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G4535

Sigma-Aldrich

[D-Lys3]-GHRP-6

synthetic, lyophilized powder

Synonym(s):

[His1, D-Lys3, Lys6]-GHRP, His-D-Trp-D-Lys-Trp-D-Phe-Lys-NH2, [D-Lys3]-Growth Hormone Releasing Peptide 6

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About This Item

MDL number:
MFCD00214665
UNSPSC Code:
12352209
PubChem Substance ID:
329799930
NACRES:
NA.32

biological source

synthetic

Quality Level

200

form

lyophilized powder

UniProt accession no.

P01286

storage temp.

−20°C

SMILES string

NCCCC[C@H](NC(=O)[C@@H](Cc1ccccc1)NC(=O)[C@H](Cc2c[nH]c3ccccc23)NC(=O)[C@@H](CCCCN)NC(=O)[C@@H](Cc4c[nH]c5ccccc45)NC(=O)[C@@H](N)Cc6c[nH]cn6)C(N)=O

InChI

1S/C49H63N13O6/c50-20-10-8-18-39(44(53)63)58-47(66)41(22-30-12-2-1-3-13-30)61-49(68)43(24-32-27-56-38-17-7-5-15-35(32)38)62-46(65)40(19-9-11-21-51)59-48(67)42(23-31-26-55-37-16-6-4-14-34(31)37)60-45(64)36(52)25-33-28-54-29-57-33/h1-7,12-17,26-29,36,39-43,55-56H,8-11,18-25,50-52H2,(H2,53,63)(H,54,57)(H,58,66)(H,59,67)(H,60,64)(H,61,68)(H,62,65)/t36-,39-,40+,41+,42+,43-/m0/s1

InChI key

MGSNWNLPMHXGDD-DFWOJPNQSA-N

Gene Information

human ... GHRH(2691)

Amino Acid Sequence

His-Trp-Lys-Trp-Phe-Lys-NH2

General description

[D-Lys3]-GHRP6 (growth hormone releasing peptide 6) is a synthetic analog of the orexigenic peptide hormone called ghrelin.

Application

[D-Lys3]-GHRP-6 has been used:
  • to study its role in incretin dysfunction and hyperglycemia in cystic fibrosis
  • as an antagonist of growth hormone secretagogue receptor (GHS-R)
  • as ghrelin receptor antagonist to study the dose-dependent effects of intraduodenal ghrelin on the glucose infusion rate (GIR) during pancreatic-euglycemic clamp procedure (PECs)

[D-Lys3]-GHRP6 has been used-
  • to treat bovine somatotropes to determine the release of GH from treated cells and non-treated or control cells
  • for intraperitoneal injection to groups of broiler chicken to determine the effect on feed intake, weight gain, and feed conversion ratio

Biochem/physiol Actions

[D-Lys3]-GHRP-6, a selective growth-hormone secretagogue receptor (GHSR) antagonist displays pro-autophagic effects on skeletal muscle. It can be used to study the dependency of GHSR-1a signalling mediated by acylated ghrelin.
[D-Lys3]-GHRP6 (growth hormone releasing peptide 6) induces the secretion of growth hormone (GH). In the membrane of clonal GC somatotropes, this peptide elevates the number of functional voltage-gated Ca2+ and Na+ channels. Chronic treatment with this peptide causes an elevation in Na+ macroscopic current in bovine pituitary somatotropes in culture, which results in an increase in the release of GH.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Adasue Magdaleno-Méndez et al.
Endocrine, 48(3), 929-936 (2014-08-26)
A variety of ion channels are expressed in the plasma membrane of somatotropes within the anterior pituitary gland. Modification of these channels is linked to intracellular Ca2+ levels and therefore to hormone secretion. Previous investigations have shown that the gut-derived
Gut ghrelin regulates hepatic glucose production and insulin signaling via a gut-brain-liver pathway
Lin Y, et al.
Cell communication and signaling : CCS, 17(1), 1-14 (2019)
K Veeraragavan et al.
Life sciences, 50(16), 1149-1155 (1992-01-01)
The synthetic hexapeptide, His-D-Trp-Ala-Trp-D-Phe-Lys-NH2 (GHRP, Growth Hormone-Releasing Peptide), has no structural similarities with any of the GH-releasing peptides known and its action in releasing GH is by a complementary but yet not clearly defined action on the pituitary as well
Incretin dysfunction and hyperglycemia in cystic fibrosis: Role of acyl-ghrelin
Journal of Cystic Fibrosis, 18(4), 557-565 (2019)
Xingshen Sun et al.
Journal of cystic fibrosis : official journal of the European Cystic Fibrosis Society, 18(4), 557-565 (2019-02-11)
Insulin secretion is insufficient in cystic fibrosis (CF), even before diabetes is present, though the mechanisms involved remain unclear. Acyl-ghrelin (AG) can diminish insulin secretion and is elevated in humans with CF. We tested the hypothesis that elevated AG contributes
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