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M8764

Sigma-Aldrich

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

≥95% (HPLC)

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About This Item

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

biological source

synthetic (organic)

Quality Level

sterility

non-sterile

Assay

≥95% (HPLC)

form

powder

solubility

0.1% aqueous TFA: 1.00-1.04 mg/mL, clear, colorless

UniProt accession no.

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)

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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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Prolonged stimulation of S91 melanoma tyrosinase by [Nle4, D-Phe7]-substituted alpha-melanotropins.
Abdel Malek ZA
Cancer Research, 45, 4735-4740 (1985)
Stefano Gatti et al.
Experimental neurology, 234(1), 230-238 (2012-01-11)
Subarachnoid hemorrhage (SAH) is still a major cause of morbidity and mortality. α-Melanocyte stimulating hormone (α-MSH) and other melanocortin peptides exert potent neuroprotective action and they might modulate key molecules involved in SAH-induced vasospasm. The aim of this research was
Aline D Lúcio et al.
Journal of fluorescence, 20(2), 473-482 (2009-11-19)
The highly hydrophobic fluorophore Laurdan (6-dodecanoyl-2-(dimethylaminonaphthalene)) has been widely used as a fluorescent probe to monitor lipid membranes. Actually, it monitors the structure and polarity of the bilayer surface, where its fluorescent moiety is supposed to reside. The present paper
Narges K Tafreshi et al.
Bioconjugate chemistry, 23(12), 2451-2459 (2012-11-03)
The incidence of malignant melanoma is rising more rapidly than that of any other cancer in the United States. The melanocortin 1 receptor (MC1R) is overexpressed in most human melanoma metastases, thus making it a promising target for imaging and
Letteria Minutoli et al.
Endocrinology, 152(10), 3852-3861 (2011-08-11)
Melanocortins (MC) trigger a vagus nerve-mediated cholinergic-antiinflammatory pathway projecting to the testis. We tested whether pharmacological activation of brain MC receptors might protect the testis from the damage induced by ischemia-reperfusion. Adult male rats were subjected to 1-h testicular ischemia

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