Efficient Photodynamic Killing of Gram-Positive Bacteria by Synthetic Curcuminoids
In our previous study, we have demonstrated that curcumin can efficiently kill the anaerobic bacterium <i>Propionibacterium acnes</i> by irradiation with low-dose blue light. The curcuminoids present in natural plant turmeric mainly include curcumin, demethoxycurcumin, and bisdemethoxycu...
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MDPI AG
2020-11-01
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| Series: | International Journal of Molecular Sciences |
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| Online Access: | https://www.mdpi.com/1422-0067/21/23/9024 |
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| author | Sung-Jen Hung Yi-An Hong Kai-Yu Lin Yi-Wen Hua Chia-Jou Kuo Anren Hu Tzenge-Lien Shih Hao-Ping Chen |
| author_facet | Sung-Jen Hung Yi-An Hong Kai-Yu Lin Yi-Wen Hua Chia-Jou Kuo Anren Hu Tzenge-Lien Shih Hao-Ping Chen |
| author_sort | Sung-Jen Hung |
| collection | DOAJ |
| description | In our previous study, we have demonstrated that curcumin can efficiently kill the anaerobic bacterium <i>Propionibacterium acnes</i> by irradiation with low-dose blue light. The curcuminoids present in natural plant turmeric mainly include curcumin, demethoxycurcumin, and bisdemethoxycurcumin. However, only curcumin is commercially available. Eighteen different curcumin analogs, including demethoxycurcumin and bisdemethoxycurcumin, were synthesized in this study. Their antibacterial activity against Gram-positive aerobic bacteria <i>Staphylococcus aureus</i> and <i>Staphylococcus epidermidis</i> was investigated using the photodynamic inactivation method. Among the three compounds in turmeric, curcumin activity is the weakest, and bisdemethoxycurcumin possesses the strongest activity. However, two synthetic compounds, (1<i>E</i>,6<i>E</i>)-1,7-bis(5-methylthiophen-2-yl)hepta-1,6-diene-3,5-dione and (1<i>E</i>,6<i>E</i>)-1,7-di(thiophen-2-yl)hepta-1,6-diene-3,5-dione, possess the best antibacterial activity among all compounds examined in this study. Their chemical stability is also better than that of bisdemethoxycurcumin, and thus has potential for future clinical applications. |
| first_indexed | 2024-03-10T14:31:19Z |
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| id | doaj.art-a5f3ebae48f64363a150fb62eb6b4091 |
| institution | Directory Open Access Journal |
| issn | 1661-6596 1422-0067 |
| language | English |
| last_indexed | 2024-03-10T14:31:19Z |
| publishDate | 2020-11-01 |
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| series | International Journal of Molecular Sciences |
| spelling | doaj.art-a5f3ebae48f64363a150fb62eb6b40912023-11-20T22:36:45ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672020-11-012123902410.3390/ijms21239024Efficient Photodynamic Killing of Gram-Positive Bacteria by Synthetic CurcuminoidsSung-Jen Hung0Yi-An Hong1Kai-Yu Lin2Yi-Wen Hua3Chia-Jou Kuo4Anren Hu5Tzenge-Lien Shih6Hao-Ping Chen7Institute of Medical Sciences, Tzu Chi University, Hualien 97004, TaiwanInstitute of Medical Sciences, Tzu Chi University, Hualien 97004, TaiwanDepartment of Chemistry, Tamkang University, New Taipei City 25137, TaiwanDepartment of Chemistry, Tamkang University, New Taipei City 25137, TaiwanDepartment of Chemistry, Tamkang University, New Taipei City 25137, TaiwanInstitute of Medical Sciences, Tzu Chi University, Hualien 97004, TaiwanDepartment of Chemistry, Tamkang University, New Taipei City 25137, TaiwanInstitute of Medical Sciences, Tzu Chi University, Hualien 97004, TaiwanIn our previous study, we have demonstrated that curcumin can efficiently kill the anaerobic bacterium <i>Propionibacterium acnes</i> by irradiation with low-dose blue light. The curcuminoids present in natural plant turmeric mainly include curcumin, demethoxycurcumin, and bisdemethoxycurcumin. However, only curcumin is commercially available. Eighteen different curcumin analogs, including demethoxycurcumin and bisdemethoxycurcumin, were synthesized in this study. Their antibacterial activity against Gram-positive aerobic bacteria <i>Staphylococcus aureus</i> and <i>Staphylococcus epidermidis</i> was investigated using the photodynamic inactivation method. Among the three compounds in turmeric, curcumin activity is the weakest, and bisdemethoxycurcumin possesses the strongest activity. However, two synthetic compounds, (1<i>E</i>,6<i>E</i>)-1,7-bis(5-methylthiophen-2-yl)hepta-1,6-diene-3,5-dione and (1<i>E</i>,6<i>E</i>)-1,7-di(thiophen-2-yl)hepta-1,6-diene-3,5-dione, possess the best antibacterial activity among all compounds examined in this study. Their chemical stability is also better than that of bisdemethoxycurcumin, and thus has potential for future clinical applications.https://www.mdpi.com/1422-0067/21/23/9024bisdemethoxycurcumincurcumincurcuminoiddemethoxycurcuminphotodynamic inactivation<i>Staphylococcus aureus</i> |
| spellingShingle | Sung-Jen Hung Yi-An Hong Kai-Yu Lin Yi-Wen Hua Chia-Jou Kuo Anren Hu Tzenge-Lien Shih Hao-Ping Chen Efficient Photodynamic Killing of Gram-Positive Bacteria by Synthetic Curcuminoids International Journal of Molecular Sciences bisdemethoxycurcumin curcumin curcuminoid demethoxycurcumin photodynamic inactivation <i>Staphylococcus aureus</i> |
| title | Efficient Photodynamic Killing of Gram-Positive Bacteria by Synthetic Curcuminoids |
| title_full | Efficient Photodynamic Killing of Gram-Positive Bacteria by Synthetic Curcuminoids |
| title_fullStr | Efficient Photodynamic Killing of Gram-Positive Bacteria by Synthetic Curcuminoids |
| title_full_unstemmed | Efficient Photodynamic Killing of Gram-Positive Bacteria by Synthetic Curcuminoids |
| title_short | Efficient Photodynamic Killing of Gram-Positive Bacteria by Synthetic Curcuminoids |
| title_sort | efficient photodynamic killing of gram positive bacteria by synthetic curcuminoids |
| topic | bisdemethoxycurcumin curcumin curcuminoid demethoxycurcumin photodynamic inactivation <i>Staphylococcus aureus</i> |
| url | https://www.mdpi.com/1422-0067/21/23/9024 |
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