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S3144

Sigma-Aldrich

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

≥95% (HPLC)

Synonym(s):

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

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1 MG
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About This Item

Empirical Formula (Hill Notation):
C79H109N19O12
CAS Number:
96736-12-8
Molecular Weight:
1516.83
MDL number:
MFCD00076802
UNSPSC Code:
12352209
PubChem Substance ID:
329824529
NACRES:
NA.32

€181.00

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Quality Level

200

Assay

≥95% (HPLC)

storage temp.

−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

InChI key

XVOCEQLNJQGCQG-ACRSGXKRSA-N

Gene Information

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

General description

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.[1]

Biochem/physiol Actions

NK-1 tachykinin receptor antagonist
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.[1][2]

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

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Certificates of Analysis (COA)

Lot/Batch Number
SLBT2690
SLBL4464V
SLBB5489V
061M1418V
011M1373V

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Rita O Kwan et al.
The Journal of trauma, 68(5), 1186-1191 (2010-01-14)
Obesity is a risk factor for poor outcomes after trauma, and circulating levels of ghrelin are decreased in obese patients. We hypothesized that ghrelin modifies microvascular permeability. The purposes of this study were to determine (1) the effect of ghrelin
F M Mitchell et al.
The Journal of biological chemistry, 270(15), 8623-8628 (1995-04-14)
Mitogenic stimulation of Swiss 3T3 fibroblasts with bombesin results in receptor-mediated activation of a complex array of effectors, including phospholipase C beta and mitogen-activated protein (MAP) kinase. Incubation of Swiss 3T3 fibroblasts with the 11-amino acid [D-Arg1,D-Phe5,D-Trp7,9,Leu11]substance P peptide inhibited
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
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
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
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