Journal article 257 views
Exploring hydrophobic diastereomeric 2,6-anhydro-glycoheptitols for their enzymatic polymerization with PEG: towards delivery applications
Vinod Khatri,
Sumati Bhatia ,
Satyanarayan Deep,
Ekta Kohli,
Rainer Haag,
Nihar Nalini Senapati,
Ashok K. Prasad
New Journal of Chemistry, Volume: 44, Issue: 36, Pages: 15369 - 15375
Swansea University Author: Sumati Bhatia
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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...
Published in: | New Journal of Chemistry |
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ISSN: | 1144-0546 1369-9261 |
Published: |
Royal Society of Chemistry (RSC)
2020
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Online Access: |
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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. |
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College: |
Faculty of Science and Engineering |
Issue: |
36 |
Start Page: |
15369 |
End Page: |
15375 |