Biophysical studies on the effect of the 13 position substitution of the anticancer alkaloid berberine on its DNA binding

Journal of Physical Chemistry B

Volumn 116, Issue 7, 2012, Pages 2314-2324

  Bhowmik, Debipreeta ^a   Hossain, Maidul ^a   Buzzetti, Franco ^b   D'Auria, Rosaria ^b   Lombardi, Paolo ^b   Kumar, Gopinatha Suresh ^a  

^a INDIAN INSTITUTE OF CHEMICAL BIOLOGY   (India)

^b Naxospharma Srl   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCHEMISTRY; CHAIN LENGTH; ENTROPY; FREE ENERGY; SODIUM; THERMODYNAMICS;

ALKYL CHAIN; BASE STACKING; BINDING AFFINITIES; BIOPHYSICAL STUDIES; CONFORMATIONAL CHANGE; COOPERATIVE BINDING; DNA BINDING; DNA HELIX; INTERCALATIVE BINDING; PHENYL GROUP; STRONG STABILIZATION; STRUCTURAL EFFECT; THERMODYNAMIC DATA; TOTAL FREE ENERGY;

BINDING ENERGY;

EID: 84857424138     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp210072a     Document Type: Article

References (88)

1. Grycová, L.; Dostál, J.; Marek, R. Phytochemistry 2007, 68, 150-175
2. Küpeli, E.; Koşar, M.; Yeşilada, E.; Başer, K. H. C.; Başer, C. Life Sci. 2002, 72, 645-657
3. Iwasa, K.; Moriyasu, M.; Tachibana, Y.; Kim, H.-S.; Wataya, Y.; Wiegrebe, W.; Bastow, K. F.; Cosentino, L. M.; Kozuka, M.; Lee, K.-H. Bioorg. Med. Chem. 2001, 9, 2871-2884
4. Nafisi, S.; Malekabady, Z. M.; Khalilzadeh, M. A. DNA Cell Biol. 2010, 29, 753-761
5. Nafisi, S.; Bonsaii, M.; Maali, P.; Khalilzadeh, M. A.; Manouchehri, F. J. Photochem. Photobiol., B 2010, 100, 84-91
6. Yin, J.; Xing, H.; Ye, J. Metabolism 2008, 57, 712-717
7. Imanshahidi, M.; Hosseinzadeh, H. Phytother. Res. 2008, 22, 999-1012
8. Cui, H.-S.; Hayasaka, S.; Zhang, X.-Y.; Hayasaka, Y.; Chi, Z.-L.; Zheng, L.-S. Jpn. J. Ophthalmol. 2007, 51, 64-67
9. Choi, B.-H.; Ahn, I.-S.; Kim, Y.-H.; Park, J.-W.; Lee, S.-Y.; Hyun, C.-K.; Do, M.-S. Exp. Mol. Med. 2006, 38, 599-605
10. Kuo, C. L.; Chi, C. W.; Liu, T. Y. Cancer Lett. 2004, 203, 127-137
11. Pasqual, M. S.; Lauer, C. P.; Moyna, P.; Henriques, J. A. Mutat. Res. 1993, 286, 243-252
12. Chiou, W.-F.; Yen, M.-H.; Chen, C.-F. Eur. J. Pharmacol. 1991, 204, 35-40
13. Hui, K. K.; Yu, J. L.; Chan, W. F.; Tse, E. Life Sci. 1991, 49, 315-324
14. Creasey, W. A. Biochem. Pharmacol. 1979, 28, 1081-1084
15. Amin, A. H.; Subbaiah, T. V.; Abbasi, K. M. Can. J. Microbiol. 1969, 15, 1067-1076
16. Stermitz, F. R.; Lorenz, P.; Tawara, J. N.; Zenewicz, L. A.; Lewis, K Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 1433-1437
