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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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spelling v2 64867 2023-11-01 Exploring hydrophobic diastereomeric 2,6-anhydro-glycoheptitols for their enzymatic polymerization with PEG: towards delivery applications a6b1181ebdbe42bd03b24cbdb559d082 0000-0002-5123-4937 Sumati Bhatia Sumati Bhatia true false 2023-11-01 CHEM 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. Journal Article New Journal of Chemistry 44 36 15369 15375 Royal Society of Chemistry (RSC) 1144-0546 1369-9261 1 9 2020 2020-09-01 10.1039/d0nj02642e http://dx.doi.org/10.1039/d0nj02642e COLLEGE NANME Chemistry COLLEGE CODE CHEM Swansea University 2024-01-02T13:13:21.2637791 2023-11-01T10:39:48.8494415 Faculty of Science and Engineering School of Engineering and Applied Sciences - Chemistry Vinod Khatri 1 Sumati Bhatia 0000-0002-5123-4937 2 Satyanarayan Deep 3 Ekta Kohli 4 Rainer Haag 5 Nihar Nalini Senapati 6 Ashok K. Prasad 0000-0003-2350-4984 7
title Exploring hydrophobic diastereomeric 2,6-anhydro-glycoheptitols for their enzymatic polymerization with PEG: towards delivery applications
spellingShingle Exploring hydrophobic diastereomeric 2,6-anhydro-glycoheptitols for their enzymatic polymerization with PEG: towards delivery applications
Sumati Bhatia
title_short Exploring hydrophobic diastereomeric 2,6-anhydro-glycoheptitols for their enzymatic polymerization with PEG: towards delivery applications
title_full Exploring hydrophobic diastereomeric 2,6-anhydro-glycoheptitols for their enzymatic polymerization with PEG: towards delivery applications
title_fullStr Exploring hydrophobic diastereomeric 2,6-anhydro-glycoheptitols for their enzymatic polymerization with PEG: towards delivery applications
title_full_unstemmed Exploring hydrophobic diastereomeric 2,6-anhydro-glycoheptitols for their enzymatic polymerization with PEG: towards delivery applications
title_sort Exploring hydrophobic diastereomeric 2,6-anhydro-glycoheptitols for their enzymatic polymerization with PEG: towards delivery applications
author_id_str_mv a6b1181ebdbe42bd03b24cbdb559d082
author_id_fullname_str_mv a6b1181ebdbe42bd03b24cbdb559d082_***_Sumati Bhatia
author Sumati Bhatia
author2 Vinod Khatri
Sumati Bhatia
Satyanarayan Deep
Ekta Kohli
Rainer Haag
Nihar Nalini Senapati
Ashok K. Prasad
format Journal article
container_title New Journal of Chemistry
container_volume 44
container_issue 36
container_start_page 15369
publishDate 2020
institution Swansea University
issn 1144-0546
1369-9261
doi_str_mv 10.1039/d0nj02642e
publisher Royal Society of Chemistry (RSC)
college_str Faculty of Science and Engineering
hierarchytype
hierarchy_top_id facultyofscienceandengineering
hierarchy_top_title Faculty of Science and Engineering
hierarchy_parent_id facultyofscienceandengineering
hierarchy_parent_title Faculty of Science and Engineering
department_str School of Engineering and Applied Sciences - Chemistry{{{_:::_}}}Faculty of Science and Engineering{{{_:::_}}}School of Engineering and Applied Sciences - Chemistry
url http://dx.doi.org/10.1039/d0nj02642e
document_store_str 0
active_str 0
description 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.
published_date 2020-09-01T13:13:23Z
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score 11.016235

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