A Convenient Route to Diversely Substituted Icosahedral Closomer Nanoscaffolds

Overview

Journal J Am Chem Soc

Publisher American Chemical Society

Specialty Chemistry

Date 2011 Jul 20

PMID 21766843

Citations 11

Authors

Satish S Jalisatgi

Vikas S Kulkarni

Betty Tang

Zachary H Houston

Mark W Lee Jr

M Frederick Hawthorne

Affiliations

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Abstract

The design and synthesis of icosahedral polyhedral borane closomer motifs based upon carbonate and carbamate anchoring groups for biomedical applications are described. Dodecacarbamate closomers containing easily accessible groups of interest at their linker termini were synthesized via activation of the B-OH vertices as aryl carbonates and their subsequent reaction with primary amines. Novel dodecacarbonate closomers were successfully synthesized for the first time by reacting [closo-B(12)(OH)(12)](2-) with an excess of respective aryl chloroformates, utilizing relatively short reaction times, mild conditions and simple purification strategies, all of which had previously presented difficulties in closomer chemistry. This methodology for the 12-fold degenerate synthesis of carbonate and carbamate closomers will greatly facilitate further exploration of closomers as monodisperse nanomolecular delivery platforms.

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