Jatrophane Diterpenes as Modulators of Multidrug Resistance. Advances of Structure-Activity Relationships and Discovery of the Potent Lead Pepluanin A

Journal of Medicinal Chemistry

Volumn 47, Issue 4, 2004, Pages 988-992

  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 UNIVERSITÉ LYON 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOYL PEROXIDE; CARBON; CARBONYL DERIVATIVE; CYCLOSPORIN A; DAUNORUBICIN; DITERPENE; EUPHORBIA EXTRACT; GLYCOPROTEIN P; GLYCOPROTEIN P INHIBITOR; HYDROXYL GROUP; JATROPHANE; PEPLUANIN A; PEPLUANIN B; PEPLUANIN C; PEPLUANIN D; PEPLUANIN E; UNCLASSIFIED DRUG;

ARTICLE; DRUG ISOLATION; EUPHORBIA; EUPHORBIA PEPLUS; STRUCTURE ACTIVITY RELATION;

ANTIBIOTICS, ANTINEOPLASTIC; BIOLOGICAL TRANSPORT; CELL LINE, TUMOR; CYCLOSPORINE; DAUNORUBICIN; DITERPENES; DRUG RESISTANCE, MULTIPLE; DRUG RESISTANCE, NEOPLASM; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; NICOTINIC ACIDS; P-GLYCOPROTEIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0842347626     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm030951y     Document Type: Article

References (14)

1. Pliny the Elder, Naturalis historia, XXVI, 45.
2. Hohmann, J.; Molnár, J.; Rédei, D.; Evanics, F.; Forgo, P. ; Kálmán, A.; Argay, G.; Szabó, Discovery and Biological evaluation of a new family of potent modulators of multidrug resistance: Reversal of multidrug resistance of mouse lymphoma cells by new natural jatrophane diterpenoids isolated from Euphorbia species. J. Med. Chem. 2002, 45, 2425-2431.
3. Juliano, R. L.; Ling, V. A surface glycoprotein modulating drug permeability in Chinese hamster ovary cell mutants. Biochim. Biophys. Acta 1976, 455, 152-62.
4. Endicott, J. A.; Ling, V. The biochemistry of P-glycoprotein-mediated multidrug resistance. Annu. Rev. Biochem. 1989, 28, 137-71.
5. Bolhuis, H.; van Veen, H. W.; Poolman, B.; Driessen, A. J. M.; Konings, W. N. Mechanisms of multidrug transporters. FEMS Microbiol. Rev. 1997, 21, 55-84.
6. Higgins, C. F. P-glycoprotein. To flip or not to flip? Curr. Biol. 1994, 4, 259-60.
7. Leveille-Webster, C. R.; Arias, I. M. The biology of the P-glycoprotein. J. Membr. Biol. 1995, 143, 89-102.
8. Sharom, F. J. The P-glycoprotein efflux pump: How does it transport drugs? J. Membr. Biol. 1997, 160, 161-175.
9. Scala, S.; Akhmed, N.; Rao, U. S.; Paull, K.; Lan, L.-B.; Dickstein, B.; Lee, J.-S., Elgemeie, G. H.; Stein, W.; Bates, S. E. The P-glycoprotein substrates and antagonists cluster into two distinct groups. Mol. Pharmacol. 1997, 51, 1024-1033.
10. Corea, G.; Fattorusso, E.; Lanzotti, V.; Taglialatela-Scafati, O.; Appendino, G.; Ballero, M.; Simon, P.-N.; Dumontet C.; Di Pietro A. Jatrophane P-Glycoprotein Inhibitors. First Insights of Structure-Activity Relationship and Discovery of a New Powerful Lead, J. Med. Chem. 2003, 46, 3395-3402.
11. Jakupovic, J.; Morgenstern, T.; Bittner, M.; Silva, M. Diterpenes from Euphorbia peplus. Phytochemistry 1998, 47, 1601-1609.
12. Appendino, G.; Jakupovic, S.; Tron, G. C.; Jakupovic, J.; Milon, V.; Ballero, M. Macrocyclic diterpenoids from Euphorbia semi-perfoliata. J. Nat. Prod. 1998, 61, 749-756.
13. 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.
14. 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, 1023-1028.