Issue 28, 2012

Non-peptidic cell-penetrating agents: synthesis of oligomeric chiral bicyclic guanidinium vectors

Abstract

Polycationic oligo(chiral bicyclic guanidines) constitute useful non-peptidic penetrating agents for cell uptake and protein surface recognition. We report herein improved and selective procedures for the preparation of oligoguanidinium scaffolds linked through thioether bonds, with similar or different groups and functions at both ends of the chain. Two synthetic strategies were developed to obtain these compounds in relatively good yields from a common thioacetate precursor: generation of a disulfide intermediate or thiolate formation. Thus, tetraguanidinium intermediates 8 and 22 are best synthesized by the disulfide route, whereas hexamer 29, octamer 31, and trimer 37 arise from a combination of both the disulfide and the thioacetate routes. Finally, tetramer 28 can be readily obtained from either strategy.

Graphical abstract: Non-peptidic cell-penetrating agents: synthesis of oligomeric chiral bicyclic guanidinium vectors

Supplementary files

Article information

Article type
Paper
Submitted
02 Mar 2012
Accepted
24 May 2012
First published
25 May 2012

Org. Biomol. Chem., 2012,10, 5417-5430

Non-peptidic cell-penetrating agents: synthesis of oligomeric chiral bicyclic guanidinium vectors

J. Valero, M. Van Gool, R. Pérez-Fernández, P. Castreño, J. Sánchez-Quesada, P. Prados and J. de Mendoza, Org. Biomol. Chem., 2012, 10, 5417 DOI: 10.1039/C2OB25467K

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