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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

Formule empirique (notation de Hill):
C78H111N21O19 · xC2HF3O2
Numéro CAS:
75921-69-6
Poids moléculaire :
1646.85 (free base basis)
Code UNSPSC :
51111800
ID de substance PubChem :
24897287
Nomenclature NACRES :
NA.32

Source biologique

synthetic (organic)

Niveau de qualité

200

Stérilité

non-sterile

Pureté

≥95% (HPLC)

Forme

powder

Solubilité

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

Numéro d'accès UniProt

P01189

Conditions d'expédition

ambient

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

BFGBZOSHJJSHTQ-CRYSLBJVSA-N

Informations sur le gène

human ... POMC(5443)

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Catégories apparentées

Amino Acid Sequence

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

Description générale

[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.

Actions biochimiques/physiologiques

[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.

Autres remarques

Lyophilized from 0.1% TFA in H2O

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Consulter la Bibliothèque de documents

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
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
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
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