DNA binding, antioxidant, cytotoxicity (MTT, lactate dehydrogenase, NO), and cellular uptake studies of structurally different nickel(II) thiosemicarbazone complexes: Synthesis, spectroscopy, electrochemistry, and X-ray crystallography

Journal of Biological Inorganic Chemistry

Volumn 18, Issue 2, 2013, Pages 233-247

  Prabhakaran, R ^a   Kalaivani, P ^a   Huang, R ^b   Poornima, P ^a   Vijaya Padma, V ^a   Dallemer, F ^c   Natarajan, K ^a  

^a BHARATHIAR UNIVERSITY   (India)

^b MICHIGAN STATE UNIVERSITY   (United States)

^c AIX MARSEILLE UNIVERSITY   (France)

Author keywords

DNA binding; Electrochemistry; Nickel(II) complexes; Thiosemicarbazones; X ray crystallography

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; 2 HYDROXY 1 NAPHTHALDEHYDE 4 (N) ETHYLTHIOSEMICARBAZONE; 2 HYDROXY 1 NAPHTHALDEHYDETHIOSEMICARBAZONE; 3 (4,5 DIMETHYL 2 THIAZOLYL) 2,5 DIPHENYLTETRAZOLIUM BROMIDE; ASCORBIC ACID; CISPLATIN; DNA; LACTATE DEHYDROGENASE; NITRIC OXIDE; SALICYLALDEHYDE 4 (N) ETHYLTHIOSEMICARBAZONE; SCAVENGER; THIOSEMICARBAZONE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; CALF (MAMMAL); CELL LINE; CELL TRANSPORT; CELLULAR DISTRIBUTION; CHELATION; COMPLEX FORMATION; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG BINDING; DRUG CYTOTOXICITY; DRUG DETERMINATION; DRUG DNA BINDING; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG UPTAKE; ELECTROCHEMICAL ANALYSIS; HUMAN; HUMAN CELL; IN VITRO STUDY; INFRARED SPECTROSCOPY; LIVER CANCER; LUNG CANCER; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; TITRIMETRY; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

ANTINEOPLASTIC AGENTS; BIPHENYL COMPOUNDS; CELL PROLIFERATION; COORDINATION COMPLEXES; CRYSTALLOGRAPHY, X-RAY; DNA; DRUG SCREENING ASSAYS, ANTITUMOR; ELECTROCHEMISTRY; FORMAZANS; FREE RADICAL SCAVENGERS; FREE RADICALS; HEP G2 CELLS; HUMANS; HYDROGEN BONDING; INHIBITORY CONCENTRATION 50; L-LACTATE DEHYDROGENASE; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NICKEL; NITRIC OXIDE; OXIDATION-REDUCTION; PICRATES; SPECTROPHOTOMETRY, INFRARED; TETRAZOLIUM SALTS; THIOSEMICARBAZONES;

EID: 84878848949     PISSN: 09498257     EISSN: 14321327     Source Type: Journal    
DOI: 10.1007/s00775-012-0969-x     Document Type: Article

References (77)

