Acid dissociation constant, a potential physicochemical factor in the inhibition of the enzyme estrone sulfatase (ES)

Sabbir Ahmed; Caroline P. Owen; Karen James; Chirag K. Patel; Mijal Patel

doi:10.1016/S0960-894X(01)00087-7

Acid dissociation constant, a potential physicochemical factor in the inhibition of the enzyme estrone sulfatase (ES)

Sabbir Ahmed, Caroline P. Owen, Karen James, Chirag K. Patel, Mijal Patel

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

Abstract

We report the initial results of the synthesis and biochemical evaluation of a series of aminosulfonate based compounds of phenol and the determination of the pKa of the parent phenol in an attempt to investigate the role of this physicochemical factor in the irreversible inhibition of the enzyme estrone sulfatase (ES). The results of the study show that there is a strong correlation between the observed pKa and inhibitory activity. We postulate that the stability of the phenoxide ion, as indicated by the acid dissociation constant, is an important factor in the irreversible inhibition of this enzyme.

Original language	English
Pages (from-to)	899-902
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	11
Issue number	7
DOIs	https://doi.org/10.1016/S0960-894X(01)00087-7
Publication status	Published - 9 Apr 2001

Keywords

steroid sulfatase
analogs
Chemistry

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10.1016/S0960-894X(01)00087-7

http://dx.doi.org/doi:10.1016/S0960-894X(01)00087-7

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title = "Acid dissociation constant, a potential physicochemical factor in the inhibition of the enzyme estrone sulfatase (ES)",

abstract = "We report the initial results of the synthesis and biochemical evaluation of a series of aminosulfonate based compounds of phenol and the determination of the pKa of the parent phenol in an attempt to investigate the role of this physicochemical factor in the irreversible inhibition of the enzyme estrone sulfatase (ES). The results of the study show that there is a strong correlation between the observed pKa and inhibitory activity. We postulate that the stability of the phenoxide ion, as indicated by the acid dissociation constant, is an important factor in the irreversible inhibition of this enzyme.",

keywords = "steroid sulfatase, analogs, Chemistry",

author = "Sabbir Ahmed and Owen, \{Caroline P.\} and Karen James and Patel, \{Chirag K.\} and Mijal Patel",

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T1 - Acid dissociation constant, a potential physicochemical factor in the inhibition of the enzyme estrone sulfatase (ES)

AU - Ahmed, Sabbir

AU - Owen, Caroline P.

AU - James, Karen

AU - Patel, Chirag K.

AU - Patel, Mijal

PY - 2001/4/9

Y1 - 2001/4/9

N2 - We report the initial results of the synthesis and biochemical evaluation of a series of aminosulfonate based compounds of phenol and the determination of the pKa of the parent phenol in an attempt to investigate the role of this physicochemical factor in the irreversible inhibition of the enzyme estrone sulfatase (ES). The results of the study show that there is a strong correlation between the observed pKa and inhibitory activity. We postulate that the stability of the phenoxide ion, as indicated by the acid dissociation constant, is an important factor in the irreversible inhibition of this enzyme.

AB - We report the initial results of the synthesis and biochemical evaluation of a series of aminosulfonate based compounds of phenol and the determination of the pKa of the parent phenol in an attempt to investigate the role of this physicochemical factor in the irreversible inhibition of the enzyme estrone sulfatase (ES). The results of the study show that there is a strong correlation between the observed pKa and inhibitory activity. We postulate that the stability of the phenoxide ion, as indicated by the acid dissociation constant, is an important factor in the irreversible inhibition of this enzyme.

KW - steroid sulfatase

KW - analogs

KW - Chemistry

UR - http://www.ncbi.nlm.nih.gov/pubmed/11294387

U2 - 10.1016/S0960-894X(01)00087-7

DO - 10.1016/S0960-894X(01)00087-7

M3 - Article

C2 - 11294387

SN - 0960-894X

VL - 11

SP - 899

EP - 902

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 7

ER -

Acid dissociation constant, a potential physicochemical factor in the inhibition of the enzyme estrone sulfatase (ES)

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Keywords

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