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Synthesis, characterization, crystal structure and DNA-binding study of four cadmium(II) pyridine-carboxamide complexes

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Abstract

Treatment of perchlorate or nitrate salt of cadmium(II) with carboxamide derivatives (L) generated four novel mononuclear metal complexes, represented as [Cd(L )4](ClO4)2 (1a and 1b) and [Cd(L)2(ONO2)2] (2a and 2b) in appreciable yields (L = L 1 = N-(furan-2-ylmethyl)-2-pyridine carboxamide and L = L 2 = N-(thiophen-2-ylmethyl)-2-pyridine carboxamide). The complexes have been characterized by FT-IR, UV-Visible, elemental analysis and single crystal X-ray crystallographic analysis which revealed eight coordinated cadmium ions, but in different coordination environments, depending on the counter anion used. In addition, electronic absorption, fluorescence spectroscopy and viscosity measurements revealed a significant interaction of the four complexes with CT-DNA via intercalative/groove binding mode. The intrinsic binding constant K b obtained varies from 0.4 × 10 4 to 1.11 × 10 5 M−1. The results suggest that neutral complexes 2a and 2b bind to DNA in an intercalative mode. On the other hand, cationic complexes 1a and 1b bind with DNA via weak electrostatic/covalent interaction.

Synthesis and characterization of four mononuclear eight coordinated cadmium(II) complexes with newly explored carboxamide derivatives and study of interaction with calf-thymus DNA are reported. The results suggest that neutral complexes 2a and 2b bind to DNA in an intercalative mode. On the other hand, cationic complexes 1a and 1b interact with DNA via weak intercalative or groove binding mode.

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References

  1. Lin J, Zhang J Y, Xu Y, Ke X K and Guo Z J 2001 N, N′-(1,2-phenylene)bis(pyridine-2-carboxamide) and N, N′-(1,2-cyclohexanediyl)bis(pyridine-2-carboxamide) toluen hemisolvate Acta Crystallogr. Sect. C 57 192

    Article  Google Scholar 

  2. Trost B M and Hachiya I 1998 Asymmetric Molybdenum-Catalyzed Alkylations J. Am. Chem. Soc. 120 1104

    Article  CAS  Google Scholar 

  3. Epperson J D, Ming L J, Baker G R and Newkome G R 2001 Paramagnetic Cobalt(II) as an NMR Probe of Dendrimer Structure: Mobility and Cooperativity of Dendritic Arms J. Am. Chem. Soc. 123 8583

    Article  CAS  Google Scholar 

  4. Collinson S R, Gelbrich T, Hursthouse M B and Tucker J H R 2001 Novel ferrocene receptors for barbiturates and ureas Chem. Commun. 555

  5. Zhang J, Liu Q, Duan C, Shao Y, Ding J, Miao Z, You X and Guo Z 2002 Structural evidence for the facile chelate-ring opening reactions of novel platinum(II)–pyridine carboxamide complexes J. Chem. Soc., Dalton Trans. 22 591

    Article  Google Scholar 

  6. Li J, Zheng M L, King I, Doyle T W and Chan S H 2001 Syntheses and Antitumor Activities of Potent Inhibitors of Ribonucleotide Reductase 3-Amino-4- Methylpyridine-2-Carboxaldehyde-Thiosemicarba-zone (3-Amp), 3-Amino-Pyridine-2-Carboxaldehyde-Thiosemicarbazone (3-Ap) and its Water-Soluble Prodrugs Curr. Med. Chem. 8 121

    Article  CAS  Google Scholar 

  7. He X M and Carter D C 1992 Atomic structure and chemistry of human serum albumin Nature 358 209

    Article  CAS  Google Scholar 

  8. Mukherjee T, Sen B, Zangrando E, Hundal G, Chattopadhyay B and Chattopadhyay P 2013 Palladium(II) and platinum(II) complexes of deprotonated N, N′-bis(2-pyridinecarboxamide)-1,2-benzene: Synthesis, structural characterization and binding interactions with DNA and BSA Inorg. Chim. Acta 406 176 and references therein

  9. Singhal R N and Jain M 1997 Cadmium-Induced Changes in the Histology of Kidneys in Common Carp, Cyprinus carpio (Cyprinidae) Bull. Environ. Contam. Toxicol. 58 456

    Article  CAS  Google Scholar 

  10. Hossain Z and Huq F 2002 Studies on the interaction between Cd 2+ ions and nucleobases and nucleotides J. Inorg. Biochem. 90 97

    Article  CAS  Google Scholar 

  11. Hossain Z and Huq F 2002 Studies on the interaction between Cd 2+ ions and DNA J. Inorg. Biochem. 90 85

    Article  CAS  Google Scholar 

  12. Genova P, Varadinova T, Matesanz A I, Marinova D and Souza P 2004 Toxic effects of bis(thiosemicarbazone) compounds and its palladium(II) complexes on herpes simplex virus growth Toxicol. Appl. Pharmacol. 197 107

