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Molecularly Imprinted Polymers Doped with Carbon Nanotube with Aid of Metal-Organic Gel for Drug Delivery Systems

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Abstract

Purpose

The incidence of breast cancer worldwide has been on the rise since the late 1970s, and it has become a common tumor that threatens women’s health. Aminoglutethimide (AG) is a common treatment of breast cancer. However, current treatments require frequent dosing that results in unstable plasma concentration and low bioavailability, risking serious adverse reactions. Our goal was to develop a molecularly imprinted polymer (MIP) based delivery system to control the release of AG and demonstrate the availability of this drug delivery system (DDS), which was doped with carbon nanotube with aid of metal-organic gel.

Methods

Preparation of MIP was optimized by key factors including composition of formula, ratio of monomers and drug loading concentration.

Results

By using multi-walled carbon nanotubes (MWCNT) and metal-organic gels (MOGs), MIP doubled the specific surface area, pore volume tripled and the IF was 1.6 times than the reference. Compared with commercial tablets, the relative bioavailability was 143.3% and a more stable release appeared.

Conclusions

The results highlight the influence of MWCNT and MOGs on MIP, which has great potential as a DDS.

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References

  1. Marasini N, Haque S, Kaminskas LM. Polymer-drug conjugates as inhalable drug delivery systems: a review. Curr Opin Colloid Interface Sci. 2017;31:18–29.

    CAS  Google Scholar 

  2. Mao S, Guo C, Shi Y, Li LC. Recent advances in polymeric microspheres for parenteral drug delivery - part 1. Exp Opin Drug Deliv. 2012;9(9):1161–76.

    CAS  Google Scholar 

  3. Forssen E, Willis M. Ligand-targeted liposomes. Adv Drug Deliv Rev. 1998;29(3):249–71.

    CAS  Google Scholar 

  4. Allen TM, Cullis PR. Drug delivery systems: entering the mainstream. Science. 2004;303(5665):1818–22.

    CAS  Google Scholar 

  5. Gagliardi M, Mazzolai B. Molecularly imprinted polymeric micro- and nano-particles for the targeted delivery of active molecules. Future Med Chem. 2015;7(2):123–38.

    CAS  Google Scholar 

  6. Lulinski P. Molecularly imprinted polymers based drug delivery devices: a way to application in modern pharmacotherapy. A review. Mater Sci Eng C-Mater Biol Appl. 2017;76:1344–53.

    CAS  Google Scholar 

  7. Tang L, Zhao C-Y, Wang X-H, Li R-S, Yang J-R, Huang Y-P, et al. Macromolecular crowding of molecular imprinting: a facile pathway to produce drug delivery devices for zero-order sustained release. Int J Pharm. 2015;496(2):822–33.

    CAS  Google Scholar 

  8. Zhang L-P, Tan X-X, Huang Y-P, Liu Z-S. Floating liquid crystalline molecularly imprinted polymer coated carbon nanotubes for levofloxacin delivery. Eur J Pharm Biopharm. 2018;127:150–8.

    CAS  Google Scholar 

  9. Tuwahatu CA, Yeung CC, Lam YW, Roy VAL. The molecularly imprinted polymer essentials: curation of anticancer, ophthalmic, and projected gene therapy drug delivery systems. J Control Release. 2018;287:24–34.

    CAS  Google Scholar 

  10. Dhanashree S, Priyanka M, Manisha K, Vilasrao K. Molecularly imprinted polymers: novel discovery for drug delivery. Curr Drug Deliv. 2016;13(5):632–45.

    CAS  Google Scholar 

  11. Xiao YH, Xiao R, Tang J, Zhu QK, Li XM, Xiong Y, et al. Preparation and adsorption properties of molecularly imprinted polymer via RAFT precipitation polymerization for selective removal of aristolochic acid I. Talanta. 2017;162:415–22.

    CAS  Google Scholar 

  12. Bagheri N, Habibi B, Khataee A, Hassanzadeh J. Application of surface molecular imprinted magnetic graphene oxide and high performance mimetic behavior of bi-metal ZnCo MOF for determination of atropine in human serum. Talanta. 2019;201:286–94.

    CAS  Google Scholar 

  13. Booker K, Bowyer MC, Holdsworth CI, McCluskey A. Efficient preparation and improved sensitivity of molecularly imprinted polymers using room temperature ionic liquids. Chem Commun. 2006;16:1730–2.

