Design and self-assembly of guanidinium-functionalized polycarbonates for increased selectivity towards pathogenic bacteria
Guanidinium-functionalized amphiphilic polycarbonates have recently been proven to be effective in treating infections caused by multidrug resistant bacteria. These positively charged polymers are able to electrostatically interact with the negatively charged microbial membrane, before translocating...
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| Format: | Thesis-Doctor of Philosophy |
| Language: | English |
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Nanyang Technological University
2023
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| Online Access: | https://hdl.handle.net/10356/164855 |
| _version_ | 1811681705091661824 |
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| author | Tan, Jason |
| author2 | Zhao Yanli |
| author_facet | Zhao Yanli Tan, Jason |
| author_sort | Tan, Jason |
| collection | NTU |
| description | Guanidinium-functionalized amphiphilic polycarbonates have recently been proven to be effective in treating infections caused by multidrug resistant bacteria. These positively charged polymers are able to electrostatically interact with the negatively charged microbial membrane, before translocating across to kill the microbe by targeting intracellular proteins and genetic materials. The design of these polymers has been tricky as it is imperative to find the right amphiphilic balance. It is common to increase their hydrophobicity for a more efficient antimicrobial activity. However, at elevated levels of hydrophobicity, they also indiscriminately disrupt healthy mammalian cell membrane due to enhanced membrane affinity. Moreover, due to their cationic nature, they often interact with the anionic salic acid, found on the surface of red blood cells, resulting in hemagglutination. This has hampered their in vivo application. In this thesis, we address these issues by looking at strategies to improve the selectivity and biocompatibility of these polymers. |
| first_indexed | 2024-10-01T03:45:11Z |
| format | Thesis-Doctor of Philosophy |
| id | ntu-10356/164855 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T03:45:11Z |
| publishDate | 2023 |
| publisher | Nanyang Technological University |
| record_format | dspace |
| spelling | ntu-10356/1648552024-08-15T02:40:56Z Design and self-assembly of guanidinium-functionalized polycarbonates for increased selectivity towards pathogenic bacteria Tan, Jason Zhao Yanli School of Chemistry, Chemical Engineering and Biotechnology Institute of Bioengineering and Bioimaging (IBB), A*STAR zhaoyanli@ntu.edu.sg Science::Chemistry Guanidinium-functionalized amphiphilic polycarbonates have recently been proven to be effective in treating infections caused by multidrug resistant bacteria. These positively charged polymers are able to electrostatically interact with the negatively charged microbial membrane, before translocating across to kill the microbe by targeting intracellular proteins and genetic materials. The design of these polymers has been tricky as it is imperative to find the right amphiphilic balance. It is common to increase their hydrophobicity for a more efficient antimicrobial activity. However, at elevated levels of hydrophobicity, they also indiscriminately disrupt healthy mammalian cell membrane due to enhanced membrane affinity. Moreover, due to their cationic nature, they often interact with the anionic salic acid, found on the surface of red blood cells, resulting in hemagglutination. This has hampered their in vivo application. In this thesis, we address these issues by looking at strategies to improve the selectivity and biocompatibility of these polymers. Doctor of Philosophy 2023-02-20T08:52:14Z 2023-02-20T08:52:14Z 2023 Thesis-Doctor of Philosophy Tan, J. (2023). Design and self-assembly of guanidinium-functionalized polycarbonates for increased selectivity towards pathogenic bacteria. Doctoral thesis, Nanyang Technological University, Singapore. https://hdl.handle.net/10356/164855 https://hdl.handle.net/10356/164855 10.32657/10356/164855 en This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License (CC BY-NC 4.0). application/pdf Nanyang Technological University |
| spellingShingle | Science::Chemistry Tan, Jason Design and self-assembly of guanidinium-functionalized polycarbonates for increased selectivity towards pathogenic bacteria |
| title | Design and self-assembly of guanidinium-functionalized polycarbonates for increased selectivity towards pathogenic bacteria |
| title_full | Design and self-assembly of guanidinium-functionalized polycarbonates for increased selectivity towards pathogenic bacteria |
| title_fullStr | Design and self-assembly of guanidinium-functionalized polycarbonates for increased selectivity towards pathogenic bacteria |
| title_full_unstemmed | Design and self-assembly of guanidinium-functionalized polycarbonates for increased selectivity towards pathogenic bacteria |
| title_short | Design and self-assembly of guanidinium-functionalized polycarbonates for increased selectivity towards pathogenic bacteria |
| title_sort | design and self assembly of guanidinium functionalized polycarbonates for increased selectivity towards pathogenic bacteria |
| topic | Science::Chemistry |
| url | https://hdl.handle.net/10356/164855 |
| work_keys_str_mv | AT tanjason designandselfassemblyofguanidiniumfunctionalizedpolycarbonatesforincreasedselectivitytowardspathogenicbacteria |