Nonapeptide-1

• CAT Number: I033426
• CAS Number: 158563-45-2
• Molecular Formula: C61H87N15O9S
• Molecular Weight: 1206.52
• Purity: 98%
• Solubility: Soluble in DMSO
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: (S)-1-(L-methionyl)-N-((R)-1-(((S)-1-(((R)-1-(((S)-1-(((S)-6-amino-1-((S)-2-(((S)-1-amino-3-methyl-1-oxobutan-2-yl)carbamoyl)pyrrolidin-1-yl)-1-oxohexan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)amino)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)amino)-5-guanidino-1-oxopentan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)pyrrolidine-2-carboxamide
• InChI: InChI=1S/C61H87N15O9S/c1-37(2)51(52(64)77)74-58(83)50-26-16-31-76(50)60(85)45(23-12-13-28-62)70-55(80)46(33-38-17-6-4-7-18-38)71-56(81)48(35-40-36-68-43-22-11-10-21-41(40)43)72-53(78)44(24-14-29-67-61(65)66)69-54(79)47(34-39-19-8-5-9-20-39)73-57(82)49-25-15-30-75(49)59(84)42(63)27-32-86-3/h4-11,17-22,36-37,42,44-51,68H,12-16,23-35,62-63H2,1-3H3,(H2,64,77)(H,69,79)(H,70,80)(H,71,81)(H,72,78)(H,73,82)(H,74,83)(H4,65,66,67)/t42-,44-,45-,46-,47+,48+,49-,50-,51-/m0/s1
• InChIKey: KNFLNGRLKALWRF-LDXSYGEZSA-N
• SMILES: CC(C)[C@@H](C(N)=O)NC([C@H]1N(C([C@H](CCCCN)NC([C@H](CC2=CC=CC=C2)NC([C@@H](CC3=CNC4=C3C=CC=C4)NC([C@H](CCCNC(N)=N)NC([C@@H](CC5=CC=CC=C5)NC([C@H]6N(C([C@H](CCSC)N)=O)CCC6)=O)=O)=O)=O)=O)=O)CCC1)=O

Nonapeptide-1 (CAT: I033426), also known as Melanostatine™ 5, is a proprietary peptide initially recognized for its antimicrobial properties. Through animal studies, it has been revealed that nonapeptide-1 possesses the ability to hinder the synthesis of melanin, making it a promising candidate for addressing specific skin conditions. Preclinical research indicates that nonapeptide-1 has the potential to effectively diminish the production of melanin, leading to a significant reduction in skin pigmentation.

