QSAR analysis on Spodoptera litura antifeedant activities for flavone derivatives

Pablo R. Duchowicz, Mohammad Goodarzi, Marco A. Ocsachoque, Gustavo P. Romanelli, Erlinda del V. Ortiz, Juan C. Autino, Daniel O. Bennardi, Diego M. Ruiz, Eduardo A. Castro

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

We establish useful models that relate experimentally measured biological activities of compounds to their molecular structure. The pED50 feeding inhibition on Spodoptera litura species exhibited by aurones, chromones, 3-coumarones and flavones is analyzed in this work through the hypothesis encompassed in the Quantitative Structure-Activity Relationships (QSAR) Theory. This constitutes a first necessary computationally based step during the design of more bio-friendly repellents that could lead to insights for improving the insecticidal activities of the investigated compounds. After optimizing the molecular structure of each furane and pyrane benzoderivative with the semiempirical molecular orbitals method PM3, more than a thousand of constitutional, topological, geometrical and electronic descriptors are calculated and multiparametric linear regression models are established on the antifeedant potencies. The feature selection method employed in this study is the Replacement Method, which has proven to be successful in previous analyzes. We establish the QSAR both for the complete molecular set of compounds and also for each chemical class, so that acceptably describing the variation of the inhibitory activities from the knowledge of their structure and thus achieving useful predictive results. The main interest of developing trustful QSAR models is that these enable the prediction of compounds having no experimentally measured activities for any reason. Therefore, the structure-activity relationships are further employed for investigating the antifeedant activity on previously synthesized 2-,7-substituted benzopyranes, which do not pose any measured values on the biological expression. One of them, 2-(α-naphtyl)-4H-1-benzopyran-4-one, results in a promising structure to be experimentally analyzed as it has predicted pED50 = 1.162.

Original languageEnglish (US)
Pages (from-to)277-285
Number of pages9
JournalScience of the Total Environment
Volume408
Issue number2
DOIs
StatePublished - Dec 20 2009

Fingerprint

flavone
antifeedant
Derivatives
Molecular structure
Benzofurans
Chromones
Flavones
Molecular orbitals
Bioactivity
Linear regression
Feature extraction
replacement
analysis
structure-activity relationship
prediction

Keywords

  • Antifeedant activity
  • Flavone derivatives
  • pED
  • QSAR Theory
  • Replacement Method

ASJC Scopus subject areas

  • Environmental Engineering
  • Environmental Chemistry
  • Waste Management and Disposal
  • Pollution

Cite this

Duchowicz, P. R., Goodarzi, M., Ocsachoque, M. A., Romanelli, G. P., Ortiz, E. D. V., Autino, J. C., ... Castro, E. A. (2009). QSAR analysis on Spodoptera litura antifeedant activities for flavone derivatives. Science of the Total Environment, 408(2), 277-285. https://doi.org/10.1016/j.scitotenv.2009.09.041

QSAR analysis on Spodoptera litura antifeedant activities for flavone derivatives. / Duchowicz, Pablo R.; Goodarzi, Mohammad; Ocsachoque, Marco A.; Romanelli, Gustavo P.; Ortiz, Erlinda del V.; Autino, Juan C.; Bennardi, Daniel O.; Ruiz, Diego M.; Castro, Eduardo A.

In: Science of the Total Environment, Vol. 408, No. 2, 20.12.2009, p. 277-285.

Research output: Contribution to journalArticle

Duchowicz, PR, Goodarzi, M, Ocsachoque, MA, Romanelli, GP, Ortiz, EDV, Autino, JC, Bennardi, DO, Ruiz, DM & Castro, EA 2009, 'QSAR analysis on Spodoptera litura antifeedant activities for flavone derivatives', Science of the Total Environment, vol. 408, no. 2, pp. 277-285. https://doi.org/10.1016/j.scitotenv.2009.09.041
Duchowicz, Pablo R. ; Goodarzi, Mohammad ; Ocsachoque, Marco A. ; Romanelli, Gustavo P. ; Ortiz, Erlinda del V. ; Autino, Juan C. ; Bennardi, Daniel O. ; Ruiz, Diego M. ; Castro, Eduardo A. / QSAR analysis on Spodoptera litura antifeedant activities for flavone derivatives. In: Science of the Total Environment. 2009 ; Vol. 408, No. 2. pp. 277-285.
@article{d32dc03d16c34639a585a1b23db437de,
title = "QSAR analysis on Spodoptera litura antifeedant activities for flavone derivatives",
abstract = "We establish useful models that relate experimentally measured biological activities of compounds to their molecular structure. The pED50 feeding inhibition on Spodoptera litura species exhibited by aurones, chromones, 3-coumarones and flavones is analyzed in this work through the hypothesis encompassed in the Quantitative Structure-Activity Relationships (QSAR) Theory. This constitutes a first necessary computationally based step during the design of more bio-friendly repellents that could lead to insights for improving the insecticidal activities of the investigated compounds. After optimizing the molecular structure of each furane and pyrane benzoderivative with the semiempirical molecular orbitals method PM3, more than a thousand of constitutional, topological, geometrical and electronic descriptors are calculated and multiparametric linear regression models are established on the antifeedant potencies. The feature selection method employed in this study is the Replacement Method, which has proven to be successful in previous analyzes. We establish the QSAR both for the complete molecular set of compounds and also for each chemical class, so that acceptably describing the variation of the inhibitory activities from the knowledge of their structure and thus achieving useful predictive results. The main interest of developing trustful QSAR models is that these enable the prediction of compounds having no experimentally measured activities for any reason. Therefore, the structure-activity relationships are further employed for investigating the antifeedant activity on previously synthesized 2-,7-substituted benzopyranes, which do not pose any measured values on the biological expression. One of them, 2-(α-naphtyl)-4H-1-benzopyran-4-one, results in a promising structure to be experimentally analyzed as it has predicted pED50 = 1.162.",
keywords = "Antifeedant activity, Flavone derivatives, pED, QSAR Theory, Replacement Method",
author = "Duchowicz, {Pablo R.} and Mohammad Goodarzi and Ocsachoque, {Marco A.} and Romanelli, {Gustavo P.} and Ortiz, {Erlinda del V.} and Autino, {Juan C.} and Bennardi, {Daniel O.} and Ruiz, {Diego M.} and Castro, {Eduardo A.}",
year = "2009",
month = "12",
day = "20",
doi = "10.1016/j.scitotenv.2009.09.041",
language = "English (US)",
volume = "408",
pages = "277--285",
journal = "Science of the Total Environment",
issn = "0048-9697",
publisher = "Elsevier",
number = "2",

