Caffeine and sulfadiazine interact differently with human serum albumin: A combined fluorescence and molecular docking study

Islam, Mullah Muhaiminul; Sonu, Vikash K.; Gashnga, Pynsakhiat Miki; Moyon, N. Shaemningwar; Mitra, Sivaprasad

doi:10.1016/j.saa.2015.07.051

Cited by 43 publications

(20 citation statements)

References 65 publications

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“…To explore this notion further, we selected caffeine as an alternative, weaker binding ligand with a reported K D value for binding to HSA varying between 0.9 mM and 1.5 mM21282930. Similar to L-tryptophan, there also exists multiple weak non-specific caffeine binding sites on HSA282930.…”

Section: Resultsmentioning

confidence: 99%

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Protein-ligand binding affinity determination by the waterLOGSY method: An optimised approach considering ligand rebinding

Huang

Bonnichon

Claridge

et al. 2017

Sci Rep

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Section: Resultsmentioning

confidence: 99%

“…Similar to L-tryptophan, there also exists multiple weak non-specific caffeine binding sites on HSA282930. Titration experiments were again conducted with varying mixing times (0.15 seconds to 2.0 seconds) and varying protein concentrations (25 μM, 50 μM and 100 μM).…”

Section: Resultsmentioning

confidence: 99%

Protein-ligand binding affinity determination by the waterLOGSY method: An optimised approach considering ligand rebinding

Huang

Bonnichon

Claridge

et al. 2017

Sci Rep

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“…All steady state fluorescence studies were carried out in Quanta Master (QM-40) apparatus (Photon Technology International, PTI), the details of which have been given in supplementary section ST2. The following relation was used to obtain the corrected fluorescence intensity after removal of the inner filter effect 40…”

Section: Methodsmentioning

confidence: 99%

Therapeutic potency of substituted chromones as Alzheimer’s drug: Elucidation of acetylcholinesterase inhibitory activity through spectroscopic and molecular modelling investigation

et al. 2019

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Introduction: Documentation on the potency of chromones as acetylcholinesterase (AChE) antagonists has paved the way for the design and usage of new chromone analogues as inhibitors of AChE modelled on the hypothesis based on cholinergic pathway of Alzheimer’s disease (AD). Here, 2 minimally substituted chromones, namely 3-cyanochromone (CyC) and 7-amino-3-methylchromone (AMC), were checked for their AChE inhibition efficacies and plasma protein modulation. Methods: Colorimetric enzymatic assay as well as fluorescence measurements were performed for obtaining the experimental results, which were further corroborated by molecular docking and simulation studies. Results: The investigated systems exhibited strong inhibition activities against AChE, with CyC (IC50= 85.12 ± 6.70 nM) acting as better inhibitor than AMC (IC50 = 103.09 ± 11.90 nM) and both having IC50 values in the range of FDA approved cholinergic drug Donepezil (IC50 = 74.13 ± 8.30 nM). Non-competitive inhibition was observed in both the cases with the inhibitors binding near the peripheral anionic site (PAS) of the enzyme. Having one planar nitrile group in CyC as compared to sp3 hybridised substituents in AMC facilitated stacking interactions in the former, accounting for its higher inhibitory efficacy. A significant decrease in the inhibition potency of CyC (~32%) was noted in comparison with AMC (~5%) when the experiments were performed in presence of human serum albumin (HSA) instead of pure aqueous buffer. Conclusion: This comparative study affirms the importance of meticulous substitution in the chromone scaffold to promote maximum inhibition potency, while considering their usage as AD drugs.

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“…Sulfadiazine (SD) is used for curing infections caused by gram-positive and gram-negative organisms [1] and it belongs to the sulfonamide category [2]. The sulfonamides are found in blood in three different forms: proteinbound, conjugated (acetylated and possibly others), and free [3]. The drug acts by the diffusion of its unbound form through the circulatory system and interacts with action sites [2].…”

Section: Introductionmentioning

confidence: 99%

Combined computational and experimental studies on cysteine-sulfadiazine adduct formation

2020

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The electrochemical characterization of sulfadiazine-cysteine (SD-CYS) adduct formation was performed in phosphate buffer (pH 7) on the basis of voltammetric current and peak potential measurements. Due to the association of cysteine with sulfadiazine, the reduction peak currents of mercuric and mercurous cysteine thiolates decreased and their peak potentials simultaneously shifted to less negative potentials. By using the current changes of mercurous cysteine thiolate, it was determined that cysteine and sulfadiazine are associated with a 1:1 stoichiometry with a conditional association constant of 1.99 ×10 4 M −1. In addition to experimental studies, a computational approach was carried out to study the geometrical parameters, electron densities, and UV-Vis absorption spectra of sulfadiazine and SD-CYS adduct in water. Calculated (B3LYP/6-311 ++ G(d,p) level) and experimental UV-Vis absorption spectra of the compounds were found to be in good agreement in water. The computational study suggests that cysteine bound to the C(5) on the pyrimidine ring via SH-group nucleophilic attack. Computational results reveal that sulfadiazine and its derivatives effectively bind cysteine and may lead to new molecules/drugs to target cysteine.

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Caffeine and sulfadiazine interact differently with human serum albumin: A combined fluorescence and molecular docking study

Cited by 43 publications

References 65 publications

Protein-ligand binding affinity determination by the waterLOGSY method: An optimised approach considering ligand rebinding

Protein-ligand binding affinity determination by the waterLOGSY method: An optimised approach considering ligand rebinding

Therapeutic potency of substituted chromones as Alzheimer’s drug: Elucidation of acetylcholinesterase inhibitory activity through spectroscopic and molecular modelling investigation

Combined computational and experimental studies on cysteine-sulfadiazine adduct formation

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