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Molecules 2016, 21(3), 335; doi:10.3390/molecules21030335

Functionalization of a Triazine Dendrimer Presenting Four Maleimides on the Periphery and a DOTA Group at the Core

Department of Chemistry and Biochemistry, Texas Christian University, Fort Worth, TX 76129, USA
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Author to whom correspondence should be addressed.
Academic Editor: Ashok Kakkar
Received: 28 January 2016 / Revised: 25 February 2016 / Accepted: 26 February 2016 / Published: 10 March 2016
(This article belongs to the Special Issue Functional Dendrimers)

Abstract

A readily and rapidly accessible triazine dendrimer was manipulated in four steps with 23% overall yield to give a construct displaying four maleimide groups and DOTA. The maleimide groups of the dendrimer are sensitive to hydrolysis under basic conditions. The addition of up to four molecules of water can be observed via mass spectrometry and HPLC. The evolution in the alkene region of the 1H-NMR—the transformation of the maleimide singlet to the appearance of two doublets—is consistent with imide hydrolysis and not the Michael addition. The hydrolysis events that proceeded over hours are sufficiently slower than the desired thiol addition reactions that occur in minutes. The addition of thiols to maleimides can be accomplished in a variety of solvents. The thiols examined derived from cysteine and include the protected amino acid, a protected dipeptide, and native oligopeptides containing either 9 or 18 amino acids. The addition reactions were monitored with HPLC and mass spectrometry in most cases. Complete substitution was observed for small molecule reactants. The model peptides containing nine or eighteen amino acids provided a mixture of products averaging between 3 and 4 substitutions/dendrimer. The functionalization of the chelate group with gadolinium was also accomplished easily. View Full-Text
Keywords: dendrimer; triazine; DOTA; maleimide; peptide; bioconjugate; theranostic dendrimer; triazine; DOTA; maleimide; peptide; bioconjugate; theranostic
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Lee, C.; Ji, K.; Simanek, E.E. Functionalization of a Triazine Dendrimer Presenting Four Maleimides on the Periphery and a DOTA Group at the Core. Molecules 2016, 21, 335.

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