The synthesis of an antifungal 1,2,4-triazole drug and the establishment of a drug delivery system based on zeolitic imidazolate frameworks

Jiao, Shulin; Li, Yaojia; Gao, Zhiguo; Chen, Ruicheng; Wang, Yan; Zou, Zhi-Hong

doi:10.1039/c9nj04432a

Cited by 20 publications

(14 citation statements)

References 43 publications

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“…The initial zero-order voriconazole release from the V-ZIFs represents a constant release in time, which is advantageous compared to frequently observed burst-release followed by long-term tail-release, as often observed for many drugs carriers, [23,24] including ZIFs. [29,30] Burst-release of azoles from ZIFs, arise because of weak coordination-binding with zinc ions. Accordingly, azoles are physically embedded in these MOFs, [29,30] opposite to the strong coordination-binding of voriconazole with zinc in our V-ZIFs.…”

Section: Release Of Inbuilt Voriconazolementioning

confidence: 99%

“…[29,30] Burst-release of azoles from ZIFs, arise because of weak coordination-binding with zinc ions. Accordingly, azoles are physically embedded in these MOFs, [29,30] opposite to the strong coordination-binding of voriconazole with zinc in our V-ZIFs. Zero-order release is assumed to be due to the relative compact architecture of V-ZIF with strong coordination-binding of voriconazole and its release due to dissociation of voriconazole from the MOF through surface corrosion.…”

Section: Release Of Inbuilt Voriconazolementioning

confidence: 99%

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Antifungal‐Inbuilt Metal–Organic‐Frameworks Eradicate Candida albicans Biofilms

Liu

et al. 2020

Adv Funct Materials

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Fungal biofilms cause a major clinical problem with a shrinking armamentarium for treatment. Here, the design and synthesis of voriconazole-inbuilt zinc 2-methylimidazolates frameworks (V-ZIF) is reported. Voriconazole is built in through coordination-binding between zinc and voriconazole. These metal-organic-frameworks with inbuilt voriconazole, reduce inadvertent voriconazole-leakage, yield a zero-order release kinetics of voriconazole, aid antifungal penetration in Candida albicans biofilms, and prevent Candida aggregation yielding better dispersal. Once accumulated in an acidic C. albicans biofilm, voriconazole dissociates from the metal-organic framework to cause membrane-damage and killing of inhabiting fungi. Moreover, in a murine model, the V-ZIFs eradicate open-wound infections caused by C. albicans better than voriconazole in solution, with negligible side effects to the healthy tissues of major organs. Thus, V-ZIFs may provide a welcome addition to the antifungal armamentarium currently available for the treatment of fungal biofilms.

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Section: Release Of Inbuilt Voriconazolementioning

confidence: 99%

Section: Release Of Inbuilt Voriconazolementioning

confidence: 99%

Antifungal‐Inbuilt Metal–Organic‐Frameworks Eradicate Candida albicans Biofilms

Liu

et al. 2020

Adv Funct Materials

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“…[21][22][23][24][25][26] Moreover, some of the trifluoromethyl-substituted and fluoro-substituted 1,2,4-triazoles, are well known potential therapeutic drugs used at present. [27][28][29] Although, there are several methods for the synthesis of mono trifluoromethylated 1,2,4-triazoles in the literature, the reported synthetic methods for bistrifluoromethylated 1,2,4-triazole derivatives are limited and also, diversity and reaction yields are low to moderate. Therefore, due to the presence of 1,2,4-triazole moiety in drug compounds and pesticides and also of their biological importance, the exploration of new and efficient methods with excellent yield to synthesize versatile trifluoromethylated 1,2,4-triazoles is very important.…”

Section: Paper Synthesismentioning

confidence: 99%

Trifluoromethylated Amidrazone Derivatives as Key Compounds for the Synthesis of 4-Aryl-3,5-bis(trifluoromethyl)-4H-1,2,4-triazoles

Zeinali¹,

Darehkordi²

2022

Synthesis

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A novel, efficient, and solvent-free approach for the synthesis of aryl-3,5-bis(trifluoromethyl)-4H-1,2,4-triazoles has been disclosed via the nucleophilic intramolecular cyclization reaction of trifluoromethylated amidrazone and 2,2,2-trifluoroacetic anhydride. Trifluoromethylated amidrazones intermediates which are used in this project have been synthesized from the reaction of N-aryl-2,2,2-trifuoroacetimidoyl chloride derivatives and hydrazine hydrate at ambient temperature in excellent yields.

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“…34 ZIF-8 not only releases metal ions, ligand 2-MI also has some antibacterial pro-perties. 35 In the current study, changes in cell membrane permeability, respiratory metabolism, cell morphology, and intracellular protein synthesis of E. coli were mainly studied. Damage to the bacterial cell membrane will affect its reproduction.…”

Section: Article the Antibacterial Mechanism Of Zn(ii) Frame Supportementioning

confidence: 99%

The Antibacterial Mechanism of Zn(II) Frame Supported on Alginate Membrane

Luo

Wang

et al. 2020

Bulletin Korean Chem Soc

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In order to solve the problem of antibiotic-resistant bacteria caused by excessive use of antibiotics, herein, an antibacterial membrane composed of natural sodium alginate (ALG), zeolite imidazolate skeleton (ZIF-8) and niflumic acid (NIF) was reported. The membrane serves as a versatile platform for local antibacterial. This report carried out in-depth research on the physical properties and antibacterial mechanism of the synthesized sodium alginate composite film. The data shows that the sodium alginate-based antibacterial film has a continuous antibacterial effect, and the release of antibacterial molecules can be controlled according to changes in the external environment. The results show that the complex has stronger mechanical and bacteriostatic properties. Niflumic acid and Zn(II) have synergistic antibacterial effect. The complex promotes bacterial death by hindering bacterial respiratory metabolism and destroying cell membrane structure.

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The synthesis of an antifungal 1,2,4-triazole drug and the establishment of a drug delivery system based on zeolitic imidazolate frameworks

Abstract: Schematic representation of a drug delivery system based on ZIF-8 for the therapy of invasive Candida albicans infections.

Cited by 20 publications

References 43 publications

Antifungal‐Inbuilt Metal–Organic‐Frameworks Eradicate Candida albicans Biofilms

Antifungal‐Inbuilt Metal–Organic‐Frameworks Eradicate Candida albicans Biofilms

Trifluoromethylated Amidrazone Derivatives as Key Compounds for the Synthesis of 4-Aryl-3,5-bis(trifluoromethyl)-4H-1,2,4-triazoles

The Antibacterial Mechanism of Zn(II) Frame Supported on Alginate Membrane

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