Inactivation of monoamine oxidase B by cis- and trans-5-aminomethyl-3-(4-methoxyphenyl)dihydrofuran-2(3H)-ones

Xingliang Lu; Richard B. Silverman

doi:10.1016/S0968-0896(98)00116-3

Inactivation of monoamine oxidase B by cis- and trans-5-aminomethyl-3-(4-methoxyphenyl)dihydrofuran-2(3H)-ones

Xingliang Lu, Richard B. Silverman^*

^*Corresponding author for this work

Chemistry

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

1 Scopus citations

Abstract

Monoamine oxidase B was previously shown to be inactivated by cis- (3) and trans-5-(aminomethyl)-3-(4-methoxyphenyl)dihydrofuran-2(3H)-one hydrochloride (4) in a time-dependent manner (Ding, Z.; Silverman, R. B. J. Med. Chem. 1992, 35, 885) and to catalyze its oxidative decarboxylation (Silverman, R. B.; Zhou, J. J. P.; Ding, C. Z.; Lu, X. J. Am. Chem. Soc. 1995, 117, 12895). By [¹⁴C]-labeling of the aryl methoxyl groups of these two inactivators, it is shown that this is not a mechanism-based inactivation and that multiple enzyme residues are labeled. Copyright (C) 1998 Elsevier Science Ltd.

Original language	English (US)
Pages (from-to)	1851-1856
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry
Volume	6
Issue number	10
DOIs	https://doi.org/10.1016/S0968-0896(98)00116-3
State	Published - Oct 1998

Keywords

2-Mercaptoethanol
Dihydrofuranone
Inactivation
Mechanism-based inactivation
Monoamine oxidase

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(98)00116-3

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title = "Inactivation of monoamine oxidase B by cis- and trans-5-aminomethyl-3-(4-methoxyphenyl)dihydrofuran-2(3H)-ones",

abstract = "Monoamine oxidase B was previously shown to be inactivated by cis- (3) and trans-5-(aminomethyl)-3-(4-methoxyphenyl)dihydrofuran-2(3H)-one hydrochloride (4) in a time-dependent manner (Ding, Z.; Silverman, R. B. J. Med. Chem. 1992, 35, 885) and to catalyze its oxidative decarboxylation (Silverman, R. B.; Zhou, J. J. P.; Ding, C. Z.; Lu, X. J. Am. Chem. Soc. 1995, 117, 12895). By [14C]-labeling of the aryl methoxyl groups of these two inactivators, it is shown that this is not a mechanism-based inactivation and that multiple enzyme residues are labeled. Copyright (C) 1998 Elsevier Science Ltd.",

keywords = "2-Mercaptoethanol, Dihydrofuranone, Inactivation, Mechanism-based inactivation, Monoamine oxidase",

author = "Xingliang Lu and Silverman, {Richard B.}",

note = "Funding Information: The authors are grateful to the National Institutes of Health (GM32634) for their financial support of this research. ",

year = "1998",

month = oct,

doi = "10.1016/S0968-0896(98)00116-3",

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AU - Lu, Xingliang

AU - Silverman, Richard B.

N1 - Funding Information: The authors are grateful to the National Institutes of Health (GM32634) for their financial support of this research.

PY - 1998/10

Y1 - 1998/10

N2 - Monoamine oxidase B was previously shown to be inactivated by cis- (3) and trans-5-(aminomethyl)-3-(4-methoxyphenyl)dihydrofuran-2(3H)-one hydrochloride (4) in a time-dependent manner (Ding, Z.; Silverman, R. B. J. Med. Chem. 1992, 35, 885) and to catalyze its oxidative decarboxylation (Silverman, R. B.; Zhou, J. J. P.; Ding, C. Z.; Lu, X. J. Am. Chem. Soc. 1995, 117, 12895). By [14C]-labeling of the aryl methoxyl groups of these two inactivators, it is shown that this is not a mechanism-based inactivation and that multiple enzyme residues are labeled. Copyright (C) 1998 Elsevier Science Ltd.

AB - Monoamine oxidase B was previously shown to be inactivated by cis- (3) and trans-5-(aminomethyl)-3-(4-methoxyphenyl)dihydrofuran-2(3H)-one hydrochloride (4) in a time-dependent manner (Ding, Z.; Silverman, R. B. J. Med. Chem. 1992, 35, 885) and to catalyze its oxidative decarboxylation (Silverman, R. B.; Zhou, J. J. P.; Ding, C. Z.; Lu, X. J. Am. Chem. Soc. 1995, 117, 12895). By [14C]-labeling of the aryl methoxyl groups of these two inactivators, it is shown that this is not a mechanism-based inactivation and that multiple enzyme residues are labeled. Copyright (C) 1998 Elsevier Science Ltd.

KW - 2-Mercaptoethanol

KW - Dihydrofuranone

KW - Inactivation

KW - Mechanism-based inactivation

KW - Monoamine oxidase

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EP - 1856

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IS - 10

ER -

Inactivation of monoamine oxidase B by cis- and trans-5-aminomethyl-3-(4-methoxyphenyl)dihydrofuran-2(3H)-ones

Abstract

Keywords

ASJC Scopus subject areas

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