TY - JOUR

T1 - Structure-activity analysis on ecdysteroids: A structural and quantum chemical approach based on two biological systems

AU - Reinard, Thomas

AU - Ferro, Noel

N1 - Funding information: The authors are thankful to: DAAD for the financial support of the academic exchange. Italian Episcopal Conference and for the financial the ground support of the computer projects to the Laboratory of Computational Biology of Plant at Pinar del Río University.

PY - 2006

Y1 - 2006

N2 - Besides their central role in the development of insects, ecdysteroids are widely found in other organisms as well. It is well established that ecdysteroids occur in various molecular forms as well as are valuable targets to identify structural requirements for the development of insecticides in favour of plant protection. Therefore, very advanced 3D- and 4D-QSAR have been applied to ecdysteroids. Our work, at present, is carried out by the arrangement use of quantum chemistry at semi-empirical level, molecular similarity measures and bio-statistical analysis. This strategy proficient gets into details of structure-activity of different ecdysteroid analogs. On the other hand, due to the analysis of a hormonal factor as multicellular scheme, in addition to the EC50 analysis in Drosophila melanogaster, the Calliphora test was taking into account. The influence of functional groups and different molecular properties (a total of 778) were cause-effect related to a set of 96 analogs for both tests. Additional theoretical analysis of hydrogen bonds and molecular orbitals were done as well. The work let to the achievement of a more realistic assessment in relation to the structure-activity, and it confirm that, geometrically, not all functional groups are important for bioactivity, only those whose contributions are involved in a quasi band of outer molecular orbitals. The discrimination of the most active molecules was done better by the use of the autosimilarity diagonal together with some other quantum and geometric variables. ?? 2005 Elsevier B.V. All rights reserved.

AB - Besides their central role in the development of insects, ecdysteroids are widely found in other organisms as well. It is well established that ecdysteroids occur in various molecular forms as well as are valuable targets to identify structural requirements for the development of insecticides in favour of plant protection. Therefore, very advanced 3D- and 4D-QSAR have been applied to ecdysteroids. Our work, at present, is carried out by the arrangement use of quantum chemistry at semi-empirical level, molecular similarity measures and bio-statistical analysis. This strategy proficient gets into details of structure-activity of different ecdysteroid analogs. On the other hand, due to the analysis of a hormonal factor as multicellular scheme, in addition to the EC50 analysis in Drosophila melanogaster, the Calliphora test was taking into account. The influence of functional groups and different molecular properties (a total of 778) were cause-effect related to a set of 96 analogs for both tests. Additional theoretical analysis of hydrogen bonds and molecular orbitals were done as well. The work let to the achievement of a more realistic assessment in relation to the structure-activity, and it confirm that, geometrically, not all functional groups are important for bioactivity, only those whose contributions are involved in a quasi band of outer molecular orbitals. The discrimination of the most active molecules was done better by the use of the autosimilarity diagonal together with some other quantum and geometric variables. ?? 2005 Elsevier B.V. All rights reserved.

U2 - 10.1016/j.theochem.2005.10.027

DO - 10.1016/j.theochem.2005.10.027

M3 - Article

VL - 2006

JO - Journal of Molecular Structure: THEOCHEM

JF - Journal of Molecular Structure: THEOCHEM

SN - 0166-1280

IS - 758:2-3

ER -