ISSN:
1438-2199
Keywords:
Amino acids
;
LHRH antagonists
;
Antiovulatory activity
;
Histamine release
;
Solid phase peptide synthesis
Source:
Springer Online Journal Archives 1860-2000
Topics:
Medicine
Notes:
Summary The amino acid, D-2-naphthylalanine, has been used by many investigators as a substituent for position one of antagonists of LHRH. We have newly designed substituents for position one in which the carboxy groups of 2-naphthoic acid, 3-quinoline- and 2-quinoxaline-carboxylic acids are linked to the five amino acids, DAla, DThr, DNVal, DSer, and Gly. The substituents in positions 2–10 were DpClPhe2, DPal3, Ser4, PicLys5, DPicLys6, Leu7, ILys8, Pro9, DAlaNH2 10. Remarkably, DThr, acylated on the amino group by 3-quinolinecarboxylic acid or by 3-quinoxalinecarboxylic acid, and introduced into position one of a relatively potent antagonist, gave a new class of antagonists of LHRH, which released as little histamine as yet recorded, and yet possessed reasonable antiovulatory activity and greatly improved solubility. These structure-activity results advance the basic knowledge of understanding the structural features of such decapeptides which cause antiovulatory activity and histamine release.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00806954
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