Reference

1: Reddon AR, O’Connor CM, Marsh-Rollo SE, Balshine S, Gozdowska M, Kulczykowska E. Brain nonapeptide levels are related to social status and affiliative behaviour in a cooperatively breeding cichlid fish. R Soc Open Sci. 2015 Feb 4;2(2):140072. doi: 10.1098/rsos.140072. eCollection 2015 Feb. PubMed PMID: 26064593; PubMed Central PMCID: PMC4448801.
2: Lema SC, Sanders KE, Walti KA. Arginine vasotocin, isotocin and nonapeptide receptor gene expression link to social status and aggression in sex-dependent patterns. J Neuroendocrinol. 2015 Feb;27(2):142-57. doi: 10.1111/jne.12239. PubMed PMID: 25425529.
3: Kelly AM, Ophir AG. Compared to what: What can we say about nonapeptide function and social behavior without a frame of reference? Curr Opin Behav Sci. 2015 Dec 1;6:97-103. PubMed PMID: 26858966; PubMed Central PMCID: PMC4742393.
4: Zabłocka A, Mitkiewicz M, Macała J, Janusz M. Neurotrophic Activity of Cultured Cell Line U87 is Up-Regulated by Proline-Rich Polypeptide Complex and Its Constituent Nonapeptide. Cell Mol Neurobiol. 2015 Oct;35(7):977-86. doi: 10.1007/s10571-015-0192-8. Epub 2015 Apr 5. PubMed PMID: 25841889; PubMed Central PMCID: PMC4572042.
5: Goodson JL. Deconstructing sociality, social evolution and relevant nonapeptide functions. Psychoneuroendocrinology. 2013 Apr;38(4):465-78. doi: 10.1016/j.psyneuen.2012.12.005. Epub 2013 Jan 4. Review. PubMed PMID: 23290368.
6: Tomaszycki ML, Richardson KK, Mann KJ. Sex and pairing status explain variations in the activation of nonapeptide receptors in song and motivation regions. Behav Neurosci. 2016 Oct;130(5):479-89. doi: 10.1037/bne0000159. Epub 2016 Aug 8. PubMed PMID: 27504854.
7: Baran NM, Sklar NC, Adkins-Regan E. Developmental effects of vasotocin and nonapeptide receptors on early social attachment and affiliative behavior in the zebra finch. Horm Behav. 2016 Feb;78:20-31. doi: 10.1016/j.yhbeh.2015.10.005. Epub 2015 Oct 23. PubMed PMID: 26476409; PubMed Central PMCID: PMC4718777.
8: Neasta J, Valmalle C, Coyne AC, Carnazzi E, Subra G, Galleyrand JC, Gagne D, M’Kadmi C, Bernad N, Bergé G, Cantel S, Marin P, Marie J, Banères JL, Kemel ML, Daugé V, Puget K, Martinez J. The novel nonapeptide acein targets angiotensin converting enzyme in the brain and induces dopamine release. Br J Pharmacol. 2016 Apr;173(8):1314-28. doi: 10.1111/bph.13424. Epub 2016 Mar 8. PubMed PMID: 27027724; PubMed Central PMCID: PMC4940823.
9: Grenács Á, Sóvágó I. Copper(II), nickel(II) and zinc(II) complexes of the N-terminal nonapeptide fragment of amyloid-β and its derivatives. J Inorg Biochem. 2014 Oct;139:49-56. doi: 10.1016/j.jinorgbio.2014.06.001. Epub 2014 Jun 10. PubMed PMID: 24973554.
10: Orcel U, De Poli M, De Zotti M, Clayden J. The N-terminal nonapeptide of cephaibols A and C: a naturally occurring example of mismatched helical screw-sense control. Chemistry. 2013 Nov 25;19(48):16357-65. doi: 10.1002/chem.201302648. Epub 2013 Oct 9. PubMed PMID: 24123376.
11: Goodson JL, Kelly AM, Kingsbury MA. Evolving nonapeptide mechanisms of gregariousness and social diversity in birds. Horm Behav. 2012 Mar;61(3):239-50. doi: 10.1016/j.yhbeh.2012.01.005. Epub 2012 Jan 13. Review. PubMed PMID: 22269661; PubMed Central PMCID: PMC3312996.
12: Lowrey EM, Tomaszycki ML. The formation and maintenance of social relationships increases nonapeptide mRNA in zebra finches of both sexes. Behav Neurosci. 2014 Feb;128(1):61-70. doi: 10.1037/a0035416. PubMed PMID: 24512066.
13: Asami T, Nishizawa N, Matsui H, Takatsu Y, Suzuki A, Kiba A, Terada M, Nishibori K, Nakayama M, Ban J, Matsumoto S, Tarui N, Ikeda Y, Yamaguchi M, Kusaka M, Ohtaki T, Kitada C. Physicochemically and pharmacokinetically stable nonapeptide KISS1 receptor agonists with highly potent testosterone-suppressive activity. J Med Chem. 2014 Jul 24;57(14):6105-15. doi: 10.1021/jm5005489. Epub 2014 Jul 7. PubMed PMID: 24918545.
14: Gu C, Liu L, He Y, Jiang J, Yang Z, Wu Q. The binding characteristics of a cyclic nonapeptide, c(CGRRAGGSC), in LNCaP human prostate cancer cells. Oncol Lett. 2012 Sep;4(3):443-449. Epub 2012 Jun 21. PubMed PMID: 22970042; PubMed Central PMCID: PMC3439175.
15: Zhang JY, Deng XM, Li FP, Wang L, Huang QY, Zhang CC, Chen WL. RNase E forms a complex with polynucleotide phosphorylase in cyanobacteria via a cyanobacterial-specific nonapeptide in the noncatalytic region. RNA. 2014 Apr;20(4):568-79. doi: 10.1261/rna.043513.113. Epub 2014 Feb 21. PubMed PMID: 24563514; PubMed Central PMCID: PMC3964918.
16: Baran NM, Tomaszycki ML, Adkins-Regan E. Early Life Manipulations of the Nonapeptide System Alter Pair Maintenance Behaviors and Neural Activity in Adult Male Zebra Finches. Front Behav Neurosci. 2016 Mar 29;10:58. doi: 10.3389/fnbeh.2016.00058. eCollection 2016. PubMed PMID: 27065824; PubMed Central PMCID: PMC4810809.
17: Goodson JL, Thompson RR. Nonapeptide mechanisms of social cognition, behavior and species-specific social systems. Curr Opin Neurobiol. 2010 Dec;20(6):784-94. doi: 10.1016/j.conb.2010.08.020. Epub 2010 Sep 17. Review. PubMed PMID: 20850965.
18: Scrima M, Grimaldi M, Di Marino S, Testa C, Rovero P, Papini AM, Chorev M, D’Ursi AM. Solvent independent conformational propensities of [1,2,3]triazolyl-bridged parathyroid hormone-related peptide-derived cyclo-nonapeptide analogues. Biopolymers. 2012;98(6):535-45. doi: 10.1002/bip.22139. PubMed PMID: 23203759.
19: Klatt JD, Goodson JL. Sex-specific activity and function of hypothalamic nonapeptide neurons during nest-building in zebra finches. Horm Behav. 2013 Nov;64(5):818-24. doi: 10.1016/j.yhbeh.2013.10.001. Epub 2013 Oct 11. PubMed PMID: 24126135.
20: Asami T, Nishizawa N, Matsui H, Nishibori K, Ishibashi Y, Horikoshi Y, Nakayama M, Matsumoto S, Tarui N, Yamaguchi M, Matsumoto H, Ohtaki T, Kitada C. Design, synthesis, and biological evaluation of novel investigational nonapeptide KISS1R agonists with testosterone-suppressive activity. J Med Chem. 2013 Nov 14;56(21):8298-307. doi: 10.1021/jm401056w. Epub 2013 Oct 17. PubMed PMID: 24047141.