Nonpeptide Luteinizing Hormone-Releasing Hormone Antagonists Derived from Erythromycin A:  Design, Synthesis, and Biological Activity of Cladinose Replacement Analogues

2004 ◽  
Vol 47 (5) ◽  
pp. 1085-1097 ◽  
Author(s):  
John T. Randolph ◽  
Philip Waid ◽  
Charles Nichols ◽  
Daryl Sauer ◽  
Fortuna Haviv ◽  
...  
Keyword(s):  
Biological Activity ◽  
Luteinizing Hormone ◽  
Design Synthesis ◽  
Luteinizing Hormone Releasing Hormone ◽  
Releasing Hormone ◽  
Erythromycin A ◽  
Hormone Antagonists

Antiovulatory Potency and Conformation of an Antagonist of the Luteinizing Hormone-Releasing Hormone Having Six D-Amino Acids

1982 ◽  
Vol 37 (7) ◽  
pp. 872-876 ◽  
Author(s):  
Karl Folkers ◽  
Cyril Y. Bowers ◽  
Frank Momany ◽  
Klaus J. Friebel ◽  
Teresa Kubiak ◽  
...  
Keyword(s):  
Amino Acids ◽  
Luteinizing Hormone ◽  
Conformational Structure ◽  
Design Synthesis ◽  
Luteinizing Hormone Releasing Hormone ◽  
Energy Calculations ◽  
Releasing Hormone ◽  
Routes Of Administration ◽  
Antiovulatory Activity

Abstract [N-Ac-Thr 1 ,D-Phe 2,D-Trp 3,6]-LHRH was the model antagonist of LHRH, which was the basis for tho design, synthesis and bioassay of seven peptides having four, five and six D-amino acids, which resulted from three single, three double, and one triple introductions of D-amino acids in positions 4, 5 and 8 of the model. Only the analog with six D-amino acids, [N-Ac-Thr 1,D-Phe 2 ,D-Trp 3,D-Ser 4, D-Tyr 5 ,D-Trp 6 ,D-Arg 8]-LHRH, had antiovulatory activity which was higher than that of the model antagonist, i.e., 70% antiovulatory activity at 25 μg/rat compared with 50% activity at 50 μg/rat, respectively. Empirical energy calculations gave a conformational structure for [N-Ac-Thr 1,D-Phe 2,D-Trp 3, D-Ser 4,D-Tyr 5,D-Arg 6,D-Arg 8]-LHRH which is similar to that calculated for previous potent antagonists. These results are a basis of new designs of antagonists having D-sub-stituents in up to ten positions toward effective inhibitors of ovulation by the parenteral and oral routes of administration.

ChemInform Abstract: SYNTHESIS AND BIOLOGICAL ACTIVITY OF PEPTIDE ANTAGONISTS OF LULIBERIN (LUTEINIZING HORMONE-RELEASING HORMONE)

1980 ◽  
Vol 11 (16) ◽  
Author(s):  
G. W. MOERSCH ◽  
M. C. REBSTOCK ◽  
E. L. WITTLE ◽  
F. J. TINNEY ◽  
E. D. NICOLAIDES ◽  
...  
Keyword(s):  
Biological Activity ◽  
Luteinizing Hormone ◽  
Luteinizing Hormone Releasing Hormone ◽  
Releasing Hormone

Metabolic stability of long-acting luteinizing hormone-releasing hormone antagonists

Amino Acids ◽  
2012 ◽  
Vol 43 (4) ◽  
pp. 1557-1566 ◽  
Author(s):  
Jin-Feng Yao ◽  
Ning Zhou ◽  
Yu-Jian Lv ◽  
Ruifeng Zhang ◽  
Ke-Liang Liu ◽  
...  
Keyword(s):  
Luteinizing Hormone ◽  
Metabolic Stability ◽  
Luteinizing Hormone Releasing Hormone ◽  
Releasing Hormone ◽  
Hormone Antagonists ◽  
Long Acting
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