TY - JOUR
T1 - Synthesis and biological actions of highly potent and prolonged acting biotin-labeled melanotropins
AU - Chaturvedi, Dhirendra N.
AU - Knittel, James J.
AU - Hruby, Victor J.
AU - Castrucci, Ana Maria de L.
AU - Hadley, Mac E.
PY - 1984/3
Y1 - 1984/3
N2 - Biocytin derivatives of a superpotent analogue of α-melanotropin, [Nle4,D-Phe7]-α-MSH, were prepared. [Naα-Bct-Ser1,Nle4,D-Phe7]-α-MSH and [12-Bct-Nα-dodecanoyl-Ser1,Nle4,D-Phe7]-α-MSH were synthesized by solid-phase techniques, and the coupling of biotin and 12-aminododecanoic acid was achieved through their succinimido esters. These melanotropins possessed almost identical actions to [Nle4,D-Phe7]-α-MSH as determined by several melanocyte bioassays. Both biocytin derivatives were highly potent agonists and exhibited prolonged biological activity as determined in the frog and lizard skin bioassays. Both biotinylated peptides were at least equipotent to α-MSH in stimulating Cloudman S91 mouse melanoma tyrosinase activity. The analogues were resistant to inactivation by α-chymotrypsin.
AB - Biocytin derivatives of a superpotent analogue of α-melanotropin, [Nle4,D-Phe7]-α-MSH, were prepared. [Naα-Bct-Ser1,Nle4,D-Phe7]-α-MSH and [12-Bct-Nα-dodecanoyl-Ser1,Nle4,D-Phe7]-α-MSH were synthesized by solid-phase techniques, and the coupling of biotin and 12-aminododecanoic acid was achieved through their succinimido esters. These melanotropins possessed almost identical actions to [Nle4,D-Phe7]-α-MSH as determined by several melanocyte bioassays. Both biocytin derivatives were highly potent agonists and exhibited prolonged biological activity as determined in the frog and lizard skin bioassays. Both biotinylated peptides were at least equipotent to α-MSH in stimulating Cloudman S91 mouse melanoma tyrosinase activity. The analogues were resistant to inactivation by α-chymotrypsin.
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U2 - 10.1021/jm00377a005
DO - 10.1021/jm00377a005
M3 - Article
C2 - 6436488
AN - SCOPUS:0021682830
SN - 0022-2623
VL - 27
SP - 1406
EP - 1410
JO - Journal of Medicinal Chemistry
JF - Journal of Medicinal Chemistry
IS - 11
ER -