Abstract
A new N-sulfonamide ligand (HL1 = N-(5-(4-methoxyphenyl)-[1,3,4]–thiadiazole–2-yl)-toluenesulfonamide) and two Cu(II) complexes, [Cu(L1)2(py)2] (C1) and [Cu(L2)2(py)2(H2O)] (C2) (HL2 = N-(5-(4-methylphenyl)-[1,3,4]–thiadiazole–2-yl)-benzenesulfonamide) were synthesized. The X-ray crystal structures of the complexes were determined. In the complex C1, the Cu(II) ion is four-coordinated, forming a CuN4 chromophore and in the complex C2, the Cu(II) ion is five-coordinated, forming a CuN4O chromophore. The ligand acts as monodentate, coordinating the Cu(II) ion through a single Nthiadiazole atom. The molecules from the reaction medium (pyridine and water) are also involved in the coordination of the Cu(II) ion. The complexes C1 and C2 are square-planar and a slightly distorted square pyramidal, respectively. The compounds were characterized by FT-IR, electronic, EPR spectroscopic and magnetic methods. The nuclease binding activity studies of the synthesized complexes confirm their capacity to cleave the DNA molecule. The cytotoxicity studies were carried out on melanoma cell line WM35 which confirm that both compounds inhibit the growth of these cells. They have a higher activity compared to a platinum drug, carboplatin.
Similar content being viewed by others
References
Sorenson J R J 1992 Free Rad. Biol. Med. 13 593
Sorenson J R J 1989 Prog. Med. Chem. 26 437
Farrell N 1989 In Transition Metal Complexes as Drugs and Chemotherapeutic Agents (Dordrecht: Kluwer Academic) p. 143
Garcia-Giménez J L, González-Álvarez M and Liu-González M J 2009 Inorg. Biochem. 103 923
Lopez T, Ortiz-Islas E, Guevara P and Gómez E 2013 Int. J. Nanomed. 8 581
Zuo J, Bi C, Fan Y, Buac D, Nardon C, Daniel K G and Dou Q P 2013 J. Inorg. Biochem. 118 83
Beckford F A, Thessing J, Stott A, Holder A A, Poluektov O G, Li L and Seeram N P 2012 Inorg. Chem. Commun. 15 225
Buac D, Schmitt S, Ventro G, Kona F R and Dou Q P 2012 Mini Rev. Med. Chem. 12 1193
Anjomshoa M and Torkzadeh-Mahani M 2015 Spectrochim. Acta, Part A 150 390
Yousuf I, Arjmand F, Tabassum S, Toupet L, Khan R A and Siddiqui M A 2015 Dalton Trans. 44 10330
Ma T, Xu J, Wang Y, Yu H, Yang Y, Liu Y, Ding W, Zhu W, Chen R, Ge Z, Tan Y, Jia L and Zhu T 2015 J. Inorg. Biochem. 144 38
Qi J, Liang S, Gou Y, Zhang Z, Zhou Z, Yang F and Liang H 2015 Eur. J. Med. Chem. 96 360
Kheirolomoom A, Mahakian L M, Lai C Y, Lindfors H A, Seo J W, Paoli E E, Watson K D, Haynam E M, Ingham E S, Xing L, Cheng R H, Borowsky A D, Cardiff R D and Ferrara K W 2010 Mol. Pharm. 7 1948
Owa T, Yoshino H, Okauchi T, Yoshimatsu K, Ozawa Y, Sugi N H, Nagasu T, Koyanagi N and Kitoh K 1999 J. Med. Chem. 42 3789
Hangan A C, Turza A, Stan R L, Stefan R and Oprean L S 2015 Russ. J. Coord. Chem. 41 365
Hangan A, Bodoki A, Oprean L, Alzuet G, Liu-Gonzalez M and Borras J 2010 Polyhedron 29 1305
Bodoki A, Hangan A, Oprean L, Borras J, Castineiras A and Bojiţă M 2008 Farmacia LVI 607
Hangan A, Bodoki A, Oprean L, Crişan O and Mihalca I 2012 Farmacia LV 932
Dolomanov O V, Bourhis L J, Gildea R J, Howard J A K and Puschmann H 2009 J. Appl. Cryst. 42 339
Palatinul L and Capuis G 2007 J. Appl. Cryst. 40 786
Sheldrick G M (. 2008 Acta Cryst A64 112
Gonzalez-Alvarez M, Alzuet G, Borras J, Marcia B and Montejo-Bernardo J M 2003 Z. Anorg. Allg. Chem. 23 15
Gutierez L, Alzuet G, Borras J, Liu-Gonzalez M, Sanz F and Castineiras A 2001 Polyhedron 20 703
Macias B, Villa M V, Gomez B, Borras J, Alzuet G, Gonzalez-Alvarez M and Castineiras A 2007 J. Bioinorg. Chem. 101 441
Allen A M, Kennard O and Watson D G 1987 Trans. Perkin. 2 S1
Desiraju G R 2003 In Crystal Design Structure and Function Perspectives in Supramolecular Chemistry (Chichester: John Wiley) p. 160
Koon N, Wong S and Colson D 1984 J. Mol. Spectrosc. 104 129
Thomas A M, Nethaji M and Chakravarty A R 2004 J. Inorg. Biochem. 98 1087
Cami G E, del C. Ramirez de Arellano M and Fustero S 2006 An. Asoc. Quim. Argent. 941
Alzuet G, Ferrer S and Borras 1993 J. Inorg. Chim. Acta 203 257
Hathaway B J 1987 In Comprehensive Coordination Chemistry (New York: Wilkinson & Gillard) ch. 9
WINEPR-Simfonia 1.25. 1994-1996 (Bruker Analytik GmbH: Karlsruhe)
Bertini I and Drago R 1980 In ESR and NMR of Paramagnetic Species in Biological and Related Systems (Dordrecht, Holland: Springer Netherlands, D Reidel Publishing Company)
Goodman A and Raynor J B 1970 Adv. Inorg. Chem. Radiochem. 13 135
Sigman D S 1986 Acc. Chem. Res. 19 180
Drevensenk P, Zupancic T, Pihlar B, Jerala R, Kolitsch U, Plaper A and Turel I 2005 J. Inorg. Biochem. 99 432
Demeter C A, Pamatong F V and Bocarsly J R 1996 Inorg. Chem. 35 6292
Demeter C A, Pamatong F V and Bocarsly J R 1997 Inorg. Chem. 36 3676
Acknowledgements
Adriana Hangan is thankful for the financial support offered by research grant Resurse Umane PNII -PD 474/2010.
Author information
Authors and Affiliations
Corresponding author
Additional information
Supplementary Information (SI)
Supplementary material has been deposited with the Cambridge Crystallographic Data Centre (nos. 1408834 (C1), 1410246 (C2) and available free of charge: eposit@ccdc.cam.ac.uk or http://www.ccdc.cam.ac.uk). All additional information pertaining to characterization of the complexes, namely, 1H-NMR, IR spectra. UV-Vis spectra, and EPR spectra (figures S1–S9) are available at www.ias.ac.in/chemsci.
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
HANGAN, A.C., TURZA, A., STAN, R.L. et al. Synthesis, crystal structure and characterization of new biologically active Cu(II) complexes with ligand derived from N-substituted sulfonamide. J Chem Sci 128, 815–824 (2016). https://doi.org/10.1007/s12039-016-1077-1
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12039-016-1077-1