Structure–activity relationships of bensulfuron methyl and its derivatives as novel agents against drug‐resistant Candida auris
With the emergence of the human pathogen Candida auris as a threat to human health, there is a strong demand to identify effective medicines to prevent the harm caused by such drug‐tolerant human fungi. Herein, a series of 33 new derivatives of bensulfuron methyl (BSM) were synthesized and character...
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| Published in: | Chemical biology & drug design Vol. 103; no. 1; pp. e14364 - n/a |
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| Main Authors: | , , , , , , , , , , , |
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01-01-2024
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| Abstract | With the emergence of the human pathogen Candida auris as a threat to human health, there is a strong demand to identify effective medicines to prevent the harm caused by such drug‐tolerant human fungi. Herein, a series of 33 new derivatives of bensulfuron methyl (BSM) were synthesized and characterized by 1H NMR, 13C NMR, and HRMS. Among the target compounds, 8a possessed the best Ki value of 1.015 μM against C. auris acetohydroxyacid synthase (CauAHAS) and an MIC value of 6.25 μM against CBS10913, a clinically isolated strain of C. auris. Taken together the structures of BSM and the synthesized compounds, it was found that methoxy groups at both meta‐position of pyrimidine ring are likely to provide desirable antifungal activities. Quantum calculations and molecular dockings were performed to understand the structure–activity relationships. The present study has hence provided some interesting clues for the discovery of novel antibiotics with this distinct mode of action.
33 novel derivatives of bensulfuron methyl were prepared and structure–activity relationships were investigated as antifungal agents against Candida auris. |
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| AbstractList | With the emergence of the human pathogen Candida auris as a threat to human health, there is a strong demand to identify effective medicines to prevent the harm caused by such drug-tolerant human fungi. Herein, a series of 33 new derivatives of bensulfuron methyl (BSM) were synthesized and characterized by 1 H NMR, 13 C NMR, and HRMS. Among the target compounds, 8a possessed the best Ki value of 1.015 μM against C. auris acetohydroxyacid synthase (CauAHAS) and an MIC value of 6.25 μM against CBS10913, a clinically isolated strain of C. auris. Taken together the structures of BSM and the synthesized compounds, it was found that methoxy groups at both meta-position of pyrimidine ring are likely to provide desirable antifungal activities. Quantum calculations and molecular dockings were performed to understand the structure-activity relationships. The present study has hence provided some interesting clues for the discovery of novel antibiotics with this distinct mode of action. With the emergence of the human pathogen Candida auris as a threat to human health, there is a strong demand to identify effective medicines to prevent the harm caused by such drug‐tolerant human fungi. Herein, a series of 33 new derivatives of bensulfuron methyl (BSM) were synthesized and characterized by 1 H NMR, 13 C NMR, and HRMS. Among the target compounds, 8a possessed the best K i value of 1.015 μM against C. auris acetohydroxyacid synthase ( Cau AHAS) and an MIC value of 6.25 μM against CBS10913, a clinically isolated strain of C. auris . Taken together the structures of BSM and the synthesized compounds, it was found that methoxy groups at both meta ‐position of pyrimidine ring are likely to provide desirable antifungal activities. Quantum calculations and molecular dockings were performed to understand the structure–activity relationships. The present study has hence provided some interesting clues for the discovery of novel antibiotics with this distinct mode of action. With the emergence of the human pathogen Candida auris as a threat to human health, there is a strong demand to identify effective medicines to prevent the harm caused by such drug-tolerant human fungi. Herein, a series of 33 new derivatives of bensulfuron methyl (BSM) were synthesized and characterized by H NMR, C NMR, and HRMS. Among the target compounds, 8a possessed the best K value of 1.015 μM against C. auris acetohydroxyacid synthase (CauAHAS) and an MIC value of 6.25 μM against CBS10913, a clinically isolated strain of C. auris. Taken together the structures of BSM and the synthesized compounds, it was found that methoxy groups at both meta-position of pyrimidine ring are likely to provide desirable antifungal activities. Quantum calculations and molecular dockings were performed to understand the structure-activity