De novo design, synthesis and spectroscopic characterization of chiral benzimidazole-derived amino acid Zn(II) complexes: Development of tryptophan-derived specific hydrolytic DNA artificial nuclease agent

Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy

Volumn 85, Issue 1, 2012, Pages 53-60

  Parveen, Shazia ^a   Arjmand, Farukh ^a  

^a ALIGARH MUSLIM UNIVERSITY   (India)

Author keywords

5 GMP and 5 TMP; Benzimidazole scaffold; Chiral dizinc(II) complexes; In vitro DNA binding; pBR322 hydrolytic cleavage

Indexed keywords

ANALYTICAL METHOD; BENZIMIDAZOLES; BIOPHYSICAL TECHNIQUES; CALF THYMUS DNA; CHIRAL DIZINC(II) COMPLEXES; CHIRAL DRUGS; COMPLEX 1; DE NOVO DESIGN; DNA BINDING; DNA CLEAVAGE; DRUG DESIGN; ETHANE-1 ,2-DIOL; HYDROLYTIC CLEAVAGE; IN VITRO DNA BINDING; L-TRYPTOPHAN; MODE OF ACTION; MOLECULAR LEVELS; NATURAL ENZYME; SEQUENCE SELECTIVITY; SPECTROSCOPIC CHARACTERIZATION; SUPERCOILED; ZN COMPLEX;

AMINO ACIDS; DNA; DRUG INTERACTIONS; ETHANE; SCAFFOLDS; THERMOMECHANICAL PULPING PROCESS; ZINC COMPOUNDS;

COMPLEXATION;

AMINO ACID; BENZIMIDAZOLE DERIVATIVE; CALF THYMUS DNA; COORDINATION COMPOUND; DNA; TRYPTOPHAN; ZINC;

ANIMAL; ARTICLE; CATTLE; CHEMISTRY; DNA CLEAVAGE; DRUG EFFECT; HYDROLYSIS; METABOLISM; SPECTROSCOPY;

AMINO ACIDS; ANIMALS; BENZIMIDAZOLES; CATTLE; COORDINATION COMPLEXES; DNA; DNA CLEAVAGE; HYDROLYSIS; SPECTRUM ANALYSIS; TRYPTOPHAN; ZINC;

EID: 81155131355     PISSN: 13861425     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.saa.2011.09.006     Document Type: Article

References (74)

