Antitumor agents. 280. Multidrug resistance-selective desmosdumotin B analogues

Journal of Medicinal Chemistry

Volumn 53, Issue 18, 2010, Pages 6699-6705

  Nakagawa Goto, Kyoko ^a   Chang, Po Cheng ^a   Lai, Chin Yu ^a   Hung, Hsin Yi ^a   Chen, Tzu Hsuan ^a   Wu, Pei Chi ^a   Zhu, Hao ^a   Sedykh, Alexander ^a   Bastow, Kenneth F ^a   Lee, Kuo Hsiung ^a,b  

^a University of North Carolina   (United States)

^b CHINA MEDICAL UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

3',5' DIMETHYL 6,8,8 TRIETHYLDESMOSDUMOTIN B; 4' METHOXY 3' METHYL 6,8,8 TRIETHYLDESMOSDUMOTIN B; 6,6,8 TRIETHYLDESMOSDUMOTIN B; ANTINEOPLASTIC AGENT; CYCLOSPORIN; DESMOSDUMOTIN B DERIVATIVE; FLAVONOID; GLYCOPROTEIN P; MULTIDRUG RESISTANCE PROTEIN; PACLITAXEL; UNCLASSIFIED DRUG; VERAPAMIL; VINCRISTINE; 6,6,8-TRIETHYLDESMOSDUMOTIN B; FLAVONE DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CHEMICAL MODIFICATION; CONTROLLED STUDY; CYTOTOXICITY; DRUG SELECTIVITY; DRUG SYNTHESIS; HEPATOMA CELL; HUMAN; HUMAN TISSUE; APOPTOSIS; BIOSYNTHESIS; CHEMISTRY; DRUG EFFECTS; DRUG RESISTANCE; DRUG SCREENING; MULTIDRUG RESISTANCE; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL LINE, TUMOR; DRUG RESISTANCE, MULTIPLE; DRUG RESISTANCE, NEOPLASM; DRUG SCREENING ASSAYS, ANTITUMOR; FLAVONES; HUMANS; P-GLYCOPROTEIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77956785606     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm100846r     Document Type: Article

References (32)

