Structure-activity relationships in C-terminal fragment analogs of pheromone biosynthesis activating neuropeptide in Helicoverpa zea.
A number of analogs of the C-terminal hexapeptide of PBAN were prepared and tested in vivo for pheromonotropic activity in Helicoverpa zea. Peptides prepared with longer-chain omega-aminocarboxylic acids (Tyr-6-aminocaproyl-Leu-NH2 and Tyr-7-aminoheptanoyl-NH2) were active at 25 and 2.5 nmol. Acetyl-Pro-Arg-Leu-NH2 was active at 1,000 pmol and represents a new minimum active fragment in the PBAN system. Addition of a bulky, hydrophobic tail (4-octylphenoxyacetyl) to the C-terminal hexapeptide of PBAN gave an analog that was active at all concentrations tested from 1 to 1,000 pmol when injected, had slight oral activity, but had no activity when applied topically. Glu-Tyr-Phe-Ser-Pro-Arg-Leu-NH2 was active at 1,000 but not at 100 pmol; at the latter dose it synergised the activity of 5 pmol of PBAN.
Kochansky
J P
JP
USDA, ARS, Insect Neurobiology and Hormone Laboratory, Beltsville, MD, USA.
Raina
A K
AK
Kempe
T G
TG
D000818:Animals; D009036:Moths; D009479:Neuropeptides / Q000737:chemistry / Q000378:metabolism*; D010446:Peptide Fragments / Q000737:chemistry / Q000378:metabolism; D012724:Sex Attractants / Q000737:chemistry / Q000378:metabolism*; D013329:Structure-Activity Relationship
D009479:Neuropeptides; D010446:Peptide Fragments; D012724:Sex Attractants; C079709:pheromone biosynthesis activating neuropeptide, Helicoverpa zea