    Article  CAS  Google Scholar 

  13. Hu W X, Zhou W, Xia C and Wen X 2006 Synthesis and anticancer activity of thiosemicarbazones Bioorg. Med. Chem. Lett. 16 2213

    Article  CAS  Google Scholar 

  14. Filipović N R, Bacchi A, Lazić M, Pelizzi G, Radulović S, Sladić D M, Todorović T R and Anđelković K K 2008 Synthesis, structure and cytotoxic activity evaluation of a dinuclear complex of Cd(II) with N ′, N ′2-bis[(1E)-1-(2-pyridyl)ethylidene]propanedihydrazide Inorg. Chem. Commun. 11 47

    Article  Google Scholar 

  15. Bjelogrlic S, Todorovic T, Bacchi A, Zec M, Sladic D, Srdic-Rajic T, Radanovic D, Radulovic S, Pelizzi G and Andelkovic K 2010 Synthesis, structure and characterization of novel Cd(II) and Zn(II) complexes with the condensation product of 2-formylpyridine and selenosemicarbazide: Antiproliferative activity of the synthesized complexes and related selenosemicarbazone complexes J. Inorg. Biochem. 104 673

    Article  CAS  Google Scholar 

  16. Bertin G and Averbeck D 2006 Cadmium: Cellular effects, modifications of biomolecules, modulation of DNA repair and genotoxic consequences (a review) Biochimie 88 1549

    Article  CAS  Google Scholar 

  17. Mondal B, Sen B, Zangrando E and Chattopadhyay P 2015 Zinc(II) complexes of carboxamide derivatives: Crystal structures and interaction with calf thymus DNA J. Chem. Sci. 127 1747

    Article  CAS  Google Scholar 

  18. Altomare A, Cascarano G, Giacovazzo C and Guagliardi A 1993 Completion and refinement of crystal structures with SIR92 J. Appl. Crystallogr. 26 343

    Article  Google Scholar 

  19. Sheldrick G M 2008 A short history of SHELX Acta Crystallogr. Sect. A: Found. Crystallogr. 64 112

    Article  CAS  Google Scholar 

  20. Farrugia L J 1999 WinGX suite for small-molecule single-crystal crystallography J. Appl. Crystallogr. 32 837

    Article  CAS  Google Scholar 

  21. Marmur J 1961 A procedure for the isolation of deoxyribonucleic acid from micro-organisms J. Mol. Biol. 3 208

    Article  CAS  Google Scholar 

  22. Reichmann M E, Rice S A, Thomas C A and Doty P 1954 A Further Examination of the Molecular Weight and Size of Desoxypentose Nucleic Acid J. Am. Chem. Soc. 76 3047

    Article  CAS  Google Scholar 

  23. Barszcz B, Jablonska-Wawrzycka A, Stadnicka K and Hodorowicz S A 2005 The synthesis and structural characterization of novel zinc and cadmium complexes of chelating alcohol Inorg. Chem. Commun. 8 951

    Article  CAS  Google Scholar 

  24. Hakimi M, Moeini K, Mardani Z and Khorrami F 2012 Crystal Structure and Characterization of a New Eight Coordinated Cadmium Complex J. Kor. Chem. Soc. 57 352

    Article  Google Scholar 

  25. Barszcz B, Hodorowicz S, Jablonska-Wawrzycka A and Stadnicka K 2005 Synthesis, X-ray structure and spectroscopic investigation of an eight-coordinate cadmium(II) complex J. Coord. Chem. 58 203

    Article  CAS  Google Scholar 

  26. Barton J K, Danishefsky A and Goldberg J 1984 Tris(phenanthroline)ruthenium(II): Stereoselectivity in binding to DNA J. Am. Chem. Soc. 106 2172

    Article  CAS  Google Scholar 

  27. Sun J, Shuo W, An Y, Liu J, Gao F, Ji L N and Mao Z W 2008 Synthesis, crystal structure and DNA-binding properties of ruthenium(II) polypyridyl complexes with dicationic 2,2 ′-dipyridyl derivatives as ligands Polyhedron 27 2845

    Article  CAS  Google Scholar 

  28. Lombardo V, Bonomi R, Sissi C and Mancin F 2010 Phosphate diesters and DNA hydrolysis by dinuclear Zn(II) complexes featuring a disulfide bridge and H-bond donors Tetrahedron 66 2189

    Article  CAS  Google Scholar 

  29. Dhara K, Ratha J, Manassero M, Wang X Y, Gao S and Banerjee P 2007 Synthesis, crystal structure, magnetic property and oxidative DNA cleavage activity of an octanuclear copper(II) complex showing water–perchlorate helical network J. Inorg. Biochem. 101 95