    Google Scholar 

  14. He CY, Long YY, Pan JL, Li K, Liu F. Molecularly imprinted silica prepared with immiscible ionic liquid as solvent and porogen for selective recognition of testosterone. Talanta. 2008;74(5):1126–31.

    CAS  Google Scholar 

  15. Li F, Chen XX, Huang YP, Liu ZS. Preparation of polyhedral oligomeric silsesquioxane based imprinted monolith. J Chromatogr A. 2015;1425:180–8.

    CAS  Google Scholar 

  16. da Silva MS, Viveiros R, Aguiar-Ricardo A, Bonifacio VDB, Casimiro T. Supercritical fluid technology as a new strategy for the development of semi-covalent molecularly imprinted materials. RSC Adv. 2012;2(12):5075–9.

    Google Scholar 

  17. da Silva MS, Viveiros R, Coelho MB, Aguiar-Ricardo A, Casimiro T. Supercritical CO2-assisted preparation of a PMMA composite membrane for bisphenol a recognition in aqueous environment. Chem Eng Sci. 2012;68(1):94–100.

    Google Scholar 

  18. Marcelo G, Ferreira IC, Viveiros R, Casimiro T. Development of itaconic acid-based molecular imprinted polymers using supercritical fluid technology for pH-triggered drug delivery. Int J Pharm. 2018;542(1–2):125–31.

    CAS  Google Scholar 

  19. Zhong DD, Liu X, Pang QQ, Huang YP, Liu ZS. Rapid preparation of molecularly imprinted polymer by frontal polymerization. Anal Bioanal Chem. 2013;405(10):3205–14.

    CAS  Google Scholar 

  20. Liang SR, Yan HY, Cao JK, Han YH, Shen SG, Bai LG. Molecularly imprinted phloroglucinol-formaldehyde-melamine resin prepared in a deep eutectic solvent for selective recognition of clorprenaline and bambuterol in urine. Anal Chim Acta. 2017;951:68–77.

    CAS  Google Scholar 

  21. Tang WY, Gao F, Duan Y, Zhu T, Row KH. Exploration of deep eutectic solvent-based molecularly imprinted polymers as solid-phase extraction sorbents for screening chloramphenicol in milk. J Chromatogr Sci. 2017;55(6):654–61.

    CAS  Google Scholar 

  22. Junqueira-Goncalves MP, Salinas GE, Bruna JE, Niranjan K. An assessment of lactobiopolymer-montmorillonite composites for dip coating applications on fresh strawberries. J Sci Food Agric. 2017;97(6):1846–53.

    CAS  Google Scholar 

  23. Du YZ, Yu M, Chen XF, Ma PX, Lei B. Development of biodegradable poly(citrate)-polyhedral Oligomeric Silsesquioxanes hybrid elastomers with high mechanical properties and Osteogenic differentiation activity. ACS Appl Mater Interfaces. 2016;8(5):3079–91.

    CAS  Google Scholar 

  24. Yin SJ, Jin ZW, Miyake T. Wearable high-powered biofuel cells using enzyme/carbon nanotube composite fibers on textile cloth. Biosens Bioelectron. 2019;141:6.

    Google Scholar 

  25. Kinloch IA, Suhr J, Lou J, Young RJ, Ajayan PM. Composites with carbon nanotubes and graphene: an outlook. Science. 2018;362(6414):547–53.

    CAS  Google Scholar 

  26. Sun XM, Sun H, Li HP, Peng HS. Developing polymer composite materials: carbon nanotubes or Graphene? Adv Mater. 2013;25(37):5153–76.

    CAS  Google Scholar 

  27. Dorraji PS, Noori M, Fotouhi L. Voltammetric determination of adefovir dipivoxil by using a nanocomposite prepared from molecularly imprinted poly(o-phenylenediamine), multi-walled carbon nanotubes and carbon nitride. Microchim Acta. 2019;186(7):8.

    Google Scholar 

  28. Amatatongchai M, Sroysee W, Sodkrathok P, Kesangam N, Chairam S, Jarujamrus P. Novel three-dimensional molecularly imprinted polymer-coated carbon nanotubes (3D-CNTs@MIP) for selective detection of profenofos in food. Anal Chim Acta. 2019;1076:64–72.

    CAS  Google Scholar 

  29. Liu XL, Yao HF, Chai MH, He W, Huang YP, Liu ZS. Green synthesis of carbon nanotubes-reinforced molecularly imprinted polymer composites for drug delivery of fenbufen. AAPS PharmSciTech. 2018;19(8):3895–906.

