Skip to main content

Applications of Glycosaminoglycans in the Medical, Veterinary, Pharmaceutical, and Cosmetic Fields

  • Chapter
  • First Online:
Industrial Applications of Renewable Biomass Products

Abstract

Glycosaminoglycans (GAGs) are complex polysaccharides ubiquitously present in the extracellular matrix of mammalian tissues, where they constitute the gelatinous material responsible for maintaining the cells together, in an intimate association with a variety of proteins. Although their structures are not strictly regular, they are composed of a repeating unit of a hexosamine-containing disaccharide. Most of them possess uronic acid residues, and with the exception of hyaluronic acid, they also carry sulfate groups. As a consequence of their high negative charge, they have an extraordinary capacity to absorb water. GAGs participate in many relevant biological processes by interaction with a plethora of proteins, and thus, a large number of applications in different fields have been conceived for GAGs and their derivatives.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 99.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 129.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 199.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  • Afratis NA, Gialeli C, Nikitovic D, Tsegenidis T, Karousou E, Theocharis AD, Pavao MS, Tzanakakis GN, Karamanos NK (2012) Glycosaminoglycans: key players in cancer cell biology and treatment. FEBS J 279:1177–1197

    Article  CAS  Google Scholar 

  • Afratis NA, Karamanos NK, Piperigkou Z, Vynios DH, Theocharis AD (2016) The role of heparins and nano-heparins as therapeutic tool in breast cancer. Glycoconj J. 2016. doi:10.1007/s10719-016-9742-7

  • Ahmad S, Ansari AA (2011) Therapeutic roles of heparin anticoagulants in cancer and related disorders. Med Chem 7:504–517

    Article  CAS  Google Scholar 

  • Aimi T, Suzuki K, Hoshino T, Mizushima T (2015) Dextran sulfate sodium inhibits amyloid-β oligomer binding to cellular prion protein. J Neurochem 134:611–617

    Article  CAS  Google Scholar 

  • Aquino SA, Park PW (2010) Diverse functions of glycosaminoglycans in infectious diseases. Prog Mol Biol Transl Sci 93:373–394

    Article  CAS  Google Scholar 

  • Aquino SA, Park PW (2016) Glycosaminoglycans and infection. Front Biosci (Landmark Ed) 21:1260–1277

    Article  Google Scholar 

  • Arevalo MT, Simpson-Haidaris PJ, Jin X, Chen H, Quinn MH (2011) Compositions and methods for inhibition of or treatment of dengue virus infection. PCT Int Appl WO 2011153458

    Google Scholar 

  • Axelsson J, Xu D, Kang BN, Nussbacher JK, Handel TM, Ley K, Sriramarao P, Esko JD (2012) Inactivation of heparan sulfate 2-O-sulfotransferase accentuates neutrophil infiltration during acute inflammation in mice. Blood 120:1742–1751

    Article  CAS  Google Scholar 

  • Bachar G, Cohen K, Hod R, Feinmesser R, Mizrachi A, Shpitzer T, Katz O, Peer D (2011) Hyaluronan-grafted particle clusters loaded with mitomycin C as selective nanovectors for primary head and neck cancers. Biomaterials 32:4840–4848

    Article  CAS  Google Scholar 

  • Badylak SF (1997) Biomaterial derived from vertebrate liver tissue. US Patent 6,379,710

    Google Scholar 

  • Badylak SF, Demeter RJ, Hiles M, Voytik SL, Knapp PM Jr (1994) Fluidized intestinal submucosa and its use as an injectable tissue graft. US Patent 5,275,826 A

    Google Scholar 

  • Badylak SF, Voytik SL, Brightman A, Waninger M (1995) Urinary bladder submucosa derived tissue graft. US Patent 5,554,389

    Google Scholar 

  • Badylak SF, Voytik-Harbin SL, Brightman AO, Tullius RS (1997) Stomach submucosa derived tissue graft. US Patent 6,099,567

    Google Scholar 

  • Barrowcliffe TJ (2012) History of heparin. Handb Exp Pharmacol 207:3–22

    Article  CAS  Google Scholar 

  • Basappa, Rangappa KS, Sugahara K (2014) Roles of glycosaminoglycans and glycanmimetics in tumor progression and metastasis. Glycoconj J 31:461–467

    Article  CAS  Google Scholar 

  • Beasley KL, Weiss M, Weiss RA (2009) Hyaluronic acid fillers: a comprehensive review. Facial Plast Surg 25:86–94

    Article  CAS  Google Scholar 

  • Bedini E, Parrilli M (2012) Synthetic and semi-synthetic chondroitin sulfate oligosaccharides, polysaccharides, and glycomimetics. Carbohydr Res 356:75–85

    Article  CAS  Google Scholar 

  • Belting M (2014) Glycosaminoglycans in cancer treatment. Thromb Res 133:S95–S101

    Article  CAS  Google Scholar 

  • Benitez A, Yates TJ, Lopez LE, Cerwinka WH, Bakkar A, Lokeshwar VB (2011) Targeting hyaluronidase for cancer therapy: antitumor activity of sulfated hyaluronic acid in prostate cancer cells. Cancer Res 71:4085–4095

    Article  CAS  Google Scholar 

  • Bernstein EF, Underhill CB, Hahn PJ, Brown DB, Uitto J (1996) Chronic sun exposure alters both the content and distribution of dermal glycosaminoglycans. Br J Dermatol 135:255–262

    Article  CAS  Google Scholar 

  • Boeriu CG, Springer J, Kooy FK, van den Broek LAM, Eggink G (2013) Production methods for hyaluronan. Int J Carbohydr Chem. Article ID 624967 2013:14

    Article  CAS  Google Scholar 

  • Bonafe F, Govoni M, Giordano E, Caldarera C, Guarnieri C, Muscari C (2014) Hyaluronan and cardiac regeneration. J Biomed Sci 21:100. 13 pp

    Article  CAS  Google Scholar 

  • Borsig L, Vlodavsky I, Ishai-Michaeli R, Torri G, Vismara E (2011) Sulfated hexasaccharides attenuate metastasis by inhibition of P-selectin and heparanase. Neoplasia 13:445–452

    Article  CAS  Google Scholar 

  • Bottegoni C, Muzzarelli RAA, Giovannini F, Busilacchi A, Gigante A (2014) Oral chondroprotection with nutraceuticals made of chondroitin sulphate plus glucosamine sulphate in osteoarthritis. Carbohydr Polym 109:126–138

