The taming of capsaicin. Reversal of the vanilloid activity of N-acylvanillamines by aromatic iodination (Articolo in rivista)

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  • The taming of capsaicin. Reversal of the vanilloid activity of N-acylvanillamines by aromatic iodination (Articolo in rivista) (literal)
Anno
  • 2005-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1021/jm050139q (literal)
Alternative label
  • Appendino G., Daddario N., Minassi A., Schiano Moriello A., De Petrocellis L. , Di Marzo V. (2005)
    The taming of capsaicin. Reversal of the vanilloid activity of N-acylvanillamines by aromatic iodination
    in Journal of medicinal chemistry; American Chemical Society, Washington (Stati Uniti d'America)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Appendino G., Daddario N., Minassi A., Schiano Moriello A., De Petrocellis L. , Di Marzo V. (literal)
Pagina inizio
  • 4663 (literal)
Pagina fine
  • 4669 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 48 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo
  • 14 (literal)
Note
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • 1. Dipartimento Sci Chim Alimentari Farmaceut & Farm, I-28100 Novara, Italy 2. CNR, Inst Biomol Chem, Endocannabinoid Res Grp, I-80078 Pozzuoli, Italy 3. CNR, Ist Cibernet Eduardo Caianiello, Endocannabinoid Res Grp, I-80078 Pozzuoli, Italy (literal)
Titolo
  • The taming of capsaicin. Reversal of the vanilloid activity of N-acylvanillamines by aromatic iodination (literal)
Abstract
  • Aromatic iodination ortho to the phenolic hydroxyl reverts the activity of the ultrapotent vanilloid agonist resiniferatoxin (RTX, 1a), generating the ultrapotent antagonist 5'-iodoRTX (1b). To better understand the role of iodine in this remarkable switch of activity, a systematic investigation on the halogenation of vanillamides, a class of compounds structurally simpler than resiniferonoids, was carried out. The results showed that (a) the antagonistic activity depends on the site of halogenation and is maximal at C-6', (b) iodine is more efficient than chlorine and bromine at reverting the agonistic activity, and (c) iodine-carbon exchange decreases antagonist activity. Iodine-induced reversal of vanilloid activity was also observed in vanillamides more powerful than capsaicin, but a poor correlation was found between agonistic and antagonistic potencies, suggesting that differences exist in the way vanillamides and their 6'-iodo derivatives bind to TRPV1 (literal)
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