Characterization of the Molecular Lipophilicity of Mycolactones A/B and C, Infectious Factors of Mycobacterium ulcerans Agent of Buruli Ulcer
Kadjo François Kassi
Laboratoire de Thermodynamique et de Physico-Chimie du Milieu, UFR SFA, Université Nangui Abrogoua, 02 BP 801 Abidjan 02, République de Côte-d’Ivoire
Jean Missa Ehouman
Laboratoire de Thermodynamique et de Physico-Chimie du Milieu, UFR SFA, Université Nangui Abrogoua, 02 BP 801 Abidjan 02, République de Côte-d’Ivoire
Mamadou Guy-Richard Koné *
Laboratoire de Thermodynamique et de Physico-Chimie du Milieu, UFR SFA, Université Nangui Abrogoua, 02 BP 801 Abidjan 02, République de Côte-d’Ivoire and Groupe Ivoirien de Recherches en Modélisation des Maladies (GIR2M), République de Côte-d’Ivoire.
Lamoussa Ouattara
Laboratoire de Thermodynamique et de Physico-Chimie du Milieu, UFR SFA, Université Nangui Abrogoua, 02 BP 801 Abidjan 02, République de Côte-d’Ivoire.
Georges Stéphane Dembélé
Laboratoire de Thermodynamique et de Physico-Chimie du Milieu, UFR SFA, Université Nangui Abrogoua, 02 BP 801 Abidjan 02, République de Côte-d’Ivoire and Groupe Ivoirien de Recherches en Modélisation des Maladies (GIR2M), République de Côte-d’Ivoire.
Nahossé Ziao
Laboratoire de Thermodynamique et de Physico-Chimie du Milieu, UFR SFA, Université Nangui Abrogoua, 02 BP 801 Abidjan 02, République de Côte-d’Ivoire and Groupe Ivoirien de Recherches en Modélisation des Maladies (GIR2M), République de Côte-d’Ivoire.
*Author to whom correspondence should be addressed.
Abstract
The work was undertaken as part of the Buruli ulcer control program. It is particularly about the determination of the lipophilicity of mycolactones A/B and C, infectious factors of Mycobacterium ulcerans, the agent of Buruli ulcer. The REKKER method and some free software such as MOLINSPIRATION, ACD/ChemSketch and EPIWED were used for the determination of the lipophilicity of mycolactones A/B and C. Very high logP values were found and respectively ranged from 12.11 to 11.41 for mycolactone A/B and 11.69 to 11.58 for mycolactone C. These values obtained from this coefficient, show that mycolactones A/B and C are naturally lipophilic and that actually reflects their effective presence in the subcutaneous fat of the infected area. These results are very encouraging and promising. They are key factors for a better understanding of the biological activities of the two mycolactones and pave the way for the proposal of a mechanism to annihilate their destructive effects.
Keywords: Mycobacterium ulcerans, mycolactone, molecular lipophilia, partition coefficient