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Gastrin-Releasing Peptide, human

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Gastrin-Releasing Peptide, human (GRP), one of the bombesin-like peptide family, is an agonist for the gastrin-releasing peptide receptor (GRPR) and it plays only a perfunctory role in the mediation of pituitary hormone release.

Category

Peptide Inhibitors

Catalog number

BAT-015776

CAS number

93755-85-2

Molecular Formula

C130H204N38O31S2

Molecular Weight

2859.38

Specification
Reference Reading

IUPAC Name

2-[[2-[[2-[[1-[2-[[2-[[6-amino-2-[[2-[[2-[[2-[[2-[[2-[[2-[[2-[2-[[1-[2-[[1-(2-amino-3-methylbutanoyl)pyrrolidine-2-carbonyl]amino]-4-methylpentanoyl]pyrrolidine-2-carbonyl]amino]propanoylamino]acetyl]amino]acetyl]amino]acetyl]amino]-3-hydroxybutanoyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-3-hydroxybutanoyl]amino]hexanoyl]amino]-4-methylsulfanylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]pyrrolidine-2-carbonyl]amino]-5-carbamimidamidopentanoyl]amino]acetyl]amino]-N-[1-[[1-[[1-[[1-[[2-[[1-[[1-[(1-amino-4-methylsulfanyl-1-oxobutan-2-yl)amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-imidazol-4-yl)-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-(1H-imidazol-4-yl)-1-oxopropan-2-yl]butanediamide

Synonyms

Gastrin-Releasing Peptide, human; H-Val-Pro-Leu-Pro-Ala-Gly-Gly-Gly-Thr-Val-Leu-Thr-Lys-Met-Tyr-Pro-Arg-Gly-Asn-His-Trp-Ala-Val-Gly-His-Leu-Met-NH2

Density

1.46±0.1 g/cm3

Sequence

VPLPAGGGXVLXKMYPRGNHWAVGHLM

Storage

Store in a cool and dry place (or refer to the Certificate of Analysis).

Solubility

DMSO

InChI

1S/C130H204N38O31S2/c1-65(2)47-86(115(185)152-82(108(134)178)38-45-200-17)156-116(186)89(52-77-56-137-63-146-77)150-101(176)62-145-123(193)104(69(9)10)163-110(180)72(14)148-114(184)88(51-76-55-140-81-28-20-19-27-80(76)81)157-117(187)90(53-78-57-138-64-147-78)158-118(188)91(54-97(132)172)151-100(175)61-144-111(181)83(30-23-41-139-130(135)136)154-121(191)95-32-25-43-167(95)128(198)93(50-75-34-36-79(171)37-35-75)160-113(183)85(39-46-201-18)153-112(182)84(29-21-22-40-131)155-125(195)107(74(16)170)165-119(189)87(48-66(3)4)159-124(194)105(70(11)12)164-126(196)106(73(15)169)162-102(177)60-142-98(173)58-141-99(174)59-143-109(179)71(13)149-120(190)94-31-24-42-166(94)127(197)92(49-67(5)6)161-122(192)96-33-26-44-168(96)129(199)103(133)68(7)8/h19-20,27-28,34-37,55-57,63-74,82-96,103-107,140,169-171H,21-26,29-33,38-54,58-62,131,133H2,1-18H3,(H2,132,172)(H2,134,178)(H,137,146)(H,138,147)(H,141,174)(H,142,173)(H,143,179)(H,144,181)(H,145,193)(H,148,184)(H,149,190)(H,150,176)(H,151,175)(H,152,185)(H,153,182)(H,154,191)(H,155,195)(H,156,186)(H,157,187)(H,158,188)(H,159,194)(H,160,183)(H,161,192)(H,162,177)(H,163,180)(H,164,196)(H,165,189)(H4,135,136,139)/t71-,72-,73+,74+,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,103-,104-,105-,106-,107-/m0/s1

