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...
| 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/ http://journalarticle.ukm.my/21545/1/S%2016.pdf |
| _version_ | 1848815378000510976 |
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| author | Pichayaporn Ratti, Jutharat Manuschai, Jiraporn Kara, Luelak Lomlim, Supawadee Naorungroj, |
| author_facet | Pichayaporn Ratti, Jutharat Manuschai, Jiraporn Kara, Luelak Lomlim, Supawadee Naorungroj, |
| author_sort | Pichayaporn Ratti, |
| building | UKM Institutional Repository |
| collection | Online Access |
| description | 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. |
| first_indexed | 2025-11-15T00:49:01Z |
| format | Article |
| id | oai:generic.eprints.org:21545 |
| institution | Universiti Kebangasaan Malaysia |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-15T00:49:01Z |
| publishDate | 2023 |
| publisher | Penerbit Universiti Kebangsaan Malaysia |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | oai:generic.eprints.org:215452023-05-09T03:44:52Z http://journalarticle.ukm.my/21545/ In Vitro antimicrobial, antiglycolytic, and antibiofilm activities of synthetic 1,4-naphthoquinone derivatives against cariogenic bacteria Pichayaporn Ratti, Jutharat Manuschai, Jiraporn Kara, Luelak Lomlim, Supawadee Naorungroj, 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. Penerbit Universiti Kebangsaan Malaysia 2023 Article PeerReviewed application/pdf en http://journalarticle.ukm.my/21545/1/S%2016.pdf Pichayaporn Ratti, and Jutharat Manuschai, and Jiraporn Kara, and Luelak Lomlim, and Supawadee Naorungroj, (2023) In Vitro antimicrobial, antiglycolytic, and antibiofilm activities of synthetic 1,4-naphthoquinone derivatives against cariogenic bacteria. Sains Malaysiana, 52 (1). pp. 199-210. ISSN 0126-6039 http://www.ukm.my/jsm/index.html |
| spellingShingle | Pichayaporn Ratti, Jutharat Manuschai, Jiraporn Kara, Luelak Lomlim, Supawadee Naorungroj, In Vitro antimicrobial, antiglycolytic, and antibiofilm activities of synthetic 1,4-naphthoquinone derivatives against cariogenic bacteria |
| title | In Vitro antimicrobial, antiglycolytic, and antibiofilm activities of synthetic 1,4-naphthoquinone derivatives against cariogenic bacteria |
| title_full | In Vitro antimicrobial, antiglycolytic, and antibiofilm activities of synthetic 1,4-naphthoquinone derivatives against cariogenic bacteria |
| title_fullStr | In Vitro antimicrobial, antiglycolytic, and antibiofilm activities of synthetic 1,4-naphthoquinone derivatives against cariogenic bacteria |
| title_full_unstemmed | In Vitro antimicrobial, antiglycolytic, and antibiofilm activities of synthetic 1,4-naphthoquinone derivatives against cariogenic bacteria |
| title_short | In Vitro antimicrobial, antiglycolytic, and antibiofilm activities of synthetic 1,4-naphthoquinone derivatives against cariogenic bacteria |
| title_sort | in vitro antimicrobial, antiglycolytic, and antibiofilm activities of synthetic 1,4-naphthoquinone derivatives against cariogenic bacteria |
| url | http://journalarticle.ukm.my/21545/ http://journalarticle.ukm.my/21545/ http://journalarticle.ukm.my/21545/1/S%2016.pdf |