Synthetic biohybrid peptidoglycan oligomers enable pan-bacteria-specific labeling and imaging : in vitro and in vivo

Peptidoglycan is the core component of the bacterial cell wall, which makes it an attractive target for the development of bacterial targeting agents. Intercepting its enzymatic assembly with synthetic substrates allows for labeling and engineering of live bacterial cells. Over the past two decades,...

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Main Authors: He Jing-Xi, Hoang, Kim Le Mai, Kho, Shu Hui, Guo, Zhong, Zhong, Wenbin, Thappeta, Kishore Reddy Venkata, Zamudio-Vázquez, Rubi, Hoo, Sin Ni, Xiong, Qirong, Duan, Hongwei, Yang, Liang, Chan-Park, Mary Bee Eng, Liu, Xue-Wei
Other Authors: School of Chemical and Biomedical Engineering
Format: Article
Language:English
Published: 2020
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Online Access:https://hdl.handle.net/10356/138576
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1385762024-03-27T01:16:52Z Synthetic biohybrid peptidoglycan oligomers enable pan-bacteria-specific labeling and imaging : in vitro and in vivo He Jing-Xi Hoang, Kim Le Mai Kho, Shu Hui Guo, Zhong Zhong, Wenbin Thappeta, Kishore Reddy Venkata Zamudio-Vázquez, Rubi Hoo, Sin Ni Xiong, Qirong Duan, Hongwei Yang, Liang Chan-Park, Mary Bee Eng Liu, Xue-Wei School of Chemical and Biomedical Engineering School of Physical and Mathematical Sciences NTU Institute for Health Technologies Science::Chemistry Peptidoglycan is the core component of the bacterial cell wall, which makes it an attractive target for the development of bacterial targeting agents. Intercepting its enzymatic assembly with synthetic substrates allows for labeling and engineering of live bacterial cells. Over the past two decades, small-molecule-based labeling agents, such as antibiotics, D-amino acids or monosaccharides have been developed for probing biological processes in bacteria. Herein, peptidoglycan oligomers, substrates for transglycosylation, are prepared for the first time using a top-down approach, which starts from chitosan as a cheap feedstock. A high efficiency of labeling has been observed in all bacterial strains tested using micromolar substrates. In contrast, uptake into mammalian cells was barely observable. Additional mechanistic studies support a hypothesis of bacteria-specific metabolic labeling rather than non-specific binding to the bacterial surface. Eventually, its practicality in bacterial targeting capability is demonstrated in resistant strain detection and in vivo infection models. MOE (Min. of Education, S’pore) Accepted version 2020-05-08T09:05:48Z 2020-05-08T09:05:48Z 2020 Journal Article He, J.-X., Hoang, K. L. M., Kho, S. H., Guo, Z., Zhong, W., Thappeta, K. R. V., . . . Liu, X.-W. (2020). Synthetic biohybrid peptidoglycan oligomers enable pan-bacteria-specific labeling and imaging : in vitro and in vivo. Chemical Science, 11(12), 3171-3179. doi:10.1039/c9sc06345e 2041-6520 https://hdl.handle.net/10356/138576 10.1039/c9sc06345e 2-s2.0-85082672981 12 11 3171 3179 en Chemical Science © 2020 The Author(s) (published by Royal Society of Chemistry) (Open Access). This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. application/pdf application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic Science::Chemistry
spellingShingle Science::Chemistry
He Jing-Xi
Hoang, Kim Le Mai
Kho, Shu Hui
Guo, Zhong
Zhong, Wenbin
Thappeta, Kishore Reddy Venkata
Zamudio-Vázquez, Rubi
Hoo, Sin Ni
Xiong, Qirong
Duan, Hongwei
Yang, Liang
Chan-Park, Mary Bee Eng
Liu, Xue-Wei
Synthetic biohybrid peptidoglycan oligomers enable pan-bacteria-specific labeling and imaging : in vitro and in vivo
description Peptidoglycan is the core component of the bacterial cell wall, which makes it an attractive target for the development of bacterial targeting agents. Intercepting its enzymatic assembly with synthetic substrates allows for labeling and engineering of live bacterial cells. Over the past two decades, small-molecule-based labeling agents, such as antibiotics, D-amino acids or monosaccharides have been developed for probing biological processes in bacteria. Herein, peptidoglycan oligomers, substrates for transglycosylation, are prepared for the first time using a top-down approach, which starts from chitosan as a cheap feedstock. A high efficiency of labeling has been observed in all bacterial strains tested using micromolar substrates. In contrast, uptake into mammalian cells was barely observable. Additional mechanistic studies support a hypothesis of bacteria-specific metabolic labeling rather than non-specific binding to the bacterial surface. Eventually, its practicality in bacterial targeting capability is demonstrated in resistant strain detection and in vivo infection models.
author2 School of Chemical and Biomedical Engineering
author_facet School of Chemical and Biomedical Engineering
He Jing-Xi
Hoang, Kim Le Mai
Kho, Shu Hui
Guo, Zhong
Zhong, Wenbin
Thappeta, Kishore Reddy Venkata
Zamudio-Vázquez, Rubi
Hoo, Sin Ni
Xiong, Qirong
Duan, Hongwei
Yang, Liang
Chan-Park, Mary Bee Eng
Liu, Xue-Wei
format Article
author He Jing-Xi
Hoang, Kim Le Mai
Kho, Shu Hui
Guo, Zhong
Zhong, Wenbin
Thappeta, Kishore Reddy Venkata
Zamudio-Vázquez, Rubi
Hoo, Sin Ni
Xiong, Qirong
Duan, Hongwei
Yang, Liang
Chan-Park, Mary Bee Eng
Liu, Xue-Wei
author_sort He Jing-Xi
title Synthetic biohybrid peptidoglycan oligomers enable pan-bacteria-specific labeling and imaging : in vitro and in vivo
title_short Synthetic biohybrid peptidoglycan oligomers enable pan-bacteria-specific labeling and imaging : in vitro and in vivo
title_full Synthetic biohybrid peptidoglycan oligomers enable pan-bacteria-specific labeling and imaging : in vitro and in vivo
title_fullStr Synthetic biohybrid peptidoglycan oligomers enable pan-bacteria-specific labeling and imaging : in vitro and in vivo
title_full_unstemmed Synthetic biohybrid peptidoglycan oligomers enable pan-bacteria-specific labeling and imaging : in vitro and in vivo
title_sort synthetic biohybrid peptidoglycan oligomers enable pan-bacteria-specific labeling and imaging : in vitro and in vivo
publishDate 2020
url https://hdl.handle.net/10356/138576
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