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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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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
Pricing and availability is not currently available.

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

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]
NK-1 tachykinin receptor antagonist

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
A Tallett et al.
Cancer research, 56(18), 4255-4263 (1996-09-15)
Small cell lung cancer (SCLC) cell growth is sustained by multiple autocrine and paracrine growth loops involving neuropeptides. The bombesin family of peptides are autocrine growth factors in H345 SCLC cells and provide a paradigm for the study of growth
O Malkesman et al.
Physiology & behavior, 90(4), 619-625 (2007-01-30)
In an attempt to explore the involvement of substance P in depression and anxiety and its' potential therapeutic effects, we measured basal plasma and hypothalamic levels of substance P in a well-studied animal model of depression--adult male Wistar Kyoto (WKY)
Birgitte Holst et al.
Molecular pharmacology, 70(3), 936-946 (2006-06-27)
[D-Arg1,D-Phe5,D-Trp7,9,Leu11]Substance P functions as a low-potency antagonist but a high-potency full inverse agonist on the ghrelin receptor. Through a systematic deletion and substitution analysis of this peptide, the C-terminal carboxyamidated pentapeptide wFwLX was identified as the core structure, which itself
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