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75921-69-6

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75921-69-6 Usage

Features

Afamelanotide is a potent, linear synthetic analog of the naturally occurring peptide hormone α-melanocyte-stimulating hormone (α-MSH).Modified to have a stronger binding affinity to melanocortin- 1 receptor (MC1R) and a smaller disassociation constant, afamelanotide has a longer half-life and subsequently exerts longer pharmacologic activity than its parent hormone.

Uses

[Nle4, D-Phe7]-α-Melanocyte Stimulating Hormone trifluoroacetate salt has been used to detect its effect on O2 consumption and CO2 production in C57BL/6 mice.1It is also used to determine its effect on leptin secretion in the primary cultures of differentiated adipocytes.

General Description

[Nle4, D-Phe7]-α-melanocyte stimulating hormone is a potent analogue of α;-melanocyte-stimulating hormone (α -MSH). αMSH is a tridecapeptide, mostly produced by the cells in the brain, pituitary and in circulation.

Biochem/physiol Actions

[Nle4, D-Phe7]-α-melanocyte stimulating hormone is 100 times more potent than α-MSH in stimulating melanoma tyrosinase, which is a rate limiting enzyme in melanin biosynthesis and is 26 times as potent as α-MSH in S91adenylate cyclase assay. α –MSH has an essential role to play in melanin production in animals. It also regulates development of several skin diseases, including cutaneous inflammation and hyper-proliferative skin diseases.

Check Digit Verification of cas no

The CAS Registry Mumber 75921-69-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,5,9,2 and 1 respectively; the second part has 2 digits, 6 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 75921-69:
(7*7)+(6*5)+(5*9)+(4*2)+(3*1)+(2*6)+(1*9)=156
156 % 10 = 6
So 75921-69-6 is a valid CAS Registry Number.
InChI:InChI=1/C78H111N21O19/c1-5-6-19-52(91-75(116)61(41-101)97-72(113)57(34-46-24-26-49(103)27-25-46)94-74(115)60(40-100)88-44(4)102)68(109)92-54(28-29-64(105)106)70(111)96-59(36-48-38-83-42-87-48)73(114)93-56(33-45-16-8-7-9-17-45)71(112)90-53(22-14-31-84-78(81)82)69(110)95-58(35-47-37-85-51-20-11-10-18-50(47)51)67(108)86-39-63(104)89-55(21-12-13-30-79)77(118)99-32-15-23-62(99)76(117)98-65(43(2)3)66(80)107/h7-11,16-18,20,24-27,37-38,42-43,52-62,65,85,100-101,103H,5-6,12-15,19,21-23,28-36,39-41,79H2,1-4H3,(H2,80,107)(H,83,87)(H,86,108)(H,88,102)(H,89,104)(H,90,112)(H,91,116)(H,92,109)(H,93,114)(H,94,115)(H,95,110)(H,96,111)(H,97,113)(H,98,117)(H,105,106)(H4,81,82,84)/t52-,53-,54-,55-,56+,57-,58-,59-,60-,61-,62-,65-/m0/s1

75921-69-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name Melanotan-1

1.2 Other means of identification

Product number -
Other names Ac-SYS-Nle-EHfRWGKPV-NH2

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:75921-69-6 SDS

75921-69-6Synthetic route

N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

Fmoc-Pro-OH
71989-31-6

Fmoc-Pro-OH

Fmoc-Ser(tBu)-OH
71989-33-8

Fmoc-Ser(tBu)-OH

(S)-2-[{({9H-fluoren-9-yl}methoxy)carbonyl}amino]pentanedioic acid
104091-09-0, 136083-74-4, 121343-82-6