17. Cernakova, M.; Kostalova, D. Folia Microbiol. 2002, 47, 375-378
18. Yu, H.-H.; Kim, K-J; Cha, J.-D.; Kim, H.-K.; Lee, Y.-E.; Choi, N.-Y.; You, Y.-O. J. Med. Food Winter 2005, 8, 454-461
19. Choi, M. S.; Oh, J. H.; Kim, S. M.; Jung, H. Y.; Yoo, H. S.; Lee, Y. M.; Moon, D. C.; Han, S. B.; Hong, J. T. Int. J. Oncol. 2009, 34, 1221-1230
20. Letasiova, S.; Jantova, S.; Cipak, L.; Muckova, M. Cancer Lett. 2006, 239, 254-262
21. Yang, I. W.; Chou, C. C.; Yung, B. Y. M. Pharmacology 1996, 354, 102-108
22. Kuo, C. L.; Chou, C. C.; Yung, B. Y. M. Cancer Lett. 1995, 93, 193-200
23. Wartenberg, M.; Budde, P.; De Marees, M.; Grunheck, F.; Tsang, S. Y.; Huang, Y.; Chen, Z. Y.; Hescheler, J.; Sauer, H. Lab. Invest. 2003, 83, 87-98
24. Iizuka, N.; Miyamoto, K.; Okita, K.; Tangoku, A.; Hayashi, H.; Yosino, S.; Abe, T.; Morioka, T.; Hazama, S.; Oka, M. Cancer Lett. 2000, 148, 19-25
25. Mantena, S. K.; Sharma, S. D.; Katyar, S. K. Mol. Cancer Ther. 2006, 5, 296-308
26. Lin, J.-P.; Yang, J-S; Lee, J.-H.; Hsieh, W.-T.; Chung, J.-G. World J. Gastroenterol. 2006, 12, 21-28
27. Peng, P. L.; Hsiesh, Y. S.; Wang, C. J.; Hsu, J. L.; Chou, F. P. Toxicol. Appl. Pharmacol. 2006, 214, 8-15
28. Kim, J. B.; Lee, K. M.; Ko, E.; Han, W.; Lee, J. E.; Shin, I.; Bae, J. Y.; Kim, S.; Noh, D. Y. Planta Med. 2008, 74, 39-42
29. Ho, Y. T.; Yang, J. S.; Lu, C. C.; Chiang, J. H.; Li, T. C.; Lin, J. J.; Lai, K. C.; Liao, C. L.; Lin, J. G.; Chung, J. G. Phytomedicine 2009, 16, 887-890
30. Sun, Y.; Xun, K.; Wang, Y.; Chen, X. Anticancer Drugs 2009, 20, 757-769
31. Mahata, S.; Bharti, A. C.; Shukla, S.; Tyagi, A.; Husain, S,A.; Das, B. C. Mol. Cancer 2011, 10, 39-52
32. Davidson, M. W.; Lopp, I.; Alexander, S.; Wilson, W. D. Nucleic Acids Res. 1977, 4, 2697-2712
33. Debnath, D.; Suresh Kumar, G.; Maiti, M. J. Biomol. Struct. Dyn. 1991, 9, 61-79
34. Saran, A.; Srivastava, S.; Coutinho, E.; Maiti, M. Indian J. Biochem. Biophys. 1995, 32, 74-77
35. Krishnan, P.; Bastow, K. F. Anti-Cancer Drug Des. 2000, 15, 255-264
36. Li, T. K.; Bathory, E.; LaVoie, E. J.; Srinivasan, A. R.; Olson, W. K.; Sauers, R. R.; Liu, L. F.; Pilch, D. S. Biochemistry 2000, 39, 7107-7116
37. Bhadra, K.; Suresh Kumar, G.; Das, S.; Islam, M. M.; Maiti., M. Bioorg. Med. Chem. 2005, 13, 4851-4856
38. Wang, Y.; Kheir, M. M.; Chai, Y.; Hu, J.; Xing, D.; Lei, F.; Du, L. PLoS ONE 2011, 6, e23495
