Research articles
ScienceAsia 50 (2024):ID 2024098 1-8 |doi:
10.2306/scienceasia1513-1874.2024.098
In vitro evaluation of 2-(chloroalkyloxy)naphthalene-1,
4-dione derivatives as anticaries agents
Kannanat Rungrojrattikorna, Jutharat Manuschaib, Paptawan Suwanhomc,d, Jiraporn Karac,d, Luelak Lomlimc,d, Supawadee Naorungrojb,e,*
ABSTRACT: Lawsone is a privileged antibacterial pharmacophore in natural and synthetic compounds. A structural
modification that increases the lipophilicity may improve its antibacterial potency. This study investigated antimicrobial, antiglycolytic, and antibiofilm activities of synthetic 2-(chloroalkyloxy)naphthalene-1,4-dione derivatives
(Compounds 1 and 2). Microdilution method and pH drop assay were used to evaluate the antibacterial and
antiglycolytic activity of Compounds 1 and 2 against three bacterial strains: Streptococcus mutans, Lacticaseibacillus
casei, and Actinomyces naeslundii. Crystal violet assay assessed the effect of Compounds 1 and 2 on S. mutans biofilm
formation. The MTT assay was employed to assess Human Gingival Fibroblast (HGF-1) cell viability. According to
minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) values, S. mutans was more
susceptible to Compounds 1 and 2 (MIC 0.78, 1.56 ?g/ml, respectively) than A. naeslundii (MIC 6.25, 12.50 ?g/ml,
respectively), while, L. casei was resistant. Only the MBC of Compound 1 against A. naeslundii (100 ?g/ml) was
found. Both Compounds 1 and 2 significantly retarded the pH declined by S. mutans, but had no effect on the pH drop
profile of A. naeslundii. Only Compound 1 significantly affected the pH drop profile of L. casei. At 12 h, all sub-MIC
concentrations (1/2 to 1/8) of Compounds 1 and 2 significantly reduced S. mutans biofilm formation. However, at
24 h, only sub-MIC 1/2 concentration significantly reduced biofilm formation. Compound 1 exhibited dose-dependent
cytotoxicity, with IC50 of 2.34 ?g/ml. By structural modification of lawsone via an alkylation reaction on the 2-hydroxyl
group, Compound 1 was more potent than Compound 2 in terms of inhibiting bacterial growth, biofilm formation, and
acid production. Both compounds could be promisingly be a potential dental caries preventive agent.
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| a |
Department of Dental Public Health, Sirindhorn College of Public Health Yala, Yala 95000 Thailand |
| b |
Department of Conservative Dentistry, Faculty of Dentistry, Prince of Songkla University, Songkhla 90110 Thailand |
| c |
Department of Pharmaceutical Chemistry, Faculty of Pharmaceutical Sciences, Prince of Songkla University,
Songkhla 90110 Thailand |
| d |
Phytomedicine and Pharmaceutical Biotechnology Excellent Center (PPBEC), Faculty of Pharmaceutical Sciences,
Prince of Songkla University, Songkhla 90110 Thailand |
| e |
Research Center of Excellence for Oral Health, Faculty of Dentistry, Prince of Songkla University, Songkhla 90110
Thailand |
* Corresponding author, E-mail: supawadee.n@psu.ac.th
Received 31 Jan 2024, Accepted 1 Sep 2024
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