Abstract
The fluorescein-labeled melanotropin [N(α)-chlorotriazinylaminofluorescein-Ser1,Nle4,D-Phe7]-α-MSH, was prepared by solid-phase techniques of peptide synthesis. The biological actions of this analogue were determined in several melanocyte bioassays and were compared with the parent peptide [Nle4,D-Phe7]-α-MSH and the native hormone α-MSH. The fluorescein compound was a superpotent agonist with ~10 times more activity than α-MSH in both the frog and the lizard skin bioassays. Murine S91 melanoma cells assayed in vitro (tyrosinase bioassay) were as responsive to the fluorescein analogue as to α-MSH. The analogue exhibited ultraprolonged biological activity and the biological activities were unaffected by treatment of the analogue with α-chymotrypsin. The fluorescein-labeled melanotropin should prove useful for melanotropin receptor characterization.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 237-240 |
| Number of pages | 4 |
| Journal | Journal of Pharmaceutical Sciences |
| Volume | 74 |
| Issue number | 3 |
| DOIs | |
| State | Published - 1985 |
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ASJC Scopus subject areas
- Drug Discovery
- Organic Chemistry
- Chemistry(all)
- Molecular Medicine
- Pharmacology
- Pharmaceutical Science
Cite this
Synthesis and biological evaluation of the superagonist [N(α)-chlorotriazinylaminofluorescein-Ser1,Nle4,D-Phe7]-α-MSH. / Chaturvedi, D. N.; Hruby, Victor J; Castrucci De, A. M L; Kreutzfeld, K. L.; Hadley, M. E.
In: Journal of Pharmaceutical Sciences, Vol. 74, No. 3, 1985, p. 237-240.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthesis and biological evaluation of the superagonist [N(α)-chlorotriazinylaminofluorescein-Ser1,Nle4,D-Phe7]-α-MSH
AU - Chaturvedi, D. N.
AU - Hruby, Victor J
AU - Castrucci De, A. M L
AU - Kreutzfeld, K. L.
AU - Hadley, M. E.
PY - 1985
Y1 - 1985
N2 - The fluorescein-labeled melanotropin [N(α)-chlorotriazinylaminofluorescein-Ser1,Nle4,D-Phe7]-α-MSH, was prepared by solid-phase techniques of peptide synthesis. The biological actions of this analogue were determined in several melanocyte bioassays and were compared with the parent peptide [Nle4,D-Phe7]-α-MSH and the native hormone α-MSH. The fluorescein compound was a superpotent agonist with ~10 times more activity than α-MSH in both the frog and the lizard skin bioassays. Murine S91 melanoma cells assayed in vitro (tyrosinase bioassay) were as responsive to the fluorescein analogue as to α-MSH. The analogue exhibited ultraprolonged biological activity and the biological activities were unaffected by treatment of the analogue with α-chymotrypsin. The fluorescein-labeled melanotropin should prove useful for melanotropin receptor characterization.
AB - The fluorescein-labeled melanotropin [N(α)-chlorotriazinylaminofluorescein-Ser1,Nle4,D-Phe7]-α-MSH, was prepared by solid-phase techniques of peptide synthesis. The biological actions of this analogue were determined in several melanocyte bioassays and were compared with the parent peptide [Nle4,D-Phe7]-α-MSH and the native hormone α-MSH. The fluorescein compound was a superpotent agonist with ~10 times more activity than α-MSH in both the frog and the lizard skin bioassays. Murine S91 melanoma cells assayed in vitro (tyrosinase bioassay) were as responsive to the fluorescein analogue as to α-MSH. The analogue exhibited ultraprolonged biological activity and the biological activities were unaffected by treatment of the analogue with α-chymotrypsin. The fluorescein-labeled melanotropin should prove useful for melanotropin receptor characterization.
UR - http://www.scopus.com/inward/record.url?scp=0021955419&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0021955419&partnerID=8YFLogxK
U2 - 10.1002/jps.2600740303
DO - 10.1002/jps.2600740303
M3 - Article
C2 - 2989482
AN - SCOPUS:0021955419
VL - 74
SP - 237
EP - 240
JO - Journal of Pharmaceutical Sciences
JF - Journal of Pharmaceutical Sciences
SN - 0022-3549
IS - 3
ER -