Web Release Date: November 1,
Design of a New Multifunctionalized PAMAM Dendrimer with Hydrazide-Terminated Spacer Arm Suitable for Metal-Carbonyl Multilabeling of Aldehyde-Containing Molecules
and
Ecole Nationale Supérieure de Chimie de Paris (ENSCP), Laboratoire de Chimie et Biochimie des Complexes Moléculaires CNRS UMR 7576, 11 rue P. et M. Curie, 75231 Paris cedex 05, France, University of Lodz, Department of Organic Chemistry, 90-136 Lodz, Narutowicza 68, Poland, ENSCP, Service de RMN, 11 rue P. et M. Curie, 75231 Paris cedex 05, France, and Institut de Chimie des Substances Naturelles (ICSN), UPR-2301 CNRS, Laboratoire de Spectrométrie de Masse, Av. de la Terrasse, 91198 Gif sur Yvette Cedex, France
Received July 20, 2007
Revised Manuscript Received September 17, 2007
Abstract:
We describe herein the synthesis of generation 4 (G4) poly(amidoamine) (PAMAM) dendrimers
bearing (1) a nitroaniline derivative as an NMR probe, (2) (
5-cyclopentadienyl)iron dicarbonyl succinimidato
complexes as infrared probes for carbonyl metallo immunoassay, (3) acetamide groups for increased solubility,
and (4) hydrazide functions at the extremity of five-carbon atom spacer arms for the labeling of aldehyde-containing
molecules. The step-by-step building of these multifunctionalized dendrimers was monitored by 1H NMR
spectroscopy, Fourier transform infrared (FT-IR) spectroscopy, and by matrix-assisted laser desorption ionization
time-of-flight (MALDI-TOF) mass spectrometry. Substitution of terminal amine groups of PAMAM dendrimers
with appropriate functional groups provides complex dendrimeric structures with a wide range of applications.
The final goal of this study is the development of new reagents suitable for the metal-carbonyl multilabeling of
immunological reagents such as antibodies.
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