scholarly journals Radical Scavenging Activity and Pharmacokinetic Properties of Coumarin–Hydroxybenzohydrazide Hybrids

2022 ◽  
Vol 23 (1) ◽  
pp. 490
Author(s):  
Marko R. Antonijević ◽  
Edina H. Avdović ◽  
Dušica M. Simijonović ◽  
Žiko B. Milanović ◽  
Ana D. Amić ◽  
...  

Free radicals often interact with vital proteins, violating their structure and inhibiting their activity. In previous studies, synthesis, characterisation, and the antioxidative properties of the five different coumarin derivatives have been investigated. In the tests of potential toxicity, all compounds exhibited low toxicity with significant antioxidative potential at the same time. In this paper, the radical scavenging activity of the abovementioned coumarin derivatives towards ten different radical species was investigated. It was found that all investigated compounds show good radical scavenging ability, with results that are in correlation with the results published in the previous study. Three additional mechanisms of radical scavenging activity were investigated. It was found that all three mechanisms are thermodynamically plausible and in competition. Interestingly, it was found that products of the Double Hydrogen Atom Transfer (DHAT) mechanism, a biradical species in triplet spin state, are in some cases more stable than singlet spin state analogues. This unexpected trend can be explained by spin delocalisation over the hydrazide bridge and phenolic part of the molecule with a low probability of spin pairing. Besides radical-scavenging activity, the pharmacokinetic and drug-likeness of the coumarin hybrids were investigated. It was found that they exhibit good membrane and skin permeability and potential interactions with P-450 enzymes. Furthermore, it was found that investigated compounds satisfy all criteria of the drug-likeness tests, suggesting they possess a good preference for being used as potential drugs.

2019 ◽  
Vol 23 (11n12) ◽  
pp. 1478-1485
Author(s):  
Senem Çolak Yazıcı ◽  
Sibel Kahraman ◽  
Salih Z. Yıldız ◽  
Mahmut D. Yılmaz

Tetra-zwitterionic-substituted nickel(II) phthalocyanine derivatives were newly synthesized starting from nonionic 2(3),9(10),16(17),23(24)-tetrakis-[2-([Formula: see text]-((3-dimethylamino)propyl)carbamate)oxyethyl)phthalocyaninato nickel (II). The novel compounds have been characterized by a combination of UV-vis, FT-IR and mass spectroscopies and elemental analysis. The critical micelle concentrations of the prepared compounds were measured, and the antioxidant activities were analyzed with radical scavenging ability of 1,1-diphenyl-2-picrylhydrazyl (DPPH) and with 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt (ABTS). The zwitterionic molecules showed aggregated spectra in the UV-vis region, and they might be good surfactant candidates for the detergent industry with their appropriate critical micelle concentration (CMC) properties in water. The compounds exhibited ABTS radical scavenging activity and thus they have antioxidant activity.


2019 ◽  
Vol 20 (19) ◽  
pp. 4735 ◽  
Author(s):  
Anja Harej ◽  
Andrijana Meščić Macan ◽  
Višnja Stepanić ◽  
Marko Klobučar ◽  
Krešimir Pavelić ◽  
...  

The novel 4-substituted 1,2,3-triazole L-ascorbic acid (L-ASA) conjugates with hydroxyethylene spacer as well as their conformationally restricted 4,5-unsaturated analogues were synthesized as potential antioxidant and antiproliferative agents. An evaluation of the antioxidant activity of novel compounds showed that the majority of the 4,5-unsaturated L-ASA derivatives showed a better antioxidant activity compared to their saturated counterparts. m-Hydroxyphenyl (7j), p-pentylphenyl (7k) and 2-hydroxyethyl (7q) substituted 4,5-unsaturated 1,2,3-triazole L-ASA derivatives exhibited very efficient and rapid (within 5 min) 2,2-diphenyl-1-picrylhydrazyl (DPPH•) radical scavenging activity (7j, 7k: IC50 = 0.06 mM; 7q: IC50 = 0.07 mM). In vitro scavenging activity data were supported by in silico quantum-chemical modelling. Thermodynamic parameters for hydrogen-atom transfer and electron-transfer radical scavenging pathways of anions deprotonated at C2-OH or C3-OH groups of L-ASA fragments were calculated. The structure activity analysis (SAR) through principal component analysis indicated radical scavenging activity by the participation of OH group with favorable reaction parameters: the C3-OH group of saturated C4-C5(OH) derivatives and the C2-OH group of their unsaturated C4=C5 analogues. The antiproliferative evaluation showed that p-bromophenyl (4e: IC50 = 6.72 μM) and p-pentylphenyl-substituted 1,2,3-triazole L-ASA conjugate (4k: IC50 = 26.91 μM) had a selective cytotoxic effect on breast adenocarcinoma MCF-7 cells. Moreover, compound 4e did not inhibit the growth of foreskin fibroblasts (IC50 > 100 μM). In MCF-7 cells treated with 4e, a significant increase of hydroxylated hypoxia-inducible transcription factor 1 alpha (HIF-1α) expression and decreased expression of nitric oxide synthase 2 (NOS2) were observed, suggesting the involvement of 4e in the HIF-1α signaling pathway for its strong growth-inhibition effect on MCF-7 cells.


