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Exploring hydrophobic diastereomeric 2,6-anhydro-glycoheptitols for their enzymatic polymerization with PEG: towards delivery applications

Vinod Khatri, Sumati Bhatia Orcid Logo, Satyanarayan Deep, Ekta Kohli, Rainer Haag, Nihar Nalini Senapati, Ashok K. Prasad Orcid Logo

New Journal of Chemistry, Volume: 44, Issue: 36, Pages: 15369 - 15375

Swansea University Author: Sumati Bhatia Orcid Logo

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DOI (Published version): 10.1039/d0nj02642e

Abstract

Two sugar PEG-based amphiphilic copolymers have been synthesized by Novozym®-435-catalyzed greener solvent free transesterification reaction of diastereomeric 2,6-anhydro-3,4,5-tri-O-benzyl-glucoheptitol and 2,6-anhydro-3,4,5-tri-O-benzyl-mannoheptitol with PEG-1000 diethyl ester in 80 and 76% yield...

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Published in: New Journal of Chemistry
ISSN: 1144-0546 1369-9261
Published: Royal Society of Chemistry (RSC) 2020
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URI: https://cronfa.swan.ac.uk/Record/cronfa64867
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Abstract: Two sugar PEG-based amphiphilic copolymers have been synthesized by Novozym®-435-catalyzed greener solvent free transesterification reaction of diastereomeric 2,6-anhydro-3,4,5-tri-O-benzyl-glucoheptitol and 2,6-anhydro-3,4,5-tri-O-benzyl-mannoheptitol with PEG-1000 diethyl ester in 80 and 76% yields, respectively. It has been observed that the configurational change at one of the carbons of diastereomeric 2,6-anhydro-heptitols has significant bearing on the degree of polymerization and characteristics of the synthesized polymers. Thus, the study of physico-chemical characteristics of synthesized anhydroglucoheptitol- and anhydromannoheptitol-PEG copolymers revealed that their aqueous solution forms spherical micelles of hydrodynamic diameters 11.2 and 6.4 nm, respectively. Micelles derived from both the amphiphilic copolymers have the potential to solubilize the hydrophobic dye, Nile red. Furthermore, a fluorescence microscopy study revealed that Nile red encapsulated micelles of synthesized amphiphilic copolymers uniformly internalized in A549 cells and thus can be used as a cargo carrier in biological systems. The viability of A549 cells was found to be very high even at a concentration of 500 μg mL−1 of copolymer indicating that they are cyto-compatible.
College: Faculty of Science and Engineering
Issue: 36
Start Page: 15369
End Page: 15375