Natural and synthetic benzophenones: Interaction with the cytosolic binding domain of P-glycoprotein

Phytochemistry

Volumn 57, Issue 4, 2001, Pages 553-557

  Rancon, Sandrine ^a   Chaboud, Annie ^a   Darbour, Nicole ^a   Comte, Gilles ^a   Bayet, Christine ^a   Simon, Pierre Noël ^a   Raynaud, Jean ^a   Di Pietro, Attilio ^b   Cabalion, Pierre ^c   Barron, Denis ^a  

^a UNIVERSITÉ LYON 1   (France)

^b INSTITUT DE BIOLOGIE ET CHIMIE DES PROTÉINES   (France)

^c INSTITUT DE RECHERCHE POUR LE DÉVELOPPEMENT   (France)

Author keywords

Benzophenones; Davallia solida; Davalliaceae; Drug resistance; P Glycoprotein

Indexed keywords

4 O BETA DEXTRO GLUCOPYRANOSYL 2,6,4' TRIHYDROXYBENZOPHENONE; BENZOPHENONE DERIVATIVE; BIOLOGICAL FACTOR; DAVALLIA SOLIDA EXTRACT; GLYCOPROTEIN P; GLYCOSIDE; PLANT EXTRACT; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; BINDING SITE; CYTOSOL; DAVALLIA SOLIDA; DRUG ISOLATION; DRUG RESISTANCE; DRUG STRUCTURE; NONHUMAN; PLANT; PROTEIN DOMAIN; PROTEIN TERTIARY STRUCTURE; SPECTROSCOPY;

BENZOPHENONES; BINDING SITES; BIOLOGICAL FACTORS; CYTOSOL; DRUG RESISTANCE, NEOPLASM; P-GLYCOPROTEIN; PLANT EXTRACTS; PROTEIN STRUCTURE, TERTIARY;

DAVALLIA SOLIDA; DAVALLIACEAE;

EID: 0035827426     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0031-9422(01)00120-0     Document Type: Article

References (17)

1. Agraval P.K. Carbon-13 NMR of Flavonoids. 1989;Elsevier, Amsterdam.
2. Agraval P.K. NMR spectroscopy in the structural elucidation of oligosaccharides and glycosides. Phytochemistry. 31:1992;3307-3330.
3. Andrus M.B., Turner T.M., Sauna Z.E., Ambudkar S.V. Synthesis and preliminary analysis of a P-glycoprotein-specific [3H]-benzophenone photoaffinity label based on (-)-stipiamide. Bioorganic and Medicinal Chemistry Letters. 10:2000;2275-2278.
4. Bennett G.J., Lee H.H. Xanthones from Guttiferae. Phytochemistry. 28:1989;967-998.
5. Breitmayer E., Voelter W. Carbon-13 NMR Spectroscopy. 1989;VCH, Weinheim.
6. Comte, G., Daskiewicz, J.B., Bayet, C., Conseil, G., Viornery-Vanier, A.,Dumontet, C., Di Pietro, A., Barron, D., 2001. C-Isoprenylation of flavonoids enhances binding affinity towards P-glycoprotein and modulation of cancer cells chemoresistance. Journal of Medicinal Chemistry 44, 763-768.
7. Conseil, G., Baubichon-Cottay, H., Dayan, G., Jault, J.M., Barron, D., Di Pietro, A., 1998. Flavonoids: a class of modulators with bifunctional interactions at vicinal ATP - and steroid binding sites on mouse P-glycoprotein. Proceedings of the National Academy of Sciences of the USA 95, 9831-9836.
8. Critchfield J.W., Welsh C.J., Phang J.M., Yeh G.C. Modulation of adriamycin in accumulation and efflux by flavonoid in HCT-15 colon cells. Activation of P-glycoprotein as a putative mechanism. Biochemical Pharmacology. 48:1994;1437-1445.
9. De Wet, H., McIntosh, D.V., Conseil, G., Baubichon-Cortay, H., Krell, T., Jault, J.M., Daskiewicz, J.B., Barron, D., Di Pietro, A., 2001. Interaction of nucleotides and flavonoids with recombinant C-terminal nucleotide binding domain of mouse multidrug resistance P-glycoprotein. Biochemistry, submitted.
10. Divita G., Goody R.S., Gautheron D.C., Di Pietro A. Structural mapping of catalytic site with respect to alpha-subunit and noncatalytic site in yeast mitochondria F1-ATPase using fluorescence resonance energy transfer. Journal of Biological Chemistry. 268:1993;13178-13186.
11. Dorman G., Prestwich G.D. Benzophenone photophores in biochemistry. Biochemistry. 33:1994;5661-5673.
12. Fleming S.A. Chemical reagents in photoaffinity labelling. Tetrahedron. 51:1995;12479-12520.
13. Gottesman M.M., Hrycyna C.A., Schoenlein P.V., German U.A., Pastan L. Genetic analysis of the multidrug transporter. Annual Revue of Genetics. 29:1993;607-649.
14. Gros P., Buschmann E. The mouse multidrug resistance gene family structural and functional analysis. International Revue of Cytology. 137:1993;169-197.
15. Noungoué-Tchamo D., Dijoux-Franca M.J., Mariotte A.M., Tsamo E., Daskiewicz J.B., Bayet C., Barron D., Conseil G., Di Pietro A. Prenylated xanthones as potential P-glycoprotein modulators. Bioorganic and Medicinal Chemistry Letters. 10:2000;1343-1345.
16. Rancon S., Chaboud A., Darbour N., Comte G., Barron D., Raynaud J., Cabalion P. A new C-glycosyl xanthone isolated from Davallia solida. Phytochemistry. 52:1999;1677-1679.
17. Shapiro A.B., Ling V. Effect of quercetin on Hoechst 33342 transport by purified and reconstituted P-glycoprotein. Biochemical Pharmacology. 53:1997;587-596.