Abstract
As part of our studies on the design of more potent antagonists of the LH-RH (luteinizing hormone-releasing hormone) decapeptide, twelve new highly soluble D-Arg6-analogs have been synthesized. These peptides contain modifications in position 1 and are typified by the general formula (N-acetyl-X1, D-p-Cl-Phe2, D-Trp3, D-Arg6, D-Ala10) LH-RH. We have found that a lypophilic, aromatic substituent is required in position 1 in order to elicit antiovulatory activity at a dose as low as 3 μg. The larger the hydrophobic amino acid (X: p-Br-Phe, β-Nal-2) in position 1, the higher is the antiovulatory activity that can be attained. Analogs with non-aromatic or hydrophilic amino acids (X: Gly, Leu, Arg, His, Glu) in position 1 generally have much lower activities in this series of LH-RH antagonists.
| Original language | English |
|---|---|
| Pages (from-to) | 969-971 |
| Number of pages | 3 |
| Journal | Peptides |
| Volume | 3 |
| Issue number | 6 |
| DOIs | |
| State | Published - Jan 1 1982 |
| Externally published | Yes |
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Keywords
- Antiovulatory activity
- LH-RH antagonists
- Peptide synthesis
ASJC Scopus subject areas
- Biochemistry
- Endocrinology
- Physiology
- Cellular and Molecular Neuroscience
Cite this
Synthesis and biological activity of LH-RH antagonists modified in position 1. / Horvath, Aniko; Coy, David H.; Nekola, Mary V.; Coy, Esther J.; Schally, Andrew V; Teplan, Istvan.
In: Peptides, Vol. 3, No. 6, 01.01.1982, p. 969-971.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthesis and biological activity of LH-RH antagonists modified in position 1
AU - Horvath, Aniko
AU - Coy, David H.
AU - Nekola, Mary V.
AU - Coy, Esther J.
AU - Schally, Andrew V
AU - Teplan, Istvan
PY - 1982/1/1
Y1 - 1982/1/1
N2 - As part of our studies on the design of more potent antagonists of the LH-RH (luteinizing hormone-releasing hormone) decapeptide, twelve new highly soluble D-Arg6-analogs have been synthesized. These peptides contain modifications in position 1 and are typified by the general formula (N-acetyl-X1, D-p-Cl-Phe2, D-Trp3, D-Arg6, D-Ala10) LH-RH. We have found that a lypophilic, aromatic substituent is required in position 1 in order to elicit antiovulatory activity at a dose as low as 3 μg. The larger the hydrophobic amino acid (X: p-Br-Phe, β-Nal-2) in position 1, the higher is the antiovulatory activity that can be attained. Analogs with non-aromatic or hydrophilic amino acids (X: Gly, Leu, Arg, His, Glu) in position 1 generally have much lower activities in this series of LH-RH antagonists.
AB - As part of our studies on the design of more potent antagonists of the LH-RH (luteinizing hormone-releasing hormone) decapeptide, twelve new highly soluble D-Arg6-analogs have been synthesized. These peptides contain modifications in position 1 and are typified by the general formula (N-acetyl-X1, D-p-Cl-Phe2, D-Trp3, D-Arg6, D-Ala10) LH-RH. We have found that a lypophilic, aromatic substituent is required in position 1 in order to elicit antiovulatory activity at a dose as low as 3 μg. The larger the hydrophobic amino acid (X: p-Br-Phe, β-Nal-2) in position 1, the higher is the antiovulatory activity that can be attained. Analogs with non-aromatic or hydrophilic amino acids (X: Gly, Leu, Arg, His, Glu) in position 1 generally have much lower activities in this series of LH-RH antagonists.
KW - Antiovulatory activity
KW - LH-RH antagonists
KW - Peptide synthesis
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UR - http://www.scopus.com/inward/citedby.url?scp=0020424937&partnerID=8YFLogxK
U2 - 10.1016/0196-9781(82)90066-3
DO - 10.1016/0196-9781(82)90066-3
M3 - Article
C2 - 6762537
AN - SCOPUS:0020424937
VL - 3
SP - 969
EP - 971
JO - Peptides
JF - Peptides
SN - 0196-9781
IS - 6
ER -