Document Detail

Prolonged pheromonotropic activity of pseudopeptide mimics of insect pyrokinin neuropeptides after topical application or injection into a moth.
MedLine Citation:
PMID:  9652976     Owner:  NLM     Status:  MEDLINE    
Amphiphilic pseudopeptide analogs of Phe-Thr-Pro-Arg-Leu-NH2, representing the active C-terminal core pentapeptide of the pyrokinin class of insect neuropeptides, were synthesized by replacement of phenylalanine with hydrocinnamic acid (Hca-Thr-Pro-Arg-Leu-NH2), or addition of 1-pyrenebutyric acid (Pba-Phe-Thr-Pro-Arg-Leu-NH2) or 9-fluoreneacetic acid (Fla-Phe-Thr-Pro-Arg-Leu-NH2). The pseudopeptides were found to stimulate sex pheromone biosynthesis when injected into females of the moth Heliothis virescens. Optimal pheromonotropic responses were obtained by injection of 0.25 pmol of Hca-Thr-Pro-Arg-Leu-NH2, 2.5 pmol of Pba-Thr-Pro-Arg-Leu-NH2 and 0.5 pmol of Fla-Thr-Pro-Arg-Leu-NH2. Topical application of each of the pseudopeptides in water to the cuticle of moths stimulated significant production of pheromone at a dose of 50 pmol with optimal stimulation occurring when 500 pmol were applied. The parent peptide, Phe-Thr-Pro-Arg-Leu-NH2, failed to stimulate significant production of pheromone when applied topically at a dose as high as 2000 pmol. Temporal studies indicated that Hca-Thr-Pro-Arg-Leu-NH2 stimulated significant production of pheromone for only 4 h after application where as continuous pheromone production for 18 h was observed when either Pba-Phe-Thr-Pro-Arg-Leu-NH2 or Fla-Phe-Thr-Pro-Arg-Leu-NH2 were applied to the abdomen. The results show that modification of the C-terminal active core of the insect pyrokinins, by addition of hydrophobic moieties, can result in production of pseudopeptides which effectively penetrate the insect cuticle and have prolonged physiological effects making them favorable candidates for use in development of alternative strategies for pest insect control.
P E Teal; R J Nachman
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Regulatory peptides     Volume:  72     ISSN:  0167-0115     ISO Abbreviation:  Regul. Pept.     Publication Date:  1997 Oct 
Date Detail:
Created Date:  1998-06-30     Completed Date:  1998-06-30     Revised Date:  2003-11-14    
Medline Journal Info:
Nlm Unique ID:  8100479     Medline TA:  Regul Pept     Country:  NETHERLANDS    
Other Details:
Languages:  eng     Pagination:  161-7     Citation Subset:  IM    
Center for Medical, Agricultural and Veterinary Entomology, USDA, ARS, Gainesville, FL 32604, USA.
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MeSH Terms
Acetic Acids / chemistry
Administration, Topical
Fluorenes / chemistry
Indicators and Reagents / chemistry
Insect Control / methods
Insect Hormones / chemical synthesis*,  pharmacology*,  physiology
Moths / metabolism*
Neuropeptides / chemical synthesis*,  pharmacology*,  physiology
Oligopeptides / chemical synthesis*,  pharmacology
Phenylpropionates / chemistry
Pheromones / biosynthesis*
Pyrenes / chemistry
Reg. No./Substance:
0/Acetic Acids; 0/Fluorenes; 0/Indicators and Reagents; 0/Insect Hormones; 0/Neuropeptides; 0/Oligopeptides; 0/Phenylpropionates; 0/Pheromones; 0/Pyrenes; 0/pyrokinin; 3443-45-6/1-pyrenebutyrate; 501-52-0/3-phenylpropionic acid; 6284-80-6/9-fluoreneacetic acid

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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