Hydration of l-glycylvaline and l-glycylvalylglycine zwitterions: Structural and vibrational studies using DFT method

Koyambo-Konzapa, Stève-Jonathan; Dhaouadi, Zoubeida; Nsangou, Mama

doi:10.1016/j.jmgm.2019.01.012

Cited by 13 publications

(3 citation statements)

References 28 publications

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“…The visualization of the structure of each compound was carried out by GaussView 5.0.9 software . Compound geometry optimizations and minimum-energy calculations were performed using Gaussian 09w software using theoretical B3LYP 6-31G(d) density functional theory (DFT). , The Ampac 8.16 software was used to convert the Gaussian output files into Ampac output files, which are compatible structure forms used for structure descriptor generation and QSAR analysis within Codessa 2.7.10 . After the molecular structures were transformed into a series of structure descriptors using Codessa 2.7.10, QSAR models were established using the heuristic method according to previous reference reports .…”

Section: Methodsmentioning

confidence: 99%

Novel Design of Citral-Thiourea Derivatives for Enhancing Antifungal Potential against Colletotrichum gloeosporioides

Zeng

Zou

Huang

et al. 2023

J. Agric. Food Chem.

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Although much progress has been made in developing botanical fungicides to combat fungal diseases in crops, there remains a great need to improve the efficiency and long-term safety of these fungicides. This study proposes a novel strategy for designing citral-thiourea derivatives that feature such desirable properties. The motivation of the work herein was to enhance the antifungal activity of citral against C. gloeosprioides by exploiting the synergistic effect that arises from combining citral and thiourea compounds, thereby producing citral-thiourea derivatives that exhibit good long-term safety. The results revealed that the generated compounds e1, e3, e6, e18, and g showed remarkable antifungal activities against C. gloeosprioides, with corresponding EC50 values reaching 0.16, 1.66, 1.37, 4.76, and 4.60 mg/L, respectively, showing that the compounds significantly outperformed both the positive control kresoxim-methyl and the commercially available fungicide carbendazim. Furthermore, compound g showed stronger protective efficacy against C. gloeosprioides than carbendazim on mango fruit at 25 mg/L. Investigating the preliminary structure–activity relationship (SAR) of the compounds also revealed that the citral-thiourea derivatives exhibited higher antifungal activities against C. gloeosprioides compared to citral and thiourea compounds. This reinforcement of antifungal activity observed in the derivatives was found to be attributable to the two characteristics of low molecular size and the presence of a fluorine atom in the meta-position of the benzene ring. Beyond this, it was determined from QSAR that two molecular descriptors (the Kier–Hall index (order 3) and Tot dipole of the molecules) were negatively related to the antifungal activity of the citral-thiourea derivatives, while one other (the maximum resonance energy of a C–H bond) was positively related to their antifungal activity. More importantly, the citral-thiourea derivatives with high antifungal activities (i.e., compounds e1, e3, e6, e14, e15, e18, and g) exhibited negligible cytotoxicity to LO2 and HEK293T cell lines. The antifungal mechanism of the generated citral-thiourea derivatives was investigated by scanning electron microscopy (SEM) and relative conductivity. The derivatives were found to affect mycelial morphology and increase fungal cell membrane permeability, thereby resulting in the destruction of fungal cell membranes. These promising results provide novel insights into the study and potential application value of citral-thiourea derivatives as high-efficiency antifungal agents against C. gloeosprioides.

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Section: Methodsmentioning

confidence: 99%

Novel Design of Citral-Thiourea Derivatives for Enhancing Antifungal Potential against Colletotrichum gloeosporioides

Zeng

Zou

Huang

et al. 2023

J. Agric. Food Chem.

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show abstract

Section: Methodsmentioning

confidence: 99%

“…The density functional theory (DFT) method of Gaussian 16 (Gaussian, Inc., Wallingford) was used to optimize the molecular structures and calculate the minimum energy of synthesized compounds. 21 Some important molecular structure properties were obtained, such as molecular energy, dipole, atomic charge distribution, molecular orbitals and orbital energies, electron density, and electrostatic potential. Then, the molecular structures and antifungal activities were linearly regressed by CODESSA software 2.7.15 (Semichem, Inc., Shawnee), and the quantitative relationship models were constructed.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

Antifungal Application of Rosin Derivatives from Renewable Pine Resin in Crop Protection

Pan

Jiang

et al. 2020

J. Agric. Food Chem.

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In the current work, we synthesized two series of dehydroabietyl amide derivatives from natural product rosin and evaluated their antifungal effects on Valsa mali, Phytophthora capsici, Botrytis cinerea, Sclerotinia sclerotiorum, and Fusarium oxysporum. In vitro and in vivo antifungal activities results indicated that rosin-based amide compounds containing thiophene heterocycles had better inhibitory effects on B. cinerea. In particular, compound 5b (5-fluoro-2-thiophene dehydroabietyl amide) exhibited the excellent antifungal properties against B. cinerea with an EC 50 of 0.490 mg/L, which was lower compared to the positive control penthiopyrad (0.562 mg/L). Physiological and biochemical studies showed that the primary action mechanism of compound 5b on B. cinerea changes mycelial morphology, increases cell membrane permeability, and inhibits the TCA pathway in respiratory metabolism. Furthermore, QSAR and SAR studies revealed that charge distribution of rosin-based amides derivatives have a key role in the antifungal activity through the hydrogen bonding, conjugation, and electrostatic interaction between the compounds and the receptors of the target. To sum up, this study contributes to the development of rosin-based antifungal agents with a novel structure and preferable biological activity.

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DFT investigation on the structural and vibrational behaviours of the non-protein amino acids in hybrid explicit/continuum solvent: a case of the zwitterions γ-aminobutyric and α − aminoisobutyric acids

Dague,

Koyambo-Konzapa,

Nose

et al. 2023

J Mol Model

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Hydration of l-glycylvaline and l-glycylvalylglycine zwitterions: Structural and vibrational studies using DFT method

Cited by 13 publications

References 28 publications

Novel Design of Citral-Thiourea Derivatives for Enhancing Antifungal Potential against Colletotrichum gloeosporioides

Novel Design of Citral-Thiourea Derivatives for Enhancing Antifungal Potential against Colletotrichum gloeosporioides

Antifungal Application of Rosin Derivatives from Renewable Pine Resin in Crop Protection

DFT investigation on the structural and vibrational behaviours of the non-protein amino acids in hybrid explicit/continuum solvent: a case of the zwitterions γ-aminobutyric and α − aminoisobutyric acids

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