    Article  CAS  Google Scholar 

  • Brougham CM, Levingstone TJ, Jockenhoevel S, Flanagan TC, O’Brien FJ (2015) Incorporation of fibrin into a collagen–glycosaminoglycan matrix results in a scaffold with improved mechanical properties and enhanced capacity to resist cell-mediated contraction. Acta Biomater 26:205–214

    Article  CAS  Google Scholar 

  • Cagno V, Donalisio M, Civra A, Volante M, Veccelli E, Oreste P, Rusnati M, Lembo D (2014) Highly sulfated K5 Escherichia coli polysaccharide derivatives inhibit respiratory syncytial virus infectivity in cell lines and human tracheal-bronchial histocultures. Antimicrob Agents Chemother 58:4782–4794

    Article  CAS  Google Scholar 

  • Campion C, Pini APJ, Gogoi RN, Gilthorpe J (2012) Sulfated oligosaccharides for use in treatment of neurodegenerative diseases. PCT Int Appl WO 2012/160337

    Google Scholar 

  • Capila I, Linhardt RJ (2002) Heparin-protein interactions. Angew Chem Int Ed Eng 41:390–412

    Article  CAS  Google Scholar 

  • Cayre Y, Allouche R (2017) Produit pour lutter contre la prolifération des cellules cancéreuse. Fr Demande FR 3039065

    Google Scholar 

  • Chang P-h (2014) Pharmaceutical formulation containing glycosaminoglycan. PCT Int Appl WO 2014142938, PCT Int Appl WO 2014143085

    Google Scholar 

  • Cheng G, Cao B (2015) Zwitterionic polysaccharide polymers having antifouling, antimicrobial and optical transparency properties. PCT Int Appl WO 2015057645 A1

    Google Scholar 

  • Conrad HE (ed) (1998) Heparin-binding proteins. Academic, San Diego

    Google Scholar 

  • Coombe DR, Kett WC (2005) Heparan sulfate-protein interactions: therapeutic potential through structure-function insights. Cell Mol Life Sci 62:410–424

    Article  CAS  Google Scholar 

  • Coppa GV, Facinelli B, Magi G, Marini E, Zampini L, Mantovani V, Galeazzi T, Padella L, Marchesiello RL, Santoro L, Coscia A, Peila C, Volpi N, Gabrielli O (2016) Human milk glycosaminoglycans inhibit in vitro the adhesion of Escherichia coli and Salmonella fyris to human intestinal cells. Pediatr Res 79:603–607

    Article  CAS  Google Scholar 

  • Cordo Russo RI, García MG, Alaniz L, Blanco G, Alvarez E, Hajos SE (2008) Hyaluronan oligosaccharides sensitize lymphoma resistant cell lines to vincristine by modulating P-glycoprotein activity and PI3K/Akt pathway. Int J Cancer 122:1012–1018

    Article  CAS  Google Scholar 

  • Crepaldi G, Fellin R, Calabrò A, Rossi A, Ventura A, Mannarino E, Senin U, Ciuffetti G, Descovich GC, Gaddi A, Rimondi S, Pozza G, Vicari A, Carandente O, Mancini M, Rubba P, Postiglione A, Strano A, Avellone G, Davì G, Novo S, Pinto A, Capurso A, Resta F, Mogavero AM, Bucci A, Antonini R, Lalloni L (1990) Double-blind multicenter trial on a new medium molecular weight glycosaminoglycan current therapeutic effects and perspectives for clinical use. Atherosclerosis 81:233–243

    Article  CAS  Google Scholar 

  • Cruz L, Meyers C (2013) Differential dependence on host cell glycosaminoglycans for infection of epithelial cells by high-risk HPV types. PLoS One 8:e68379

    Article  CAS  Google Scholar 

  • Da Costa Dias B, Jovanovic K, Gonsalves D, Weiss SFT (2011) Structural and mechanistic commonalities of amyloid-β and the prion protein. Prion 5:126–137

    Article  CAS  Google Scholar 

  • Davis DAS, Parish CR (2013) Heparan sulfate: a ubiquitous glycosaminoglycan with multiple roles in immunity. Front Immunol 4:470. 7 pp

    Google Scholar 

  • De Vita D, Giordano S (2012) Effectiveness of intravesical hyaluronic acid/chondroitin sulfate in recurrent bacterial cystitis: a randomized study. Int Urogynecol J 23:1707–1713

    Article  Google Scholar 

  • DeAngelis PL, Lane RS (2016) Heparosan/therapeutic prodrug complexes and methods of making and using same. WO 2016/065309

    Google Scholar 

  • DeAngelis PL, Liu J, Linhardt RJ (2013) Chemoenzymatic synthesis of glycosaminoglycans: re-creating, re-modeling and re-designing nature’s longest or most complex carbohydrate chains. Glycobiology 23:764–777

    Article  CAS  Google Scholar 

  • Della Valle F, Romeo A (1989) Esters of hyaluronic acid. US Patent 4,851,521

    Google Scholar 

  • Dicker KT, Gurski LA, Pradhan-Bhatt S, Witt RL, Farach-Carson MC, Jia X (2014) Hyaluronan: a simple polysaccharide with diverse biological functions. Acta Biomater 10:1558–1570

    Article  CAS  Google Scholar 

  • Eklund E, Ekman-Ordeberg G, Malmstrom A (2013) Treatment of cytokine mediated conditions. Can Pat Appl CA 2779838

    Google Scholar 

  • Esko JD (2001) Special considerations for proteoglycans and glycosaminoglycans and their purification. Curr Protoc Mol Biol 17:17.2.1–17.2.9

    Google Scholar 

  • Fabricius H-A (2015) Sulfated polysaccharides for use in the treatment of cancer. PCT Int Appl WO 2015/059177

    Google Scholar 

  • Finelli I, Chiessi E, Galesso D, Renier D, Paradossi G (2009) Gel-like structure of a hexadecyl derivative of hyaluronic acid for the treatment of osteoarthritis. Macromol Biosci 9:646–653

    Article  CAS  Google Scholar 

  • Fitton H, Gardiner V (2011) Anti-viral formulations. PCT Int Appl WO 2011/100805

    Google Scholar 

  • Flores Salgado F, Benitez Jimenez AF, Costa Rierola M, Flores Costa R, Flores Costa L (2013) Partially depolymerized glycosaminoglycan silver and gold salts. PCT Int Appl WO 2013/121001

    Google Scholar 

  • Freudenberg U, Zieris A, Chwalek K, Tsurkan MV, Maitz MF, Atallah P, Levental KR, Eming SA, Werner C (2015) Heparin desulfation modulates VEGF release and angiogenesis in diabetic wounds. J Control Release 220(Part A):79–88