InChI Key

PUBCCFNQJQKCNC-XKNFJVFFSA-N

Canonical SMILES

CC(C)CC(C(=O)NC(CCSC)C(=O)N)NC(=O)C(CC1=CNC=N1)NC(=O)CNC(=O)C(C(C)C)NC(=O)C(C)NC(=O)C(CC2=CNC3=CC=CC=C32)NC(=O)C(CC4=CNC=N4)NC(=O)C(CC(=O)N)NC(=O)CNC(=O)C(CCCNC(=N)N)NC(=O)C5CCCN5C(=O)C(CC6=CC=C(C=C6)O)NC(=O)C(CCSC)NC(=O)C(CCCCN)NC(=O)C(C(C)O)NC(=O)C(CC(C)C)NC(=O)C(C(C)C)NC(=O)C(C(C)O)NC(=O)CNC(=O)CNC(=O)CNC(=O)C(C)NC(=O)C7CCCN7C(=O)C(CC(C)C)NC(=O)C8CCCN8C(=O)C(C(C)C)N

1. Human gastrin-releasing peptide: biological potency in humans

B Werth, P Hildebrand, C Beglinger, J B Jansen, K Gyr, C B Lamers, F Delco Regul Pept . 1991 Nov 26;36(3):423-33. doi: 10.1016/0167-0115(91)90075-r.

Gastrin-releasing peptide (GRP) was infused in graded doses (1-27 pmol/kg per h) to healthy human volunteers to study the effects on gastric, pancreatic and gallbladder functions as well as on gastrin, CCK and PP release. The results were compared to equimolar doses of synthetic bombesin. GRP significantly (P less than 0.05) stimulated gastric and pancreatic secretory responses, gallbladder contraction and gastro-enteropancreatic hormone release in a dose-dependent manner. GRP was found to be equipotent to bombesin with respect to gastric acid secretion, pancreatic enzyme output, gallbladder contraction and plasma hormone release. We conclude (a) that human GRP has similar biologic effects as synthetic bombesin; (b) as GRP is localized exclusively in nerve tissue and has potent effects on different organs, it is a likely candidate for peptidergic control of human gastric, pancreatic and gallbladder functions.

2. Gastrin-releasing peptide and cancer

Graham S Baldwin, Oneel Patel, Arthur Shulkes Biochim Biophys Acta . 2006 Aug;1766(1):23-41. doi: 10.1016/j.bbcan.2006.01.003.

Over the past 20 years, abundant evidence has been collected to suggest that gastrin-releasing peptide (GRP) and its receptors play an important role in the development of a variety of cancers. In fact, the detection of GRP and the GRP receptor in small cell lung carcinoma (SCLC), and the demonstration that anti-GRP antibodies inhibited proliferation in SCLC cell lines, established GRP as the prototypical autocrine growth factor. All forms of GRP are generated by processing of a 125-amino acid prohormone; recent studies indicate that C-terminal amidation of GRP18-27 is not essential for bioactivity, and that peptides derived from residues 31 to 125 of the prohormone are present in normal tissue and in tumors. GRP receptors can be divided into four classes, all of which belong to the 7 transmembrane domain family and bind GRP and/or GRP analogues with affinities in the nM range. Over-expression of GRP and its receptors has been demonstrated at both the mRNA and protein level in many types of tumors including lung, prostate, breast, stomach, pancreas and colon. GRP has also been shown to act as a potent mitogen for cancer cells of diverse origin both in vitro and in animal models of carcinogenesis. Other actions of GRP relevant to carcinogenesis include effects on morphogenesis, angiogenesis, cell migration and cell adhesion. Future prospects for the use of radiolabelled and cytotoxic GRP analogues and antagonists for cancer diagnosis and therapy appear promising.

3. Gastrin-releasing peptide as a molecular target for inflammatory diseases: an update

Fabricia Petronilho, Rafael Roesler, Felipe Dal-Pizzol, Gilberto Schwartsmann, Lucineia Gainski Danielski Inflamm Allergy Drug Targets . 2013 Jun;12(3):172-7. doi: 10.2174/1871528111312030003.

Gastrin-releasing peptide (GRP) is a neuropeptide that acts through G protein coupled receptors and is involved in signal transmission in both the central and peripheral nervous systems. Its receptor, gastrin-releasing peptide receptor (GRPR), is expressed by various cell types, and it is overexpressed in cancer cells. In recent years, studies have suggested the relationship of GRP and inflammatory diseases. RC-3095, a selective GRPR antagonist, was found to have antiinflammatory properties in models of arthritis, gastritis, uveitis and sepsis. Furthermore, GRP mediates air pollutioninduced airway hyperreactivity and airway inflammation in mice. In conclusion, GRP and its receptor are relevant to the inflammatory response, being a potential therapeutic target several diseases are related to inflammation.