Conformational dependence of serotonin theoretical pKa prediction

Jaturong Pratuangdejkul; Wichit Nosoongnoen; Georges Alexandre Guérin; Sylvan Loric; Marc Conti; Jean Marie Launay; Philippe Manivet

doi:10.1016/j.cplett.2006.01.035

Conformational dependence of serotonin theoretical pK_a prediction

Jaturong Pratuangdejkul
, Wichit Nosoongnoen
, Georges Alexandre Guérin
, Sylvan Loric
, Marc Conti
, Jean Marie Launay
, Philippe Manivet

Department of Microbiology

E.A. 3621
Hôpital Lariboisière
BioQuanta
Hôpital Henri Mondor
Hôpital Bicêtre

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

62 Citations (Scopus)

Abstract

In the present work we used quantum mechanics calculations to predict the two pK_a's of 5-hydrotryptamine (5-HT). Proton dissociation reaction succeeded to predict the experimental pK_a1 corresponding to ionization of the protonated amine group but failed for pK_a2 corresponding to ionization of the 5-hydroxyl group. For pK_a2, a cluster-continuum model including three water molecules in the first hydration shell around 5-hydroxyl and 5-hydroxide groups enabled us to reproduce the experimental pK_a2 value. Furthermore, we demonstrated that specific conformations of acid/base pair of 5-HT is critical to predict accurately the experimental pK_a's of the flexible 5-HT molecule.

Original language	English
Pages (from-to)	538-544
Number of pages	7
Journal	Chemical Physics Letters
Volume	420
Issue number	4-6
DOIs	https://doi.org/10.1016/j.cplett.2006.01.035
Publication status	Published - 21 Mar 2006

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10.1016/j.cplett.2006.01.035

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title = "Conformational dependence of serotonin theoretical pKa prediction",

abstract = "In the present work we used quantum mechanics calculations to predict the two pKa's of 5-hydrotryptamine (5-HT). Proton dissociation reaction succeeded to predict the experimental pKa1 corresponding to ionization of the protonated amine group but failed for pKa2 corresponding to ionization of the 5-hydroxyl group. For pKa2, a cluster-continuum model including three water molecules in the first hydration shell around 5-hydroxyl and 5-hydroxide groups enabled us to reproduce the experimental pKa2 value. Furthermore, we demonstrated that specific conformations of acid/base pair of 5-HT is critical to predict accurately the experimental pKa's of the flexible 5-HT molecule.",

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T1 - Conformational dependence of serotonin theoretical pKa prediction

AU - Pratuangdejkul, Jaturong

AU - Nosoongnoen, Wichit

AU - Guérin, Georges Alexandre

AU - Loric, Sylvan

AU - Conti, Marc

AU - Launay, Jean Marie

AU - Manivet, Philippe

PY - 2006/3/21

Y1 - 2006/3/21

N2 - In the present work we used quantum mechanics calculations to predict the two pKa's of 5-hydrotryptamine (5-HT). Proton dissociation reaction succeeded to predict the experimental pKa1 corresponding to ionization of the protonated amine group but failed for pKa2 corresponding to ionization of the 5-hydroxyl group. For pKa2, a cluster-continuum model including three water molecules in the first hydration shell around 5-hydroxyl and 5-hydroxide groups enabled us to reproduce the experimental pKa2 value. Furthermore, we demonstrated that specific conformations of acid/base pair of 5-HT is critical to predict accurately the experimental pKa's of the flexible 5-HT molecule.

AB - In the present work we used quantum mechanics calculations to predict the two pKa's of 5-hydrotryptamine (5-HT). Proton dissociation reaction succeeded to predict the experimental pKa1 corresponding to ionization of the protonated amine group but failed for pKa2 corresponding to ionization of the 5-hydroxyl group. For pKa2, a cluster-continuum model including three water molecules in the first hydration shell around 5-hydroxyl and 5-hydroxide groups enabled us to reproduce the experimental pKa2 value. Furthermore, we demonstrated that specific conformations of acid/base pair of 5-HT is critical to predict accurately the experimental pKa's of the flexible 5-HT molecule.

UR - https://www.scopus.com/pages/publications/33644686042

U2 - 10.1016/j.cplett.2006.01.035

DO - 10.1016/j.cplett.2006.01.035

M3 - Article

AN - SCOPUS:33644686042

SN - 0009-2614

VL - 420

SP - 538

EP - 544

JO - Chemical Physics Letters

JF - Chemical Physics Letters

IS - 4-6

ER -

Conformational dependence of serotonin theoretical pK_a prediction

Abstract

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