    Article  CAS  Google Scholar 

  • Fu L, Suflita M, Linhardt RJ (2016) Bioengineered heparins and heparan sulfates. Adv Drug Deliv Rev 97:237–249

    Article  CAS  Google Scholar 

  • Fukuda T, Matsumoto E, Miura Y (2015) Interaction between multimeric sulfated saccharides and Alzheimer amyloid β (1-42). Chem Lett 44:1482–1484

    Article  CAS  Google Scholar 

  • Funderburgh JL (2000) Keratan sulfate: structure, biosynthesis, and function. Glycobiology 10:951–958

    Article  CAS  Google Scholar 

  • Fux L, Ilan N, Sanderson RD, Vlodavsky I (2009) Heparanase: busy at the cell surface. Trends Biochem Sci 34:511–519

    Article  CAS  Google Scholar 

  • Galus A, Mallet J-M, Lembo D, Cagno V, Djabourov M, Lortat-Jacob H, Bouchemal K (2016) Hexagonal-shaped chondroitin sulfate self-assemblies have exalted anti-HSV-2 activity. Carbohydr Polym 136:113–120

    Article  CAS  Google Scholar 

  • García B, Merayo-Lloves J, Martin C, Alcalde I, Quirós LM, Vazquez F (2016) Surface proteoglycans as mediators in bacterial pathogens infections. Front Microbiol 7:220. 11 pp

    Google Scholar 

  • Genco T, Zemljič LF, Bračič M, Stana-Kleinschek K, Heinze T (2012) Physicochemical properties and bioactivity of a novel class of cellulosics: 6-deoxy-6-amino cellulose sulfate. Macromol Chem Phys 213:539–548

    Article  CAS  Google Scholar 

  • Gilbert TW, Sellaro TL, Badylak SF (2006) Decellularization of tissues and organs. Biomaterials 27:3675–3683

    CAS  Google Scholar 

  • Gomes AM, Stelling MP, Pavão MSG (2013, 2013) Heparan sulfate and heparanase as modulators of breast cancer progression. BioMed Res Int:852093. 11 pp

    Google Scholar 

  • Gomes AM, Kozlowski EO, Borsig L, Teixeira FCOB, Vlodavsky I, Pavão MSG (2015) Antitumor properties of a new non-anticoagulant heparin analog from the mollusk Nodipecten nodosus: effect on P-selectin, heparanase, metastasis and cellular recruitment. Glycobiology 25:386–393

    Article  CAS  Google Scholar 

  • Gray E, Hogwood J, Mulloy B (2012) The anticoagulant and antithrombotic mechanisms of heparin. Handb Exp Pharmacol 207:43–61

    Article  CAS  Google Scholar 

  • Grohmann S, Hildebrand G, Liefeith K (2014) Active substance-loaded biocompatible polyelectrolyte multilayers based on sulfated glycosaminoglycans, methods for producing the multilayers, and use of the multilayers. PCT Int Appl WO 2014/147080; Ger Offen DE 102013204742

    Google Scholar 

  • Harenberg J (1998) Review of pharmacodynamics, pharmacokinetics, and therapeutic properties of sulodexide. Med Res Rev 18:1–20

    Article  CAS  Google Scholar 

  • Hendricks GL, Velazquez L, Pham S, Qaisar N, Delaney JC, Viswanathan K, Albers L, Comolli JC, Shriver Z, Knipe DM, Kurt-Jones EA, Fygenson DK, Trevejo JM, Wang JP, Finberg RW (2015) Heparin octasaccharide decoy liposomes inhibit replication of multiple viruses. Antivir Res 116:34–44

    Article  CAS  Google Scholar 

  • Herrero LJ, Foo S-S, Sheng K-C, Chen W, Forwood MR, Bucala R, Mahalingam S (2015) Pentosan polysulfate: a novel glycosaminoglycan-like molecule for the effective treatment of alphavirus-induced cartilage destruction and inflammatory disease. J Virol 89:8063–8076

    Article  CAS  Google Scholar 

  • Herrero-Mendez A, Palomares T, Castro B, Herrero J, Granado MH, Bejar JM, Alonso-Varona A (2015) HR007: a family of biomaterials based on glycosaminoglycans for tissue repair. J Tissue Eng Regen Med. doi:10.1002/term.1998

  • Hidari KI, Abe T, Suzuki T (2013) Carbohydrate-related inhibitors of dengue virus entry. Viruses 5:605–618

    Article  CAS  Google Scholar 

  • Hoshiba T, Chen G, Endo C, Maruyama H, Wakui M, Nemoto E, Kawazoe N, Tanaka M (2016) Decellularized extracellular matrix as an in vitro model to study the comprehensive roles of the ECM in stem cell differentiation. Stem Cells Int. Article ID 6397820, 10 pp

    Google Scholar 

  • Huang Y, Yao X, Zhang R, Ouyang L, Jiang R, Liu X, Song C, Zhang G, Fan Q, Wang L, Huang W (2014) Cationic conjugated polymer/fluoresceinamine-hyaluronan complex for sensitive fluorescence detection of CD44 and tumor-targeted cell imaging. ACS Appl Mater Interfaces 6:19144–19153

    Article  CAS  Google Scholar 

  • Jia X, Kiick KL (2009) Hybrid multicomponent hydrogels for tissue engineering. Macromol Biosci 9:140–156

    Article  CAS  Google Scholar 

  • Jinno-Oue A, Tanaka A, Shimizu N, Mori T, Sugiura N, Kimata K, Isomura H, Hoshino H (2013) Inhibitory effect of chondroitin sulfate type E on the binding step of human T-cell leukemia virus type 1. AIDS Res Hum Retrovir 29:621–629

    Article  CAS  Google Scholar 

  • Kallestrup E, Jørgensen S, Nordling J, Hald T (2005) Treatment of interstitial cystitis with Cystistat®, a hyaluronic acid product. Scand J Urol Nephrol 39:143–147

    Article  CAS  Google Scholar 

  • Kavasi RM, Berdiaki A, Spyridaki I, Corsini E, Tsatsakis A, Tzanakakis G, Nikitovic D (2017) HA metabolism in skin homeostasis and inflammatory disease. Food Chem Toxicol 101:128–138

    Article  CAS  Google Scholar 

  • Keane TJ, Swinehart IT, Badylak SF (2015) Methods of tissue decellularization used for preparation of biologic scaffolds and in vivo relevance. Methods 84:25–34