1. Debra CQ, Kathy AK, Earl RK (2006) Antiviral Res 71:24-30
2. Teitz Y, Ronen D, Vansover A, Stematsky T, Riggs JL (1994) Antiviral Res 24:305-314
3. Arguelles MCR, Silva ECL, SanmartIn J, Pelagatti P, Zani F (2005) J Inorg Biochem 99:2231-2239
4. Arguelles MCR, Silva ECL, SanmartIn J, Bacchi A, Pelizzi C, Zani F (2004) Inorg Chim Acta 357:2543-2552
5. Cukurovali A, Yilmaz I, Gur S, Kazaz C (2006) Eur J Med Chem 41:201-207
6. Murugkar A, Unnikrishnan B, Padhye S, Bhonde R, Teat S, Triantafillou E, Sinn E (1999) Met Based Drugs 6:177-182
7. Teitz Y, Barko N, Abramoff M, Ronen D (1994) Chemotherapy (Tokyo) 40:195-200
8. Hu WX, Zhou W, Xia C, Wen X (2006) Bioorg Med Chem Lett 16:2213-2218
9. Afrasiabi Z, Sinn E, Padhye S, Dutta S, Newton C, Anson CE, Powell AK (2003) J Inorg Biochem 95:306-314
10. Bal T, Atasever B, Solakoglu Z, Kuruca SE, Ulkuseven B (2007) Eur J Med Chem 42:161-167
11. Campana M, Laborie C, Barbier G, Assan R, Milcent R (1991) Eur J Med Chem 26:273-278
12. Campbell MJ (1975) Coord Chem Rev 15:279-319
13. Prabhakaran R, Huang R, Karvembu R, Jayabalakrishnan C, Natarajan K (2007) Inorg Chim Acta 360:691-694
14. Prabhakaran R, Huang R, Renukadevi SV, Karvembu R, Zeller M, Natarajan K (2008) Inorg Chim Acta 361:2547-2552
15. Prabhakaran R, Anantharaman S, Thilagavathi M, Kaveri MV, Kalaivani P, Karvembu R, Dharmaraj N, Bertagnolli H, Natarajan K (2011) Spectrochim Acta 78:844-853
16. Prabhakaran R, Kalaivani P, Jayakumar R, Zeller M, Hunter AD, Renukadevi SV, Ramachandran E, Natarajan K (2011) Metallomics 3:42-48
17. Prabhakaran R, Kalaivani P, Huang R, Sieger M, Kaim W, Viswanathamurthi P, Dallemer F, Natarajan K (2011) Inorg Chim Acta 376:317-324
18. Kalaivani P, Prabhakaran R, Ramachandran E, Dallemer F, Paramaguru G, Renganathan R, Poornima P, Vijaya Padma V, Natarajan K (2012) Dalton Trans 41:2486-2499
19. Prabhakaran R, Kalaivani P, Poornima P, Dallemer F, Paramaguru G, Vijaya Padma V, Renganathan R, Natarajan K (2012) Dalton Trans 41:9323-9336
20. Chen J, Huang YW, Liu G, Afrasiabi Z, Sinn E, Padhye S, Ma Y (2004) Toxicol Appl Pharmacol 197:40-48
21. Zheng LM, Li J, King I, Doyle TW, Chen SH (2001) Curr Med Chem 8:121-133
22. Hall MD, Salam NK, Hellawell JL, Fales HM, Kensler CB, Ludwig JA, Szakacs G, Hibbs DE, Gottesman MM (2009) J Med Chem 52:3191-3204
23. Gelasco A, Lippard SJ (1999) In: Clarke MJ, Sadler PJ (eds) Topics in biological inorganic chemistry, vol 1. Springer, New York, p 1
24. Piper T, Borsky K, Keppler BK (1999) In: Clarke MJ, Sadler PJ (eds) Topics in biological inorganic chemistry, vol 1. Springer, New York, p 171
25. Reedijk J (2008) Platinum Met Rev 52:2-11
26. Hall MD, Okabe M, Shen DW, Liang XJ, Gottesman MM (2008) Annu Rev Pharmacol Toxicol 48:495-535
27. Gao X, Wang X, Ding J, Lin L, Li Y, Guo Z (2006) Inorg Chem Commun 9:722-726
28. Huq F, Yu JQ, Daghriri H, Beale P (2004) J Inorg Biochem 98:1261-1270
29. Tayyem H, Huq F, Yu JQ, Beale P, Fisher K (2008) ChemMedChem 3:145-151
30. Rabik CA, Dolan ME (2007) Cancer Treat Rev 33:9-23
31. Momekov G, Bakalova A, Karaivanova M (2005) Curr Med Chem 12:2177-2191
32. Zutphen SV, Reedijk J (2005) Coord Chem Rev 249:2845-2853
33. Purohit S, Kolay AP, Prasad LS, Manoharan PT, Ghosh S (1989) Inorg Chem 28:3735-3742
34. Venanzi J (1958) J Chem Soc 43:719-724
35. Vogel AI (1989) Textbook of practical organic chemistry, 5th edn. Longman. London
36. Sheldrick GM (1997) SHELXL-97, release 97-2. University of Göttingen, Göttingen
37. Wolfe A, Shimer GH, Meehan T (1987) Biochemistry 26:6392-6396
