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GHRP-6

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GHRP-6 is a synthetic met-enkephalin analogue that binds to growth hormone secretagogue receptor (GHSR).

Category
Peptide Inhibitors
Catalog number
BAT-006112
CAS number
87616-84-0
Molecular Formula
C46H56N12O6
Molecular Weight
873.01
GHRP-6
Size Price Stock Quantity
25 mg $298 In stock
IUPAC Name
(2S)-6-amino-2-[[(2R)-2-[[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-amino-3-(1H-imidazol-5-yl)propanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]propanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-3-phenylpropanoyl]amino]hexanamide
Synonyms
growth hormone releasing hexapeptide; H-His-D-Trp-Ala-Trp-D-Phe-Lys-NH2; GHRP-6 Acetate
Appearance
Lyophilized Powder
Purity
98%
Density
1.333±0.06 g/cm3(Predicted)
Boiling Point
1407.0±65.0°C(Predicted)
Sequence
H-His-D-Trp-Ala-Trp-D-Phe-Lys-NH2
Storage
Store at -20°C
InChI
InChI=1S/C46H56N12O6/c1-27(54-44(62)39(20-29-23-51-35-15-7-5-13-32(29)35)57-43(61)34(48)22-31-25-50-26-53-31)42(60)56-40(21-30-24-52-36-16-8-6-14-33(30)36)46(64)58-38(19-28-11-3-2-4-12-28)45(63)55-37(41(49)59)17-9-10-18-47/h2-8,11-16,23-27,34,37-40,51-52H,9-10,17-22,47-48H2,1H3,(H2,49,59)(H,50,53)(H,54,62)(H,55,63)(H,56,60)(H,57,61)(H,58,64)/t27-,34-,37-,38+,39+,40-/m0/s1
InChI Key
WZHKXNSOCOQYQX-FUAFALNISA-N
Canonical SMILES
CC(C(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)NC(CC3=CC=CC=C3)C(=O)NC(CCCCN)C(=O)N)NC(=O)C(CC4=CNC5=CC=CC=C54)NC(=O)C(CC6=CN=CN6)N
1. Growth hormone releasing hexapeptide-6 (GHRP-6) test in the diagnosis of GH-deficiency
M Pombo, A Leal-Cerro, J Barreiro, A Peñalva, R Peino, F Mallo, C Dieguez, F F Casanueva J Pediatr Endocrinol Metab. 1996 Jun;9 Suppl 3:333-8.
Pituitary GH reserve can be assessed by substances that act directly at the somatotroph, such as GHRH, or by a variety of metabolic and neuropharmacological tests acting at the hypothalamic level, such as hypoglycemia, clonidine or L-Dopa. In order to evaluate GHRP-6 as a test of pituitary GH reserve, we studied GH responses of i.v. administered GHRP-6 in a group of short-statured children, as well as in a group of adults diagnosed with growth hormone deficiency (GHD) by conventional GH testing. Although we found that the GH response to GHRP-6 was lower in patients with GHD than in normal children, on an individual basis a considerable degree of overlap was observed between the two groups. In contrast, we found an almost complete blockade of GH response to either GHRP-6 or GHRH plus GHRP-6 in patients with pituitary stalk transection, suggesting that this could be a cost-effective test for the diagnosis of this condition. A similar finding was also obtained in GH response to the combined administration of GHRH plus GHRP-6 in patients with GHD of adult onset; this test may well prove valuable in the diagnosis of this clinical entity.
2. Regulation of growth hormone secretion by the growth hormone releasing hexapeptide (GHRP-6)
D Micic, F Mallo, R Peino, F Cordido, A Leal-Cerro, R V Garcia-Mayor, F F Casanueva J Pediatr Endocrinol. 1993 Jul-Dec;6(3-4):283-9. doi: 10.1515/jpem.1993.6.3-4.283.
Growth hormone (GH) secretion is regulated by a complex system of central and peripheral signals. Recently, a new GH-releasing hexapeptide (His-D-Trp-Ala-Trp-D-Phe-Lys-NH2) called GHRP-6 which specifically releases GH has been studied. In the present work the mechanism of action of GHRP-6 has been addressed in experimental animal models as well as in obese subjects. GHRP-6 releases GH independently of the hypothalamic factors GHRH and somatostatin and is a powerful GH releaser in obesity.
3. [D-Lys3]-GHRP-6 exhibits pro-autophagic effects on skeletal muscle
Angus P Yu, Xiao M Pei, Thomas K Sin, Shea P Yip, Benjamin Y Yung, Lawrence W Chan, Cesar S Wong, Parco M Siu Mol Cell Endocrinol. 2015 Feb 5;401:155-64. doi: 10.1016/j.mce.2014.09.031. Epub 2014 Oct 29.
[D-Lys3]-GHRP-6 is regarded as a highly selective growth-hormone secretagogue receptor (GHSR) antagonist and has been widely used to investigate the dependency of GHSR-1a signalling mediated by acylated ghrelin. However, [D-Lys3]-GHRP-6 has been reported to influence other cellular processes which are unrelated to GHSR-1a. This study aimed to examine the effects of [D-Lys3]-GHRP-6 on autophagic and apoptotic cellular signalling in skeletal muscle. [D-Lys3]-GHRP-6 enhanced the autophagic signalling demonstrated by the increases in protein abundances of beclin-1 and LC3 II-to-LC3 1 ratio in both normal muscle and doxorubicin-injured muscle. [D-Lys3]-GHRP-6 reduced the activation of muscle apoptosis induced by doxorubicin. No histological abnormalities were observed in the [D-Lys3]-GHRP-6-treated muscle. Intriguingly, the doxorubicin-induced increase in centronucleated muscle fibres was not observed in muscle treated with [D-Lys3]-GHRP-6, suggesting the myoprotective effects of [D-Lys3]-GHRP-6 against doxorubicin injury. The [D-Lys3]-GHRP-6-induced activation of autophagy was found to be abolished by the co-treatment of CXCR4 antagonist, suggesting that the pro-autophagic effects of [D-Lys3]-GHRP-6 might be mediated through CXCR4. In conclusion, [D-Lys3]-GHRP-6 exhibits pro-autophagic effects on skeletal muscle under both normal and doxorubicin-injured conditions.
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