39. Maiti, M.; Suresh Kumar, G. Med. Res. Rev. 2007, 27, 649-695
40. Qina, Y.; Pang, J. Y.; Chen, W. H.; Zhao, Z. Z.; Liu, L.; Jiang, Z. H. Chem. Biodiversity 2007, 4, 481-487
41. Bhadra, K.; Suresh Kumar, G. Med. Res. Rev. 2011, 31, 821-862
42. Debnath, D.; Suresh Kumar, G.; Nandi, R.; Maiti, M. Indian J. Biochem. Biophys. 1989, 26, 201-208
43. Bhadra, K.; Maiti, M.; Suresh Kumar, G. Biochim. Biophys. Acta 2008, 1780, 1054-1061
44. Li, W. Y.; Lu, H.; Xu, C. X.; Zhang, J. B.; Lu, Z. H. Spectrosc. Lett. 1998, 3l, 1287-1298
45. Mazzini, S.; Bellucci, M. C.; Mondelli, R. Bioorg. Med. Chem. 2003, 11, 505-514
46. Ferraroni, M.; Bazzicalupi, C.; Bilia, A. R.; Gratteri, P. Chem. Commun. 2011, 47, 4917-4919
47. Naasani, I.; Seimiya, H.; Yamori, T.; Tsuruo, T. Cancer Res. 1999, 59, 4004-4011
48. Franceschin, M.; Rossetti, L.; D'Ambrosio, A.; Schirripa, S.; Bianco, A.; Ortaggi, G.; Savino, M.; Schultes, C.; Neidle, S. Bioorg. Med. Chem. Lett. 2006, 16, 1707-1711
49. Zhang, W. J.; Ou, T. M.; Lu, Y. J.; Huang, Y. Y.; Wu, W. B.; Huang, Z. S.; Zhou, J. L.; Wong, K. Y.; Gu, L. Q. Bioorg. Med. Chem. 2007, 15, 5493-5501
50. Gornall, K. C.; Samosorn, S.; Tanwirat, B.; Suksamrarn, A.; Bremner, J. B.; Kelso, M. J.; Beck, J. L. Chem. Commun. 2010, 46, 6602-6604
51. Iwasa, K.; Kamigauchi, M.; Ueki, M.; Taniguchi, M. Eur. J. Med. Chem. 1996, 31, 469-478
52. Iwasa, K.; Nanba, H.; Lee, D. U.; Kang, S. I. Planta Med. 1998, 64, 748-751
53. Lee, D. U.; Kang, Y. J.; Park, M. K.; Lee, Y. S.; Seo, H. G.; Kim, T. S.; Kim, C. H.; Chang, K. C. Life Sci. 2003, 73, 1401-1412
54. Park, K. D.; Lee, J. H.; Kim, S. H.; Kang, T. H.; Moona, J. S.; Kima, S. U. Bioorg. Med. Chem. Lett. 2006, 16, 3913-3916
55. Samosorn, S.; Tanwirat, B.; Muhamad, N.; Casadei, G.; Tomkiewicz, D.; Lewis, K.; Suksamrarn, A.; Pramananan, T.; Gornall, K. C.; Beck, J. L; Bremner, J. B. Bioorg. Med. Chem. 2009, 17, 3866-3872
56. Cui, J. S.; Xu, F.; Pang, J. Y.; Chen, W. H.; Jiang, Z. H. Chem. Biodiversity 2010, 7, 2908-16
57. Islam, M. M.; Basu, A.; Hossain, M.; Suresh Kumar, G.; Hotha, S.; Suresh Kumar, G. DNA Cell Biol. 2011, 30, 123-133
58. Islam, M. M.; Basu, A.; Suresh Kumar, G. Med. Chem. Commun. 2011, 2, 631-637
59. Samosorn, S.; Tanwirat, B.; Muhamad, N.; Casadei, G.; Tomkiewicz, D.; Lewis, K.; Suksamrarn, A.; Prammananan, T.; Gornall, K. C.; Beck, J. L.; Bremner, J. B. Bioorg. Med. Chem. 2009, 17, 3866-3872
