Enhanced DNA binding of 9-ω-amino alkyl ether analogs from the plant alkaloid berberine

DNA and Cell Biology

Volumn 30, Issue 2, 2011, Pages 123-133

  Islam, Md Maidul ^a,c   Basu, Anirban ^a   Hossain, Maidul ^a   Sureshkumar, Gopalsamy ^b   Hotha, Srinivas ^b   Suresh Kumar, Gopinatha ^a  

^a INDIAN INSTITUTE OF CHEMICAL BIOLOGY   (India)

^b NATIONAL CHEMICAL LABORATORY   (India)

^c Alia University   (India)

Author keywords

[No Author keywords available]

Indexed keywords

9 OMEGA AMINO ALKYL ETHER DERIVATIVE; ANTINEOPLASTIC AGENT; BERBERINE; BERBERINE DERIVATIVE; DOUBLE STRANDED DNA; ISOQUINOLINE ALKALOID; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CALF (MAMMAL); CIRCULAR DICHROISM; CONTROLLED STUDY; DERIVATIZATION; DRUG DESIGN; DRUG DNA BINDING; ENTROPY; FLUORESCENCE; ISOTHERMAL TITRATION CALORIMETRY; MOLECULAR RECOGNITION; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; THERMODYNAMICS; THYMUS; ULTRAVIOLET SPECTROSCOPY;

ABSORPTION; ANIMALS; BERBERINE; CALORIMETRY; CATTLE; CIRCULAR DICHROISM; DNA; ETHERS; ETHIDIUM; NUCLEIC ACID DENATURATION; PLANTS; SPECTROMETRY, FLUORESCENCE; STRUCTURE-ACTIVITY RELATIONSHIP; TRANSITION TEMPERATURE;

EID: 79551653334     PISSN: 10445498     EISSN: None     Source Type: Journal    
DOI: 10.1089/dna.2010.1109     Document Type: Article

References (49)