relationships. The present study has hence provided some interesting clues for the discovery of novel antibiotics with this distinct mode of action. With the emergence of the human pathogen Candida auris as a threat to human health, there is a strong demand to identify effective medicines to prevent the harm caused by such drug‐tolerant human fungi. Herein, a series of 33 new derivatives of bensulfuron methyl (BSM) were synthesized and characterized by 1H NMR, 13C NMR, and HRMS. Among the target compounds, 8a possessed the best Ki value of 1.015 μM against C. auris acetohydroxyacid synthase (CauAHAS) and an MIC value of 6.25 μM against CBS10913, a clinically isolated strain of C. auris. Taken together the structures of BSM and the synthesized compounds, it was found that methoxy groups at both meta‐position of pyrimidine ring are likely to provide desirable antifungal activities. Quantum calculations and molecular dockings were performed to understand the structure–activity relationships. The present study has hence provided some interesting clues for the discovery of novel antibiotics with this distinct mode of action. 33 novel derivatives of bensulfuron methyl were prepared and structure–activity relationships were investigated as antifungal agents against Candida auris. |
| Author | Li, Hao‐Ran Lin, Xin Liu, Yixuan Agnew‐Francis, Kylie A. Tang, Jin‐Yin Fraser, James A. Wang, Xiaofang Guddat, Luke W. Sun, Xue‐Wen Sun, Zhi‐Juan Wang, Jian‐Guo Xu, Qing |
| Author_xml | – sequence: 1 givenname: Xue‐Wen surname: Sun fullname: Sun, Xue‐Wen organization: Nankai University – sequence: 2 givenname: Yixuan orcidid: 0009-0000-6394-1797 surname: Liu fullname: Liu, Yixuan organization: The University of Queensland – sequence: 3 givenname: Xiaofang surname: Wang fullname: Wang, Xiaofang organization: Newish Technology (Beijing) Co., Ltd – sequence: 4 givenname: Hao‐Ran surname: Li fullname: Li, Hao‐Ran organization: Nankai University – sequence: 5 givenname: Xin surname: Lin fullname: Lin, Xin organization: The University of Queensland – sequence: 6 givenname: Jin‐Yin surname: Tang fullname: Tang, Jin‐Yin organization: Nankai University – sequence: 7 givenname: Qing surname: Xu fullname: Xu, Qing organization: Nankai University – sequence: 8 givenname: Kylie A. orcidid: 0000-0002-7701-9143 surname: Agnew‐Francis fullname: Agnew‐Francis, Kylie A. organization: The University of Queensland – sequence: 9 givenname: James A. orcidid: 0000-0001-5724-5285 surname: Fraser fullname: Fraser, James A. organization: The University of Queensland – sequence: 10 givenname: Zhi‐Juan surname: Sun fullname: Sun, Zhi‐Juan organization: Newish Technology (Beijing) Co., Ltd – sequence: 11 givenname: Luke W. orcidid: 0000-0002-8204-8408 surname: Guddat fullname: Guddat, Luke W. email: luke.guddat@uq.edu.au organization: The University of Queensland – sequence: 12 givenname: Jian‐Guo orcidid: 0000-0001-7577-1502 surname: Wang fullname: Wang, Jian‐Guo email: nkwjg@nankai.edu.cn organization: Nankai University |
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| Cites_doi | 10.1016/j.mib.2022.102208 10.1016/j.ejmech.2018.11.005 10.1128/AAC.01719‐20 10.1016/j.ejmech.2015.03.014 10.1002/ps.5739 10.1111/j.1742‐4658.2009.06863.x 10.3390/antibiotics12020323 10.1016/s1130‐1406(08)70027‐5 10.1021/ci3004545 10.1126/science.224.4656.1443 10.1016/j.bmc.2012.04.045 10.5694/j.1326‐5377.2007.tb01313.x 10.1016/j.drudis.2022.04.021 10.1021/bi047980a 10.1021/acsinfecdis.0c00229 10.1007/s00253‐016‐7809‐9 10.1007/s00726‐005‐0297‐3 10.1128/AAC.01809‐12 10.1021/ci200227u 10.2174/13816128113199990009 10.1111/lam.12820 10.1021/jm301501k 10.1002/anie.201511985 10.1111/j.1348‐0421.2008.00083.x 10.1104/pp.75.3.827 10.1021/acs.jafc.1c02081 10.1021/acs.jafc.8b00665 10.1111/cbdd.14114 10.1006/jmbi.1996.0477 10.1073/pnas.1714392115 10.1128/AAC.41.4.763 10.1111/j.1742‐4658.2012.08505.x 10.1073/pnas.1809422115 10.1038/s41467‐022‐31023‐x |
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| Keywords | Candida auris antifungal agent drug resistance acetohydroxyacidsynthase bensulfuron methyl derivative |
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| Snippet | With the emergence of the human pathogen Candida auris as a threat to human health, there is a strong demand to identify effective medicines to prevent the... |
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| SubjectTerms | acetohydroxyacidsynthase antifungal agent Antifungal Agents - pharmacology bensulfuron methyl derivative Candida Candida auris drug resistance Humans Microbial Sensitivity Tests Structure-Activity Relationship Sulfonylurea Compounds |
| Title | Structure–activity relationships of bensulfuron methyl and its derivatives as novel agents against drug‐resistant Candida auris |
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