    Article  CAS  Google Scholar 

  • Khaderi K (2014) Compositions and methods for treating injuries to the visual system of a human. US Patent 0,212,404 A1

    Google Scholar 

  • Khanlari A, Detamore MS, Gehrke SH (2013) Increasing cross-linking efficiency of methacrylated chondroitin sulfate hydrogels by copolymerization with oligo(ethylene glycol) diacrylates. Macromolecules 46:9609–9617

    Article  CAS  Google Scholar 

  • Khanlari A, Suekama TC, Gehrke SH (2015a) Structurally versatile glycosaminoglycan hydrogels for biomedical applications. Macromol Symp 358:67–77

    Article  CAS  Google Scholar 

  • Khanlari A, Suekama TC, Detamore MS, Gehrke SH (2015b) Structurally diverse and readily tunable photocrosslinked chondroitin sulfate based copolymers. J Polym Sci Part B Polym Phys 53:1070–1079

    Article  CAS  Google Scholar 

  • Khanlari A, Schulteis JE, Suekama TC, Detamore MS, Gehrke SH (2015c) Designing crosslinked hyaluronic acid hydrogels with tunable mechanical properties for biomedical applications. J Appl Polym Sci 132. doi:10.1002/APP.42009

  • Kim E, Okumura M, Sawa H, Miyazaki T, Fujikura D, Yamada S, Sugahara K, Sasaki M, Kimura T (2011) Paradoxical effects of chondroitin sulfate-E on Japanese encephalitis viral infection. Biochem Biophys Res Commun 409:717–722

    Google Scholar 

  • Kim S-H, Turnbull J, Guimond SJ (2011) Extracellular matrix and cell signalling: the dynamic cooperation of integrin, proteoglycan and growth factor receptor. Endocrinology 209:139–151

    Google Scholar 

  • Kirn-Safran CB, D’Souza SS, Carson DD (2008) Heparan sulfate proteoglycans and their binding proteins in embryo implantation and placentation. Semin Cell Dev Biol 19:187–193

    Article  CAS  Google Scholar 

  • Kobayashi F, Yamada S, Taguwa S, Kataoka C, Naito S, Hama Y, Tani H, Matsuura Y, Sugahara K (2012) Specific interaction of the envelope glycoproteins E1 and E2 with liver heparan sulfate involved in the tissue tropismatic infection by hepatitis C virus. Glycoconj J 29:211–220

    Article  CAS  Google Scholar 

  • Kozlowski EO, Pavao MSG (2011) Effect of sulfated glycosaminoglycans on tumor invasion and metastasis. Front Biosci Sch Ed S3:1541–1551

    Article  CAS  Google Scholar 

  • Kozlowski EO, Pavao MSG, Borsig L (2011) Ascidian dermatan sulfates attenuate metastasis, inflammation and thrombosis by inhibition of P-selectin. J Thromb Haemost 9:1807–1815

    Article  CAS  Google Scholar 

  • Krichen F, Volpi N, Sila A, Maccari F, Mantovani V, Galeotti F, Ellouz-Chaabouni S, Bougatef A (2017) Purification, structural characterization and antiproliferative properties of chondroitin sulfate/dermatan sulfate from tunisian fish skins. Int J Biol Macromol 95:32–39

    Article  CAS  Google Scholar 

  • Kroma A, Feliczak-Guzik A, Nowak I (2012) The use of glycosaminoglycans in cosmetic products. Chemik 66:136–139

    CAS  Google Scholar 

  • Kwok JCF, Warren P, Fawcett JW (2012) Chondroitin sulfate: a key molecule in the brain matrix. Int J Biochem Cell Biol 44:582–586

    Article  CAS  Google Scholar 

  • Ladet S (2013) Multilayer implants for delivery of therapeutic agents. PCT Int Appl WO 2013046057

    Google Scholar 

  • Lee EC, Davis-Poynter N, Nguyen CTH, Peters AA, Monteith GR, Strounina E, Popat A, Ross BP (2016) GAG mimetic functionalised solid and mesoporous silica nanoparticles as viral entry inhibitors of herpes simplex type 1 and type 2 viruses. Nanoscale 8:16192–16196

    Article  CAS  Google Scholar 

  • Lee-Sayer SSM, Dong Y, Arif AA, Olsson M, Brown KL, Johnson P (2015) The where, when, how, and why of hyaluronan binding by immune cells. Front Immunol 6:150

    Article  CAS  Google Scholar 

  • Ley K, Cerrito M, Arfors KE (1991) Sulfated polysaccharides inhibit leukocyte rolling in rabbit mesentery venules. Am J Phys 260:1667–1673

    Google Scholar 

  • Li Y, Liu Y, Xia W, Lei D, Voorhees JJ, Fisher GJ (2013) Age-dependent alterations of decorin glycosaminoglycans in human skin. Sci Rep 3:2422. 8 pp

    Article  Google Scholar 

  • Lian W, Wu M, Huang N, Gao N, Xiao C, Li Z, Zhang Z, Zheng Y, Peng W, Zhao J (2013) Anti-HIV-1 activity and structure-activity-relationship study of a fucosylated glycosaminoglycan from an echinoderm by targeting the conserved CD4 induced epitope. Biochim Biophys Acta 1830:4681–4691

    Article  CAS  Google Scholar 

  • Liang Y, Kiick KL (2014) Heparin-functionalized polymeric biomaterials in tissue engineering and drug delivery applications. Acta Biomater 10:1588–1600

    Article  CAS  Google Scholar 

  • Liaw PC, Becker DL, Stafford AR, Fredenburgh JC, Weitz JI (2001) Molecular basis for the susceptibility of fibrin-bound thrombin to inactivation by heparin cofactor II in the presence of dermatan sulfate but not heparin. J Biol Chem 276:20959–20965

    Article  CAS  Google Scholar 

  • Lin H-Y (2015) Compound of glycosaminoglycan, preparation method and use thereof. PCT Int Appl WO 2015/028172 A1; US Patent Appl Publ US 20150065446

    Google Scholar 

  • Liu L, Liu Y, Li J, Du G, Chen J (2011) Microbial production of hyaluronic acid: current state, challenges, and perspectives. Microb Cell Factories 10:99–108

    Article  CAS  Google Scholar 

  • Liu C-C, Zhao N, Kanekiyo T, Yamaguchi Y, Cirrito JR, Holtzman DM, Bu G (2016) Neuronal heparan sulfates promote amyloid pathology by modulating brain amyloid-β clearance and aggregation in Alzheimer’s disease. Sci Transl Med 8:332ra44