1. Arora, A., Balasubramanian, C., Kumar, N., Agarwal, S., Ojha, R.P., and Maiti, S. (2008). Binding of berberine to human telomeric quadruplex- spectroscopic, calorimetric and molecular modeling studies. FEBS J 275, 3971-3983.
2. Bhadra, K., Maiti, M., and Kumar, G.S. (2008a). DNA-binding cytotoxic alkaloids: comparative study of the energetics of binding of berberine, palmatine, and coralyne. DNA Cell Biol 27, 675-685.
3. Bhadra, K., Maiti, M., and Kumar, G.S. (2008b). Thermodynamics of the binding of cytotoxic protoberberine molecule coralyne to deoxyribonucleic acids. Biochim Biophys Acta 1780, 298-306.
4. Bhadra, K., Maiti, M., and Kumar, G.S. (2008c). Berberine-DNA complexation: new insights into the cooperative binding and energetic aspects. Biochim Biophys Acta 1780, 1054-1061.
5. Bhadra, K., and Kumar, G.S. (2010). Therapeutic potential of nucleic acid-binding isoquinoline alkaloids: binding aspects and implications for drug design. Med Res Rev 2010 Jan 14. [Epub ahead of print]
6. Birdsall, T.C., and Kelly, G.S. (1997). Berberine: therapeutic potential of an alkaloid found in several medicinal plants. Altern Med Rev 2, 94-103.
7. Chen, W.H., Pang, J.Y., Qin, Y., Peng, Q., Cai, Z., and Jiang, Z.H. (2005). Synthesis of linked berberine dimers and their remarkably enhanced DNA-binding affinities. Bioorg Med Chem Lett 15, 2689-2692.
8. Chiou, W.F., Yen, M.H., and Chen, C.F. (1991). Mechanism of vasodilatory effect of berberine in rat mesenteric artery. Eur J Pharmacol 204, 35-40.
9. Choi, M.S., Oh, J.H., Kim, S.M., Jung, H.Y., Yoo, H.S., Lee, Y.M., Moon, D.C., Han, S.B., and Hong, J.T. (2009). Berberine inhibits p53-dependent cell growth through induction of apoptosis of prostate cancer cells. Int J Oncol 34, 1221-1230.
10. Elford, B.C. (1986). L-Glutamine influx in malaria-infected erythrocytes: a target for antimalarials? Parasitol Today 2, 309-312.
11. Foye, W.O., Karnik, P.S., and Sengupta, S.K. (1986). DNAbinding abilities of bisguanylhydrazones of anthracene-9,10- dicarboxaldehyde. Anticancer Drug Des 1, 65-71.
12. Franceschin, M., Rossetti, L., D'Ambrosio, A., Schirripa, S., Bianco, A., Ortaggi, G., Savino, M., Schultes, C., and Neidle, S. (2006). Natural and synthetic G-quadruplex interactive berberine derivatives. Bioorg Med Chem 16, 1707-1711.
13. Ghosh, A.K., Bhattacharyya, F.K., and Ghosh, D.K. (1985). Leishmania donovani: amastigote inhibition and mode of action of berberine. Exp Parasitol 60, 404-413.
14. Gornall, K.C., Samosorn, S., Tanwirat, B., Suksamaran, A., Bremner, J.B., Kelso, M.J., and Beck, J.L. A mass spectrometric investigation of novel quadruplex DNA-selective berberine derivatives. Chem Com (Camb) 2010 Sept 21 [Epub ahead of print].
15. Graves, D.E., and Velea, L.M. (2000). Intercalative binding of small molecules to nucleic acids. Curr Org Chem 4, 915-929.
16. Grycova, L., Dostal, J., and Marek, R. (2007). Quaternary protoberberine alkaloids. Phytochemistry 68, 150-175.
17. Halimani, M., Chandran, S.P., Kashyap, S., Jadhav, V.M., Prasad, B.L.V., Hotha, S., and Maiti, S. (2009). Dendritic effect of ligand-coated nanoparticles: enhanced apoptotic activity of silica-berberine nanoconjugates. Langmuir 25, 2339-2347.
18. 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., and Chung, J.G. (2009). Berberine inhibits human tongue squamous carcinoma cancer tumor growth in a murine xenograft model. Phytomedicine 16, 887-890.
19. Hui, K.K., Yu, J.L., Chan, W.F., and Tsc, E. (1991). Interaction of berberine with human platelet alpha 2 adrenoceptors. Life Sci 49, 315-324.
20. Iizuka, N., Miyamoto, K., Okita, K., Tangoku, A., Hayashi, H., Yosino, S., Abe, T., Morioka, S., and Oka, M. (2000). Inhibitory effect of Coptidis Rhizoma and berberine on the proliferation of human esophageal cancer cell lines. Cancer Lett 148, 19-25.
21. Imanshahidi, M., and Hosseinzadeh, H. (2008). Pharmacological and therapeutic effects of Berberis vulgaris and its active constituent, berberine. Phytotherapy Res 22, 999-1012.
22. Islam, M.M., Pandya, P., Kumar, S., and Kumar, G.S. (2009). RNA targeting through binding of small molecules: studies on t-RNA binding by the cytotoxic protoberberine alkaloid coralyne. Mol Biosystems 5, 244-254.
23. Krishnan, P., and Bastov, K.F. (2000). The 9-position in berberine analogs is an important determinant of DNA topoisomerase II inhibition. Anticancer Drug Des 15, 255-264.
24. Kuo, C.L., Chou, C.C., and Yung, B.Y. (1995). Berberine complexes with DNA in the berberine-induced apoptosis in human leukemic HL-60 cells. Cancer Lett 93, 193-200.
25. Letasiova, S., Jantova, S., Cipak, L., and Muckova, M. (2006). Berberine-antiproliferative activity in vitro and induction of apoptosis/necrosis of the U937 and B16 cells. Cancer Lett 239, 254-262.
26. Li, T.K., Batahry, E., La Voie, E.J., Srinivasan, A.R., Olson, W.K., and Sauer, R.R. (2000). Human topoisomerase I poisoning by protoberberines: potential roles for both drug-DNA and drugenzyme interactions. Biochemistry 39, 7107-7116.