1. I. Agranat, H. Caner, and J. Caldwell Nat. Rev. Drug Discov. 1 2002 753 768
2. K. Isele, V. Broughton, C.J. Matthews, A.F. Williams, G. Bernardinelli, P. Franz, and S. Decurtins J. Chem. Soc., Dalton Trans. 389 2002 9 3905
3. J.K. Barton Science 233 1986 727 734
4. S. Dhar, D. Senapati, P.A.N. Reddy, P.K. Das, and A.R. Chakravarty Chem. Commun. 245 2003 2 2453
5. F. Arjmand, and M. Chauhan Helv. Chim. Acta 88 2005 2413 2423
6. F. Arjmand, and M. Chauhan J. Organomet. Chem. 692 2007 5156 5164
7. F. Arjmand, B. Mohani, and S. Ahmad Eur. J. Med. Chem. 40 2005 1103 1110
8. M.K. Teng, N. Usman, C.A. Frederick, and A.H.J. Wang Nucleic Acids Res. 16 1988 2671 2690
9. J.A. Parkinson, J. Barber, K.T. Douglas, J. Rosamond, and D. Sharples Biochemistry 29 1990 10181 10190
10. A. Fede, A. Labhardt, W. Bannwarth, and W. Leupin Biochemistry 30 1991 11377 11388
11. F. Mancina, and P. Tecilla New J. Chem. 31 2007 800 817
12. N. Raman, A. Selvan, and S. Sudharsa Spectrochim. Acta A 79 2011 873 883
13. L.A. Basile, A.L. Raphael, and J.K. Barton J. Am. Chem. Soc. 109 1987 7550 7551
14. L.M. Berreau Adv. Phys. Org. Chem. 41 2006 79 181
15. A. Schiller, R. Scopelliti, and K. Severin Dalton Trans. 2006 3858 3867
16. Y. An, Y.Y. Lin, H. Wang, H.Z. Sun, M.L. Tong, L.N. Ji, and Z.W. Mao Dalton Trans. 2007 1250 1254
17. A.K. Patra, T. Bhowmick, S. Ramakumar, M. Nethaji, and A.K. Chakravarty Dalton Trans. 2008 6966 6976
18. E.L. Hegg, and J.N. Burstyn Coord. Chem. Rev. 173 1998 133 165
19. D.M. Boghaei, and M. Gharagozlou Spectrochim. Acta A 67 2007 944 949
20. J. Marmur J. Mol. Biol. 3 1961 208 214
21. M.E. Reicmann, S.A. Rice, C.A. Thomas, and P. Doty Am. Chem. Soc. 76 1954 3047 3053
22. A. Wolfe, G.H. Shimer, and T. Meehan Biochemistry 26 1987 6392 6396
23. J.R. Lakowiez, and G. Webber Biochemistry 12 1973 4161 4170
24. F. Arjmand, and M. Aziz Eur. J. Med. Chem. 44 1 2009 834 844
25. F. Arjmand, and M. Muddassir Eur. J. Med. Chem. 45 2010 3549 3557
26. F. Arjmand, and M. Muddassir Chirality 23 2011 250 259
27. Y. Xie, W. Bu, A.S. Chi Chan, X. Xu, Q. Liu, Z. Zhang, J. Yu, and Y. Fan Inorg. Chim. Acta 310 2000 257 260
28. S.M. Annigeri, A.D. Naik, U.B. Gangadharmath, V.K. Revankar, and V.B. Mahale Trans. Met. Chem. 27 2002 316 320
29. G.F. de Sousa, V.M. Deflon, M.T.P. Gambardella, R.H.P. Francisco, J.D. Ardisson, and E. Niquet Inorg. Chem. 45 2006 4518 4525
30. S. Yurdakul, and S. Badoglu Struct. Chem. 20 2009 423 434
31. P.R. Reddy, and A.M. Reddy Indian J. Chem. 41 2002 2083 2087
32. M. Casadesus, M.P. Coogan, E. Davies, and L.-l. Ooi Inorg. Chim. Acta 361 2008 63 78
33. C.T. Yang, B. Moubaraki, K.S.J. Murray, and J. Vittal Dalton Trans. 2003 880 889
34. A.I. Anzellotti, M. Sabat, and N. Farrell Inorg. Chem. 45 2006 1638 1645
35. G.M. Mamardashvili, O.E. Storonkina, and N.Zh. Mamardashvili Russ. J. Coord. Chem. 30 2004 388 391
36. C.S. Hwang, N. Lee, Y.A. Kim, and Y.B. Park Bull. Korean Chem. Soc. 27 2006 1809 1814
37. C. Cativiela, L.R. Falvello, J.C. Gines, R. Navarro, and E.P. Urriolabeitia New J. Chem. 25 2001 344 352
38. F. Arjmand, and M. Muddassir J. Photochem. Photobiol. B 101 2010 37 46