    Article  CAS  Google Scholar 

  • Lompardía SL, Díaz M, Papademetrio DL, Mascaró M, Pibuel M, Álvarez E, Hajos SE (2016) Hyaluronan oligomers sensitize chronic myeloid leukemia cell lines to the effect of Imatinib. Glycobiology 26:343–352

    Article  CAS  Google Scholar 

  • Lundin A, Bergström T, Andrighetti-Fröhner CR, Bendrioua L, Ferro V, Trybala E (2012) Potent anti-respiratory syncytial virus activity of a cholestanol-sulfated tetrasaccharide conjugate. Antivir Res 93:101–109

    Article  CAS  Google Scholar 

  • Manveen K, Sethi MK, Zaia J (2017) Extracellular matrix proteomics in schizophrenia and Alzheimer’s disease. Anal Bioanal Chem 409:379–394

    Article  CAS  Google Scholar 

  • Marchi E, Tamagnone G (1994) Method of treatment of diabetic nephropathy by means of sulodexide of medicines containing it. US Patent 5,496,807

    Google Scholar 

  • Martín R, Martín C, Escobedo S, Suárez JE, Quirós LM (2013) Surface glycosaminoglycans mediate adherence between HeLa cells and lactobacillus salivarius Lv72. BMC Microbiol 13:210. 11 pp

    Article  CAS  Google Scholar 

  • Martinez P, Vergoten G, Colomb F, Bobowski M, Steenackers A, Carpentier M, Allain F, Delannoy P, Julien S (2013) Over-sulfated glycosaminoglycans are alternative selectin ligands: insights into molecular interactions and possible role in breast cancer metastasis. Clin Exp Metastasis 30:919–931

    Article  CAS  Google Scholar 

  • Matheny RG (2015) Compositions and methods for preventing cardiac arrhythmia. US Patent 2015/0164959 A1

    Google Scholar 

  • Mathieu C, Dhondt KP, Chalons M, Mely S, Raoul H, Negre D, Cosset F-L, Gerlier D, Vives RR, Horvat B (2015) Heparan sulfate-dependent enhancement of henipavirus infection. MBio 6:1–10

    Article  CAS  Google Scholar 

  • Memi E, Karakiulakis G, Goma F, Papakonstantinou E (2012) The functional role of glycosaminoglycans in the pathophysiology of the thyroid gland and their putative role as prognostic, diagnostic and therapeutic agents in thyroid pathologies. Rev Clin Pharmacol Pharmacokinet Int Ed 26:61–86

    CAS  Google Scholar 

  • Mikami T, Kitagawa H (2013) Biosynthesis and function of chondroitin sulfate. Biochim Biophys Acta Gen Subj 1830:4719–4733

    Article  CAS  Google Scholar 

  • Misra S, Hascall VC, Markwald RR, Ghatak S (2015) Interactions between hyaluronan and its receptors (CD44, RHAMM) regulate the activities of inflammation and cancer. Front Immunol 6:201. 31 pp

    Article  CAS  Google Scholar 

  • Mizumoto S, Sugahara (2013) Glycosaminoglycans are functional ligands for receptor for advanced glycation end-products in tumors. FEBS J 280:2462–2470

    Article  CAS  Google Scholar 

  • Mizumoto S, Takahashi J, Sugahara K (2012) Receptor for advanced glycation end products (RAGE) functions as receptor for specific sulfated glycosaminoglycans, and anti-RAGE antibody or sulfated glycosaminoglycans delivered in vivo inhibit pulmonary metastasis of tumor cells. J Biol Chem 287:18985–18994

    Article  CAS  Google Scholar 

  • Monfort J, Pelletier J-P, Garcia-Giralt N, Martel-Pelletier J (2008) Biochemical basis of the effect of chondroitin sulphate on osteoarthritis articular tissues. Ann Rheum Dis 67:735–740

    Article  CAS  Google Scholar 

  • Mousa SA (2015) Composition and method for sulfated non-anticoagulant low molecular weight heparins in cancer and tumor metastasis. US Patent Appl Publ US 20150132399

    Google Scholar 

  • Mousa SA (2016) Composition and method of use for combinations of anti-viral protease, polymerase inhibitors and natural bioactive compounds in the treatment of hepatitis C infection. US Patent Appl Publ US20160346308 A1

    Google Scholar 

  • Murphy CM, Duffy GP, Schindeler A, O’Brien FJ (2016) Effect of collagen-glycosaminoglycan scaffold pore size on matrix mineralization and cellular behavior in different cell types. J Biomed Mater Res Part A 104:291–304

    Article  CAS  Google Scholar 

  • Nakano T, Betti M, Pietrasik Z (2010) Extraction, isolation and analysis of chondroitin sulfate glycosaminoglycans. Recent Pat Food Nutr Agric 2:61–74

    Article  CAS  Google Scholar 

  • Nickel JC, Egerdie RB, Steinhoff G, Palmer B, Hanno P (2010) A multicenter, randomized, double-blind, parallel group pilot evaluation of the efficacy and safety of intravesical sodium chondroitin sulfate versus vehicle control in patients with interstitial cystitis/painful bladder syndrome. Urology 76:804–809

    Article  Google Scholar 

  • Nikitovic D, Chatzinikolaou G, Tsiaoussis J, Tsatsakis A, Karamanos NK, Tzanakakis GN (2012) Insights into targeting colon cancer cell fate at the level of proteoglycans/glycosaminoglycans. Curr Med Chem 19:4247–4258

    Article  CAS  Google Scholar 

  • Nishimura Y, Shudo H, Seto H, Hoshino Y, Miura Y (2013) Syntheses of sulfated glycopolymers and analyses of their BACE-1 inhibitory activity. Bioorg Med Chem Lett 23:6390–6395

    Article  CAS  Google Scholar 

  • Nugent MA (2000) Heparin sequencing brings structure to the function of complex oligosaccharides. Proc Natl Acad Sci U S A 97:10301–10303

    Article  CAS  Google Scholar 

  • O'Hearn A, Wang M, Cheng H, Lear-Rooney CM, Koning K, Rumschlag-Booms E, Varhegyi E, Olinger G, Rong L (2015) Role of EXT1 and glycosaminoglycans in the early stage of filovirus entry. J Virol 89:5441–5449

    Article  CAS  Google Scholar 

  • Papakonstantinou E, Roth M, Karakiulakis G (2012) Hyaluronic acid: a key molecule in skin aging. Dermato-Endocrinol 4:253–258

    Article  CAS  Google Scholar 

  • Papy-Garcia D, Christophe M, Huynh MB, Sineriz F, Sissoeff L, Sepulveda-Diaz JE, Raisman-Vozari R (2011) Glycosaminoglycans, protein aggregation and neurodegeneration. Curr Protein Pept Sci 12:258–268

    Article  CAS  Google Scholar 

  • Papy-Garcia D, Huynh MB, Soussi-Yanicostas N, Vozari R, Sineriz F, Yanicostas C (2013) Method of diagnosis, prognosis, or treatment of neurodegenerative diseases. PCT Int Appl WO 2013/053954.

