TY - JOUR
T1 - IMPROVEMENT OF HEAD-TO-TAIL RGD PEPTIDE CYCLIZATION EFFICIENCY COMBINING LOW TEMPERATURE AND LITHIUM CHLORIDE
AU - Gauna, Adriana
AU - Sanchez-Hoyos, Fredys
AU - Huerta, Maycol
AU - Kogan, Marcelo J.
AU - Araya, Eyleen
N1 - Publisher Copyright:
© 2024 Sociedad Chilena de Quimica. All rights reserved.
PY - 2024
Y1 - 2024
N2 - RGD-containing peptides (linear and cyclic) have been developed to target some types of cancer cells through interaction with the αvβ3 Integrin. Due to their reduced conformational freedom, cyclic peptides exhibit improved metabolic stability and binding affinity/specificity to their molecular targets. However, macrocyclization is considered a significant synthetic challenge that is affected by the ring size, peptide sequence, and reaction conditions, making tetra- and pentapeptides more difficult to cyclize. In this work, we report some optimized cyclization conditions for the obtention of a cyclic RGDfK peptide that combine the use of low reaction temperature and the addition of LiCl, a combination not yet reported that resulted in a reduction of the formation of oligomers and an improvement of the cyclization efficiency.
AB - RGD-containing peptides (linear and cyclic) have been developed to target some types of cancer cells through interaction with the αvβ3 Integrin. Due to their reduced conformational freedom, cyclic peptides exhibit improved metabolic stability and binding affinity/specificity to their molecular targets. However, macrocyclization is considered a significant synthetic challenge that is affected by the ring size, peptide sequence, and reaction conditions, making tetra- and pentapeptides more difficult to cyclize. In this work, we report some optimized cyclization conditions for the obtention of a cyclic RGDfK peptide that combine the use of low reaction temperature and the addition of LiCl, a combination not yet reported that resulted in a reduction of the formation of oligomers and an improvement of the cyclization efficiency.
KW - Cyclic(RGDfK)
KW - Head-to-tail cyclization
KW - Integrins
KW - peptide cyclization conditions
KW - Targeting
UR - http://www.scopus.com/inward/record.url?scp=85210539832&partnerID=8YFLogxK
U2 - 10.4067/s0717-97072024000106038
DO - 10.4067/s0717-97072024000106038
M3 - Article
AN - SCOPUS:85210539832
SN - 0717-9324
VL - 69
SP - 6038
EP - 6041
JO - Journal of the Chilean Chemical Society
JF - Journal of the Chilean Chemical Society
IS - 1
ER -