38. Cohen G, Eisenberg H (1969) Biopolymers 8:45-55
39. Blios MS (1958) Nature 26:1199-1200
40. Mossman T (1983) J Immunol Methods 65:55-63
41. Wacker WEC, Ulmer DD, Valee BL (1956) J Med 255:449-456
42. Stueher DJ, Marletta MA (1987) J Immunol 139:518-525
43. Xiong XB, Ma Z, Lai R, Lavasanifar A (2010) Biomaterials 31:757-768
44. West DX, Billeh IS, Jasinski JP, Jasinski JM, Butcher RJ (1998) Transit Met Chem 23:209-224
45. Prabhakaran R, Krishnan V, Pasumpon K, Sukanya D, Wendel E, Jayabalakrishnan C, Bertagnolli H, Natarajan K (2006) Appl Organometal Chem 20:203-213
46. Prabhakaran R, Renukadevi SV, Karvembu R, Huang R, Mautz J, Huttner G, Subashkumar R, Natarajan K (2008) Eur J Med Chem 43:268-273
47. Chikate RC, Padhye SB (2005) Polyhedron 24:1689-1700
48. Alomar K, Khan MA, Allain M, Bouet GM (2009) Polyhedron 28:1273-1280
49. Archaryya R, Basuli F, Peng SM, Lee GH, Falvello LR, Bhattacharya S (2006) Inorg Chem 45:1252-1259
50. Tojal JG, Dizarro JL, Orad AG, Sanz ARP, Ugalda M, Diaz AA, Serra JL, Arriortua MI, Rojo T (2001) J Inorg Biochem 86:627-633
51. Naik AD, Annigeri SM, Gangadharmathy VB, Revankar VK, Mahale VB (2002) J Mol Stuct 616:119-127
52. Rodrigues C, Batista AA, Aucélio RQ, Teixeira LR, Visentin LC, Beraldo H (2008) Polyhedron 27:3061-3066
53. Jouad EM, Riou A, Allain M, Khan MA, Bouet GM (2001) Polyhedron 20:67-74
54. Kalaivani P, Prabhakaran R, Dallemer F, Poornima P, Vaishnavi E, Ramachandran E, Vijaya Padma V, Renganathan R, Natarajan K (2012) Metallomics 4:101-113
55. Prabhakaran R, Sivasamy R, Angayarkanni J, Huang R, Kalaivani P, Karvembu R, Dallemer F, Natarajan K (2011) Inorg Chim Acta 374:647-653
56. Klayman DL, Scovill JP, Brtosevich JF, Bruce J (1983) J Med Chem 26:35-39
57. Prabhakaran R, Karvembu R, Hashimoto T, Shimizu K, Natarajan K (2005) Inorg Chim Acta 358:2093-2096
58. Ferrari MB, Capacchi S, Bisceglie F, Pelosi G, Tarasconi P (2001) Inorg Chim Acta 312:81-87
59. Fostiak LM, Gracia I, Swearinger JK, Bermejo E, Castineivas A, West DX (2003) Polyhedron 22:83-92
60. Hua LZ, Ying DC, Hui LJ, Jiang LY, Hua MY, Zeng YX (2000) New J Chem 24:1057-1062
61. Novakovi SB, Bogdanovic GA, Leovac VM (2005) Inorg Chem Commun 8:9-13
62. Hathaway BJ (1987) Comprehensive coordination chemistry, vol 5. Pergamon, Oxford
63. Patterson GS, Holm RH (1975) Bioinorg Chem 4:257-275
64. Kryatov SV, Mohanraj BS, Tarasov VV, Kryatova OP, Akimova EVR, Nuthakki B, Rusling JF, Staples RJ, Nazarenko AY (2002) Inorg Chem 41:923-930
65. Desbois MH, Astruc D (1989) Organometallics 8:1841-1847
66. Heinze J (1984) Angew Chem Int Ed Engl 23:831-847
67. Long EC, Barton JK (1990) Acc Chem Res 23:271-273
68. Pasternack RF, Gibbs EJ, Villafranca JJ (1983) Biochemistry 22:2406-2414
69. Selvi PT, Evans HS, Palanaindavar M (2005) J Inorg Biochem 99:2110-2118
70. Chauhan M, Arjmand F, Banerjee K (2007) Inorg Chem 46:3072-3082
71. Singh R, Singh S, Kumar S, Arora S (2007) Food Chem 103:1403-1410
72. Mahakunakoran P, Tohda M, Murakami Y, Matsumoto K, Watanabe H (2004) Biol Pharm Bull 27:38-46
73. Naik GH, Priyadarsini KI, Satav JG, Banavalikar MM, Sohoni PP, Biyani MK (2003) Phytochemistry 63:97-104
74. Rekka E, Kourounakis PN (1991) J Pharm Pharmacol 43:486-491
75. Pavanato A, Tunon MJ, Campos SS, Marroni CA, Llesuy S, Gallego JG, Marroni N (2003) Dig Dis Sci 48:824-829
76. Hartinger CG, Casini A, Duhot C, Tsybin YO, Messori L, Dyson PJ (2008) J Inorg Biochem 102:2136-2141
77. Prabhakaran R, Geetha A, Thilagavathi M, Karvembu R, Krishnan V, Bertagnolli H, Natarajan K (2004) J Inorg Biochem 98:2131-2140