60. Iwasa, K.; Moriyasu, M.; Yamori, T.; Turuo, T.; Lee, D. U. J. Nat. Prod. 2001, 64, 896-898
61. Gornall, K. C.; Samosorn, S.; Tanwirat, B.; Suksamrarn, A.; Bremner, J. B.; Kelso, M. J.; Beck, J. L. Chem. Commun. 2010, 46, 6602-6604
62. Naxospharma srl, US Patent appl. US 12/458,657, filed July 20, 2009; published as US 2011/015222 A1 on January 20, 2011.
63. Chaires, J. B. Biochemistry 1983, 22, 4204-4211
64. Bhadra, K.; Maiti, M.; Suresh Kumar, G. Biochim. Biophys. Acta 2007, 1770, 1071-1080
65. Islam, M. M.; Roy Chowdhury, S.; Suresh Kumar, G. J. Phys. Chem. B 2009, 113, 1210-1224
66. Sinha, R.; Islam, M. M.; Bhadra, K.; Suresh Kumar, G.; Banerjee, A.; Maiti, M. Bioorg. Med. Chem. 2006, 14, 800-814
67. Islam, M. M.; Sinha, R.; Suresh Kumar, G. Biophys. Chem. 2007, 125, 508-520
68. McGhee, J. D.; von Hippel, P. H. J. Mol. Biol. 1974, 86, 469-489
69. Job, P. Ann. Chim. 1928, 9, 113-203
70. Huang, C. Y. Methods Enzymol. 1982, 87, 509-525
71. Giri, P.; Suresh Kumar, G. Arch. Biochem. Biophys. 2008, 474, 183-192
72. Giri, P.; Suresh Kumar, G. Mol. BioSyst. 2008, 4, 341-348
73. Islam, M. M.; Pandya, P.; Kumar, S.; Suresh Kumar, G. Mol. BioSyst. 2009, 5, 244-254
74. Sinha, R.; Suresh Kumar, G. J. Phys. Chem. B 2009, 113, 13410-13420
75. Müller, W.; Crothers, D. M. J. Mol. Biol. 1968, 35, 251-290
76. Islam, M. M.; Pandya, P.; Roy Chowdhury, S.; Kumar, S.; Suresh Kumar, G. J. Mol. Struct. 2008, 891, 498-507
77. Bhadra, K.; Maiti, M.; Suresh Kumar, G. DNA Cell Biol. 2008, 27, 675-685
78. Crothers, D. M. Biopolymers 1968, 6, 575-584
79. O'Brien, R.;; Haq, I. In Applications of Biocalorimetry: Binding, Stability and Enzyme Kinetics; Ladbury, J. E.; Doyle, M., Eds.; Biocalorimetry 2; John Wiley and Sons Ltd: Chichester, U.K., 2004; pp 1-34.
80. Buurma, N. J.; Haq, I. Methods 2007, 42, 162-172
81. Matthew, W. F.; Edwin, A. L. Methods Cell. Biol. 2008, 84, 79-113
82. Bhadra, K.; Suresh Kumar, G. Mini Rev. Med. Chem. 2010, 10, 1235-1247
83. Haq, I. Arch. Biochem. Biophys. 2002, 403, 1-15
84. Chaires, J. B. Arch. Biochem. Biophys. 2006, 453, 26-31
85. Hossain, M.; Suresh Kumar, G. Mol. BioSyst. 2009, 5, 1311-1322
86. Saha, I.; Hossain, M.; Suresh Kumar, G. Phys. Chem. Chem. Phys. 2010, 12, 12771-12779
87. Chaires, J. B. Ann. Rev. Biophys. 2008, 37, 135-151
88. Record, M. T., Jr; Anderson, C. F.; Lohman, T. M. Q. Rev. Biophys. 1978, 11, 103-178