Mimetic insect kinin analogs for insect control
AssigneeThe United States of America as represented by the Secretary of Agriculture
InventorsRonald J. Nachman, Grant Mark Holman
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Abstract
Novel pseudopeptide analogs of the insect kinin neuropeptide family which possess biological activity mimicking that of the naturally occurring neuropeptides are disclosed. By substituting a sterically hindered amino acid which is compatible with a turn conformation, for the Xaa.sup.2 amino acid of the insect kinin C-terminal pentapeptide (i.e. Ser, Pro, or Ala), analogs are produced which exhibit resistance to degradation by angiotensin converting enzyme (ACE) while still retaining biological activity. The analogs may be used for insect control by disrupting the diuretic and/or myotropic activity in insects.
Claims18
A compound of the formula
- R--X.sub.1 --X.sub.2 --Trp--Gly--NH.sub.2
- wherein:
- (a) X.sub.1 is selected from the group consisting of Asn, His, Phe, Ser and Tyr;
- (b) X.sub.2 is an amino acid having the structure:
- ##STR2## where R.sub.1 and R.sub.2 are hydrocarbon groups independently selected from the group consisting of -alkyl and -alkylphenyl, where said alkyl comprises optionally halogenated alkyl hydrocarbon groups which may be branched or straight chain, and said phenyl may be optionally substituted with one or more halogens and/or other optionally halogenated alkyl hydrocarbon groups;
- and
- (c) R is selected from the group consisting of:
- (i) hydrocinnamic acid,
- (ii) Cb--(CH.sub.2).sub.n --C(O)-- where:
- (i) Cb is a carborane, and
- (ii) n is 1, 2, or 3;
- (iii) H--X.sub.3 --Phe--, and
- (iv) (R.sub.3).sub.y --L.sub.m --X.sub.3 --Phe--where:
- (i) X.sub.3 is selected from the group consisting of a bond, an amino acid, and a polypeptide, said polypeptide comprising all or a portion of an insect kinin neuropeptide which is naturally contiguous to the C terminal pentapeptide --Phe--X.sub.1 --X.sub.4 --Trp--Gly--NH.sub.2, where X.sub.4 is Ala, Ser or Pro;
- (ii) R.sub.3 is selected from the group consisting of hydrophobic aromatic amines, hydrophobic aromatic acids, and pyroglutamic acid, said hydrophobic aromatic amines and said hydrophobic aromatic acids being effective to render said compound hydrophobic or amphiphilic or both;
- (iii) y is 1 or 2;
- (iv) m is 0 or 1;
- and
- (v) L is a spacer which, when R.sub.3 is a hydrophobic aromatic acid, said spacer is selected from the group consisting of non-polar hydrocarbons having a free amino group and free carboxyl group, and uncharged .alpha.-amino acids, or when R.sub.3 is a hydrophobic aromatic amine, said spacer is a diacid.
Dependencies are inferred from the claim text.