Synthesis and in vitro evaluation of a novel iodinated resiniferatoxin derivative that is an agonist at the human vanilloid VR1 receptor

Synthesis and in vitro evaluation of a novel iodinated resiniferatoxin derivative that is an agonist at the human vanilloid VR1 receptor

Using a 'directed' iodination procedure, novel iodo-resiniferatoxin congeners were synthesized from 4-acetoxy-3-methoxyphenylacetic acid and resiniferinol- 9,13,14-ortho-phenylacetate (ROPA). The 2-iodo-4-hydroxy-5-methoxyphenylacetic acid ester of resiniferinol 5 displayed high affinity b...

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Veröffentlicht in:Bioorganic & medicinal chemistry letters 2002-04, Vol.12 (8), p.1189-1192
Hauptverfasser: MCDONNELL, Mark E, ZHANG, Sui-Po, DUBIN, Adrienne E, DAX, Scott L
Format: Artikel
Sprache:eng
Schlagworte:
Biological and medical sciences
Diterpenes - chemical synthesis
Diterpenes - chemistry
Diterpenes - pharmacology
Drug Evaluation, Preclinical
Humans
In Vitro Techniques
Iodine - chemistry
Medical sciences
Miscellaneous
Neuropharmacology
Neurotransmitters. Neurotransmission. Receptors
Pharmacology. Drug treatments
Receptors, Drug - agonists
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Zusammenfassung:Using a 'directed' iodination procedure, novel iodo-resiniferatoxin congeners were synthesized from 4-acetoxy-3-methoxyphenylacetic acid and resiniferinol- 9,13,14-ortho-phenylacetate (ROPA). The 2-iodo-4-hydroxy-5-methoxyphenylacetic acid ester of resiniferinol 5 displayed high affinity binding (K(i)=0.71 nM) for the human vanilloid VR1 receptor and functioned as a partial agonist.
ISSN:0960-894X
1464-3405
DOI:10.1016/S0960-894X(02)00127-0