}

TY - JOUR

T1 - QSAR analysis on Spodoptera litura antifeedant activities for flavone derivatives

AU - Duchowicz, Pablo R.

AU - Goodarzi, Mohammad

AU - Ocsachoque, Marco A.

AU - Romanelli, Gustavo P.

AU - Ortiz, Erlinda del V.

AU - Autino, Juan C.

AU - Bennardi, Daniel O.

AU - Ruiz, Diego M.

AU - Castro, Eduardo A.

PY - 2009/12/20

Y1 - 2009/12/20

N2 - We establish useful models that relate experimentally measured biological activities of compounds to their molecular structure. The pED50 feeding inhibition on Spodoptera litura species exhibited by aurones, chromones, 3-coumarones and flavones is analyzed in this work through the hypothesis encompassed in the Quantitative Structure-Activity Relationships (QSAR) Theory. This constitutes a first necessary computationally based step during the design of more bio-friendly repellents that could lead to insights for improving the insecticidal activities of the investigated compounds. After optimizing the molecular structure of each furane and pyrane benzoderivative with the semiempirical molecular orbitals method PM3, more than a thousand of constitutional, topological, geometrical and electronic descriptors are calculated and multiparametric linear regression models are established on the antifeedant potencies. The feature selection method employed in this study is the Replacement Method, which has proven to be successful in previous analyzes. We establish the QSAR both for the complete molecular set of compounds and also for each chemical class, so that acceptably describing the variation of the inhibitory activities from the knowledge of their structure and thus achieving useful predictive results. The main interest of developing trustful QSAR models is that these enable the prediction of compounds having no experimentally measured activities for any reason. Therefore, the structure-activity relationships are further employed for investigating the antifeedant activity on previously synthesized 2-,7-substituted benzopyranes, which do not pose any measured values on the biological expression. One of them, 2-(α-naphtyl)-4H-1-benzopyran-4-one, results in a promising structure to be experimentally analyzed as it has predicted pED50 = 1.162.

AB - We establish useful models that relate experimentally measured biological activities of compounds to their molecular structure. The pED50 feeding inhibition on Spodoptera litura species exhibited by aurones, chromones, 3-coumarones and flavones is analyzed in this work through the hypothesis encompassed in the Quantitative Structure-Activity Relationships (QSAR) Theory. This constitutes a first necessary computationally based step during the design of more bio-friendly repellents that could lead to insights for improving the insecticidal activities of the investigated compounds. After optimizing the molecular structure of each furane and pyrane benzoderivative with the semiempirical molecular orbitals method PM3, more than a thousand of constitutional, topological, geometrical and electronic descriptors are calculated and multiparametric linear regression models are established on the antifeedant potencies. The feature selection method employed in this study is the Replacement Method, which has proven to be successful in previous analyzes. We establish the QSAR both for the complete molecular set of compounds and also for each chemical class, so that acceptably describing the variation of the inhibitory activities from the knowledge of their structure and thus achieving useful predictive results. The main interest of developing trustful QSAR models is that these enable the prediction of compounds having no experimentally measured activities for any reason. Therefore, the structure-activity relationships are further employed for investigating the antifeedant activity on previously synthesized 2-,7-substituted benzopyranes, which do not pose any measured values on the biological expression. One of them, 2-(α-naphtyl)-4H-1-benzopyran-4-one, results in a promising structure to be experimentally analyzed as it has predicted pED50 = 1.162.

KW - Antifeedant activity

KW - Flavone derivatives

KW - pED

KW - QSAR Theory

KW - Replacement Method

UR - http://www.scopus.com/inward/record.url?scp=71749103679&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=71749103679&partnerID=8YFLogxK

U2 - 10.1016/j.scitotenv.2009.09.041

DO - 10.1016/j.scitotenv.2009.09.041

M3 - Article

VL - 408

SP - 277

EP - 285

JO - Science of the Total Environment

JF - Science of the Total Environment

SN - 0048-9697

IS - 2

ER -