    CAS  Google Scholar 

  30. Chen J-F, Liu X, Ma J-F, Han B-B, Ding J-D, Lin Q, et al. A pillar 5 arene-based multiple-stimuli responsive metal-organic gel was constructed for facile removal of mercury ions. Soft Matter. 2017;13(30):5214–8.

    CAS  Google Scholar 

  31. Wei Q, James SL. A metal-organic gel used as a template for a porous organic polymer. Chem Commun. 2005;12:1555–6.

    Google Scholar 

  32. Barman S, Garg JA, Blacque O, Venkatesan K, Berke H. Triptycene based luminescent metal-organic gels for chemosensing. Chem Commun. 2012;48(90):11127–9.

    CAS  Google Scholar 

  33. Ma L, Tang L, Li RS, Huang YP, Liu ZS. Water-compatible molecularly imprinted polymers prepared using metal-organic gel as porogen. RSC Adv. 2015;5(103):84601–9.

    CAS  Google Scholar 

  34. Geisler J, Johannessen DC, Anker G, Lonning PE. Treatment with formestane alone and in combination with aminoglutethimide in heavily pretreated breast cancer patients: clinical and endocrine effects. Eur J Cancer. 1996;32A(5):789–92.

    CAS  Google Scholar 

  35. Umpleby RJ, Baxter SC, Chen YZ, Shah RN, Shimizu KD. Characterization of molecularly imprinted polymers with the Langmuir-Freundlich isotherm. Anal Chem. 2001;73(19):4584–91.

    CAS  Google Scholar 

  36. Ceglowski M, Hoogenboom R. Molecularly imprinted poly(2-oxazoline) based on cross-linking by direct amidation of methyl ester side chains. Macromolecules. 2018;51(16):6468–75.

    CAS  Google Scholar 

  37. Yin JF, Yang GL, Wang HL, Chen Y. Macroporous polymer monoliths fabricated by using a metal-organic coordination gel template. Chem Commun. 2007;44:4614–6.

    Google Scholar 

  38. Rampey AM, Umpleby RJ, Rushton GT, Iseman JC, Shah RN, Shimizu KD. Characterization of the imprint effect and the influence of imprinting conditions on affinity, capacity, and heterogeneity in molecularly imprinted polymers using the Freundlich isotherm-affinity distribution analysis. Anal Chem. 2004;76(4):1123–33.

    CAS  Google Scholar 

  39. Thommes M, Kaneko K, Neimark AV, Olivier JP, Rodriguez-Reinoso F, Rouquerol J, et al. Physisorption of gases, with special reference to the evaluation of surface area and pore size distribution (IUPAC technical report). Pure Appl Chem. 2015;87(9–10):1051–69.

    CAS  Google Scholar 

  40. Ritger PL, Peppas NA. A simple equation for description of solute release I. Fickian and non-fickian release from non-swellable devices in the form of slabs, spheres, cylinders or discs. J Control Release. 1987;5(1):23–36.

    CAS  Google Scholar 

  41. Liu Z, Davis C, Cai W, He L, Chen X, Dai H. Circulation and long-term fate of functionalized, biocompatible single-walled carbon nanotubes in mice probed by Raman spectroscopy. PNAS. 2008;105:1410–5.

    CAS  Google Scholar 

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Author notes

  1. Long Zhao, Mei-Hong Chai and Hong-Fei Yao contributed equally to this work.

Authors and Affiliations

  1. Tianjin Key Laboratory on Technologies Enabling Development of Clinical Therapeutics and Diagnostics (Theranostics), School of Pharmacy, Tianjin Medical University, Tianjin, 300070, China

    Long Zhao, Mei-Hong Chai, Hong-Fei Yao, Yan-Ping Huang & Zhao-Sheng Liu

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  1. Long Zhao
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  2. Mei-Hong Chai
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  3. Hong-Fei Yao
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  4. Yan-Ping Huang
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  5. Zhao-Sheng Liu
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Correspondence to Yan-Ping Huang or Zhao-Sheng Liu.

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Zhao, L., Chai, MH., Yao, HF. et al. Molecularly Imprinted Polymers Doped with Carbon Nanotube with Aid of Metal-Organic Gel for Drug Delivery Systems. Pharm Res 37, 193 (2020). https://doi.org/10.1007/s11095-020-02902-z

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