Synthesis and In Vitro Evaluation of 8‐Hydroxyquinolines as Dental Plaque Inhibitors

Warner, Victor D.; Musto, Joseph D.; Turesky, Samuel; Soloway, Barbara

doi:10.1002/jps.2600640934

Cited by 12 publications

(10 citation statements)

References 7 publications

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“…8-hydroxyquinoline (HQ) is a well-studied, privileged structure, with activity against a wide range of cell types (Prachayasittikul, Prachayasittikul, Ruchirawat, & Prachayasittikul, 2013;Song, Xu, Chen, Zhan, & Liu, 2015), including anticancer activity (Barilli et al, 2014;Bhat, Shim, Zhang, Chong, & Liu, 2012;Chang, Chen, Wang, Tzeng, & Chen, 2010;Feng et al, 2015;Li et al, 2016;Moret et al, 2009;Mrozek-Wilczkiewicz et al, 2015;Sosi c et al, 2013;Spaczy nska, Tabak, Malarz, & Musiol, 2014), antifungal activity (Cieslik et al, 2012;Musiol et al, 2006), and antibacterial activity (Warner, Musto, Turesky, & Soloway, 1975). The HQ are active against several bacterial species including Staphylococcus aureus and Staphylococcus epidermidis (Abouelhassan et al, 2014(Abouelhassan et al, , 2015Basak et al, 2016;Garrison et al, 2017;Lam et al, 2014), Enterococcus faecium (Basak et al, 2016;Garrison et al, 2017), Burkholderia pseudomallei (Wangtrakuldee et al, 2013), Neisseria gonorrhoeae, (Lawung et al, 2018), Listeria monocytogenes (Cherdtrakulkiat et al, 2016), and Mycobacterium avium (Hongmanee, Rukseree, Buabut, Somsri, & Palittapongarnpim, 2007;Kos et al, 2015).…”

Section: Introductionmentioning

confidence: 99%

8‐Hydroxyquinolines are bactericidal against Mycobacterium tuberculosis

Odingo

Early

Smith

et al. 2019

Drug Development Research

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There is an urgent need for new treatments effective against Mycobacterium tuberculosis, the causative agent of tuberculosis. The 8‐hydroxyquinoline series is a privileged scaffold with anticancer, antifungal, and antibacterial activities. We conducted a structure–activity relationship study of the series regarding its antitubercular activity using 26 analogs. The 8‐hydroxyquinolines showed good activity against M. tuberculosis, with minimum inhibitory concentrations (MIC90) of <5 μM for some analogs. Small substitutions at C5 resulted in the most potent activity. Substitutions at C2 generally decreased potency, although a sub‐family of 2‐styryl‐substituted analogs retained activity. Representative compounds demonstrated bactericidal activity against replicating M. tuberculosis with >4 log kill at 10× MIC over 14 days. The majority of the compounds demonstrated cytotoxicity (IC50 of <100 μM). Further development of this series as antitubercular agents should address the cytotoxicity liability. However, the 8‐hydroxyquinoline series represents a useful tool for chemical genomics to identify novel targets in M. tuberculosis.

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Section: Introductionmentioning

confidence: 99%

8‐Hydroxyquinolines are bactericidal against Mycobacterium tuberculosis

Odingo

Early

Smith

et al. 2019

Drug Development Research

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“…8-Hydroxyquinolines have been shown to be some of the most potent in vitro inhibitors of S. mutans No. 6715.5 7 Initial studies indicated that 8-hydroxyquinolines with log P values between 1 and 4 display the best activity against this organism.5 As part of our continuing studies of dental plaque inhibitors, we synthesized and tested a series of 5-substituted 8-hydroxyquinolines.6•7 These analogues were chosen since the substituent would be some distance from the portion of the molecule involved in chelation. It has been shown that chelation with iron or copper ions is required for antibacterial activity.…”

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confidence: 99%

Quantitative structure-activity relations for 5-substituted 8-hydroxyquinolines as inhibitors of dental plaque

Warner¹,

Musto²,

Sane³

et al. 1977

J. Med. Chem.

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Fourteen 8-hydroxyquinolines were tested for antiplaque activity by measuring their minimum inhibitory concentrations [MIC (M)] against Streptococcus mutans No. 6715. Linear regression analysis was conducted with the MIC (M) values and hydrophobic (log P), electronic (beta, pKaOH, pKaN), and steric [molar refractivity (MR), molecular weight (mol wt)] parameters. The best correlation (r2 = 0.90) was obtained with MR, log P, and beta. The smaller the steric contribution of the 5-substituent, the more active the compound. The parent 8-hydroxyquinoline was the most active. The negative contribution toward activity by 5-substituents larger than hydrogen can be overcome by the positive contributions of groups that are lipophilic and electron withdrawing; for example, the 5-chloro derivative is as active as the parent 8-hydroxyquinolines.

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“…Earlier studies demonstrated that various 8-hydroxyquinoline derivatives inhibited in vitro accumulation of the cariogenic microorganism Streptococcus mutans on cleaned enamel surfaces which had been repeatedly immersed in these agents (11,12). In the study reported herein, attempts were made to determine the efficacy in vitro of three 8-hydroxyquinoline compounds, viz., 8-hydroxyquinoline sulfate (HQS; Eastman Organic), 5-chloro-7-iodo-8-quinolinol (CIQ; Pfaltz and Bauer), and 5,7-dichloro-8-hydroxyquinoline (DCHQ; Aldrich Chemical), against preformed intact plaques of pure cultures of S. mutans 6715-13, S. sanguis ATCC 10558, Actinomyces viscosus M-100, and A. naeslundii ATCC 12104.…”

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confidence: 98%

“…Other investigators have employed dimethyl sulfoxide to dissolve these compounds (11,12). However, in these studies, such a procedure was deemed unsatisfactory because dimethyl sulfoxide was found to inhibit culture acid production, but this was not so for polyethylene glycol 200.…”

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confidence: 99%