39. J.M. Kelly, A.B. Tossi, D.J. Mcconnell, and C. OhUigin Nucleic Acids Res. 13 17 1985 6017 6034
40. P.J. Cox, G. Psomas, and C.A. Bolos Bioorg. Med. Chem. 17 2009 6054 6062
41. J.K. Barton, A.T. Danishefsky, and J.M. Goldberg J. Am. Chem. Soc 106 1984 2172 2176
42. C.S. Chow, and J.K. Barton Method Enzymol. 212 1992 219 242
43. S. Ramakrishnan, and M. Palaniandavar Dalton Trans. 2008 3866 3878
44. P.R. Chetana, R. Rao, M. Roy, and A.K. Patra Inorg. Chim. Acta 362 2009 4692 4698
45. Y. Schimazaki, M. Takani, and O. Yamauchi Dalton Trans. 2009 7854 7869
46. S. Zhang, Y. Zhu, C. Tu, H. Wei, Z. Yang, L. Lin, J. Ding, J. Zhang, and Z. Guo J. Inorg. Biochem. 98 2004 2099 2106
47. M. Chauhan, F. Arjmand, and K. Banerjee Inorg. Chem. 46 2007 3072 3082
48. T. Matsubara, and K. Hirao J. Mol. Struct. (Theochem) 581 2002 203 213
49. M.J. Waring J. Mol. Biol. 13 1965 269 282
50. J.B. Lepecq, and C. Paoletti J. Mol. Biol. 27 1967 87 106
51. P.T. Selvi, H.S. Evans, and M. Palaniandavar J. Inorg. Biochem. 99 2005 2110 2118
52. S. Satyanarayana, J.C. Dabrowiak, and J.B. Chaires Biochemistry 31 1992 9319 9324
53. M. Cusumano, M.L. Di Pietro, and A. Giannetto Inorg. Chem. 45 2006 230 235
54. D. Ghosh, H. Ahmad, and J.A. Thomas Chem. Commun. 294 2009 7 2949
55. C. Rajput, R. Rutkaite, L. Swanson, I. Haq, and J.A. Thomas Chem. Eur. J. 12 2006 4611 4619
56. A.M. Polyanichko, V.V. Andrushchenko, E.V. Chikhirzhina, V. Vorobev, and H. Wieser Nucleic Acids Res. 32 2004 989 996
57. K. Karidi, A. Garoufis, A. Tsipis, N. Hadjiliadis, H. Dulk, and J. Reedijik Dalton Trans. 2005 1176 1187
58. M.-V.J. de, J. Lorenzo, A.M. Montana, V. Morenzo, and F.X. Aviles J. Inorg. Biochem. 102 2008 973 987
59. K. Karidi, A. Garoufis, N. Hadjiliadis, and J. Reedijk Dalton Trans. 2005 728 734
60. M.S. Melvin, J.T. Tomlinson, G.R. Saluta, G.L. Kucera, N. Lindquist, and R.A. Manderville J. Am. Chem. Soc. 122 2000 6333 6334
61. Y. Jung, and S.J. Lippard Chem. Rev. 107 2007 1387 1407
62. X. Dong, X. Wang, M. Lin, H. Sun, X. Yang, and Z. Guo Inorg. Chem. 49 2010 2541 2549
63. C.A. Detmer III, F.V. Pamatong, and J.R. Bocarsly Inorg. Chem. 36 1997 3676 3682
64. E. Trotta, G. Del, N. Erba, and M. Paci Biochemistry 39 2000 6799 6808
65. P. Wittung, P. Nielsen, and B. Norden J. Am. Chem. Soc. 118 1996 7049 7054
66. C. Bailly, G. Chessari, C. Carrasco, A. Joubert, J. Mann, W.D. Wilson, and S. Niedle Nucleic Acids Res. 31 2003 1514 1524
67. C.E.B. Smith, and M.S. Searle Nucleic Acids Res. 27 1999 1619 1624
68. M.S. Melvin, M.W. Calcutt, R.E. Noftle, and R.A. Manderville Chem. Res. Toxicol. 15 2002 742 748
69. C.J. Burrows, and J.G. Muller Chem. Rev. 98 1998 1109 1152
70. B. Selvakumar, V. Rajendiran, U. Maheswari, H. Stoeckli-Evans, and M. Palaniandavar J. Inorg. Biochem. 100 2006 316 330
71. T. Afrati, A.A. Pantazaki, C.D. Samara, C. Raptopoulou, A. Terzisb, and D.P. Kessissoglou Dalton Trans. 39 2010 765 775
72. M.S.S. Babu, K.H. Reddy, and P.G. Krishna Polyhedron 26 2007 572 580
73. T. Jun, W. Bochua, and Z. Liancai Bioorg. Med. Chem. Lett. 17 2007 1197 1199
74. D. Mandal, M. Chauhan, F. Arjmand, G. Aromi, and D. Ray Dalton Trans. 2009 9183 9191