ISSN:
1573-1561
Keywords:
Haloacetate
;
pheromone analog
;
catabolic protein
;
EAG
;
Plutella xylostella
;
Lepidoptera
;
Yponomeutidae
;
inhibition
Source:
Springer Online Journal Archives 1860-2000
Topics:
Biology
,
Chemistry and Pharmacology
Notes:
Abstract A series of mono-, di-, and trihalogenated acetate analogs of Zl 1–16: Ac were prepared and examined for electrophysiological activity in antennae of males of the diamondback moth,Plutella xylostella. In addition, two potential affinity labels, a diazoacetate (Dza) and a trifluoromethyl ketone (Tfp), were evaluated for EAG activity. The Z11–16∶Ac showed the highest activity in EAG assays, followed by the fluorinated acetates, but other halo-acetates were essentially inactive. The polar diazoacetate and the trifluoromethyl ketone were also very weak EAG stimulants. The effects of these analogs on the hydrolysis of [3H]Z11–16∶Ac to [3H]Z11–16∶OH by antennal esterases was also examined. The three fluorinated acetates showed the greatest activity as inhibitors in competition assays, with rank order F2Ac 〉 F3Ac 〉 FAc 〉 Ac 〉 Cl2Ac 〉 ClAc 〉 Dza 〉 Br2Ac 〉 BrAc 〉 Tfp 〉 I 〉 Cl3Ac 〉 Br3Ac 〉 OH. The relative polarities of the haloacetates, as determined by TLC mobility, are in the order mono- 〉 di- 〉 trihalo, but F, Cl, Br, and I all confer similar polarities within a substitution group. Thus, the steric size appears to be the predominant parameter affecting the interactions of the haloacetate analogs with both receptor and catabolic proteins inP. xylostella males.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF01018789
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