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Synthesis and characterization of pH responsive D-glucosamine based molecular gelators

Small molecular gelators are a class of compounds with potential applications for soft biomaterials. Low molecular weight hydrogelators are especially useful for exploring biomedical applications. Previously, we found that 4,6-O-benzylidene acetal protected D-glucose and D-glucosamine are well-suite...

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Autores principales: Goyal, Navneet, Mangunuru, Hari P R, Parikh, Bargav, Shrestha, Sonu, Wang, Guijun
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4311663/
https://www.ncbi.nlm.nih.gov/pubmed/25670980
http://dx.doi.org/10.3762/bjoc.10.328
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author Goyal, Navneet
Mangunuru, Hari P R
Parikh, Bargav
Shrestha, Sonu
Wang, Guijun
author_facet Goyal, Navneet
Mangunuru, Hari P R
Parikh, Bargav
Shrestha, Sonu
Wang, Guijun
author_sort Goyal, Navneet
collection PubMed
description Small molecular gelators are a class of compounds with potential applications for soft biomaterials. Low molecular weight hydrogelators are especially useful for exploring biomedical applications. Previously, we found that 4,6-O-benzylidene acetal protected D-glucose and D-glucosamine are well-suited as building blocks for the construction of low molecular weight gelators. To better understand the scope of D-glucosamine derivatives as gelators, we synthesized and screened a novel class of N-acetylglucosamine derivatives with a p-methoxybenzylidene acetal protective group. This modification did not exert a negative influence on the gelation. On the contrary, it actually enhanced the gelation tendency for many derivatives. The introduction of the additional methoxy group on the phenyl ring led to low molecular weight gelators with a higher pH responsiveness. The resulting gels were stable at neutral pH values but degraded in an acidic environment. The release profiles of naproxen from the pH responsive gels were also analyzed under acidic and neutral conditions. Our findings are useful for the design of novel triggered release self-assembling systems and can provide an insight into the influence of the the structure on gelation.
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spelling pubmed-43116632015-02-10 Synthesis and characterization of pH responsive D-glucosamine based molecular gelators Goyal, Navneet Mangunuru, Hari P R Parikh, Bargav Shrestha, Sonu Wang, Guijun Beilstein J Org Chem Full Research Paper Small molecular gelators are a class of compounds with potential applications for soft biomaterials. Low molecular weight hydrogelators are especially useful for exploring biomedical applications. Previously, we found that 4,6-O-benzylidene acetal protected D-glucose and D-glucosamine are well-suited as building blocks for the construction of low molecular weight gelators. To better understand the scope of D-glucosamine derivatives as gelators, we synthesized and screened a novel class of N-acetylglucosamine derivatives with a p-methoxybenzylidene acetal protective group. This modification did not exert a negative influence on the gelation. On the contrary, it actually enhanced the gelation tendency for many derivatives. The introduction of the additional methoxy group on the phenyl ring led to low molecular weight gelators with a higher pH responsiveness. The resulting gels were stable at neutral pH values but degraded in an acidic environment. The release profiles of naproxen from the pH responsive gels were also analyzed under acidic and neutral conditions. Our findings are useful for the design of novel triggered release self-assembling systems and can provide an insight into the influence of the the structure on gelation. Beilstein-Institut 2014-12-23 /pmc/articles/PMC4311663/ /pubmed/25670980 http://dx.doi.org/10.3762/bjoc.10.328 Text en Copyright © 2014, Goyal et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Goyal, Navneet
Mangunuru, Hari P R
Parikh, Bargav
Shrestha, Sonu
Wang, Guijun
Synthesis and characterization of pH responsive D-glucosamine based molecular gelators
title Synthesis and characterization of pH responsive D-glucosamine based molecular gelators
title_full Synthesis and characterization of pH responsive D-glucosamine based molecular gelators
title_fullStr Synthesis and characterization of pH responsive D-glucosamine based molecular gelators
title_full_unstemmed Synthesis and characterization of pH responsive D-glucosamine based molecular gelators
title_short Synthesis and characterization of pH responsive D-glucosamine based molecular gelators
title_sort synthesis and characterization of ph responsive d-glucosamine based molecular gelators
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4311663/
https://www.ncbi.nlm.nih.gov/pubmed/25670980
http://dx.doi.org/10.3762/bjoc.10.328
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