Crystal structures, in-silico study and anti-microbial potential of synthetic monocarbonyl curcuminoids

Din, Zia Ud; Serrano, Nadja Fernanda Gonzaga; Ademi, Kastriot; Sousa, Cristina Paiva de; Deflon, Victor M.; Maia, Pedro Ivo da Silva; Rodrigues‐Filho, Edson

doi:10.1016/j.molstruc.2017.05.061

Cited by 8 publications

(2 citation statements)

References 29 publications

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“…Subsequently, both compounds were molecularly docked to several key bacterial enzymes, and the result suggested that the most relevant target of compounds 2 and 3 is D ‐alanyl‐ D ‐alanine carboxypeptidase (PDB ID: 1PW1). In agreement with the in vitro assay, compounds 2 and 3 showed the best binding affinity of −8.0 and −8.5 kcal/mol, respectively, with hydrogen bonding and hydrophobic interactions observed with several amino acid residues, [ 132 ] which resembled the same space occupancy in the active site of the co‐crystallized ligand and ciprofloxacin. Besides that, the inhibition constant ( K i ) was calculated for compounds 2 and 3 with correspondingly smaller K i values of 2.65 and 2.14 μM, indicating greater binding affinity and high enzyme inhibition.…”

Section: Bioactivity Of Diarylpentanoids: Anti‐infective Propertiessupporting

confidence: 57%

“…[131] Moreover, this study proves the importance of increasing the flexibility of the C5-linker compared to the C3-linker of the chalcone in further enhance the selectivity and efficacy of the compounds. hydrophobic interactions observed with several amino acid residues, [132] which resembled the same space occupancy in the active site of the co-crystallized ligand and ciprofloxacin. Besides that, the inhibition constant (K i ) was calculated for compounds 2 and 3 with correspondingly smaller K i values of 2.65 and 2.14 μM, indicating greater binding affinity and high enzyme inhibition.…”

Section: Diarylpentanoidsmentioning

confidence: 67%

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Diarylpentanoids, the privileged scaffolds in antimalarial and anti‐infectives drug discovery: A review

Ramli,

Mohd Faudzi

2023

Archiv der Pharmazie

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Asia is a hotspot for infectious diseases, including malaria, dengue fever, tuberculosis, and the pandemic COVID‐19. Emerging infectious diseases have taken a heavy toll on public health and the economy and have been recognized as a major cause of morbidity and mortality, particularly in Southeast Asia. Infectious disease control is a major challenge, but many surveillance systems and control strategies have been developed and implemented. These include vector control, combination therapies, vaccine development, and the development of new anti‐infectives. Numerous newly discovered agents with pharmacological anti‐infective potential are being actively and extensively studied for their bioactivity, toxicity, selectivity, and mode of action, but many molecules lose their efficacy over time due to resistance developments. These facts justify the great importance of the search for new, effective, and safe anti‐infectives. Diarylpentanoids, a curcumin derivative, have been developed as an alternative with better bioavailability and metabolism as a therapeutic agent. In this review, the mechanisms of action and potential targets of antimalarial drugs as well as the classes of antimalarial drugs are presented. The bioactivity of diarylpentanoids as a potential scaffold for a new class of anti‐infectives and their structure–activity relationships are also discussed in detail.

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Section: Bioactivity Of Diarylpentanoids: Anti‐infective Propertiessupporting

confidence: 57%

Section: Diarylpentanoidsmentioning

confidence: 67%

Diarylpentanoids, the privileged scaffolds in antimalarial and anti‐infectives drug discovery: A review

Ramli,

Mohd Faudzi

2023

Archiv der Pharmazie

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Crystal and Quantum Chemical Exploration of the Potent Monocarbonyl Curcuminoids to Unveil Their Structural and Intriguing Electronic Properties

et al. 2020

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The two isomeric trifluoromethane and nitro containing monocarbonylcurcuminoids: (1E,4E)‐2‐methyl‐1‐(4‐nitrophenyl)‐5‐(4 (trifluoromethyl)phenyl)penta‐1,4‐dien‐3‐one (DI‐MNTDO ) and (1E,4E)‐2‐methyl‐5‐(4‐nitrophenyl)‐1‐(4‐(trifluoromethyl)phenyl)penta‐1,4‐dien‐3‐one (MO‐MNTDO)have been prepared by two consecutive aldol condensation reactions. The chemical structures of the DI‐MNTDO and MO‐MNTDO have been determined using X‐ray crystallographic and spectrometric methods. The single crystal X‐Ray diffraction (SC‐XRD) data reveals that DI‐MNTDO contains two geometrically different molecules in the asymmetric unit, while, MO‐MNTDO contains one molecule in the asymmetric unit. Additionally, molecular geometric parameters, vibrational spectral analysis, as well as electronic properties of the above‐mentioned molecules have been studied utilizing DFT/B3LYP/6‐31G (d, p) approach. The UV‐Vis spectral analysis was performed utilizing the time‐dependent density functional theory (TD‐DFT) with the same level. The natural bond orbitals (NBOs) investigation has been carried out at the B3LYP/6‐311+G(d,p) approach to explain the intramolecular hyper conjugative interactions. A plausible concurrence is acquired between experimental and theoretical findings. The frontier molecular orbitals (FMOs) have been achieved by above‐mentioned level of theory. Subsequently, the global reactivity parameters are calculated using the energies of FMOs. The chemical potential (μ) order: [MO‐MNTDO (μ=‐5.0785 eV)] < [DI‐MNTDO (μ=‐4.9465 eV)]. The obtained findings in context of stability as well as reactivity indicate that DI‐MNTDO is more stable and less reactive as compared to MO‐MNTDO.

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Antibacterial potential of chalcones and its derivatives against Staphylococcus aureus

Silva¹,

Donato²,

Gonçalves³

et al. 2022

3 Biotech

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Crystal structures, in-silico study and anti-microbial potential of synthetic monocarbonyl curcuminoids

Cited by 8 publications

References 29 publications

Diarylpentanoids, the privileged scaffolds in antimalarial and anti‐infectives drug discovery: A review

Diarylpentanoids, the privileged scaffolds in antimalarial and anti‐infectives drug discovery: A review

Crystal and Quantum Chemical Exploration of the Potent Monocarbonyl Curcuminoids to Unveil Their Structural and Intriguing Electronic Properties

Antibacterial potential of chalcones and its derivatives against Staphylococcus aureus

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