3′-O, 4′-O-aromatic acyl substituted 7,8-pyranocoumarins: A new class of P-glycoprotein modulators

Journal of Pharmacy and Pharmacology

Volumn 64, Issue 1, 2012, Pages 90-100

  Shen, Xiaoling ^a   Chen, Guangying ^b   Zhu, Guoyuan ^c   Cai, Jiazhong ^a   Wang, Lu ^a   Hu, Yingjie ^a   Fong, Wang Fun ^c  

^a GUANGZHOU UNIVERSITY OF CHINESE MEDICINE   (China)

^b HAINAN NORMAL UNIVERSITY   (China)

^c HONG KONG BAPTIST UNIVERSITY   (Hong Kong)

Author keywords

( ) Praeruptorin A; 7, 8 pyranocoumarin; multidrug resistance; P glycoprotein

Indexed keywords

3' O,4' O DICYNNAMOYL KHELLACTONE; ADENOSINE TRIPHOSPHATASE; ANTINEOPLASTIC AGENT; DMDCK; DOXORUBICIN; GLYCOPROTEIN P; GLYCOPROTEIN P INHIBITOR; PACLITAXEL; PRAERUPTORIN A; PUROMYCIN; PYRANOCOUMARIN DERIVATIVE; UNCLASSIFIED DRUG; VERAPAMIL; VINBLASTINE; COUMARIN DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CANCER INHIBITION; CELL PROLIFERATION; CONTROLLED STUDY; DRUG ACCUMULATION; DRUG CYTOTOXICITY; DRUG MECHANISM; DRUG POTENTIATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; FEMALE; HUMAN; HUMAN CELL; HYDROGEN BOND; IC 50; IN VITRO STUDY; IN VIVO STUDY; MOUSE; MULTIDRUG RESISTANCE; NONHUMAN; PROTEIN INTERACTION; STRUCTURE ACTIVITY RELATION; TUMOR CELL CULTURE; TUMOR VOLUME; TUMOR XENOGRAFT; ANIMAL; BAGG ALBINO MOUSE; CHEMICAL STRUCTURE; DRUG EFFECT; DRUG RESISTANCE; METABOLISM; NUDE MOUSE; STATISTICS;

ANIMALS; ANTINEOPLASTIC AGENTS; COUMARINS; DRUG RESISTANCE, MULTIPLE; DRUG RESISTANCE, NEOPLASM; FEMALE; MICE; MICE, INBRED BALB C; MICE, NUDE; MODELS, ANIMAL; MOLECULAR STRUCTURE; P-GLYCOPROTEIN; PYRANOCOUMARINS; STATISTICS AS TOPIC; TUMOR CELLS, CULTURED;

EID: 83555168247     PISSN: 00223573     EISSN: 20427158     Source Type: Journal    
DOI: 10.1111/j.2042-7158.2011.01378.x     Document Type: Article

References (19)

1. Stavrovskaya AA,. Cellular mechanisms of multidrug resistance of tumor cells. Biochemistry (Mosc) 2000; 65: 95-106.
2. Gottesman MM, et al,. Multidrug resistance in cancer: role of ATP-dependent transporters. Nat Rev Cancer 2002; 2: 48-58. (Pubitemid 37328807)
3. Choi CH,. ABC transporters as multidrug resistance mechanisms and the development of chemosensitizers for their reversal. Cancer Cell Int 2005; 5: 30.
4. Krishna R, Mayer LD,. Multidrug resistance (MDR) in cancer. Mechanisms, reversal using modulators of MDR and the role of MDR modulators in influencing the pharmacokinetics of anticancer drugs. Eur J Pharm Sci 2000; 11: 265-283.
5. Tsuruo T, et al,. Overcoming of vincristine resistance in P388 leukemia in vivo and in vitro through enhanced cytotoxicity of vincristine and vinblastine by verapamil. Cancer Res 1981; 41: 1967-1972. (Pubitemid 11114605)
6. Robert J, Jarry C,. Multidrug resistance reversal agents. J Med Chem 2003; 46: 4805-4187.
7. Goldmann B,. Multidrug resistance: can new drugs help chemotherapy score against cancer? J Natl Cancer Inst 2003; 95: 255-257.
8. Pajeva IK, Wiese M,. Pharmacophore model of drugs involved in P-glycoprotein multidrug resistance: explanation of structural variety (hypothesis). J Med Chem 2002; 45: 5671-5686. (Pubitemid 35453760)
9. Pajeva IK, et al,. Structure-function relationships of multidrug resistance P-glycoprotein. J Med Chem 2004; 47: 2523-2533. (Pubitemid 38580090)
10. Seelig A,. A general pattern for substrate recognition by P-glycoprotein. Eur J Biochem 1998; 251: 252-261. (Pubitemid 28081437)
11. Seelig A, Landwojtowicz E,. Structure-activity relationship of P-glycoprotein substrates and modifiers. Eur J Biochem 2000; 12: 31-40.
12. Wu JY, et al,. Reversal of multidrug resistance in cancer cells by pyranocoumarins isolated from Radix Peucedani. Eur J Pharmacol 2003; 473: 9-17. (Pubitemid 36851623)
13. Shen XL, et al,. (±)-3′-O, 4′-O-dicynnamoyl-cis- khellactone, a derivative of (±)-Praeruptorin A, reverses P-glycoprotein mediated multidrug resistance in cancer cells. Bioorg Med Chem 2006; 14: 7138-7145.
14. Fong WF, et al,. Methoxylation of 3′, 4′-aromatic side chains improves P-glycoprotein inhibitory and multidrug resistance reversal activities of 7, 8-pyranocoumarin against cancer cells. Bioorg Med Chem 2008; 16: 3694-3703.
15. Wu XL, et al,. [Studies on structure modification of (+)-praeruptorin A.]. Acta Pharm Sin 2002; 37: 527-534 [In Chinese].
16. Kong LY, et al,. [Semi-synthesis of derivatives with C-3′and C-4′ transconfiguration from (+)-praeruptorin A.]. Acta Pharm Sin 2003; 38: 358-363 [In Chinese].
17. Mechetner EB, et al,. P-glycoprotein function involves conformational transitions detectable by differential immunoreactivity. Proc Natl Acad Sci USA 1997; 94: 12908-12913. (Pubitemid 27518450)
18. Nagy H, et al,. P-Glycoprotein conformational changes detected by antibody competition. Eur J Biochem 2001; 268: 2416.
19. Maki N, et al,. Allosteric modulation of human P-glycoprotein. Inhibition of transport by preventing substrate translocation and dissociation. J Biol Chem 2003; 278: 18132-18319.