TY - JOUR T1 - 4(R/S)-Amino/guanidino-substituted proline peptides: design, synthesis and DNA transfection properties JF - Chimia Y1 - 2012 A1 - Umashankara, M. A1 - Nanda, Manaswini A1 - Sonar, Mahesh A1 - Ganesh, Krishna N. KW - 4-Aminoproline peptides KW - 4-Guanidino proline peptides KW - Cationic collagen mimetics KW - Cell penetrating peptides AB -

Collagen is a major structural protein found in the connective tissues of higher organisms and mammals and its biomechanical properties are related to the high thermal stability of its triple helical structure. The primary structure of collagen is composed of the repeating tripeptide motif of Pro-Hyp-Gly, where Hyp is 4R-hydroxy proline. Cationic collagen mimetics consisting of [Pro(X)-Pro(Y)-Gly](6) where Pro(X) and Pro(Y) are 4(R/S)-amino/guanidine proline have been synthesized and shown to form triplexes more stable than the unmodified collagen peptide [Pro-Hyp-Gly](6). The origin of hyperstability is due to conformational pre-organization of proline pucker arising from the electronegativity of the cationic group. These cationic collagen peptides are shown to be effective cell penetrating and plasmid DNA transfecting agents. The results have potential for design of new collagen mimetics for biomaterial applications and efficient cell penetrating agents for drug delivery applications.

PB - SWISS CHEMICAL SOC CY - SCHWARZTORSTRASSE 9, CH-3007 BERN, SWITZERLAND VL - 66 IS - 12 U3 - Foreign U4 - 1.045 ER -