Theoretical proton affinities of α1 adrenoceptor ligands

Gemma K. Kinsella; Graeme W. Watson; Isabel Rozas

doi:10.1016/j.bmc.2005.10.007

Theoretical proton affinities of α1 adrenoceptor ligands

Gemma K. Kinsella, Graeme W. Watson, Isabel Rozas

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

Abstract

A systematic study has been performed of the proton affinity of a large family of agonists and antagonists of the α1-adrenoceptor at the B3LYP/6-31G* level of theory. After a conformational search, all the N atoms were considered as protonation sites and protonation energy values were determined. The inclusion of solvation by means of the Onsager model yielded stabilization in the proton affinity values obtained. In addition, a good correlation was found between the proton affinity values corresponding to the first protonation in gas phase of some of the compounds and their corresponding experimental affinity constants K_i for the α1A adrenergic receptor.

Original language	English
Pages (from-to)	1580-1587
Number of pages	8
Journal	Bioorganic and Medicinal Chemistry
Volume	14
Issue number	5
DOIs	https://doi.org/10.1016/j.bmc.2005.10.007
Publication status	Published - 1 Mar 2006
Externally published	Yes

Keywords

Adrenoceptor
Density Functional Theory
Proton affinity
α1

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10.1016/j.bmc.2005.10.007

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abstract = "A systematic study has been performed of the proton affinity of a large family of agonists and antagonists of the α1-adrenoceptor at the B3LYP/6-31G* level of theory. After a conformational search, all the N atoms were considered as protonation sites and protonation energy values were determined. The inclusion of solvation by means of the Onsager model yielded stabilization in the proton affinity values obtained. In addition, a good correlation was found between the proton affinity values corresponding to the first protonation in gas phase of some of the compounds and their corresponding experimental affinity constants Ki for the α1A adrenergic receptor.",

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AU - Watson, Graeme W.

AU - Rozas, Isabel

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N2 - A systematic study has been performed of the proton affinity of a large family of agonists and antagonists of the α1-adrenoceptor at the B3LYP/6-31G* level of theory. After a conformational search, all the N atoms were considered as protonation sites and protonation energy values were determined. The inclusion of solvation by means of the Onsager model yielded stabilization in the proton affinity values obtained. In addition, a good correlation was found between the proton affinity values corresponding to the first protonation in gas phase of some of the compounds and their corresponding experimental affinity constants Ki for the α1A adrenergic receptor.

AB - A systematic study has been performed of the proton affinity of a large family of agonists and antagonists of the α1-adrenoceptor at the B3LYP/6-31G* level of theory. After a conformational search, all the N atoms were considered as protonation sites and protonation energy values were determined. The inclusion of solvation by means of the Onsager model yielded stabilization in the proton affinity values obtained. In addition, a good correlation was found between the proton affinity values corresponding to the first protonation in gas phase of some of the compounds and their corresponding experimental affinity constants Ki for the α1A adrenergic receptor.

KW - Adrenoceptor

KW - Density Functional Theory

KW - Proton affinity

KW - α1

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VL - 14

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JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

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ER -

Theoretical proton affinities of α1 adrenoceptor ligands

Abstract

Keywords

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