Synthesis, crystal structures, and biological activities of 2-thiophene N(4)-methylthiosemicarbazone and its unusual hexanuclear silver(I) cluster

Inorganic Chemistry Communications

Volumn 13, Issue 11, 2010, Pages 1268-1271

  Li, Ming Xue ^a   Zhang, Dong ^a   Zhang, Li Zhi ^a   Niu, Jing Yang ^a  

^a HENAN UNIVERSITY   (China)

Author keywords

Crystal structure; Cytotoxic activity; Silver(I); Thiosemicarbazone

Indexed keywords

EID: 77956931013     PISSN: 13877003     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.inoche.2010.07.012     Document Type: Article

References (51)

1. S.B. Padhye, and G.B. Kauffman Coord. Chem. Rev. 63 1985 127
2. D.X. West, A.E. Liberta, S.B. Padhye, R.C. Chikate, P.B. Sonawane, A.S. Kumbhar, and R.G. Xerande Coord. Chem. Rev. 123 1993 49
3. A. Murugkar, S. Padhye, S. Guha-Roy, and U. Wagh Inorg. Chem. Commun. 2 1999 545
4. M. Baldini, M. Belicchi-Ferrari, F. Bisceglie, G. Pelosi, S. Pinelli, and P. Tarasconi Inorg. Chem. 42 2003 2049
5. S. Padhye, Z. Afrasiabi, E. Sinn, J. Fok, K. Mehta, and N. Rath Inorg. Chem. 44 2005 1154
6. C.R. Kowol, R. Trondl, P. Heffeter, V.B. Arion, M.A. Jakupec, A. Roller, M. Galanski, W. Berger, and B.K. Keppler J. Med. Chem. 52 2009 5032
7. A.P. Rebolledo, M. Vieites, D. Gambino, O.E. Piro, E.E. Castellano, C.L. Zani, E.M. Souza-Fagundes, L.R. Teixeira, A.A. Batista, and H. Beraldo J. Inorg. Biochem. 99 2005 698
8. D.X. West, G.A. Bain, R.J. Butcher, J.P. Jasinski, Y. Li, R.Y. Pozdniakiv, J. Valdes-Martinez, R.A. Toscano, and S. Hernandes-Ortega Polyhedron 15 1996 665
9. D. Kovala-Demertzi, A. Domopoulou, M. Demertzis, C.P. Paptopoulou, and A. Terzis Polyhedron 13 1994 1917
10. N. Farrell Coord. Chem. Rev. 232 2002 1
11. D. Kovala-Demertzi, A. Papageorgiou, L. Papathanasis, A. Alexandratos, P. Dalezis, J.R. Miller, and M.A. Demertzis Bioorg. Med. Chem. Lett. 44 2009 1296
12. Z. Iakovidou, E. Mioglou, D. Mourelatos, A. Kotsis, M.A. Demertzis, A. Papagoergiou, J.R. Miller, and D. Kovala-Demertzi Anticancer Drugs 12 2001 65
13. E. López-Torres, M.A. Mendiola, C.J. Pastor, and B.S. Pérez Inorg. Chem. 43 2004 5222
14. I. Pal, F. Basuli, T.C.W. Mak, and S. Bhattacharya Angew. Chem. Int. Ed. 40 2001 2923
15. R. Curran, J. Lenehan, M. McCann, K. Kavanagh, M. Devereux, D.A. Egan, G. Clifford, K. Keane, B.S. Creaven, and V. McKee Inorg. Chem. Commun. 10 2007 1149
16. K. Nomiya, S. Takahashi, and R. Noguchi 2000 J. Chem. Soc Dalton Trans 2091
17. K. Nomiya, S. Takahashi, S.R. Noguchi, S. Nemoto, T. Takayama, and M. Oda Inorg. Chem. 39 2000 3301
18. W. Su, M. Hong, J. Weng, Y. Liang, Y. Zhao, R. Cao, Z. Zhou, and A.S.C. Chan Inorg. Chim. Acta 331 2002 8
19. T.S. Lobana, R. Sharma, and R.J. Butcher Polyhedron 27 2008 1375
20. B. Liu, G.-W. Zhou, M.-L. Fu, L. Xu, G.-C. Guo, and J.-S. Huang Bull. Korean Chem. Soc. 25 2004 1937
21. M.-X. Li, C.-L. Chen, C.-S. Ling, J. Zhou, B.-S. Ji, Y.-J. Wu, and J.-Y. Niu Bioorg. Med. Chem. Lett. 19 2009 2704
22. M.-X. Li, Y. Bai, B.-G. Zhang, C.-Y. Duan, J. Xu, and Q.-J. Meng Inorg. Chem. 44 2005 5459
23. M.-X. Li, Q.-Z. Sun, Y. Bai, C.-Y. Duan, B.-G. Zhang, and Q.-J. Meng Dalton Trans. 2006 2572
24. M.-X. Li, J. Zhou, C.-L. Chen, and J.-P. Wang Z. Naturforsch. 63b 2008 280
25. M.-X. Li, J. Zhou, Z.-L. Wang, and J.-P. Wang Chinese J. Struct. Chem. 27 2008 281
