M8764

[Nle⁴, D-Phe⁷]-α-Melanocyte Stimulating Hormone trifluoroacetate salt

≥95% (HPLC)

• Empirical Formula (Hill Notation): C₇₈H₁₁₁N₂₁O₁₉ · xC₂HF₃O₂
• CAS Number: 75921-69-6
• Molecular Weight: 1646.85 (free base basis)
• UNSPSC Code: 51111800
• PubChem Substance ID: 24897287
• NACRES: NA.32

Properties

• biological source: synthetic (organic)
• Quality Level: 200
• sterility: non-sterile
• assay: ≥95% (HPLC)
• form: powder
• solubility: 0.1% aqueous TFA: 1.00-1.04 mg/mL, clear, colorless
• UniProt accession no.: P01189
• shipped in: ambient
• storage temp.: −20°C
• SMILES string: OC(=O)C(F)(F)F.CCCC[C@H](NC(=O)[C@H](CO)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CO)NC(C)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](Cc2c[nH]cn2)C(=O)N[C@H](Cc3ccccc3)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](Cc4c[nH]c5ccccc45)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N6CCC[C@H]6C(=O)N[C@@H](C(C)C)C(N)=O
• InChI: 1S/C78H111N21O19.C2HF3O2/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;3-2(4,5)1(6)7/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);(H,6,7)/t52-,53-,54-,55-,56+,57-,58-,59-,60-,61-,62-,65-;/m0./s1
• InChI key: BFGBZOSHJJSHTQ-CRYSLBJVSA-N
• Gene Information: human ... POMC(5443)

Description

Amino Acid Sequence

Ac-Ser-Tyr-Ser-Nle-Glu-His-Phe-Arg-Trp-Gly-Lys-Pro-Val-NH2

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.

Application

[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.

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.

Other Notes

Lyophilized from 0.1% TFA in H2O

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)