Coulomb and Overlap Self-Similarities

A Comparative Selectivity Analysis of Structure-Function Relationships for Auxin-like Molecules

verfasst von

Noel Ferro, Ana Gallegos, Patrick Bultinck, Hans Jörg Jacobsen, Ramón Carbó-Dorca, Thomas Reinard

Abstract

Auxins are defined mainly by a set of physiological actions, but the structure-effect relationship still is based on chemical intuition. Currently a well-defined auxin molecular structure is not available. The existence of different auxin binding proteins and mechanisms of auxin action, the wide diversity of the auxin molecules, and the pleiotropic effects of auxin imply a completely different mechanism as described for the animal hormone concept. Here, we present a computational approach dealing with semiempirical optimizations of the auxin molecules themselves, which represent a number of about 250 different chemical structures. Our approach uses molecular quantum similarity measures and additional quantum variables for the analysis of auxin-like molecules. The finding of similarities in molecules by focusing basically on their electron structure results in new insights in the relationship of the different auxin groups. Additional statistical analysis allows the identification of relationships between similarity groups and their biological activity, respectively. It is postulated that the auxin-like molecular recognition depends more on specific molecular assembling states than on a specific ring system or side chain.

Organisationseinheit(en)

Institut für Pflanzengenetik

Externe Organisation(en)

University of Pinar del Río (UPR)
University of Girona
Universiteit Gent

Typ

Artikel

Journal

Journal of Chemical Information and Modeling

Band

46

Seiten

1751-1762

Anzahl der Seiten

12

ISSN

1549-9596

Publikationsdatum

01.07.2006

Publikationsstatus

Veröffentlicht

Peer-reviewed

Ja

ASJC Scopus Sachgebiete

Allgemeine Chemie, Allgemeine chemische Verfahrenstechnik, Angewandte Informatik, Bibliotheks- und Informationswissenschaften

Elektronische Version(en)

https://doi.org/10.1021/ci050491c (Zugang: Geschlossen)