    Google Scholar 

  • Paul TJ, Kelly H, Zuchniarz J, Ahmed T, Prabhakar R (2016) Design of heparin oligosaccharide based molecules for inhibition of Alzheimer amyloid beta (Aβ40) aggregation. Can J Chem 94:1090–1098

    Article  CAS  Google Scholar 

  • Peer D (2015) Liposomal formulations for delivery of nucleic acids. Int Appl WO 2015/198326

    Google Scholar 

  • Persson A, Tykesson E, Westergren-Thorsson G, Malmström A, Ellervik U, Mani K (2016) Xyloside-primed chondroitin sulfate/dermatan sulfate from breast carcinoma cells with a defined disaccharide composition has cytotoxic effects in vitro. J Biol Chem 291:14871–14882

    Article  CAS  Google Scholar 

  • Petrey AC, de la Motte CA (2014) Hyaluronan, a crucial regulator of inflammation. Front Immunol 5:101

    Article  CAS  Google Scholar 

  • Pisano C, Vlodavsky I, Ilan N, Zunino F (2014) The potential of heparanase as a therapeutic target in cancer. Biochem Pharmacol 89:12–19

    Article  CAS  Google Scholar 

  • Pomin VH (2015a) A dilemma in the glycosaminoglycan-based therapy: synthetic or naturally unique molecules? Med Res Rev 35:1195–1219

    Article  CAS  Google Scholar 

  • Pomin VH (2015b) Sulfated glycans in inflammation. Eur J Med Chem 92:353–369

    Article  CAS  Google Scholar 

  • Pomin VH, Mulloy B (2015) Current structural biology of the heparin interactome. Curr Opin Struct Biol 34:17–25

    Article  CAS  Google Scholar 

  • Prestwich GD, Kennedy TP (2011) Methods for treating or preventing the spread of cancer using semi-synthetic glycosaminoglycosan ethers. PCT Int Appl WO 2011/094149

    Google Scholar 

  • Prestwich GD, Oottamasathein S, Kennedy T (2011) Applications of partially and fully sulfated hyaluronan. PCT Int Appl WO 2011/156445

    Google Scholar 

  • Prestwich GD, Oottamasathien S, Kennedy TP (2013) Applications of partially and fully sulfated hyaluronan. US Patent Appl 0,209,531

    Google Scholar 

  • Puperi DS, O’Connell RW, Punske ZE, Wu Y, West JL, Grande-Allen KJ (2016) Hyaluronan hydrogels for a biomimetic spongiosa layer of tissue engineered heart valve scaffolds. Biomacromolecules 17:1766–1775

    Article  CAS  Google Scholar 

  • Pye DA, Ogundipe OD (2016) Pharmaceutical extracts and uses thereof. PCT Int Appl WO 2016/067008

    Google Scholar 

  • Qian W, Tao L, Wang Y, Zhang F, Li M, Huang S, Wang A, Chen W, Yue Z, Chen L, Liu Y, Huang C, Zhang L, Li Y, Lu Y (2015) Downregulation of integrins in cancer cells and anti-platelet properties are involved in holothurian glycosaminoglycan-mediated disruption of the interaction of cancer cells and platelets in hematogenous metastasis. J Vasc Res 52:197–209

    Article  CAS  Google Scholar 

  • Radhakrishnan K, Tripathy J, Datey A, Chakravortty D, Raichur AM (2015) Mesoporous silica-chondroitin sulphate hybrid nanoparticles for targeted and bio-responsive drug delivery. New J Chem 39:1754–1760

    Article  CAS  Google Scholar 

  • Rankin KS, Frankel D (2016) Hyaluronan in cancer – from the naked mole rat to nanoparticle therapy. Soft Matter 12:3841–3848

    Article  CAS  Google Scholar 

  • Rawat M, Hsieh-Wilson L (2014) Glycosaminoglycan mimetics. US Patent 8,912,149 B1

    Google Scholar 

  • Reinmueller J, Dirting K (2012) Antiinfective composition. PCT Int Appl WO 2012/168462; Ger Offen DE 102011077393

    Google Scholar 

  • Ren X, Weisgerber DW, Bischoff D, Lewis MS, Reid RR, He T-C, Yamaguchi DT, Miller TA, Harley BAC, Lee JC (2016) Nanoparticulate mineralized collagen scaffolds and BMP-9 induce a long-term bone cartilage construct in human mesenchymal stem cells. Adv Healthc Mater 5:1821–1830

    Article  CAS  Google Scholar 

  • Rilla K, Tiihonen R, Kultti A, Tammi M, Tammi R (2008) Pericellular hyaluronan coat visualized in live cells with a fluorescent probe is scaffolded by plasma membrane protrusions. J Histochem Cytochem 56:901–910

    Article  CAS  Google Scholar 

  • Ritchie JP, Ramani VC, Ren Y, Naggi A, Torri G, Casu B, Penco S, Pisano C, Carminati P, Tortoreto M, Zunino F, Vlodavsky I, Sanderson RD, Yang Y (2011) SST0001, a chemically modified heparin, inhibits myeloma growth and angiogenesis via disruption of the heparanase/syndecan-1 axis. Clin Cancer Res 17:1382–1393

    Article  CAS  Google Scholar 

  • Ronca F, Palmieri L, Panicucci P, Ronca G (1998) Anti-inflammatory activity of chondroitin sulfate. Osteoarthr Cartil 6(Suppl A):14–21

    Article  Google Scholar 

  • Said JS, Trybala E, Görander S, Ekblad M, Liljeqvist J-A, Jennische E, Lange S, Bergström T (2016) The cholestanol-conjugated sulfated oligosaccharide PG545 disrupts the lipid envelope of herpes simplex virus particles. Antimicrob Agents Chemother 60:1049–1057

    Article  CAS  Google Scholar 

  • Sakiyama-Elbert SE (2014) Incorporation of heparin into biomaterials. Acta Biomater 10:1581–1587

