Structure-activity relationships for euphocharacins A-L, a new series of jatrophane diterpenes, as inhibitors of cancer cell P-glycoprotein

Planta Medica

Volumn 70, Issue 7, 2004, Pages 657-665

  Corea, Gabriella ^a   Fattorusso, Ernesto ^a   Lanzotti, Virginia ^b   Motti, Riccardo ^a   Simon, Pierre Noël ^c   Dumontet, Charles ^c   Di Pietro, Attilio ^d  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^b UNIVERSITY OF MOLISE   (Italy)

^c INSERM   (France)

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

Author keywords

Diterpenes; Euphorbia characias; Euphorbiaceae; Jatrophanes; P glycoprotein; SAR studies

Indexed keywords

CYCLOSPORIN; DAUNORUBICIN; DITERPENE; EUPHOCHARACIN A; EUPHOCHARACIN B; EUPHOCHARACIN C; EUPHOCHARACIN D; EUPHOCHARACIN E; EUPHOCHARACIN F; EUPHOCHARACIN G; EUPHOCHARACIN H; EUPHOCHARACIN I; EUPHOCHARACIN J; EUPHOCHARACIN K; EUPHOCHARACIN L; EUPHORBIA EXTRACT; GLYCOPROTEIN P; GLYCOPROTEIN P INHIBITOR; HYDROXYL GROUP; PROPANE; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL; CHEMICAL STRUCTURE; CORRELATION ANALYSIS; DRUG ACTIVITY; EFFUSION; EUPHORBIA CHARACIAS; MASS SPECTROMETRY; MEDICINAL PLANT; NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; CELL LINE, TUMOR; DITERPENES; EUPHORBIA; HUMANS; P-GLYCOPROTEIN; PHYTOTHERAPY; PLANT EXTRACTS; STRUCTURE-ACTIVITY RELATIONSHIP;

EUPHORBIA; EUPHORBIA CHARACIAS; EUPHORBIACEAE;

EID: 3542993310     PISSN: 00320943     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-827191     Document Type: Article

References (15)

1. Leveille-Webster CR, Arias IM. The biology of the P-glycoprotein. J Membrane Biol 1995; 143: 89-102
2. Sharom FJ. The P-glycoprotein efflux pump: how does it transport drugs? J Membrane Biol 1997; 160: 161-75
3. Scala S, Akhmed N, Rao US, Paull K, Lan LB, Dickstein B, Lee JS, Elgemeie GH, Stein W, Bates SE. The P-glycoprotein substrates and antagonists cluster into two distinct groups. Mol Pharmacol 1997; 51: 1024-33
4. Juliano RL, Ling V. A surface glycoprotein modulating drug permeability in Chinese hamster ovary cell mutants. Biochim Biophys Acta 1976; 455: 152-62
5. Endicott JA, Ling V. The biochemistry of P-glycoprotein-mediated multidrug resistance. Annu Rev Biochemistry 1989; 58: 137-71
6. Wang RB, Kuo CL, Lien LL, Lien EJ. Structure-activity relationship: analyses of P-glycoprotein substrates and inhibitors. J Clin Pharm Ther 2003; 28: 203-228
7. Robert J, Jarry C. Multidrug resistance reversal agents. J Med Chem 2003; 46: 4805-17
8. Hohmann J, Molnár J, Rédei D, Evanics F, Forgo P, Kálmán A, Argay G, Szabó P. Discovery and biological evaluation of a new family of potent modulators of mutidrug resistance: reversal of multidrug resistance of mouse lymphoma cells by new natural jatrophane diterpenoids isolated from Euphorbia species. J Med Chem 2002; 45: 2425-31
9. Corea G, Fattorusso E, Lanzotti V, Tagliatatela-Scafati O, Appendino G, Ballero M, Simon P-N, Dumontet C, Di Pietro A. Jatrophane diterpenes as P-glycoprotein inhibitors. First insights of structure-activity relationship and discovery of a new powerful lead. J Med Chem 2003; 46: 3395-402
10. Corea G, Fattorusso E, Lanzotti V, Taglialatela-Scafati O, Appendino G, Ballero M, Simon P-N, Dumontet C, Di Pietro A. Modified jatrophane diterpenes as modulators of multidrug resistance from Euphorbia dendroides L. Bioorg & Med Chem 2003; 11: 5221-7
11. Corea G, Fattorusso E, Lanzotti V, Motti R, Simon P-N, Dumontet C, Di Pietro A. Jatrophane diterpenes as modulators of multidrug resistance. Advances of structure-activity relationship and discovery of the potent lead pepluanin A. J Med Chem 2004; 47: 988-92
12. Comte G, Daskiewicz J-B, Bayet C, Conseil G, Viornery-Vanier A, Dumontet C, Di Pietro A, Barron D. C-Isoprenylation of flavonoids enhances binding affinity toward P-glycoprotein and modulation of cancer cell chemoresistance. J Med Chem 2001; 44: 763-768
13. Simon P-N, Chaboud A, Darbour N, Di Pietro A, Dumontet C, Lurel F, Raynaud J, Barron D. Modulation of cancer cell multidrug resistance by an extract of Ficus citrifolia. Anticancer Res 2001; 21: 1023-8
14. Hohmann J, Vasas A, Gunther G, Mathe I, Evanics F, Dombi G, Jerkovich G. Macrocyclic diterpene polyester of the jatrophane type from Euphorbia esula. J Nat Prod 1997; 60: 331-5
15. Appendino G, Jakupovic S, Tron GC, Jakupovic J, Milon V, Ballero M. Macrocyclic diterpenoids from Euphorbia semiperfoliata. J Nat Prod 1998; 61: 749-56