Synthesis and molecular interaction study of a diphenolic hidrazinyl-thiazole compound with strong antioxidant and antiradical activity with HSA

Mic, Mihaela; Pı̂rnău, Adrian; Floare, Călin G.; Marc, Gabriel; Franchini, Ana H.; Oniga, Ovidiu; Vlase, Laurian; Bogdan, M.

doi:10.1016/j.molstruc.2021.131278

Cited by 18 publications

(28 citation statements)

References 46 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Recent docking studies for drug-protein interactions analysis encompass, for example, oral anticoagulants [169], the anticancer drug gemcitabine [170], the antihypertensive drug telmisartan [171], among others. Regarding other bioactive compounds, some recent examples include the dihydroxy-phenyl-thiazol-hydrazinium chloride (antioxidant and antiradical activities) [172], hydrazone ligand derived Cu(II) and VO(IV) complexes (antibacterial and antifungal activities) [173], uranyl complexes of alkyl substituted isothiosemicarbazone (anticancer features) [174], 7-amino coumarin derivative (analgesic, anticancer, and anticoagulant activities) [175], among others. Our group also, recently, evaluated the recognition mechanisms and protein binding affinity of chiral derivatives of xanthones on HSA by diverse methods, including docking approach (Figure 6) [98,163].…”

Section: In Silico Methodsmentioning

confidence: 99%

Enantioresolution and Binding Affinity Studies on Human Serum Albumin: Recent Applications and Trends

et al. 2021

View full text Add to dashboard Cite

The interaction between proteins and drugs or other bioactive compounds has been widely explored over the past years. Several methods for analysis of this phenomenon have been developed and improved. Nowadays, increasing attention is paid to innovative methods, such as high performance affinity liquid chromatography (HPALC) and affinity capillary electrophoresis (ACE), taking into account various advantages. Moreover, the development of separation methods for the analysis and resolution of chiral drugs has been an area of ongoing interest in analytical and medicinal chemistry research. In addition to bioaffinity binding studies, both HPALC and ACE al-low one to perform other type of analyses, namely, displacement studies and enantioseparation of racemic or enantiomeric mixtures. Actually, proteins used as chiral selectors in chromatographic and electrophoretic methods have unique enantioselective properties demonstrating suitability for the enantioseparation of a large variety of chiral drugs or other bioactive compounds. This review is mainly focused in chromatographic and electrophoretic methods using human serum albumin (HSA), the most abundant plasma protein, as chiral selector for binding affinity analysis and enantioresolution of drugs. For both analytical purposes, updated examples are presented to highlight recent applications and current trends.

show abstract

Section: In Silico Methodsmentioning

confidence: 99%

Enantioresolution and Binding Affinity Studies on Human Serum Albumin: Recent Applications and Trends

et al. 2021

View full text Add to dashboard Cite

show abstract

“…The route followed for synthesizing the intermediate and final compounds is presented in Scheme 1 . The synthesis of intermediate compounds 3a and 3b and that of final compound 5a were previously reported in the literature [ 3 , 13 , 14 ]. To a methanol solution (60 mL) of 2,4-dihydroxybenzaldehyde 1b or 2,4-dihydroxyacetophenone 1a (20 mmol) was added a hot aqueous solution (30 mL) of thiosemicarbazide 2 (20 mmol) and to the resulted mixtures was added a drop of concentrated H 2 SO 4 .…”

Section: Methodsmentioning

confidence: 99%

“…The resulting precipitates (compounds 3a and 3b ) were filtered off and vacuum dried. The synthesis of all final compounds was performed according to a method already described in the literature [ 3 , 15 ]. A quantity of 10 mmol of compound 3a-b was mixed with 70 mL of hot anhydrous acetone in a round bottom glass flask under magnetic stirring until solubilization, then 10 mmol of the corresponding compound 4a-d was added.…”