    Article  CAS  Google Scholar 

  • Salbach J, Rachner TD, Rauner M, Hempel U, Anderegg U, Franz S, Simon J-C, Hofbauer LC (2012) Regenerative potential of glycosaminoglycans for skin and bone. J Mol Med 90:625–635

    Article  Google Scholar 

  • Savage JR, Pulsipher A, Rao NV, Kennedy TP, Prestwich GD, Ryan ME, Lee WY (2016) A modified glycosaminoglycan, GM-0111, inhibits molecular signaling involved in periodontitis. PLoS One 11:e0157310/1

    CAS  Google Scholar 

  • Sayari N, Balti R, Ben Mansour M, Ben Amor I, Graiet I, Gargouri J, Bougatef A (2016) Anticoagulant properties and cytotoxic effect against HCT116 human colon cell line of sulfated glycosaminoglycans isolated from the Norway lobster (Nephrops norvegicus) shell. Biomed Pharmacother 80:322–330

    Article  CAS  Google Scholar 

  • Schaefer L, Schaefer RM (2010) Proteoglycans: from structural compounds to signaling molecules. Cell Tissue Res 339:237–246

    Article  CAS  Google Scholar 

  • Schnabelrauch M, Scharnweber D, Schiller J (2013) Sulfated glycosaminoglycans as promising artificial extracellular matrix components to improve the regeneration of tissues. J Curr Med Chem 20:2501–2523

    Article  CAS  Google Scholar 

  • Schwoerer R, Zubkova OV, Turnbull JE, Tyler PC (2013) Synthesis of a targeted library of heparan sulfate hexa- to dodecasaccharides as inhibitors of β-secretase: potential therapeutics for Alzheimer’s disease. Chem Eur J 19:6817–6823

    Google Scholar 

  • Scott IR (1988) Skin treatment composition. EP 0295092 B1

    Google Scholar 

  • Seki Y, Mizukura M, Ichimiya T, Suda Y, Nishihara S, Masuda M, Takase-Yoden S (2012) O-sulfate groups of heparin are critical for inhibition of ecotropic murine leukemia virus infection by heparin. Virology 424:56–66

    Article  CAS  Google Scholar 

  • Silva LA, Khomandiak S, Ashbrook AW, Weller R, Heise MT, Morrison TE, Dermody TS (2014) A single-amino-acid polymorphism in chikungunya virus E2 glycoprotein influences glycosaminoglycan utilization. J Virol 88:2385–2397

    Article  CAS  Google Scholar 

  • Simionescu D, Mercuri JJ (2016). Shape-memory sponge hydrogel biomaterial. US Patent 9,283,301

    Google Scholar 

  • Spero M, Weiss MS, Kopp JB (2005) Methods using glycosaminoglycans for the treatment of kidney disease. PCT Int Appl WO 2006039709 A1

    Google Scholar 

  • Staples GO, Zaia J (2011) Mass spectrometry in carbohydrate sequencing and binding analysis. In: Wang B, Boons G-J (eds) Carbohydrate recognition: biological problems, methods, and applications. Wiley, Hoboken, pp 257–300

    Chapter  Google Scholar 

  • Stern R, Maibach HI (2008) Hyaluronan in skin: aspects of aging and its pharmacologic modulation. Clin Dermatol 26:106–122

    Article  Google Scholar 

  • Stewart KL, Hughes E, Yates EA, Akien GR, Huang T-Y, Lima MA, Rudd TR, Guerrini M, Hung S-C, Radford SE, Middleton DA (2016) Atomic details of the interactions of glycosaminoglycans with amyloid β fibrils. J Am Chem Soc 138:8328–8331

    Article  CAS  Google Scholar 

  • Ströh LJ, Stehle T (2014) Glycan engagement by viruses: receptor switches and specificity. Ann Rev Virol 1:285–306

    Article  CAS  Google Scholar 

  • Tangso KJ, da Cunha PHCD, Spicer P, Li J, Boyd BJ (2016) Antimicrobial activity from colistin-heparin lamellar-phase complexes for the coating of biomedical devices. ACS Appl Mater Interfaces 8:31321–31329

    Article  CAS  Google Scholar 

  • Theocharis AD, Skandalis SS, Gialeli C, Karamanos NK (2016) Extracellular matrix structure. Adv Drug Deliv Rev 97:4–27

    Article  CAS  Google Scholar 

  • Turley E (2010) Topically administered, skin-penetrating glycosaminoglycan formulations suitable for use in cosmetic and pharmaceutical applications. CA 2703532 A1; PCT Int Appl WO 2011/140630 A1

    Google Scholar 

  • Tyler PC, Guimond SE, Turnbull JE, Zubkova OV (2015) Single-entity heparan sulfate glycomimetic clusters for therapeutic applications. Angew Chem Int Ed 54:2718–2723

    Article  CAS  Google Scholar 

  • Verges Milano J, Garcia Garcia A, Ruhi Roura R, Montell Bonaventura E, Garcia Lopez M, Alaez Verson CR, Escaich Ferrer J, Egea Maiquez J, Lorrio Gonzalez S, Negredo Madrigal P (2011) Sulphated disaccharides for the treatment of neurodegenerative and/or neurovascular diseases. PCT Int. Appl. WO 2011/080203

    Google Scholar 

  • Vistoli G, De Maddis D, Cipak A, Zarkovic N, Carini M, Aldini G (2013) Advanced glycoxidation and lipoxidation end products (AGEs and ALEs): an overview of their mechanisms of formation. Free Radic Res 47:3–27

    Article  CAS  Google Scholar 

  • Volpi N, Schiller J, Stern R, Soltes L (2009) Role, metabolism, chemical modifications and applications of hyaluronan. Curr Med Chem 16:1718–1745

    Article  CAS  Google Scholar 

  • Von Recum HA, Hijaz A (2014) Glycosaminoglycans for chemokine drug delivery. U.S. Pat. Appl. Publ. US 20140364360

    Google Scholar 

  • Vuillermoz B, Wegrowski Y, Contet-Audonneau J-L, Danoux L, Pauly G, Maquart F-X (2005) Influence of aging on glycosaminoglycans and small leucine-rich proteoglycans production by skin fibroblasts. Mol Cell Biochem 277:63–72

    Article  CAS  Google Scholar 

  • Wang P, Ding K (2014) Proteoglycans and glycosaminoglycans in misfolded proteins formation in Alzheimer’s disease. Protein Pept Lett 21:1048–1056

