In Vitro antimicrobial, antiglycolytic, and antibiofilm activities of synthetic 1,4-naphthoquinone derivatives against cariogenic bacteria
This study investigated the potential anticaries properties of synthetic 1,4-naphthoquinone derivatives. Synthetic 1,4-naphthoquinone derivatives (2-4) were designed and synthesized by employing lawsone methyl ether (LME, 1), a plant-derived 1,4-naphthoquinone, as a lead compound. The synthetic co...
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| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
Penerbit Universiti Kebangsaan Malaysia
2023
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| Online Access: | http://journalarticle.ukm.my/21545/1/S%2016.pdf http://journalarticle.ukm.my/21545/ http://www.ukm.my/jsm/index.html |
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| Institution: | Universiti Kebangsaan Malaysia |
| Language: | English |
| Summary: | This study investigated the potential anticaries properties of synthetic 1,4-naphthoquinone derivatives. Synthetic
1,4-naphthoquinone derivatives (2-4) were designed and synthesized by employing lawsone methyl ether (LME, 1),
a plant-derived 1,4-naphthoquinone, as a lead compound. The synthetic compounds were characterized by infrared
spectroscopy, 1H-nuclear magnetic spectroscopy, 13C- nuclear magnetic spectroscopy, and high-resolution mass
spectrometry. Minimum inhibitory concentration (MIC), minimum bactericidal concentration (MBC), and growth
curves were determined to assess their antibacterial effects against Streptococcus mutans, Lacticaseibacillus
casei, and Actinomyces naeslundii. The pH drop assay was also performed on these three bacterial species. The
effect on S. mutans biofilm formation was evaluated by crystal violet assay. From the microdilution assay, 2-(prop-
2-ynyloxy)naphthalene-1,4-dione (compound 2) showed potent antimicrobial activity against S. mutans and A.
naeslundii (MIC of 1.56 and 3.125 μg/mL, respectively) in the same range as chlorhexidine (MIC of 1.95 and 1.95
μg/mL, respectively). The 1,4-naphthoquinone derivatives showed low antibacterial activity against L. casei. LME
(compound 1) and 2-(prop-2-ynyloxy)naphthalene-1,4-dione (compound 2) inhibited pH reduction from S. mutans.
The compounds at sub-MIC concentrations showed a potent inhibitory effect against S. mutans biofilm formation
in a dose- and time-dependent manner. These results suggested that the synthetic 1,4-naphthoquinone derivatives
are promising compounds that could be developed as a novel alternative or adjunctive anticaries therapies. |
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