Design, Synthesis, Antifungal Activity and Molecular Docking of Thiochroman-4-one Derivatives

Zhong, Yifan; Han, Xiaoyan; Li, Shengbin; Qi, Hui; Song, Yali; Qiao, Xiaoqiang

doi:10.1248/cpb.c17-00274

Cited by 13 publications

(8 citation statements)

References 27 publications

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“…Inhibitor of fungal NMT was also found among a series of synthesized novel thiochroman-4-one derivatives (Fig. 12 , compound 11 ), which showed antifungal activity against C. albican s and C. neoformans with MIC of 0.5 µg mL −1 and 1 µg mL −1 , respectively, values similar to those for amphotericin B (Zhong et al 2017 ). The structure–activity relationship and molecular docking analysis indicated that the binding model of the found inhibitor to C. albicans NMT was consistent with the original NMT ligand R64.…”

Section: Aminoacyl-trna Synthetasesmentioning

confidence: 96%

Molecular targets for antifungals in amino acid and protein biosynthetic pathways

Kuplińska

Rząd

2021

Amino Acids

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Fungi cause death of over 1.5 million people every year, while cutaneous mycoses are among the most common infections in the world. Mycoses vary greatly in severity, there are long-term skin (ringworm), nail or hair infections (tinea capitis), recurrent like vaginal candidiasis or severe, life-threatening systemic, multiorgan infections. In the last few years, increasing importance is attached to the health and economic problems caused by fungal pathogens. There is a growing need for improvement of the availability of antifungal drugs, decreasing their prices and reducing side effects. Searching for novel approaches in this respect, amino acid and protein biosynthesis pathways appear to be competitive. The route that leads from amino acid biosynthesis to protein folding and its activation is rich in enzymes that are descriptive of fungi. Blocking the action of those enzymes often leads to avirulence or growth inhibition. In this review, we want to trace the principal processes of fungi vitality. We present the data of genes encoding enzymes involved in amino acid and protein biosynthesis, potential molecular targets in antifungal chemotherapy, and describe the impact of inhibitors on fungal organisms.

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Section: Aminoacyl-trna Synthetasesmentioning

confidence: 96%

Molecular targets for antifungals in amino acid and protein biosynthetic pathways

Kuplińska

Rząd

2021

Amino Acids

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“…(E,Z)-1,2-diethylidenecyclopentane was only emitted by the non-toxigenic strain and is a known compound of Laurus nobilis essential oil, which has shown antifungal activities and caused inhibition of AFB1 in vitro [46]. The thiochroman-4-one emitted by the non-AFB1-producing strain was known to be an antifungal agent involved in population regulation [47].…”

Section: Mvocsmentioning

confidence: 99%

Volatile Organic Compounds Emitted by Aspergillus flavus Strains Producing or Not Aflatoxin B1

Josselin

Clerck

Boevre

et al. 2021

Toxins

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Aspergillus flavus is a phytopathogenic fungus able to produce aflatoxin B1 (AFB1), a carcinogenic mycotoxin that can contaminate several crops and food commodities. In A. flavus, two different kinds of strains can co-exist: toxigenic and non-toxigenic strains. Microbial-derived volatile organic compounds (mVOCs) emitted by toxigenic and non-toxigenic strains of A. flavus were analyzed by solid phase microextraction (SPME) coupled with gas chromatography–mass spectrometry (GC-MS) in a time-lapse experiment after inoculation. Among the 84 mVOCs emitted, 44 were previously listed in the scientific literature as specific to A. flavus, namely alcohols (2-methylbutan-1-ol, 3-methylbutan-1-ol, 2-methylpropan-1-ol), aldehydes (2-methylbutanal, 3-methylbutanal), hydrocarbons (toluene, styrene), furans (2,5-dimethylfuran), esters (ethyl 2-methylpropanoate, ethyl 2-methylbutyrate), and terpenes (epizonaren, trans-caryophyllene, valencene, α-copaene, β-himachalene, γ-cadinene, γ-muurolene, δ-cadinene). For the first time, other identified volatile compounds such as α-cadinol, cis-muurola-3,5-diene, α-isocomene, and β-selinene were identified as new mVOCs specific to the toxigenic A. flavus strain. Partial Least Square Analysis (PLSDA) showed a distinct pattern between mVOCs emitted by toxigenic and non-toxigenic A. flavus strains, mostly linked to the diversity of terpenes emitted by the toxigenic strains. In addition, the comparison between mVOCs of the toxigenic strain and its non-AFB1-producing mutant, coupled with a semi-quantification of the mVOCs, revealed a relationship between emitted terpenes (β-chamigrene, α-corocalene) and AFB1 production. This study provides evidence for the first time of mVOCs being linked to the toxigenic character of A. flavus strains, as well as terpenes being able to be correlated to the production of AFB1 due to the study of the mutant. This study could lead to the development of new techniques for the early detection and identification of toxigenic fungi.

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“…Research has shown that the NMT gene is essential for vegetative growth and survival of Candida albicans and Cryptococcus neoformans [9][10]. In addition, NMT is a promising target protein for the development of new fungicidal drugs and has a broad spectrum of antifungal [11]. Osh4 is an important antifungal target protein which plays a role in sterol membrane regulation [12].…”

Section: ■ Experimental Section Materialsmentioning

confidence: 99%

<i>In Silico</i> Study on Interaction and Preliminary Toxicity Prediction of <i>Eleutherine americana</i> Components as an Antifungal and Antitoxoplasmosis Candidate

et al. 2020

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Red bulbs of Eleutherine americana (Aubl.) Merr. ex K. Heyne has been known for its high content of naphthoquinones that have antifungal and antiparasitic activities. In this research, in silico interaction study was performed between 31 compounds reported to be found in E. americana with the selected target proteins for antifungal and antitoxoplasmosis activity using the molecular docking method. An ORPs (OSBP-related proteins), Osh4 (PDB ID: 1ZHX), and N-myristoyltransferase (Nmt, PDB ID: 1IYL) were used as the antifungal target proteins. Toxoplasma gondii purine nucleoside phosphorylase (TgPNP, PDB ID: 3MB8) and calcium-dependent protein kinase-1 (TgCDPK1, PDB ID: 4M84) were used as antitoxoplasmosis target proteins. Three-dimensional structures of the test compounds were made and optimized using GaussView 6.0 and Gaussian 09W. The target proteins were prepared using the Discovery Studio 2016 Program. Aquatic toxicity prediction as the preliminary assessment of the safety of the compounds was performed using ECOSAR v2.0. The results suggest that the compound having both the smallest free binding energy compared with positive control and other test compounds and low predicted toxicity is β-sitosterol with a free binding energy of ‒11.55 and ‒11.18 kcal/mol towards Osh4 and Nmt and ‒8.06 and ‒10.29 kcal/mol towards TgPNP and TgCDPK1, respectively.

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Design, Synthesis, Antifungal Activity and Molecular Docking of Thiochroman-4-one Derivatives

Cited by 13 publications

References 27 publications

Molecular targets for antifungals in amino acid and protein biosynthetic pathways

Molecular targets for antifungals in amino acid and protein biosynthetic pathways

Volatile Organic Compounds Emitted by Aspergillus flavus Strains Producing or Not Aflatoxin B1

<i>In Silico</i> Study on Interaction and Preliminary Toxicity Prediction of <i>Eleutherine americana</i> Components as an Antifungal and Antitoxoplasmosis Candidate

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