59481-26-4

Basic information

• Product Name: cyclo(3-14)H-Ala-Gly-Cys-Lys-Asn-Phe-Phe-D-Tyr-Lys-Thr-Phe-Thr-Ser-Cys-OH
• CAS NO: 59481-26-4
• Molecular Weight: 1614.87
• Mol File: 59481-26-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: cyclo(3-14)H-Ala-Gly-Cys-Lys-Asn-Phe-Phe-D-Tyr-Lys-Thr-Phe-Thr-Ser-Cys-OH(CAS DataBase Reference)
• NIST Chemistry Reference: cyclo(3-14)H-Ala-Gly-Cys-Lys-Asn-Phe-Phe-D-Tyr-Lys-Thr-Phe-Thr-Ser-Cys-OH(59481-26-4)
• EPA Substance Registry System: cyclo(3-14)H-Ala-Gly-Cys-Lys-Asn-Phe-Phe-D-Tyr-Lys-Thr-Phe-Thr-Ser-Cys-OH(59481-26-4)

Safety Data

• Hazardous Substances Data: 59481-26-4(Hazardous Substances Data)

Upstream product

• 4530-20-5 BOC-glycine 
• 15761-38-3 L-N-Boc-Ala 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 15260-10-3 N-Boc-O-benzyl-L-threonine 
• 23680-31-1 BOC-O-benzyl-L-serine 
• 18942-46-6 N-(tert-butyloxycarbonyl)-S-(4-methoxybenzyl)cysteine 
• 54613-99-9 Boc-(S)-Lys(2-Cl-Z)-OH 
• 81189-61-9 Boc-D-Tyr(2-BrZ)-OH 
• 65420-40-8 (S)-2-tert-Butoxycarbonylamino-N-(9H-xanthen-9-yl)-succinamic acid 

Relevant articles and documents

N-Imidazolebenzyl-histidine substitution in somatostatin and in its octapeptide analogue modulates receptor selectivity and function

Despite 3 decades of focused chemical, biological, structural, and clinical developments, unusual properties of somatostatin (SRIF, 1) analogues are still being uncovered. Here we report the unexpected functional properties of 1 and the octapeptide cyclo(3-14)H-Cys-Phe-Phe-Trp8-Lys-Thr-Phe-Cys-OH (somatostatin numbering; OLT-8, 9) substituted by imBzl-l- or -d-His at position 8. These analogues were tested for their binding affinity to the five human somatostatin receptors (sst1-5), as well as for their functional properties (or functionalities) in an sst3 internalization assay and in an sst3 luciferase reporter gene assay. While substitution of Trp8 in somatostatin by imBzl-l- or -d-His8 results in sst3 selectivity, substitution of Trp8 in the octapeptide 9 by imBzl-l- or -d-His8 results in loss of binding affinity for sst1,2,4,5 and a radical functional switch from agonist to antagonist.