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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

Patricia René et al.
The Journal of pharmacology and experimental therapeutics, 335(3), 520-532 (2010-09-10)
Heterozygous null mutations in the melanocortin-4 receptor (MC4R) cause early-onset obesity in humans, indicating that metabolic homeostasis is sensitive to quantitative variation in MC4R function. Most of the obesity-causing MC4R mutations functionally characterized so far lead to intracellular retention of
E A Langan et al.
The British journal of dermatology, 163(3), 451-455 (2010-06-16)
While ultraviolet radiation (UVR) is a major cause of skin ageing and carcinogenesis, public pursuit of a novel tanning strategy circumventing the need for UVR is increasingly reported in the media and scientific press. This involves the subcutaneous self-administration of
Christine G Joseph et al.
Peptides, 31(12), 2304-2313 (2010-09-14)
The melanocortin system has been implicated in a multitude of physiological pathways including obesity, satiety, energy homeostasis, sexual behavior, pigmentation, sodium regulation, hypertension, and many others. Based upon studies of the endogenous melanocortin receptor agonists at the cloned human melanocortin
The role of alpha-melanocyte-stimulating hormone in cutaneous biology.
Luger TA
The Journal of Investigative Dermatology. Symposium Proceedings / The Society for Investigative Dermatology, Inc. [and] European Society for Dermatological Research, 2, 87-93 (1997)
Peripherally administered [Nle4,D-Phe7]-?-melanocyte stimulating hormone increases resting metabolic rate, while peripheral agouti-related protein has no effect, in wild type C57BL/6 and ob/ob mice
Hoggard N
Journal of Molecular Endocrinology, 33, 693-703 (2004)
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