872718-97-3

Basic information

• Product Name: [D-Tyr⁴⁶,D-Pya⁽⁴⁾⁴⁷,Ala⁴⁸,azaGly⁵¹,Arg(Me)⁵³,Trp⁵⁴]metastin(46-54)
• CAS NO: 872718-97-3
• Molecular Weight: 1161.33
• Mol File: 872718-97-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: [D-Tyr⁴⁶,D-Pya⁽⁴⁾⁴⁷,Ala⁴⁸,azaGly⁵¹,Arg(Me)⁵³,Trp⁵⁴]metastin(46-54)(CAS DataBase Reference)
• NIST Chemistry Reference: [D-Tyr⁴⁶,D-Pya⁽⁴⁾⁴⁷,Ala⁴⁸,azaGly⁵¹,Arg(Me)⁵³,Trp⁵⁴]metastin(46-54)(872718-97-3)
• EPA Substance Registry System: [D-Tyr⁴⁶,D-Pya⁽⁴⁾⁴⁷,Ala⁴⁸,azaGly⁵¹,Arg(Me)⁵³,Trp⁵⁴]metastin(46-54)(872718-97-3)

Safety Data

• Hazardous Substances Data: 872718-97-3(Hazardous Substances Data)

Upstream product

• 205528-30-9 Fmoc-D-3-(4-pyridyl)Ala-OH 
• 35661-60-0 Fmoc-Leu-OH 
• 35661-39-3 N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine 
• 47672-25-3 N-trityl-L-phenylalanine 
• 71989-33-8 Fmoc-Ser(tBu)-OH 
• 118488-18-9 Fmoc-D-Tyr(O-tBu)-OH 

Relevant articles and documents

Physicochemically and pharmacokinetically stable nonapeptide kiss1 receptor agonists with highly potent testosterone-suppressive activity

Modifications of metastin(45-54) produced peptide analogues with higher metabolic stability than metastin(45-54). N-terminally truncated nonapeptide 4 ([d-Tyr46,d-Pya(4)47,azaGly51,Arg(Me) 53]metastin(46-54)) is a representative compound with both potent agonistic activity and metabolic stability. Although 4 had more potent testosterone-suppressant activity than metastin, it possessed physicochemical instability at pH 7 and insufficient in vivo activity. Instability at pH 7 was dependent upon Asn48 and Ser49; substitution of Ser 49 with Thr49 reduced this instability and maintained KISS1 receptor agonistic activity. Furthermore, [d-Tyr46,d-Trp 47,Thr49,azaGly51,Arg(Me)53,Trp 54]metastin(46-54) (14) showed 2-fold greater [Ca2+] i-mobilizing activity than metastin(45-54) and an apparent increase in physicochemical stability. N-terminal acetylation of 14 resulted in the most potent analogue, 22 (Ac-[d-Tyr46,d-Trp47,Thr 49,azaGly51,Arg(Me)53,Trp54] metastin(46-54)). With continuous administration, 22 possessed 10-50-fold more potent testosterone-suppressive activity in rats than 4. These results suggested that a controlled release of short-length KISS1 receptor agonists can suppress the hypothalamic-pituitary-gonadal axis and reduce testosterone levels. Compound 22 was selected for further preclinical evaluation for hormone-dependent diseases.