Next Article in Journal
Chitosan Nanoparticles as Carriers for the Delivery of ΦKAZ14 Bacteriophage for Oral Biological Control of Colibacillosis in Chickens
Next Article in Special Issue
Fluoride-Promoted Esterification (FPE) Chemistry: A Robust Route to Bis-MPA Dendrons and Their Postfunctionalization
Previous Article in Journal
Coumarins, Xanthones and Related Compounds
Previous Article in Special Issue
Comparison of Properties among Dendritic and Hyperbranched Poly(ether ether ketone)s and Linear Poly(ether ketone)s
Article Menu
Issue 3 (March) cover image

Export Article

Open AccessArticle
Molecules 2016, 21(3), 335;

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
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)
Full-Text   |   PDF [3255 KB, uploaded 10 March 2016]   |  


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

Figure 1

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

Supplementary material


Share & Cite This Article

MDPI and ACS Style

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.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics



[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top