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S3144

Sigma-Aldrich

[D-Arg1, D-Phe5, D-Trp7,9, Leu11]-Substance P

≥95% (HPLC)

Synonym(e):

D-Arg-Pro-Lys-Pro-D-Phe-Gln-D-Trp-Phe-D-Trp-Leu-Leu-NH2, Antagonist D

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About This Item

Empirische Formel (Hill-System):
C79H109N19O12
CAS-Nummer:
96736-12-8
Molekulargewicht:
1516.83
MDL-Nummer:
MFCD00076802
UNSPSC-Code:
12352209
PubChem Substanz-ID:
329824529
NACRES:
NA.32

Qualitätsniveau

200

Assay

≥95% (HPLC)

Lagertemp.

−20°C

SMILES String

CC(C)C[C@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](Cc1c[nH]c2ccccc12)NC(=O)[C@H](Cc3ccccc3)NC(=O)[C@@H](Cc4c[nH]c5ccccc45)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](Cc6ccccc6)NC(=O)[C@@H]7CCCN7C(=O)[C@H](CCCCN)NC(=O)[C@@H]8CCCN8C(=O)[C@H](N)CCCNC(N)=N)C(N)=O

InChI

1S/C79H109N19O12/c1-46(2)38-59(68(83)100)91-70(102)60(39-47(3)4)92-73(105)64(43-51-45-88-56-28-14-12-25-53(51)56)95-72(104)61(40-48-20-7-5-8-21-48)93-74(106)63(42-50-44-87-55-27-13-11-24-52(50)55)94-69(101)57(32-33-67(82)99)89-71(103)62(41-49-22-9-6-10-23-49)96-76(108)66-31-19-37-98(66)78(110)58(29-15-16-34-80)90-75(107)65-30-18-36-97(65)77(109)54(81)26-17-35-86-79(84)85/h5-14,20-25,27-28,44-47,54,57-66,87-88H,15-19,26,29-43,80-81H2,1-4H3,(H2,82,99)(H2,83,100)(H,89,103)(H,90,107)(H,91,102)(H,92,105)(H,93,106)(H,94,101)(H,95,104)(H,96,108)(H4,84,85,86)/t54-,57+,58+,59+,60+,61+,62-,63-,64-,65+,66+/m1/s1

InChIKey

XVOCEQLNJQGCQG-ACRSGXKRSA-N

Angaben zum Gen

human ... TAC1(6863) , TACR1(6869)
mouse ... TAC1(21333) , TACR1(21336)
rat ... TAC1(24806) , TACR1(24807)

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Amino Acid Sequence

Arg-Pro-Lys-Pro-Phe-Gln-Trp-Phe-Trp-Leu-Leu-NH2

Allgemeine Beschreibung

The somatostatin gene codes for a peptide hormone containing 14 and 28 amino acid moieties. SST-14 is highly expressed in the central nervous system and peripheral organs. SST-28 is mainly expressed in enteroendocrine cells of the intestine.

Biochem./physiol. Wirkung

Somatostatin plays an important role in regulating the metabolism of other hormones such as growth hormone, insulin, IGF-1 (insulin-like growth factor 1), glucagon, glucagon-like peptide and gastrin. Somatostatin has both regulatory and inhibitory functions. It retards gastrointestinal motility and gallbladder contraction, suppresses gut exocrine secretion and reduces epithelial proliferation. Somatostatin is associated with intestinal nutrient absorption and blood flow regulation. This peptide hormone is believed to inhibit cell proliferation and promote apoptosis. Somatostatin acts as a neurotransmitter and neuromodulator, and is also associated in maintaining water balance.
NK-1 tachykinin receptor antagonist

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)

Analysenzertifikate (COA)

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J Cummings et al.
Journal of chromatography. B, Biomedical applications, 653(2), 195-203 (1994-03-04)
The neuropeptide growth factor antagonists [D-Arg1,D-Phe5,D-Trp7,9,Leu11]-substance P (D) and [Arg6,D-Trp7,9, [corrected] N-MePhe8]-substance P(6-11) (G) are currently undergoing preclinical evaluation as potential anticancer agents and clinical trials are planned for G in the near future. A reversed-phase high-performance liquid chromatographic separation
H Houben et al.
Peptides, 14(1), 109-115 (1993-01-01)
The effect of peptide and nonpeptide substance P antagonists on prolactin (PRL) and growth hormone (GH) secretion was evaluated in three-dimensional rat anterior pituitary cell aggregates. [D-Arg1,D-Phe5,D-Trp7,9,Leu11]Substance P inhibited basal growth hormone (GH) release at a concentration range of 1-10
Michael Patterson et al.
Peptides, 32(11), 2290-2294 (2011-08-13)
Ghrelin is a peptide hormone secreted into circulation from the stomach. It has been postulated to act as a signal of hunger. Ghrelin administration acutely increases energy intake in lean and obese humans and chronically induces weight gain and adiposity
X H Gu et al.
Biochemical and biophysical research communications, 179(1), 130-133 (1991-08-30)
The specific binding of [125I]ET-1 to rat cardiac membrane fragments was inhibited by [D-Arg1,D-Phe, D-Try7,9,Leu11] substance P [substance P(D)], a potent bombesin antagonist. This inhibitory effect required high concentrations (greater than 3X10(-6)M) of substance P(D) and was accompanied by a
S Langdon et al.
Cancer research, 52(16), 4554-4557 (1992-08-15)
The proliferation of small cell lung cancer (SCLC) cells appears sustained by multiple autocrine and paracrine circuits involving Ca2+ mobilizing neuropeptides. Consequently, broad spectrum neuropeptide antagonists which inhibit SCLC growth in vitro have been suggested as potential anticancer agents. Here
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