27. Lin, S., Tsai, S.C., Lee, C.C., Wang, B.W., Liou, J.Y., and Shyu, K.G. (2004). Berberine inhibits HIF-1alpha expression via enhanced proteolysis. Mol Pharmacol 66, 612-619.
28. Liu, Z., Liu, Q., Xu, B., Wu, J., Guo, C., Zhu, F., Yang, Q., Gao, G., Gong, Y., and Shao, C. (2009). Berberine induces p53- dependent cell cycle arrest and apoptosis of human osteosarcoma cells by inflicting DNA damage. Mutat Res 662, 75-83.
29. Ma, Y., Ou, T.M., Hou, J.Q., Lu, I.J., Tan, J.H., Gu, L.Q., and Huang, Z.S. (2008). 9-N-Substituted berberine derivatives: stabilization of G-quadruplex DNA and down-regulation of oncogene c-myc. Bioorg Med Chem 16, 7582-7591.
30. Ma, Y., Ou, T.M., Tan, J.H., Hou, J.Q., Huang, S.L., Gu, L.Q., and Huang, Z.S. (2009). Synthesis and evaluation of 9-Osubstituted berberine derivatives containing aza-aromatic terminal group as highly selective telomeric G-quadruplex stabilizing ligands. Bioorg Med Chem Lett 19, 3414-3417.
31. Maiti, M., and Kumar, G.S. (2007a). Molecular aspects on the interaction of protoberberine, benzophenanthridine, and aristolochia group of alkaloids with nucleic acid structures and biological perspectives. Med Res Rev 27, 649-695.
32. Maiti, M., and Kumar, G.S. (2007b). Protoberberine alkaloids: physicochemical and nucleic acid binding properties. Top Heterocycl Chem 10, 155-209.
33. Mazzini, S., Bellucci, M.C., and Mondelli, R. (2003). Mode of binding of the cytotoxic alkaloid berberine with the double helix oligonucleotide D(AAGAATTCTT)2. Bioorg Med Chem 11, 505-514.
34. McGhee, J.D., and von Hippel, P.H. (1974). Theoretical aspects of DNA-protein interactions: co-operative and non-co-operative binding of large ligands to a one-dimensional homogeneous lattice. J Mol Biol 86, 469-489.
35. Pang, J.Y., Long, Y.H., Chen, W.H., and Jiang, Z.H. (2007). Amplification of DNA-binding affinities of protoberberine alkaloids by appended polyamines. Bioorg Med Chem 17, 1018-1021.
36. Pang, J.Y., Qin, Y., Chen, W.H., Luo, G.A., and Jiang, Z.H. (2005). Synthesis and DNA-binding affinities of monomodified berberines. Bioorg Med Chem 13, 5835-5840.
37. Pasqual, M.S., Lauer, C.P., Moyna, P., and Henriques, J.A. (1993). Genotoxicity of the isoquinoline alkaloid berberine in prokaryotic and eukaryotic organisms. Mutat Res 286, 243-252.
38. Peng, P.L., Hsieh, Y.S., Wang, C.J., Hsu, J.L., and Chou, F.P. (2006). Inhibitory effect of berberine on the invasion of human lung cancer cells via decreased productions of urokinaseplasminogen activator and matrix metalloproteinase-2. Toxicol Appl Pharmacol 214, 8-15.
39. Pilch, D.S., Yu, C., Makhey, D., La Voie, E.J., Srinivasan, A.R., Olson, W.K., and Sauers, R.R. (1997). Minor groove-directed and intercalative ligand-DNA interactions in the poisoning of human DNA topoisomerase I by protoberberine analogs. Biochemistry 36, 12542-12553.
40. Qin, Y., Chen, W.H., Pang, J.Y., Zhao, Z.Z., Liu, L., and Jiang, Z.H. (2007). DNA-binding affinities and sequence specificities of protoberberine alkaloids and their demethylated derivatives: a comparative study. Chem Biodivers 4, 145-153.
41. Sinha, R., and Kumar, G.S. (2009). Interaction of isoquinoline alkaloids with an RNA triplex: structural and thermodynamic studies of berberine, palmatine, and coralyne binding to poly(U).poly(A)*poly(U). J Phys Chem B 113, 13410-13420.
42. Sun, Y., Xun, K., Wang, Y., and Chen, X. (2009). A systematic review of the anticancer properties of berberine, a natural product from Chinese herbs. Anticancer Drugs 20, 757-769.
43. Tan, J.H., Lu, Y.J., Huang, Z.S., Gu, L.Q., and Wu, J.Y. (2007). Spectroscopic studies of DNA binding modes of cationsubstituted anthrapyrazoles derived from emodin. Eur J Med Chem 42, 1169-1175.
44. Tang, J., Feng, Y., Tsao, S., Wang, N., Curtain, R., and Wang, Y. (2009). Berberine and Coptidis Rhizoma as novel antineoplastic agents: a review of traditional use and biomedical investigations. J Ethanopharmacol 126, 5-17.
45. Urbanova, J., Lubal, P., Slaninova, I., Taborska, E., and Taborsky, P. (2009). Fluorescence properties of selected benzo [c] phenantridine alkaloids and studies of their interaction with CT DNA. Anal Bioanal Chem 349, 997-1002.
46. Vennerstrom, J.L., and Klayman, D.L. (1988). Protoberberine alkaloids as antimalarials. J Med Chem 31, 1084-1087.
47. Wartenberg, M., Budde, P., De Marees, M., Grunheck, F., Tsang, S.Y., Huang, Y., Chen, Z.Y., Hescheler, J., and Sauer, H. (2003). Inhibition of tumor-induced angiogenesis and matrixmetalloproteinase expression in confrontation cultures of embryoid bodies and tumor spheroids by plant ingredients used in traditional Chinese medicine. Lab Invest 83, 87-98.
48. Yang, I.W., Chou, C.C., and Yung, B.Y. (1996). Dose-dependent effects of berberine on cell cycle pause and apoptosis in Balb/c 3T3 cells. Naunyn Schmiedebergs Arch Pharmacol 354, 102-108.
49. Zhang, R., Dougherty, D.V., and Rosenblum, M.L. (1990). Laboratory studies of berberine used alone and in combination with 1,3-bis(2-chloroethyl)- 1-nitrosourea to treat malignant brain tumors. Chin Med J 103, 658-665.