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FunctionalizationofNanotubeswithAzoicO-glycoside

ConferencePaper·September2014

DOI:10.13140/2.1.2553.7609

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Functionalization of Nanotubes with Azoic O-glycoside

Ivan Flores Rosales, Pamela Hurtado Ponce, Marco Brito-Arias*

Biotechnology Unit

National Polytechnic Institute of Mexico (UPIBI-IPN)

Avenida Acueducto s/n, La Laguna Ticoman, Mexico City DF, 07340

Email: mbrito@ipn.mx

Keywords: Phenylazonaphtyl glycosides, nanotubes, TEM microscopy, azoic glycosides.

Abstract Text: This work describes the coupling reaction between an azoic O-glycoside with a single wall nanotube acyl chloride to generate the nanotube-azoic O-glycoside complex which was analyzed by

TEM microscopy. The study showed the presence of nodules or aggregates along the cylindrical

nanotube, suggesting the functionalization through a covalent interaction.

Introduction

Nanotubes are defined as coaxial cylindrical units nanoscale graphite (1 to 100 nm) with walls composed of carbon hexagonal mesh with both ends rounded. Nanotubes have had a major impact in biomedical

areas such as molecules with potential use as drug carriers, biosensors, encapsulating enzymes, neuronal

and bone growth among others. Because of the particular importance of the coupling of carbohydrates to nanotubes to improve solubility, increase the biocompatibility and specificity towards specific targets, we

propose the synthesis of nanotubes (SWNT) linked to azoic O-glycosides using a covalent approach. The

presence of the dye will also allow the detection of the nanotubes complex by spectroscopy or confocal microscopy which will allow us to find the nanotubes within cells.[1]

Methodology

The strategy employed for the preparation of the complex nanotube-azoic glycoside consisted in the

coupling reaction between the nanotube acyl chloride with Sudan II-β-D-galactopyranoside as depicted

in scheme. The reaction conditions used were sonication in THF at room temperature. The nanotube was centrifuged and washed (3 x 2 mL) with THF until the solution was colorless. The nanotubes obtained as

pellet were dried in oven, suspended in isopropanol and analyzed by TEM microscopy.

Results and Discussion

The azoic glycoside was synthesized by direct coupling reaction between acetobromo glucose with Sudan

II under the Koenigs-Knorr conditions, and deprotected under Zemplen conditios.[2] The resulting azoic glycoside was condensed with nanotube previously derivatized to the acyl chloride form. The

reaction was repeatedly washed and centrifuged to assure that the nanotubes were free of unreacted

glycoside. The suspended nanotubes were analyzed by TEM microscopy, observing for the unreacted nanotube a uniform surface without the presence of aggregates around the cylinder. On the other hand for

the complex nanotube- azoic O-glycosides it was observed the presence of small bundles around the

cylindrical nanotubes at different resolutions in agreement with those reported by Wu et al for the reaction with glycodendrimers [3] (figures 2 and 3).

Scheme

Cl

O

nO

OHOH

HO

OH

O

N

N

+

O

n

O

HOHO

OH

O

N

N

O

Scheme. Synthetic approach for the preparation

of complex nanotube-azoic glycoside.

Figure 1. Non functionalized single wall nanotube.

Figure 2. Functionalized nanotube with glycoside

coating the SWNT.

Figure 3. Functionalized nanotube.

References

[1] H. Sun, P. She, G. Lu, K. Xu, W. Zhang, Z. Liu. Recent advances in the development of functionalized carbon nanotubes: a versatile vector for drug delivery. J Mater Sci 2014 49:6845–

6854.

[2] Marco Brito-Arias Synthesis and Characterization of Glycosides Ed Springer 2007, 73-74.

[3] P. Wu, X. Chen, N. Hu, U. Tam, O. Blixt, Al. Zettl, and C. R. Bertozzi. Biocompatible Carbon

Nanotubes Generated by Functionalizationwith Glycodendrimers. Angew. Chem. Int. Ed. 2008, 47,

5022 –5025.