26. M.-X. Li, J. Zhou, H. Zhao, C.-L. Chen, and J.-P. Wang J. Coord. Chem. 62 2009 1423
27. D. Zhang, Q. Li, M.-X. Li, D.-Y. Chen, and J.-Y. Niu J. Coord. Chem. 63 2010 1063
28. M.-X. Li, C.-L. Chen, D. Zhang, J.-Y. Niu, and B.-S. Ji Eur. J. Med. Chem. 45 2010 3169
29. A. Castiñeiras, I. García-Santos, S. Dehnen, and P. Sevillano Polyhedron 25 2006 3653
30. L.J. Ashfield, A.R. Cowley, J.R. Dilworth, and P.S. Donnelly Inorg. Chem. 43 2004 4121
31. R. Pedrido, M.J. Romero, M.R. Bermejo, M. Martínez-Calvo, A.M. González-Noya, and G. Zaragoza Dalton Trans. 2009 8329
32. T.S. Lobana, R. Sharma, and R.J. Butcher Polyhedron 28 2009 1103
33. Synthesis of HL: Thiophene-2-carboxaldehyde (0.45 g, 4.0 mmol) was added dropwise to an ethanol solution (30 mL) of 4-methyl-3-thiosemicarbazide (0.44 g, 4.0 mmol) with five drops of acetic acid as catalyst. After refluxed for 2 h, the resultant solution was filtered. Brown crystals suitable for X-ray studies were obtained by slow evaporation of its ethanol solution. Anal. Calcd. for C7H9N3S2: C 42.15, H 4.52, N 21.07; found C 42.02, H 4.34, N 20.85.
34. Synthesis of 1: AgNO3(0.07 g, 0.4 mmol) and 2-thiophene N(4)-methylthiosemicarbazone (0.08 g, 0.4 mmol) were suspended in 30 mL of ethanol and refluxed for 0.5 h with stirring. The resulting precipitate was filtered off, washed with cold ethanol and dried in a vacuum. Brown crystals suitable for X-ray diffraction were obtained by slow evaporation of its DMF solution. Anal. Calcd. for C54H76Ag6N22O4S12: C 30.43, H 3.57, N 14.46; found C 30.21, H 3.71, N 14.19.
35. Crystal data for HL: C7H9N3S2 (199.29), Crystal dimensions 0.36 × 0.31 × 0.27 mm3, monoclinic, P21/c, a = 8.0897(7) Å, b = 13.286(1) Å, c = 9.454 (1) Å, β = 98.770(2)°, V = 1004.3(1) Å 3, Z = 4, ρcalcd = 1.318 Mg m-3, 5020 reflections collected, 1447 unique (Rint = 0.0212), R1 = 0.0498 [I > 2σ (I)], wR2 = 0.1608 (all data). The data were collected on a Bruker APEX-II CCD diffractometer (MoKa, λ = 0.71073 Å) at 293(2) K. All structures were solved by the direct method and refined by the full-matrix least-squares on F2 using the SHELXL-97 [28, 29]. All of the non-hydrogen atoms were refined anisotropically.
36. G.M. Sheldrick SHELXS 97, Program for Crystal Structure Solution 1997 University of Göttingen Göttingen
37. G.M. Sheldrick SHELXL 97, Program for Crystal Structure Refinement 1997 University of Göttingen Göttingen
38. A. Sreekanth, and M.R.P. Kurup Polyhedron 23 2004 969
39. D.X. West, G.A. Bain, R.J. Butcher, J.P. Jasinski, Y. Li, and R.Y. Pordniakiv Polyhedron 15 1996 665
40. Crystal data for 1: C54H76Ag6N22O4S12 (2129.31), Crystal dimensions 0.29 × 0.21 × 0.13 mm3, triclinic, space group P-1, a = 10.718(2) Å, b = 14.654(1) Å, c = 15.048 (1) Å, α = 118.851(1)°, β = 95.800(2)°, γ = 99.383(2)°, V = 1997.7(4) Å 3, Z = 1, ρcalcd = 1.770 Mg.m-3, 10408 reflections collected, 5000 unique (Rint = 0.0779), R1 = 0.0507 [I > 2σ (I)], wR2 = 0.1190 (all data). The data were collected on a Bruker APEX-II CCD diffractometer (MoKa, λ = 0.71073 Å) at 293(2) K. All structures were solved by the direct method and refined by the full-matrix least-squares on F2 using the SHELXL-97. All of the non-hydrogen atoms were refined anisotropically.
41. Y.-B. Dong, H.-Y. Wang, J.-P. Ma, D.-Z. Shen, and R.-Q. Huang Inorg. Chem. 44 2005 4679