    Article  CAS  Google Scholar 

  • Weigel PH, Fuller GM, LeBoeuf RD (1986) A model for the role of hyaluronic acid and fibrin in the early events during the inflammatory response and wound healing. J Theor Biol 119:219–234

    Article  CAS  Google Scholar 

  • Wu RL, Huang L, Zhao H-C, Geng X-P (2017) Hyaluronic acid in digestive cancers. J Cancer Res Clin Oncol 143:1–16

    Article  CAS  Google Scholar 

  • Xiao L, Tong Z, Chen Y, Pochan DJ, Sabanayagam CR, Jia X (2013) Hyaluronic acid-based hydrogels containing covalently integrated drug depots: implication for controlling inflammation in mechanically stressed tissues. Biomacromolecules 14:3808–3819

    Article  CAS  Google Scholar 

  • Xu D, Olson J, Cole JN, van Wijk XM, Brinkmann V, Zychlinsky A, Nizet V, Esko JD, Chang Y-C (2015) Heparan sulfate modulates neutrophil and endothelial function in antibacterial innate immunity. Infect Immun 83:3648–3656

    Article  CAS  Google Scholar 

  • Yang R-M, Fu C-P, Li N-N, Wang L, Xu X-D, Yang D-Y, Fang J-Z, Jiang X-Q, Zhang L-M (2014) Glycosaminoglycan-targeted iron oxide nanoparticles for magnetic resonance imaging of liver carcinoma. Mater Sci Eng C Mater Biol Appl 45:556–563

    Article  CAS  Google Scholar 

  • Yang X, Du H, Liu J, Zhai G (2015) Advanced nanocarriers based on heparin and its derivatives for cancer management. Biomacromolecules 16:423–436

    Article  CAS  Google Scholar 

  • Yip GW, Smollich M, Götte M (2006) Therapeutic value of glycosaminoglycans in cancer. Mol Cancer Ther 5:2139–2148

    Article  CAS  Google Scholar 

  • Yue Z, Wang A, Zhu Z, Tao L, Li Y, Zhou L, Chen W, Lu Y (2015) Holothurian glycosaminoglycan inhibits metastasis via inhibition of P-selectin in B16F10 melanoma cells. Mol Cell Biochem 410:143–154

    Article  CAS  Google Scholar 

  • Yuk SH, Oh KS, Cho SH, Lee BS, Kim SY, Kwak BK, Kim K, Kwon IC (2011) Glycol chitosan/heparin immobilized iron oxide nanoparticles with a tumor-targeting characteristic for magnetic resonance imaging. Biomacromolecules 12:2335–2343

    Article  CAS  Google Scholar 

  • Zhang Q, Li J, Liu C, Song C, Li P, Yin F, Xiao Y, Jiang W, Zong A, Zhang X, Wang F (2015) Protective effects of low molecular weight chondroitin sulfate on amyloid beta (Aβ)-induced damage in vitro and in vivo. Neuroscience 305:169–182

    Article  CAS  Google Scholar 

  • Zhang RR, Strebe JK, Kuo JS (2016) Heparan sulfates promote amyloid pathology in Alzheimer disease. Neurosurgery 79:N12–N13

    Google Scholar 

  • Zhang X, Zhao X, Lang Y, Li Q, Liu X, Cai C, Hao J, Li G, Yu G (2016) Low anticoagulant heparin oligosaccharides as inhibitors of BACE-1, the Alzheimer’s β-secretase. Carbohydr Polym 151:51–59

    Google Scholar 

  • Zhao W, McCallum SA, Xiao Z, Zhang F, Linhardt RJ (2012) Binding affinities of vascular endothelial growth factor (VEGF) for heparin-derived oligosaccharides. Biosci Rep 32:71–81

    Article  CAS  Google Scholar 

  • Zheng S, Jin Z, Han J, Cho S, Nguyen VD, Young Ko S, Park J-O, Park S (2016) Preparation of HIFU-triggered tumor-targeted hyaluronic acid micelles for controlled drug release and enhanced cellular uptake. Colloids Surf B: Biointerfaces 143:27–36

    Article  CAS  Google Scholar 

  • Zhong WP, Chin HG, Lee EJ, Guo S, Yip GW, Lam Y (2015) Divergent synthesis of chondroitin sulfate disaccharides and identification of sulfate motifs that inhibit triple negative breast cancer. Sci Rep 5:14355. 8 pp

    Article  CAS  Google Scholar 

  • Zhou X, Jin L (2016) The structure-activity relationship of glycosaminoglycans and their analogues with β-amyloid peptide. Protein Pept Lett 23:358–364

    Article  CAS  Google Scholar 

  • Zhou H, Roy S, Cochran E, Zouaoui R, Chu CL, Duffner J, Zhao G, Smith S, Galcheva-Gargova Z, Karlgren J, Dussault N, Kwan RY, Moy E, Barnes M, Long A, Honan C, Qi YW, Shriver Z, Ganguly T, Schultes B, Venkataraman G, Kishimoto TK (2011) M402, a novel heparan sulfate mimetic, targets multiple pathways implicated in tumor progression and metastasis. PLoS One 6:e21106

    Article  CAS  Google Scholar 

  • Zhu M, Feng Q, Sun Y, Li G, Bian L (2016) Effect of cartilaginous matrix components on the chondrogenesis and hypertrophy of mesenchymal stem cells in hyaluronic acid hydrogels. J Biomed Mater Res Part B Appl Biomater. doi:10.1002/jbm.b.33760

  • Zieris A, Dockhorn R, Röhrich A, Zimmermann R, Müller M, Welzel PB, Tsurkan MV, Sommer J-U, Freudenberg U, Werner C (2014) Biohybrid networks of selectively desulfated glycosaminoglycans for tunable growth factor delivery. Biomacromolecules 55:4439–4446

    Article  CAS  Google Scholar 

  • Zimmer R, Courty J (2012) Compositions comprising multivalent synthetic ligands of surface nucleolin and glycosaminoglycans. PCT Int Appl WO 2012/045750

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to María Laura Uhrig .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2017 Springer International Publishing AG

About this chapter

Cite this chapter

Kovensky, J., Grand, E., Uhrig, M.L. (2017). Applications of Glycosaminoglycans in the Medical, Veterinary, Pharmaceutical, and Cosmetic Fields. In: Goyanes, S., D’Accorso, N. (eds) Industrial Applications of Renewable Biomass Products. Springer, Cham. https://doi.org/10.1007/978-3-319-61288-1_5

Download citation

Publish with us

Policies and ethics