Section: Methodsmentioning

confidence: 99%

“…The reducing power of the tested compounds was determined using the FRAP assay, according to a modified method proposed initially by Benzie and Strain, which was previously reported by our group [ 3 , 17 , 19 , 23 ]. The reducing power of compounds was calculated as percent of the reference compounds, using Equation (4):

…”

Section: Methodsmentioning

confidence: 99%

“…The very good antioxidant and antiradical properties identified for the compound Dihydroxy-Phenyl-Thiazol-Hydrazinium chloride (DPTH), developed by our team and named in this paper 5a , were the starting point for the present research [ 3 ].…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Phenolic Thiazoles with Antioxidant and Antiradical Activity. Synthesis, In Vitro Evaluation, Toxicity, Electrochemical Behavior, Quantum Studies and Antimicrobial Screening

et al. 2021

Self Cite

View full text Add to dashboard Cite

Oxidative stress represents the underlying cause of many chronic diseases in human; therefore, the development of potent antioxidant compounds for preventing or treating such conditions is useful. Starting from the good antioxidant and antiradical properties identified for the previously reported Dihydroxy-Phenyl-Thiazol-Hydrazinium chloride (DPTH), we synthesized a congeneric series of phenolic thiazoles. The radical scavenging activity, and the antioxidant and chelation potential were assessed in vitro, a series of quantum descriptors were calculated, and the electrochemical behavior of the synthesized compounds was studied to evaluate the impact on the antioxidant and antiradical activities. In addition, their antibacterial and antifungal properties were evaluated against seven aerobic bacterial strains and a strain of C. albicans, and their cytotoxicity was assessed in vitro. Compounds 5a-b, 7a-b and 8a-b presented remarkable antioxidant and antiradical properties, and compounds 5a-b, 7a and 8a displayed good Cu+2 chelating activity. Compounds 7a and 8a were very active against P. aeruginosa ATCC 27853 compared to norfloxacin, and proved less cytotoxic than ascorbic acid against the human keratinocyte cell line (HaCaT cells, CLS-300493). Several phenolic compounds from the synthesized series presented excellent antioxidant activity and notable anti-Pseudomonas potential.

show abstract

Probing the combination of erlotinib hydrochloride, an anticancer drug, and human serum albumin: Spectroscopic, molecular docking, and molecular dynamic analyses

et al. 2023

View full text Add to dashboard Cite

Human serum albumin (HSA) is a globular and monomeric protein in plasma that transports many drugs and compounds. Binding of some drugs to HSA can lead to changes in its stability and biological function. We investigated the binding interactions between erlotinib hydrochloride (Erlo) and HSA. Erlo is used to treat lung, pancreatic, and some other cancers. Experimental data showed that the fluorescence emission of the protein was quenched by Erlo using a static quenching mechanism. The calculation of the binding constant, K b (1.57 Â 10 5 M À1 at 300 K), confirmed the existence of a moderate binding interaction between Erlo and HSA.The interaction was enthalpy driven, spontaneous, and exothermic. The calculated thermodynamic parameters in agreement with simulation and molecular docking data showed that van der Waals and hydrogen bond forces played an important role in the interaction process. Molecular docking results indicated that Erlo has more affinity to bind to subdomain IIA (site I) of HSA. Molecular dynamics simulation analysis showed that the protein is stable in the presence of Erlo under simulation conditions.

show abstract

Synthesis and molecular interaction study of a diphenolic hidrazinyl-thiazole compound with strong antioxidant and antiradical activity with HSA

Cited by 18 publications

References 46 publications

Enantioresolution and Binding Affinity Studies on Human Serum Albumin: Recent Applications and Trends

Enantioresolution and Binding Affinity Studies on Human Serum Albumin: Recent Applications and Trends

Phenolic Thiazoles with Antioxidant and Antiradical Activity. Synthesis, In Vitro Evaluation, Toxicity, Electrochemical Behavior, Quantum Studies and Antimicrobial Screening

Probing the combination of erlotinib hydrochloride, an anticancer drug, and human serum albumin: Spectroscopic, molecular docking, and molecular dynamic analyses

Contact Info

Product

Resources

About