Structure-activity relationships of the ultrapotent vanilloid resiniferatoxin (RTX): The homovanillyl moiety

Giovanni Appendino; Abdellah Ech-Chahad; Alberto Minassi; Sara Bacchiega; Luciano De Petrocellis; Vincenzo Di Marzo

doi:10.1016/j.bmcl.2006.09.077

Structure-activity relationships of the ultrapotent vanilloid resiniferatoxin (RTX): The homovanillyl moiety

Giovanni Appendino
, Abdellah Ech-Chahad
, Alberto Minassi
, Sara Bacchiega
, Luciano De Petrocellis
, Vincenzo Di Marzo

Dipartimento di Scienze del Farmaco

Risultato della ricerca: Contributo su rivista › Articolo in rivista › peer review

Abstract

Starting from ROPA (2), analogues of RTX (1a) modified on the acyl side chain were prepared and evaluated for vanilloid activity in HEK-293 cells over-expressing the human recombinant TRPV1. The ROPA motif provided an enhancement of potency sufficient to expand the range of vanillyl surrogates to structural elements (e.g., an unsubstituted phenyl ring) that afford inactive analogues in compounds from the capsaicin series.

Lingua originale	Inglese
pagine (da-a)	132-135
Numero di pagine	4
Rivista	Bioorganic and Medicinal Chemistry Letters
Volume	17
Numero di pubblicazione	1
DOI	https://doi.org/10.1016/j.bmcl.2006.09.077
Stato di pubblicazione	Pubblicato - 1 gen 2007

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10.1016/j.bmcl.2006.09.077

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title = "Structure-activity relationships of the ultrapotent vanilloid resiniferatoxin (RTX): The homovanillyl moiety",

abstract = "Starting from ROPA (2), analogues of RTX (1a) modified on the acyl side chain were prepared and evaluated for vanilloid activity in HEK-293 cells over-expressing the human recombinant TRPV1. The ROPA motif provided an enhancement of potency sufficient to expand the range of vanillyl surrogates to structural elements (e.g., an unsubstituted phenyl ring) that afford inactive analogues in compounds from the capsaicin series.",

keywords = "Capsaicin, Resiniferatoxin (RTX), Structure-activity relationships, TRPV1, Vanilloids",

author = "Giovanni Appendino and Abdellah Ech-Chahad and Alberto Minassi and Sara Bacchiega and Petrocellis, \{Luciano De\} and Marzo, \{Vincenzo Di\}",

note = "Funding Information: We gratefully acknowledge Indena S.p.A. for financial support.",

year = "2007",

month = jan,

day = "1",

doi = "10.1016/j.bmcl.2006.09.077",

language = "English",

volume = "17",

pages = "132--135",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Ltd.",

number = "1",

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TY - JOUR

T1 - Structure-activity relationships of the ultrapotent vanilloid resiniferatoxin (RTX)

T2 - The homovanillyl moiety

AU - Appendino, Giovanni

AU - Ech-Chahad, Abdellah

AU - Minassi, Alberto

AU - Bacchiega, Sara

AU - Petrocellis, Luciano De

AU - Marzo, Vincenzo Di

N1 - Funding Information: We gratefully acknowledge Indena S.p.A. for financial support.

PY - 2007/1/1

Y1 - 2007/1/1

N2 - Starting from ROPA (2), analogues of RTX (1a) modified on the acyl side chain were prepared and evaluated for vanilloid activity in HEK-293 cells over-expressing the human recombinant TRPV1. The ROPA motif provided an enhancement of potency sufficient to expand the range of vanillyl surrogates to structural elements (e.g., an unsubstituted phenyl ring) that afford inactive analogues in compounds from the capsaicin series.

AB - Starting from ROPA (2), analogues of RTX (1a) modified on the acyl side chain were prepared and evaluated for vanilloid activity in HEK-293 cells over-expressing the human recombinant TRPV1. The ROPA motif provided an enhancement of potency sufficient to expand the range of vanillyl surrogates to structural elements (e.g., an unsubstituted phenyl ring) that afford inactive analogues in compounds from the capsaicin series.

KW - Capsaicin

KW - Resiniferatoxin (RTX)

KW - Structure-activity relationships

KW - TRPV1

KW - Vanilloids

UR - https://www.scopus.com/pages/publications/33845777090

U2 - 10.1016/j.bmcl.2006.09.077

DO - 10.1016/j.bmcl.2006.09.077

M3 - Article

SN - 0960-894X

VL - 17

SP - 132

EP - 135

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 1

ER -

Structure-activity relationships of the ultrapotent vanilloid resiniferatoxin (RTX): The homovanillyl moiety

Abstract

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