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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 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

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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Upregulation of Voltage-Gated Calcium Channel Cav1.3 in Bovine Somatotropes Treated with Ghrelin
Salinas ZVM, et al.
Journal of signal transduction (2013)
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
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
Incretin dysfunction and hyperglycemia in cystic fibrosis: Role of acyl-ghrelin
Journal of Cystic Fibrosis, 18(4), 557-565 (2019)
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