Antibacterial Profile in vitro and in vivo of New 1,4-Naphthoquinones Tethered to 1,2,3-1H-Triazoles against the Planktonic Growth of Streptococcus mutans

Abstract

The cariogenic processes are mainly caused by the bacterium Streptococcus mutans (S. mutans) and consist of the demineralization of the tooth that occurs when the acid production overcomes the natural repair or if a problem occurs in the last one. In this work, we performed the synthesis of twenty-one 1,4-naphthoquinones tethered to 1,2,3-1H-triazoles (8a-8k and 9a-9j), antibacterial evaluation against the S. mutans in vitro and the acute toxicity of the better ones in vivo. We observed strong inhibition results in the disc diffusion test ranging, the halos of inhibitions, from 18.66 (± 0.57) to 29 (± 2.64) mm, and good values in the minimum inhibitory concentration (5 to 50 μg), for the compounds 9e, 9h, 9i and 9j. Furthermore, they do not have a cytotoxic effect at the concentrations tested. Besides that, in the in vivo test, they show some slight alteration in the histopathological analyses and the biochemistry. Thus, we found four potential candidates to become instruments for the treatment of cavities.

Synthetic and Semisynthetic Compounds as Antibacterials Targeting Virulence Traits in Resistant Strains: A Narrative Updated Review

“…Among 4-(4-formyl-3-phenyl-1 H -pyrazol-1-yl)benzoic acid derivatives, some of the identified compounds showed antibacterial activity against A. baumanii with an MIC of 4 µg/mL [ 28 ]. Furthermore, according to Gomes et al [ 43 ], of twenty-one freshly synthesized 1,4-naphthoquinones linked to 1,2,3-1 H -triazoles, four ( 9e , 9h , 9i and 9j ) proved to possess antibacterial activity against S. mutans from oral cavities with IZs of 18.66–29.00 mm. The results also showed no toxic effects for these compounds, which possibly increases their potential for application in practice.…”

The Relevance and Insights on 1,4-Naphthoquinones as Antimicrobial and Antitumoral Molecules: A Systematic Review

“…The hydroxyl-1,4 naphthoquinones such as juglone 2, lawsone 3, plumbagin 4, and lapachol 5 are natural NQs isolated from plants extensively used in traditional Indian medicine [15][16][17][18]. In the past decades, the substitution of diverse groups and modifications in the NQs ring have provided many derivatives with enhanced biological activity [19][20][21][22][23][24][25][26][27][28][29][30][31][32]. In this respect, lawsone derivatives, 3-(aminomethyl)-2-hydroxy-1,4-naphthoquinones 6, or amino naphthoquinone Mannich bases have been synthesized and evaluated as anticancer, antimalarial, antiviral, antifungal, and antibacterial molecules [19,20]; amino 7, and thioether 8 NQs (Figure 1), as well as the NQs with aromatic amines in carbon two or three, may tune their antifungal and antibacterial activity and anticancer activity, being the case for 2-acetyl-3-aminophenyl-1,4-naphthoquinones 9, which has been evaluated for in vitro antiproliferative activity against several types of human cancer cells with very promising results [21].…”

“…To enhance the biological effects induced by NQs, some approaches include incorporating two biologically active groups in the same molecule. For instance, several compounds containing NQ and triazole nuclei in their structure have shown a more potent Many biologically active compounds contain an indole heterocyclic structure [22][23][24]. Examples of this type of compound are mitomycin A 10 and 7-methoxymitosene 11 (Figure 1).…”

“…As a result, different compounds containing substituted indole and quinone in their structure show diverse biological activity. The indole quinone subunit is an important framework of the mitomycin family of antitumor agents [22][23][24][25]. Hence, efforts to develop methods to assemble polycyclic compounds containing pyrrole and quinone have been conducted by researchers [26,32].…”