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``Clickable'', Trifunctional Magnetite Nanoparticles and Their Chemoselective Biofunctionalization

Das, Manasmita and Bandyopadhyay, Debarati and Mishra, Debasish and Datir, Satyajit and Dhak, Prasanta and Jain, Sanyog and Maiti, Tapas Kumar and Basak, Amit and Pramanik, Panchanan (2011) ``Clickable'', Trifunctional Magnetite Nanoparticles and Their Chemoselective Biofunctionalization. In: Bioconjugate Chemistry, 22 (6). pp. 1181-1193.

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Official URL: http://pubs.acs.org/doi/abs/10.1021/bc2000484


A multifunctional iron oxide based nanoformulation for combined cancer-targeted therapy and multimodal imaging has been meticulously designed and synthesized using a chemoselective ligation approach. Novel superparamagnetic magnetite nanoparticles simultaneously functionalized with amine, carboxyl, and azide groups were fabricated through a sequence of stoichiometrically controllable partial succinylation and Cu (II) catalyzed diazo transfer on the reactive amine termini of 2-aminoethylphosphonate grafted magnetite nanoparticles (MNPs). Functional moieties associated with MNP surface were chemoselectively conjugated with rhodamine B isothiocyanate (RITC), propargyl folate (FA), and paclitaxel (PTX) via tandem nucleophic addition of amine to isothithiocyanates, Cu (I) catalyzed azide-alkyne click chemistry and carbodiimide-promoted esterification. An extensive in vitro study established that the bioactives chemoselectively appended to the magnetite core bequeathed multifunctionality to the nanoparticles without any loss of activity of the functional molecules. Multifunctional nanoparticles, developed in the course of the study, could selectively target and induce apoptosis to folate-receptor (FR) overexpressing cancer cells with enhanced efficacy as compared to the free drug. In addition, the dual optical and magnetic properties of the synthesized nanoparticles aided in the real-time tracking of their intracellular pathways also as apoptotic events through dual fluorescence and MR-based imaging.

Item Type: Journal Article
Publication: Bioconjugate Chemistry
Publisher: American Chemical society
Additional Information: Copyright of this article belongs to American Chemical society.
Department/Centre: Division of Biological Sciences > Molecular Biophysics Unit
Date Deposited: 29 Jun 2011 09:54
Last Modified: 29 Jun 2011 09:54
URI: http://eprints.iisc.ac.in/id/eprint/38644

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