ghrp 6 - 87616-84-0

ghrp 6

Catalog Number: EVT-242346
CAS Number: 87616-84-0
Molecular Formula: C46H56N12O6
Molecular Weight: 873 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction

Description

Growth hormone-releasing peptide 6 (GHRP-6) is a synthetic hexapeptide known for its potent ability to stimulate the secretion of growth hormone (GH). Its unique mechanism of action and the resulting physiological effects have made it a subject of interest in various fields of medical research. GHRP-6 has been shown to exert its effects through pathways that are distinct from those of growth hormone-releasing hormone (GHRH), and it has been observed to have synergistic effects when administered with GHRH23710.

Mechanism of Action

GHRP-6 induces GH secretion through a complex mechanism that involves different pathways. It has been demonstrated that GHRP-6 can stimulate phosphatidylinositol (PI) turnover in human pituitary somatotroph cells, which leads to the activation of protein kinase C (PKC) and mobilization of intracellular calcium reserves, independent of the cAMP pathway4. Additionally, GHRP-6 has been shown to induce a biphasic calcium response in rat pituitary somatotrophs, suggesting that the peptide mobilizes intracellular calcium stores and also causes calcium influx through voltage-dependent calcium channels6. This biphasic response is dose-dependent and involves a PKC-dependent process6. Furthermore, GHRP-6 does not increase intracellular cyclic AMP (cAMP) levels in ovine and rat somatotrophs, indicating that its action is cAMP-independent5. The peptide's effect on GH secretion is also influenced by the endogenous somatostatinergic tone, as shown by its interactions with atropine and pyridostigmine2.

Applications in Various Fields

Cardiology

In cardiology, GHRP-6 has been investigated for its cardioprotective effects. A study on female Cuban Creole pigs demonstrated that GHRP-6 administration reduced myocardial infarct size following acute coronary occlusion. The treatment led to a significant reduction in infarct mass and thickness, and more than half of the treated pigs did not exhibit pathological Q waves in any of the ECG leads. The reduction in myocardial necrosis was confirmed by quantitative histopathology and serum levels of creatine kinase MB (CK-MB) and C-reactive protein (CRP). The study suggested that GHRP-6 exerts antioxidant effects, which may contribute to the reduction of myocardial ischemic damage1.

Endocrinology

In endocrinology, GHRP-6 has been studied for its GH-releasing properties in both healthy individuals and patients with GH deficiencies. It has been found to be more efficacious than GHRH and exhibits a synergistic action when both compounds are administered together23. However, in patients with neonatal pituitary stalk transection, GHRP-6 did not induce GH secretion, indicating that its action may not be solely at the hypothalamic level3. In acromegalic patients, GHRP-6 and GHRH both elicited a strong response, suggesting that GH-secreting pituitary adenomas respond well to these peptides7.

Pediatrics

GHRP-6 has also been explored in pediatric research, particularly in children with short stature. Oral administration of GHRP-6 induced a GH response comparable to that elicited by intravenous GHRH. The study also investigated the interaction between oral GHRP-6 and arginine, finding that the combination could potentiate the GH rise in children8.

Oncology

The peptide's action has been examined in various types of human pituitary adenomas. GHRP-6 was found to increase intracellular calcium concentrations in cultured cells from these adenomas, with the exception of corticotrophs. This indicates that GHRP-6's pituitary action is not restricted to somatotroph lineage and may have implications for the treatment of pituitary tumors9.

Properties

CAS Number

87616-84-0

Product Name

ghrp 6

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

Molecular Formula

C46H56N12O6

Molecular Weight

873 g/mol

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

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

Synonyms

(D-Lys)GHRP-6
(D-Trp(2)-D-Phe(5))GHRP
GH-releasing hexapeptide 6
GH-releasing peptide-6
GHRP, His(1)-Lys(6)-
GHRP-6
growth hormone releasing hexapeptide
His(1)-Lys(6)-GHRP
His-Trp-Ala-Trp-Phe-LysNH2
histidyl-tryptophyl-alanyl-tryptophyl-phenylalanyl-lysinamide
SK and F 110679
SK and F-110679
SKF 110679

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

Isomeric SMILES

C[C@@H](C(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)N[C@H](CC3=CC=CC=C3)C(=O)N[C@@H](CCCCN)C(=O)N)NC(=O)[C@@H](CC4=CNC5=CC=CC=C54)NC(=O)[C@H](CC6=CN=CN6)N

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