(S)-2-[{({9H-fluoren-9-yl}methoxy)carbonyl}amino]pentanedioic acid

Fmoc-Tyr(tBu)-OH
71989-38-3

Fmoc-Tyr(tBu)-OH

Fmoc-Lys-OH
105047-45-8

Fmoc-Lys-OH

Fmoc-D-Phe-OH
86123-10-6

Fmoc-D-Phe-OH

Fmoc-His(Trt)-OH
109425-51-6

Fmoc-His(Trt)-OH

Fmoc-(S)-2-aminohexanoic acid
77284-32-3

Fmoc-(S)-2-aminohexanoic acid

3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester
143824-78-6

3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester

Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine

Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine

NDP-MSH
75921-69-6

NDP-MSH

Conditions
ConditionsYield
Stage #1: Fmoc-Val-OH With 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 0.5h;
Stage #2: With piperidine In N,N-dimethyl-formamide for 0.333333h;
Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Pro-OH; Fmoc-Ser(tBu)-OH; (S)-2-[{({9H-fluoren-9-yl}methoxy)carbonyl}amino]pentanedioic acid; Fmoc-Tyr(tBu)-OH; Fmoc-Lys-OH; Fmoc-D-Phe-OH; Fmoc-His(Trt)-OH; Fmoc-(S)-2-aminohexanoic acid; 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine Further stages;
NDP-MSH
75921-69-6

NDP-MSH

[125I]2,3,5,6-tetrafluorophenyl 4-fluoro-3-iodobenzoate

[125I]2,3,5,6-tetrafluorophenyl 4-fluoro-3-iodobenzoate

[125I][Nle4, D-Phe7, FIB-Lys11]α-MSH

[125I][Nle4, D-Phe7, FIB-Lys11]α-MSH

Conditions
ConditionsYield
With borate buffer In acetonitrile at 45℃; for 0.5h; pH=8;
NDP-MSH
75921-69-6

NDP-MSH

[18F]2,3,5,6-tetrafluorophenyl 4-fluoro-3-iodobenzoate

[18F]2,3,5,6-tetrafluorophenyl 4-fluoro-3-iodobenzoate

[18F][Nle4, D-Phe7, FIB-Lys11]α-MSH

[18F][Nle4, D-Phe7, FIB-Lys11]α-MSH

Conditions
ConditionsYield
With borate buffer In acetonitrile at 50℃; for 0.166667h; pH=8;
NDP-MSH
75921-69-6

NDP-MSH

2,3,5,6-tetrafluorophenyl 4-fluoro-3-iodobenzoate

2,3,5,6-tetrafluorophenyl 4-fluoro-3-iodobenzoate

C85H113FIN21O20

C85H113FIN21O20

Conditions
ConditionsYield
With borate buffer In acetonitrile at 20℃; for 1.5h; pH=8.6;0.18 mg

75921-69-6Downstream Products

75921-69-6Relevant articles and documents

Design of MC1R Selective γ-MSH Analogues with Canonical Amino Acids Leads to Potency and Pigmentation

Zhou, Yang,Mowlazadeh Haghighi, Saghar,Zoi, Ioanna,Sawyer, Jonathon R.,Hruby, Victor J.,Cai, Minying

, p. 9320 - 9329 (2017)

Melanoma is a lethal form of skin cancer. Skin pigmentation, which is regulated by the melanocortin 1 receptor (MC1R), is an effective protection against melanoma. However, the endogenous MC1R agonists lack selectivity for the MC1R and thus can have side effects. The use of noncanonical amino acids in previous MC1R ligand development raises safety concerns. Here we report the development of the first potent and selective hMC1R agonist with only canonical amino acids. Using γ-MSH as a template, we developed a peptide, [Leu3, Leu7, Phe8]-γ-MSH-NH2 (compound 5), which is 16-fold selective for the hMC1R (EC50 = 4.5 nM) versus other melanocortin receptors. Conformational studies revealed a constrained conformation for this linear peptide. Molecular docking demonstrated a hydrophobic binding pocket for the melanocortin 1 receptor. In vivo pigmentation study shows high potency and short duration. [Leu3, Leu7, Phe8]-γ-MSH-NH2 is ideal for inducing short-term skin pigmentation without sun for melanoma prevention.

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