Effect of alkynyloxy derivatives of lawsone as an antifungal spray for acrylic denture base: An in vitro study

Luelak Lomlim; Jutharat Manuschai; Pichayaporn Ratti; Jiraporn Kara; Athip Sakunphueak; Pharkphoom Panichayupakaranant; Supawadee Naorungroj

doi:10.1016/j.heliyon.2023.e13919

Effect of alkynyloxy derivatives of lawsone as an antifungal spray for acrylic denture base: An in vitro study

Heliyon. 2023 Feb 20;9(3):e13919. doi: 10.1016/j.heliyon.2023.e13919. eCollection 2023 Mar.

Authors

Luelak Lomlim^{1

2}, Jutharat Manuschai³, Pichayaporn Ratti⁴, Jiraporn Kara^{1

2}, Athip Sakunphueak^{2

5}, Pharkphoom Panichayupakaranant^{2

5}, Supawadee Naorungroj³

Affiliations

¹ Department of Pharmaceutical Chemistry, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Hat Yai, Songkhla, 90112, Thailand.
² Phytomedicine and Pharmaceutical Biotechnology Excellent Center (PPBEC), Faculty of Pharmaceutical Sciences, Prince of Songkla University, Hat Yai, Songkhla, 90112, Thailand.
³ Department of Conservative Dentistry, Faculty of Dentistry, Prince of Songkla University, Hat Yai, Songkhla, 90112, Thailand.
⁴ Department of Dental Public Health, Sirindhorn College of Public Health Yala, Muang Yala, Yala, 95000, Thailand.
⁵ Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Hat Yai, Songkhla, 90112, Thailand.

Abstract

Objective: The purpose of this study was to (i) synthesize and develop an alkynyloxy derivative of lawsone as an antifungal spray and (ii) assess the antifungal spray's effectiveness in reducing the viability of Candida albicans (C. albicans) on polymethylmethacrylate (PMMA) specimens.

Methods: Lawsone methyl ether (LME) and its derivative, 2-(prop-2-ynyloxy)naphthalene-1,4-dione (compound 1) were synthesized and characterized. The synthetic compounds were screened for antimicrobial activities against C. albicans using the microtiter broth dilution method to determine the minimum inhibitory concentration (MIC) and minimum fungicidal concentration (MFC). Compound 1 was further formulated as an antifungal spray in three concentrations (100, 200, and 400 μg/mL). C. albicans biofilms were developed for 48 h on PMMA specimens. The efficacy of using an antifungal spray for 1 and 3 min to remove biofilm was assessed using colony counting and scanning electron microscopy (SEM). Chlorhexidine gluconate (CHX), polident®, and distilled water were used as positive and negative control cleansing solutions, respectively.

Results: LME and compound 1 showed comparable inhibition against C. albicans with a MIC of 25 μg/mL and MFC of 50 μg/mL. For immediate treatment, C. albicans was not detected on PMMA specimens when expose to 2% CHX and compound 1 (100, 200, and 400 μg/mL) antifungal spray for 3 min. However, after recolonization, a small number of viable cells were observed in denture soaked in compound 1 antifungal spray for 3 min group. Following recolonization, polident® and distilled water had comparable viable cell counts of C. albicans to the no treatment group. Scanning electron microscope (SEM) images revealed that CHX, polident®, and compound 1 caused cell damage in various forms.

Conclusion: Denture spray containing synthetic alkynyloxy derivative of lawsone is a promising antifungal agent for C. albicans biofilm removal from the PMMA surface.

Keywords: Antifungal activity; Biofilm removal; Candida species; Denture hygiene; Lawsone derivative.