New 8-hydroxyquinoline derivatives highlight the potential of this class for treatment of fungal infections

Joaquim, Angélica Rocha; Reginatto, Paula; Lopes, Marcela Silva; Bazana, Luana Candice Genz; Gionbelli, Mariana Pies; Cesare, Maycon Antonio de; Kaminski, Taís Fernanda Andrzejewski; Teixeira, Mário Lettieri; Abegg, Maxwel Adriano; Andrade, Saulo Fernandes de

doi:10.1039/d0nj06188c

Cited by 7 publications

(6 citation statements)

References 49 publications

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“…Regarding the antifungal activity, in a recent study, 7-substituted derivatives were evaluated against Candida sp. and dermatophyte strains ( 27a – d , Figure ), and two of them (containing the pyrimidine ring) deserve to be highlighted . Compound 27b was promising against Microsporum sp.…”

Section: Structural Changes At the 8hq Core Based On The Microorganis...mentioning

confidence: 99%

“…Interestingly, the 8-methylated series (represented by 27c – d ) showed reduced activity, which suggests that the 8-hydroxyl is important for the antifungal effect. The MIC values of 27a increase in the presence of metal ions, suggesting this compound acts as an ion scavenger in fungal cells …”

Section: Structural Changes At the 8hq Core Based On The Microorganis...mentioning

confidence: 99%

“…and dermatophyte strains (27a−d, Figure 27), and two of them (containing the pyrimidine ring) deserve to be highlighted. 112 Compound 27b was promising against Microsporum sp. and Trichophyton sp., with MIC values ranging from 3.35 to 6.70 μM.…”

Section: ■ Introductionmentioning

confidence: 99%

“…The MIC values of 27a increase in the presence of metal ions, suggesting this compound acts as an ion scavenger in fungal cells. 112 Position 7 of the 8HQ nucleus is of interest, since there are few works that provide an antimicrobial SAR. Modifications in this position are attractive as it is found in close proximity to the phenolic hydroxyl, which may contribute to the chelating capacity of 8HQ, depending on the substituent.…”

Section: ■ Introductionmentioning

confidence: 99%

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Novel Antimicrobial 8-Hydroxyquinoline-Based Agents: Current Development, Structure–Activity Relationships, and Perspectives

et al. 2021

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The search for new antimicrobials is imperative due to the emergent resistance of new microorganism strains. In this context, revisiting known classes like 8-hydroxyquinolines could be an interesting strategy to discover new agents. The 8-hydroxyquinoline derivatives nitroxoline and clioquinol are used to treat microbial infections; however, these drugs are underused, being available in few countries or limited to topical use. After years of few advances, in the last two decades, the potent activity of clioquinol and nitroxoline against several targets and the privileged structure of 8-hydroxyquinoline nucleus have prompted an increased interest in the design of novel antimicrobial, anticancer, and anti-Alzheimer agents based on this class. Herein, we discuss the current development and antimicrobial structure–activity relationships of this class in the perspective of using the 8-hydroxyquinoline nucleus for the search for novel antimicrobial agents. Furthermore, the most investigated molecular targets concerning 8-hydroxyquinoline derivatives are explored in the final section.

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Section: Structural Changes At the 8hq Core Based On The Microorganis...mentioning

confidence: 99%

Section: Structural Changes At the 8hq Core Based On The Microorganis...mentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Novel Antimicrobial 8-Hydroxyquinoline-Based Agents: Current Development, Structure–Activity Relationships, and Perspectives

et al. 2021

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“…Given this scenario, it is time to explore new molecules with antimicrobial activity, which offer safety in their use, not only in efficacy against pathogens but also in low adverse reactions to patients (Joaquim et al 2021 ). In some cases, researchers have worked in different ways with drugs that were forgotten for decades by the pharmaceutical industry, such as clioquinol and nitroxoline (Fig.…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial activity of clioquinol and nitroxoline: a scoping review

Wykowski

Andrade

2022

Arch Microbiol

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Clioquinol and nitroxoline, two drugs with numerous pharmacological properties fallen into disuse for many decades. The first was considered dangerous due to contraindications and the second mainly because was taken as ineffective, despite its known antibacterial activity. In the last decades, the advances in pharmaceutical chemistry, molecular biology, toxicology and genetics allowed to better understand the cellular action of these compounds, some toxicological issues and/or activity scopes. Thus, a new opportunity for these drugs to be considered as potential antimicrobial agents has arisen. This review contemplates the trajectory of clioquinol and nitroxoline from their emergence to the present day, emphasizing the new studies that indicate the possibility of reintroduction for specific cases.

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Identification of antimycobacterial 8-hydroxyquinoline derivatives as in vitro enzymatic inhibitors of Mycobacterium tuberculosis enoyl-acyl carrier protein reductase

Joaquim,

Lopes,

Fortes

et al. 2024

Bioorganic Chemistry

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New 8-hydroxyquinoline derivatives highlight the potential of this class for treatment of fungal infections

Abstract: Compound 5h has interesting antifungal activity and a good toxicity profile and seems to act as an ion scavenger in fungi.

Cited by 7 publications

References 49 publications

Novel Antimicrobial 8-Hydroxyquinoline-Based Agents: Current Development, Structure–Activity Relationships, and Perspectives

Novel Antimicrobial 8-Hydroxyquinoline-Based Agents: Current Development, Structure–Activity Relationships, and Perspectives

Antimicrobial activity of clioquinol and nitroxoline: a scoping review

Identification of antimycobacterial 8-hydroxyquinoline derivatives as in vitro enzymatic inhibitors of Mycobacterium tuberculosis enoyl-acyl carrier protein reductase

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