Abstract
A series of C-terminally fluorinated analogs of luteinizing hormone-releasing hormone (LH-RH) was synthesized by a combination of solid-phase and classical techniques and found to have interesting properties when assayed for LH- and FSH-releasing activities over a prolonged period of time in immature male rats. One of the peptides, desGly10-LH-RH-2,2,2-trifluoroethylamide, was found to be about nine times more effective than LH-RH in releasing LH, or approximately twice as active as the corresponding alkylamide peptide, desGly10-LH-RH-ethylamide. However, desGly10-LH-RH-2,2,3,3,3-pentafluoropropylamide was only slightly more active than LH-RH and considerably less active than the corresponding propylamide analog. A family of peptides was also prepared containing D-alanine in position six of the chain in conjunction with the C-terminal modifications. D-Ala6,desGly10-LH-RH-2,2,2-trifluoroethylamide, surprisingly, gave patterns of gonadotropin release which were only as intense and virtually identical with those obtained with D-Ala6,desGly10-LH-RH-ethylamide which in turn releases about 20 times more LH than a similar dose of LH-RH. D-Ala6,desGly10-LH-RH-propylamide also gave almost identical patterns of gonadotropin release. D-Ala6,desGly10,LH-RH-2,2,3,3,3-pentafluoropropylamide was considerably less potent, being only five times more effective than LH-RH.
| Original language | English |
|---|---|
| Pages (from-to) | 1848-1851 |
| Number of pages | 4 |
| Journal | Biochemistry |
| Volume | 14 |
| Issue number | 9 |
| State | Published - Dec 1 1975 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Biochemistry
Cite this
Polyfluoroalkylamine derivatives of luteinizing hormone-releasing hormone. / Coy, David H.; Vilchez-Martinez, Jesus A.; Coy, Esther J.; Nishi, Nozumu; Arimura, Akira; Schally, Andrew V.
In: Biochemistry, Vol. 14, No. 9, 01.12.1975, p. 1848-1851.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Polyfluoroalkylamine derivatives of luteinizing hormone-releasing hormone
AU - Coy, David H.
AU - Vilchez-Martinez, Jesus A.
AU - Coy, Esther J.
AU - Nishi, Nozumu
AU - Arimura, Akira
AU - Schally, Andrew V
PY - 1975/12/1
Y1 - 1975/12/1
N2 - A series of C-terminally fluorinated analogs of luteinizing hormone-releasing hormone (LH-RH) was synthesized by a combination of solid-phase and classical techniques and found to have interesting properties when assayed for LH- and FSH-releasing activities over a prolonged period of time in immature male rats. One of the peptides, desGly10-LH-RH-2,2,2-trifluoroethylamide, was found to be about nine times more effective than LH-RH in releasing LH, or approximately twice as active as the corresponding alkylamide peptide, desGly10-LH-RH-ethylamide. However, desGly10-LH-RH-2,2,3,3,3-pentafluoropropylamide was only slightly more active than LH-RH and considerably less active than the corresponding propylamide analog. A family of peptides was also prepared containing D-alanine in position six of the chain in conjunction with the C-terminal modifications. D-Ala6,desGly10-LH-RH-2,2,2-trifluoroethylamide, surprisingly, gave patterns of gonadotropin release which were only as intense and virtually identical with those obtained with D-Ala6,desGly10-LH-RH-ethylamide which in turn releases about 20 times more LH than a similar dose of LH-RH. D-Ala6,desGly10-LH-RH-propylamide also gave almost identical patterns of gonadotropin release. D-Ala6,desGly10,LH-RH-2,2,3,3,3-pentafluoropropylamide was considerably less potent, being only five times more effective than LH-RH.
AB - A series of C-terminally fluorinated analogs of luteinizing hormone-releasing hormone (LH-RH) was synthesized by a combination of solid-phase and classical techniques and found to have interesting properties when assayed for LH- and FSH-releasing activities over a prolonged period of time in immature male rats. One of the peptides, desGly10-LH-RH-2,2,2-trifluoroethylamide, was found to be about nine times more effective than LH-RH in releasing LH, or approximately twice as active as the corresponding alkylamide peptide, desGly10-LH-RH-ethylamide. However, desGly10-LH-RH-2,2,3,3,3-pentafluoropropylamide was only slightly more active than LH-RH and considerably less active than the corresponding propylamide analog. A family of peptides was also prepared containing D-alanine in position six of the chain in conjunction with the C-terminal modifications. D-Ala6,desGly10-LH-RH-2,2,2-trifluoroethylamide, surprisingly, gave patterns of gonadotropin release which were only as intense and virtually identical with those obtained with D-Ala6,desGly10-LH-RH-ethylamide which in turn releases about 20 times more LH than a similar dose of LH-RH. D-Ala6,desGly10-LH-RH-propylamide also gave almost identical patterns of gonadotropin release. D-Ala6,desGly10,LH-RH-2,2,3,3,3-pentafluoropropylamide was considerably less potent, being only five times more effective than LH-RH.
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UR - http://www.scopus.com/inward/citedby.url?scp=0016757247&partnerID=8YFLogxK
M3 - Article
C2 - 1092343
AN - SCOPUS:0016757247
VL - 14
SP - 1848
EP - 1851
JO - Biochemistry
JF - Biochemistry
SN - 0006-2960
IS - 9
ER -