Hexarelin

A synthetic six-residue peptide bearing a non-canonical D-2-methyltryptophan substitution and a C-terminal amide.

Molecular Profile

Type
Synthetic peptide (hexapeptide)
Molecular formula
C47H58N12O6
Molecular weight
887.04 g/mol
CAS number
140703-51-1
Amino acids
6
Sequence
His-D-2-MeTrp-Ala-Trp-D-Phe-Lys-NH2
Modification
D-2-methyltryptophan; D-Phe; C-terminal amide.

Mechanism & Target Class

A synthetic peptidyl hexapeptide of the GHRP series that engages two structurally distinct membrane-protein binding partners. The first is a class A G-protein-coupled receptor characterized in binding and photoaffinity-labeling studies of brain and pituitary membranes. The second is CD36, a heavily glycosylated class B membrane glycoprotein of roughly 472 residues, identified through photoaffinity cross-linking as a binding partner whose contact interface maps to a lysine-rich extracellular segment (residues Gln155-Lys183). The molecule's defining structural feature is substitution of the position-2 tryptophan of the parent GHRP-6 sequence with D-2-methyl-tryptophan, a non-canonical residue that confers conformational rigidity and resistance to proteolytic degradation; a conserved core and a turn-stabilized backbone are recurring pharmacophore elements across the GHRP series.

Storage & Handling

Lyophilized
-20°C; typically stable 24-36 months desiccated.
Handling
Avoid freeze-thaw; aliquot; protect from light and moisture.

Primary Database

PubChem CID 6918297 ↗

References (22)

  1. Reviews

    1

    Ishida J, et al. (2020). JCSM Rapid Communications

    DOI: 10.1002/rco2.9

  2. 2

    Proulx C, et al. (2020). Biomedicines

    DOI: 10.3390/biomedicines8080241PubMed 32717955

  3. 3

    Mao Y, et al. (2014). J Geriatr Cardiol

    DOI: 10.11909/j.issn.1671-5411.2014.03.007PubMed 25278975

  4. 4

    Demers A, et al. (2008). PPAR Research

    DOI: 10.1155/2008/364784PubMed 18288286

  5. Clinical

    5

    Arvat E, et al. (1997). Peptides

    DOI: 10.1016/s0196-9781(97)00016-8PubMed 9285939

  6. 6

    Arvat E, et al. (1997). Eur J Endocrinol

    DOI: 10.1530/eje.0.1370635PubMed 9437229

  7. 7

    Ghigo E, et al. (1994). J Clin Endocrinol Metab

    DOI: 10.1210/jcem.78.3.8126144PubMed 8126144

  8. 8

    Imbimbo BP, et al. (1994). Eur J Clin Pharmacol

    DOI: 10.1007/BF00191904PubMed 7912186

  9. Primary research

    9

    McDonald H, et al. (2020). Biomed Pharmacother

    DOI: 10.1016/j.biopha.2020.110165PubMed 32403043

  10. 10

    Cheng XL, et al. (2019). Peptides

    DOI: 10.1016/j.peptides.2019.170122PubMed 31386895

  11. 11

    McDonald H, et al. (2018). Physiol Rep

    DOI: 10.14814/phy2.13699

  12. 12

    Mao Y, et al. (2013). Endocrinology

    DOI: 10.1210/en.2013-1291PubMed 23861368

  13. 13

    Proulx C, et al. (2012). J Med Chem

    DOI: 10.1021/jm300557tPubMed 22712585

  14. 14

    Sabatino D, et al. (2011). J Am Chem Soc

    DOI: 10.1021/ja203007uPubMed 21692501

  15. 15

    Demers A, et al. (2004). Biochem J

    DOI: 10.1042/BJ20040036PubMed 15176951

  16. 16

    Bodart V, et al. (2002). Circ Res

    DOI: 10.1161/01.res.0000016164.02525.b4PubMed 11988484

  17. 17

    Tivesten Å, et al. (2000). Endocrinology

    DOI: 10.1210/endo.141.1.7249PubMed 10614623

  18. 18

    Locatelli V, et al. (1999). Endocrinology

    DOI: 10.1210/endo.140.9.6948PubMed 10465272

  19. 19

    Bodart V, et al. (1999). Circ Res

    DOI: 10.1161/01.res.85.9.796PubMed 10532947

  20. 20

    Muccioli G, et al. (1998). J Endocrinol

    DOI: 10.1677/joe.0.1570099PubMed 9614363

  21. 21

    Torsello A, et al. (1996). Neuroendocrinology

    PubMed 8921832

  22. 22

    Deghenghi R, et al. (1994). Life Sci

    DOI: 10.1016/0024-3205(94)00510-9PubMed 7910650