Quantitative structure-activity relationship of rubiscolin analogues as δ opioid peptides using comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA)

Julio Caballero, Mario Saavedra, Michael Fernández, Fernando D. González-Nilo

Research output: Contribution to journalArticlepeer-review

33 Citations (Scopus)

Abstract

Three-dimensional quantitative structure-activity relationship (3D-QSAR) studies were carried out on a series of 38 rubiscolins as δ opioid peptides using comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA). Quantitative information on structure-activity relationships is provided for further rational development and direction of selective synthesis. All models were carried out over a training set including 30 peptides. The best CoMFA model included electrostatic and steric fields and had a moderate Q2 = 0.503. CoMSIA analysis surpassed the CoMFA results: the best CoMSIA model included only the hydrophobic field and had a Q2 = 0.661. In addition, this model predicted adequately the peptides contained in the test set. Our model identified that the potency of δ opioid activity of rubiscolin analogues essentially exhibited a significant relationship with local hydrophobic and hydrophilic characteristics of amino acids at positions 3, 4, 5, and 6.

Original languageEnglish
Pages (from-to)8101-8104
Number of pages4
JournalJournal of Agricultural and Food Chemistry
Volume55
Issue number20
DOIs
Publication statusPublished - 3 Oct 2007

Keywords

  • CoMFA
  • CoMSIA
  • Quantitative structure-activity relationships
  • Rubiscolin analogues

ASJC Scopus subject areas

  • Agricultural and Biological Sciences (miscellaneous)
  • Food Science
  • Chemistry (miscellaneous)
  • Agricultural and Biological Sciences(all)
  • Chemistry(all)

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