    Article  CAS  Google Scholar 

  30. Dhara K, Roy P, Ratha J, Manassero M and Banerjee P 2007 Synthesis, crystal structure, magnetic property and DNA cleavage activity of a new terephthalate-bridged tetranuclear copper(II) complex Polyhedron 26 4509

    Article  CAS  Google Scholar 

  31. Bloomfield V A, Crothers D M and Tinoco I 1974 In Physical Chemistry of Nucleic Acids (New York: Harper and Row) p. 432

  32. Tysoe S A, Morgan R J, Baker A D and Strekas T C 1993 Spectroscopic investigation of differential binding modes of .DELTA.- and.LAMBDA.-Ru(bpy )2(ppz )2+ with calf thymus DNA J. Phys. Chem. 97 1707

    Article  CAS  Google Scholar 

  33. Selvi P T, Stoeckli-Evans H and Palaniandavar M 2005 Synthesis, structure and DNA interaction of cobalt(III) bis-complexes of 1,3-bis(2-pyridylimino) isoindoline and 1,4,7-triazacyclononane J. Inorg. Biochem. 99 2110

    Article  Google Scholar 

  34. Kelly J M, Tossi A B, McConnell D J and OhUigin C 1985 A study of the interactions of some polypyridylrutheniumn(I) complexes with DNA using fluorescence spectroscopy, topoisomerisation and thermal denaturation Nucl. Acids. Res. 13 6017

    Article  CAS  Google Scholar 

  35. Wolfe A, Shimer G and Meehan T 1987 Polycyclic aromatic hydrocarbons physically intercalate into duplex regions of denatured DNA Biochemistry 26 6392

    Article  CAS  Google Scholar 

  36. Lu J, Sun Q, Li J L, Gu W, Tianab J L, Liuab X and Yan S P 2013 Synthesis, characterization, and DNA-binding of two new Cd(II) complexes with 8-[(2-pyridylmethyl)amino]-quinoline J. Coord. Chem. 66 3280

    Article  CAS  Google Scholar 

  37. Wu H L, Wang K T, Kou F, Jia F, Liu B, Yuan J K and Bai Y 2011 A six-coordinate picrate cadmium(II) complex with a new V-shaped ligand 1,3-bis(1-ethylbenzimidazol-2-yl)-2-thiapropane: Synthesis, crystal structure, and DNA-binding properties J. Coord. Chem. 64 2676

    Article  CAS  Google Scholar 

  38. Wu H L, Wang K, Jia F, Liu B, Kou F, Yuan J and Kong J 2010 Synthesis, characterization, and DNA band of a five-coordinate cadmium(II) complex with 1,3-bis(1-benzylbenzimidazol-2-yl)-2-thiapropane J. Coord. Chem. 63 4113

    Article  CAS  Google Scholar 

  39. Wu H L, Yuan J, Huang X C, Kou F, Liu B, Jia F, Wang K T and Bai Y 2012 Two zinc(II) and cadmium(II) complexes based on the V-shaped ligand 2, 6-bis(2-benzimidazolyl)pyridine: Synthesis, crystal structure, DNA-binding properties and antioxidant activities Inorg. Chim. Acta 390 12

    Article  CAS  Google Scholar 

  40. Pyle A M, Rehmann J P, Meshoyrer R, Kumar C V, Turro N J and Barton J K 1989 Mixed-ligand complexes of ruthenium(II): Factors governing binding to DNA J. Am. Chem. Soc. 111 3051

    Article  CAS  Google Scholar 

  41. Vijayalakshmi R, Kanthimathi M, Subramanian V and Nair B U 2000 Interaction of DNA with [Cr(Schiff base)(H2 O)2]ClO4 Biochim. Biophys. Acta 1475 157

    Article  CAS  Google Scholar 

  42. Stern O and Volmer M 1919 Über die Abklingzeit der Fluoreszenz Physik. Zeitschr. 20 183

    CAS  Google Scholar 

  43. Kathiravan A and Renganathan R 2009 Photoinduced interactions between colloidal TiO2 nanoparticles and calf thymus-DNA Polyhedron 28 1374

    Article  CAS  Google Scholar 

  44. Wang B, Yang Z Y, Crewdson P and Wang D 2007 Synthesis, crystal structure and DNA-binding studies of the Ln(III) complex with 6-hydroxychromone-3-carbaldehyde benzoyl hydrazone J. Inorg. Biochem. 101 1492

    Article  CAS  Google Scholar 

  45. Li D, Tian J, Gu W, Liu X and Yan S 2010 A novel 1,2,4-triazole-based copper(II) complex: Synthesis, characterization, magnetic property and nuclease activity J. Inorg. Biochem. 104 171