42. M.C. Biagini, M. Laufranchi, L. Marchiò, and M.A. Pellinghelli Inorg. Chim. Acta 305 2000 95
43. M. Yazdanbakhsh, M. Hakimi, M.M. Heravi, M. Ghassemzadeh, and B. Neumüller Z. Anorg. Allg. Chem. 631 2005 924
44. F. Adhami, M. Ghassemzadeh, M.M. Heravi, and A. Taeb Z. Anorg. Allg. Chem. 625 1999 1411
45. H.-B. Bürg, J.D. Dunitz, Structure Correlations 1994 VCH Weinheim, Germany 780
46. A. Mishra, N.K. Kaushik, A.K. Verma, and R. Gupta Eur. J. Med. Chem. 43 2008 2189
47. M. Joseph, M. Kuriakose, M.R.P. Kurup, E. Suresh, A. Kishore, and S.G. Bhat Polyhedron 25 2006 61
48. M. Joseph, V. Suni, M.R.P. Kurup, M. Nethaji, A. Kishore, and S.G. Bhat Polyhedron 23 2004 3069
49. The in vitro antibacterial activity of the free ligand and its silver complex was investigated against several representative Gram positive bacteria (Bacillus subtilis, Staphylococcus aureus, and Agrobacterium tumefaciens) and Gram negative bacteria (Escherichia coli, Salmonella typhimurium, and Pseudomonas aeruginosa). The antifungal activity was assayed against mould (Aspergillus niger, Mucor mucedo, and Penicillium oxalicum) and yeast (Candida lusitaniae, Candida albicans). The minimal inhibitory concentrations (MIC, mg/mL) were estimated by the disk diffusion method [42]. The final concentration of all cultures in Mueller-Hinon agar (MHA) for bacteria and potato dextrose agar (PDA) and Sabouraud dextrose agar (SDA) for mould spores and yeast cells was adjusted to 106 cfu/mL (bacteria) or 2 × 105 cfu/mL (mould spores and yeast cells) and used for inoculation in the MIC test. Serial dilutions of the test compounds, previously dissolved in dimethyl sulfoxide (DMSO) were prepared at concentrations of 0-2000 μg/mL. To each plate was inoculated with 0.1 mL of the prepared bacterial and fungi cultures. Similarly, each plate carried a blank disc, with solvent DMSO only in the center to serve as negative control. The inoculated plates were then incubated at either 37 °C for 18-20 h (bacteria) or 28 °C for 48-96 h (fungi), respectively. The minimal inhibitory concentration (MIC) was detected as the lowest concentration of drug in plate for which no visible growth took place by macroscopic evaluation. All determinations were performed in triplicate and confirmed by three separate experiments.
50. S.A. Khan, and K. Saleem Z. Khan. Eur. J. Med. Chem. 42 2007 103
51. SMMC-7721, a human liver cancer cell line (purchased from the Institute of Biochemistry and Cell Biology, SIBS, CAS), was cultured in RPMI-1640 medium supplemented with 10% FBS, 100 U mL-1 of penicillin, 100 μg (200 μL per well) of streptomycin at 37 °C in humid air atmosphere of 5% CO2. Cell cytotoxicity was assessed by the MTT assay. Briefly, cells were placed into a 96-well-plate (5 × 103 cells per well). The next day the compound diluted in culture medium at various concentrations was added (200 μL per well) to the wells. 48 h later 20 μL of MTT (0.5 mg mL-1 MTT in PBS) was added and cells were incubated for a further 4 h. 200 μL of DMSO was added to each culture to dissolve the MTT crystals. The MTT-formazan product dissolved in DMSO was estimated by measuring absorbance at 570 nm with a micro plate reader. Then the inhibitory percentage of each compound at various concentrations was calculated, and the IC50 value was determined.