1. Lage, H. An overview of cancer multidrug resistance: a still unsolved problem Cell. Mol. Life Sci. 2008, 65, 3145-3167
2. Perez-Tomas, R. Multidrug resistance: retrospect and prospects in anti-cancer drug treatment Curr. Med. Chem. 2006, 13, 1859-1876
3. Fojo, T.; Bates, S. Strategies for reversing drug resistance Oncogene 2003, 22, 7512-7523
4. Tsuruo, T.; Naito, M.; Tomida, A.; Fujita, N.; Mashima, T.; Sakamoto, H. Molecular targeting therapy of cancer: drug resistance, apoptosis and survival signal Cancer Sci. 2003, 94, 15-21
5. Endicott, J. A.; Ling, V. The biochemistry of P-glycoprotein-mediated multidrug resistance Annu. Rev. Biochem. 1989, 58, 137-171
6. Cole, S. P.; Bhardwaj, G.; Gerlach, J. H.; Mackie, J. E.; Grant, C. E.; Almquist, K. C.; Stewart, A. J; Kurz, E. U.; Duncan, A. M.; Deeley, R. G. Overexpression of a transporter gene in a multidrug-resistant human lung cancer cell line Science 1992, 258, 1650-1654
7. Doyle, L. A.; Yang, W.; Abruzzo, L. V.; Krogmann, T.; Gao, Y.; Rishi, A. K.; Ross, D. D. A multidrug resistance transporter from human MCF-7 breast cancer cells Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 15665-15670
8. Allikmets, R.; Schriml, L. M.; Hutchinson, A.; Romano-Spica, V.; Dean, M. A human placenta-specific ATPbinding cassette gene (ABCP) on chromosome 4q22 that is involved in multidrug resistance Cancer Res. 1998, 58, 5337-5339
9. Miyake, K.; Mickley, L.; Litman, T.; Zhan, Z.; Robey, R.; Cristensen, B.; Brangi, M.; Greenberger, L.; Dean, M.; Fojo, T.; Bates, S. E. Molecular cloning of cDNAs which are highly overexpressed in mitoxantrone-resistant cells: demonstration of homology to ABC transport genes Cancer Res. 1999, 59, 8-13
10. Recent review for ABC transporters: Eckford, P. D. W.; Sharom, F. J. ABC efflux pump-based resistance to chemotherapy drugs Chem. Rev. 2009, 109, 2989-3011
11. Sharom, F. J. ABC multidrug transporters: structure, function and role in chemoresistance Future Med. 2008, 9, 105-127
12. Crowley, E.; Callaghan, R. Multidrug efflux pumps: drug binding-gates or cavity? FEBS J. 2010, 277, 530-539
13. Aller, S. G.; Yu, J.; Ward, A.; Weng, Y.; Chittaboina, S.; Zhuo, R.; Harrell, P. M.; Trinh, Y. T.; Zhang, Q.; Urbatsch, I. L.; Chang, G. Structure of P-glycoprotein reveals a molecular basis for poly-specific drug binding Science 2009, 323, 1718-1722
14. Kimura, Y.; Morita, S.; Matsuo, M.; Ueda, K. Mechanism of multidrug recognition by MDR1/ABCB1 Cancer Sci. 2007, 98, 1303-1310
15. Ambudkar, S. V; Kimchi-Sarfaty, C.; Sauna, Z. E.; Gottesman, M. M. P-glycoprotein: from genomics to mechanism Oncogene 2003, 22, 7468-7485
16. Modok, S.; Mellor, H. R.; Callaghan, R. Modulation of multidrug resistance efflux pump activity to overcome chemoresistance in cancer Curr. Opin. Pharmacol. 2006, 6, 350-354
17. Takara, K.; Sakaeda, T.; Okumura, K. An update on overcoming MDR1-mediated multidrug resistance in cancer chemotherapy Curr. Pharm. Des. 2006, 12, 273-286
18. Avendaño, C.; Menéndez, J. C. Recent advance in multidrug resistance modulators Med. Chem. Rev. 2004, 1, 419-444
19. Kawase, M.; Motohashi, N. New multidrug resistance reversal agents Curr. Drug Targets 2003, 4, 31-43
20. Lehne, G. P-glycoprotein as a drug target in the treatment of multidrug resistant cancer Curr. Drug Targets 2000, 1, 85-99
21. Coley, H. M. Overcoming multidrug resistance in cancer: clinical studies of P-glycoprotein inhibitors Methods Mol. Biol. 2010, 549, 341-358
22. Havsteen, B. H. The biochemistry and medical significance of the flavonoids Pharmacol. Ther. 2002, 96, 67-202
23. Alvarez, A. I.; Real, R.; Pérez, M.; Mendoza, G.; Prieto, J. G.; Merino, G. Modulation of the activity of ABC transporters (P-glycoprotein, MRP2, BCRP) by flavonoids and drug response J. Pharm. Sci. 2010, 99, 598-617
24. Bansal, T.; Jaggil, M.; Khar, R. K.; Talegaonkar, S. Emerging significance of flavonoids as P-glycoprotein inhibitors in cancer chemotherapy J. Pharm. Pharm. Sci. 2009, 12, 46-78
25. Morris, M. E.; Zhang, S. Flavonoid-drug interactions: effects of flavonoids on ABC transporters Life Sci. 2006, 78, 2116-2130
26. Boumendjel, A.; Di Pietro, A.; Dumontet, C.; Barron, D. Recent advances in the discovery of flavonoids and analogs with high-affinity binding to P-glycoprotein responsible for cancer cell multidrug resistance Med. Res. Rev. 2002, 22, 512-529
27. Nakagawa-Goto, K.; Bastow, K. F.; Wu, J.-H.; Tokuda, H.; Lee, K. H. Total synthesis and bioactivity of unique flavone desmosdumotin B and its analogs Bioorg. Med. Chem. Lett. 2005, 15, 3016-3019
28. Nakagawa-Goto, K.; Bastow, K. F.; Cgen, T. H.; Morris-Natschke, S. L.; Lee, K. H. Antitumor agents. 260. New desmosdumotin B analogues with inproved in vitro anticancer activity J. Med. Chem. 2009, 51, 3297-3303
29. Szybalski, W.; Bryson, V. Genetic studies on microbial cross resistance to toxic agents. I. Cross resistance of Escherichia coli to fifteen antibiotics J. Bacteriol. 1952, 64, 489-499
30. Hall, M. D.; Handley, M. D.; Gottesman, M. M. Is resistance useless? Multidrug resistance and collateral sensitivity Trends Pharmacol. Sci. 2009, 30, 546-556. Note: The structure of desmosdumotin analogue 11 in Figure 3 is missing a triethyl group on the A-ring; it should be the same as 3 in this article
31. Ludwig, J. A.; Szakács, G.; Martin, S. E.; Chu, B. F.; Cardarelli, C.; Sauna, Z. E.; Caplen, N. J.; Fales, H. M.; Ambudkar, S. V.; Weinstein, J. N.; Gottesman, M. M. Selective toxicity of NSC73306 in MDR1-positive cells as a new strategy to circumvent multidrug resistance in cancer Cancer Res. 2006, 66, 4808-4815
32. Hall, M. D.; Salam, N. K.; Hellawell, J. L.; Fales, H. M.; Kensler, C. B.; Ludwig, J. A.; Szakács, G.; Hibbs, D. E.; Gottesman, M. M. Synthesis, activity, and pharmacophore development for isatin-β-thiosemicarbazones with selective activity toward multidrug-resistant cells J. Med. Chem. 2009, 52, 3191-3204