Preparation and biological properties of biotinylated PhTX derivatives

Masaru Hashimoto; Ying Liu; Kan Fang; Hong Yu Li; Giuseppe Campiani; Koji Nakanishi

doi:10.1016/S0968-0896(99)00054-1

Preparation and biological properties of biotinylated PhTX derivatives

Masaru Hashimoto, Ying Liu, Kan Fang, Hong Yu Li, Giuseppe Campiani, Koji Nakanishi

Research output: Contribution to journal › Article › peer-review

13 Scopus citations

Abstract

We report the synthesis of several highly functionalized biotinylated philanthotoxin (PhTX) analogues (7, 8, 10, 13-16) designed on the basis of earlier structure-activity relationship studies. Despite the extensive modifications, the binding to nicotinic acetylcholine receptor (nAChR) is in the low micromolar range according to an inhibition assay using ³H-thienylcyclohexyl-piperidine (TCP). A patch clamp functional assay gave comparable results. Compounds exemplified by 16, which consists of a biotinylated ligand linked to a bifunctional photoaffinity probe (BPP), represent a new type of probe which should find use in photo-cross-linking studies of ligand-receptor interactions. Copyright (C) 1999 Elsevier Science Ltd.

Original language	English (US)
Pages (from-to)	1181-1194
Number of pages	14
Journal	Bioorganic and Medicinal Chemistry
Volume	7
Issue number	6
DOIs	https://doi.org/10.1016/S0968-0896(99)00054-1
State	Published - Jun 1999
Externally published	Yes

Keywords

Biotin-labeling
Philanthotoxin
Photoaffinity
nAChR

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/S0968-0896(99)00054-1

Cite this

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title = "Preparation and biological properties of biotinylated PhTX derivatives",

abstract = "We report the synthesis of several highly functionalized biotinylated philanthotoxin (PhTX) analogues (7, 8, 10, 13-16) designed on the basis of earlier structure-activity relationship studies. Despite the extensive modifications, the binding to nicotinic acetylcholine receptor (nAChR) is in the low micromolar range according to an inhibition assay using 3H-thienylcyclohexyl-piperidine (TCP). A patch clamp functional assay gave comparable results. Compounds exemplified by 16, which consists of a biotinylated ligand linked to a bifunctional photoaffinity probe (BPP), represent a new type of probe which should find use in photo-cross-linking studies of ligand-receptor interactions. Copyright (C) 1999 Elsevier Science Ltd.",

keywords = "Biotin-labeling, Philanthotoxin, Photoaffinity, nAChR",

author = "Masaru Hashimoto and Ying Liu and Kan Fang and Li, {Hong Yu} and Giuseppe Campiani and Koji Nakanishi",

year = "1999",

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TY - JOUR

T1 - Preparation and biological properties of biotinylated PhTX derivatives

AU - Hashimoto, Masaru

AU - Liu, Ying

AU - Fang, Kan

AU - Li, Hong Yu

AU - Campiani, Giuseppe

AU - Nakanishi, Koji

PY - 1999/6

Y1 - 1999/6

N2 - We report the synthesis of several highly functionalized biotinylated philanthotoxin (PhTX) analogues (7, 8, 10, 13-16) designed on the basis of earlier structure-activity relationship studies. Despite the extensive modifications, the binding to nicotinic acetylcholine receptor (nAChR) is in the low micromolar range according to an inhibition assay using 3H-thienylcyclohexyl-piperidine (TCP). A patch clamp functional assay gave comparable results. Compounds exemplified by 16, which consists of a biotinylated ligand linked to a bifunctional photoaffinity probe (BPP), represent a new type of probe which should find use in photo-cross-linking studies of ligand-receptor interactions. Copyright (C) 1999 Elsevier Science Ltd.

AB - We report the synthesis of several highly functionalized biotinylated philanthotoxin (PhTX) analogues (7, 8, 10, 13-16) designed on the basis of earlier structure-activity relationship studies. Despite the extensive modifications, the binding to nicotinic acetylcholine receptor (nAChR) is in the low micromolar range according to an inhibition assay using 3H-thienylcyclohexyl-piperidine (TCP). A patch clamp functional assay gave comparable results. Compounds exemplified by 16, which consists of a biotinylated ligand linked to a bifunctional photoaffinity probe (BPP), represent a new type of probe which should find use in photo-cross-linking studies of ligand-receptor interactions. Copyright (C) 1999 Elsevier Science Ltd.

KW - Biotin-labeling

KW - Philanthotoxin

KW - Photoaffinity

KW - nAChR

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JO - Bioorganic and Medicinal Chemistry

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Preparation and biological properties of biotinylated PhTX derivatives

Abstract

Keywords

ASJC Scopus subject areas

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