    Article  CAS  Google Scholar 

  46. Garcia-Gimenez J L, Gonzalez-Alvarez M, Liu-Gonzalez M, Macias B, Borras J and Alzuet G 2009 Toward the development of metal-based synthetic nucleases: DNA binding and oxidative DNA cleavage of a mixed copper(II) complex with N-(9H-purin-6-yl)benzenesulfonamide and 1,10-phenantroline. Antitumor activity in human Caco-2 cells and Jurkat T lymphocytes. Evaluation of p53 and Bcl-2 proteins in the apoptotic mechanism J. Inorg. Biochem. 103 923

    Article  Google Scholar 

  47. Tolia C, Papadopoulos A N, Raptopoulou C P, Psycharis V, Garino C, Salassa L and Psomas G 2013 Copper(II) interacting with the non-steroidal antiinflammatory drug flufenamic acid: Structure, antioxidant activity and binding to DNA and albumins J. Inorg. Biochem. 123 53

    Article  CAS  Google Scholar 

  48. Satyanarayana S, Daborusak J C and Chaires J B 1993 Tris(phenanthroline)ruthenium(II) enantiomer interactions with DNA: Mode and specificity of binding Biochemistry 32 2573

    Article  CAS  Google Scholar 

  49. Satyanarayana S, Daborusak J C and Chaires J B 1992 Neither.DELTA.- nor.LAMBDA.-tris(phenanthroline) ruthenium(II) binds to DNA by classical intercalation Biochemistry 31 9319

    Article  CAS  Google Scholar 

  50. Yuan C-X, Wu Y-B, Wei Y-B, Yang P and Zhu M L 2007 Studies on the Interaction of Dinitratobis(phen) Cadmium Complex with DNA Chin. J. Chem. 25 1267

    Article  CAS  Google Scholar 

  51. Gao C, Ma X, Tian J, Li D and Yan S 2010 Synthesis, structure, and DNA binding of three reduced amino-acid Schiff-base zinc(II), nickel(II), and cadmium(II) complexes J. Coord. Chem. 63 115

    Article  CAS  Google Scholar 

  52. Ma X-F, Li D-D, Tian J-L, Kou Y-Y and Yan S-P 2009 DNA binding and cleavage activity of reduced amino-acid Schiff base complexes of cobalt(II), copper(II), and cadmium(II) Trans. Met. Chem. 34 475

    Article  CAS  Google Scholar 

  53. Park H, Kwon J H, Cho T, Kim J M, Hwang I H, Kim C, Kim S, Kim J and Kim S K 2013 Real-time detection of DNA cleavage induced by [M(2,2′-bipyridine )2(NO3)](NO3) (M = Cu(II), Zn(II) and Cd(II)) complexes using linear dichroism technique J. Inorg. Biochem. 127 46

    Article  CAS  Google Scholar 

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Acknowledgements

Financial support from the Council of Scientific and Industrial Research (CSIR), New Delhi, India [CSIR Scheme No. 01(2685)/12/EMR-II dated 03-10-2012] is gratefully acknowledged.

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Authors and Affiliations

  1. Department of Chemistry, Burdwan University, Golapbag, Burdwan, West Bengal, 713 104, India

    BIPLAB MONDAL, BUDDHADEB SEN, SANDIPAN SARKAR & PABITRA CHATTOPADHYAY

  2. Department of Chemical and Pharmaceutical Sciences, Via Licio Giorgieri 1, 34127, Trieste, Italy

    ENNIO ZANGRANDO

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  1. BIPLAB MONDAL
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Correspondence to PABITRA CHATTOPADHYAY.

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Supplementary Information (SI)

Crystallographic data for the structural analyses of complexes 1a and 2b have been deposited with the Cambridge Crystallographic Data Centre bearing the CCDC Nos. 1438356 and 1438357, respectively. Copies of this information are available on request at free of charge from CCDC, Union Road, Cambridge, CB21EZ, UK (fax: + 44-1223-336-033; e-mail: deposit@ccdc.ac.uk or http://www.ccdc.cam.ac.uk). NMR spectra (Figures S1–S4), plots of DNA binding experiments for complex 2b from the absorbance and emission study and its comparison with the complex 1 and other reported cadmium(II) complexes, and CIF files of complexes 1a and 2b are available at http://www.ias.ac.in/chemsci.

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MONDAL, B., SEN, B., SARKAR, S. et al. Synthesis, characterization, crystal structure and DNA-binding study of four cadmium(II) pyridine-carboxamide complexes. J Chem Sci 129, 45–55 (2017). https://doi.org/10.1007/s12039-016-1215-9

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  • DOI: https://doi.org/10.1007/s12039-016-1215-9

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