2012 ◽  
Vol 189 ◽  
pp. 225-231
Author(s):  
Xiang Peng Guo ◽  
Rui Fa Jin

The structural and electronic properties of alkannin and its derivatives and their radicals were investigated at density functional level. It turned out that the presence of the dihydroxy functionality increases the radical stability through hydrogen bond formation. The hydrogen atom transfer for alkannin derivatives is difficult to occur compared with zero compound phenol. However, alkannin derivatives appear to be good candidates for the one-electron-transfer, particularly for alkannin derivatives with –OCOCH=CH(CH3)2 and –OCOCH2CH(CH3)2 groups. It suggests that 1–7 are expected to be the promising candidates for radical scavenging activity compounds because The ionization potential (IP) values of 1–7 are lower than that of the zero compound phenol.


2020 ◽  
Vol 83 (2) ◽  
pp. 365-376
Author(s):  
MINGJUN YAO ◽  
IFTIKHAR ALI KHAN ◽  
YIQUN CHENG ◽  
YUN ANG ◽  
XINGHU ZHOU ◽  
...  

ABSTRACT The effects of different grilling methods and tea marinades on the formation of heterocyclic amines (HCAs) and benzo[a]pyrene (BaP) in grilled chicken drumsticks were investigated. This study showed that both the grilling method and type of charcoal used in charcoal grilling had a significant effect on the formation of HCAs and BaP. The total content of HCAs and BaP detected in drumsticks was the lowest under electric roasting, at 7.25 and 0.04 ng/g, respectively; thus, the electric grill can be used as an alternative grilling method to meet consumer demands for safety. The free radical scavenging ability of tea infusion was significantly higher than that of spice infusion. The white tea marinade significantly increased radical scavenging activity and prevented formation of HCAs and BaP more than the green tea marinade; thus, tea marinade can be applied to flavoring as a pretreatment to preserve the quality of meat and to decrease the generation of HCAs and BaP during cooking. HIGHLIGHTS


RSC Advances ◽  
2017 ◽  
Vol 7 (67) ◽  
pp. 42225-42232 ◽  
Author(s):  
Qing Li ◽  
Lishushi Qiu ◽  
Wenqiang Tan ◽  
Guodong Gu ◽  
Zhanyong Guo

A new class of inulin derivatives possessing 1,2,3-triazolium charged units by associating “click reaction” with efficient 1,2,3-triazole quaternization were designed and synthesized. The synthesized inulin derivatives possess excellent free radical-scavenging ability.


2011 ◽  
Vol 344 (9) ◽  
pp. 588-594 ◽  
Author(s):  
Mehdi Khoobi ◽  
Saeed Emami ◽  
Gholamreza Dehghan ◽  
Alireza Foroumadi ◽  
Ali Ramazani ◽  
...  

2017 ◽  
pp. 13-38 ◽  
Author(s):  
Nirjhar Dasgupta ◽  
Paramita Nandy ◽  
Chandan Sengupta ◽  
Sauren Das

Mangrove, a specialized group of plant communities, provide immense ecological and protective benefits to the coastal areas of the tropical and subtropical world where they thrive. Demographic obligation and climatic hostilities have massively altered their vegetation pattern and, even ruined some key species to large extent. The present study aims to consider Reactive Oxygen Species (ROS) scavenging skills in some degrading mangrove taxa of Indian Sundarbans (Xylocarpus granatum and Heritiera fomes) compared with some opulently growing ones (Excoecaria agallocha, Bruguiera gymnorrhiza and Phoenix paludosa) in increasing salinity gradient, in relation to their sustainability. Non-enzymatic antioxidants (secondary metabolites) Proanthocyanidin and Tannin were estimated and Free radical scavenging ability was evaluated by Singlet Oxygen Scavenging Activity Assay, Reducing power assay, effects on Peroxynitrite, Nitric Oxide Radical Scavenging, Hydrogen Peroxide Scavenging Activity Assay, Reaction with Hypochlorous Acid, Superoxide Radical Scavenging Activity Assay and Hydroxyl Radical Scavenging Activity. Relatively higher occurrence of secondary metabolites and improved antioxidant ability were recorded in E. agallocha, B. gymnorrhiza and P. paludosa; than the other two plants X. granatum and H. fomes; where the trend showed a decline in the ROS scavenging after a certain increase in salinity. Strong positive correlation of both secondary metabolites and radical scavenging ability with salinity pose the three stable taxa more viable in the higher salty environment of the Indian Sundarbans. But relatively less ROS scavenging ability in more saline zones, may be the potential reason for the unfavorable existence of the two red listed plants, which would ultimately lead to gradual natural extinction of them from the Indian Sundarbans.


Author(s):  
SAMRAJ RATTANADILOK NA PHUKET ◽  
TITIMA SANGKAEW ◽  
PIYATIDA CHANAPAN ◽  
SURACHAI TECHAOEI

Objective: The objective of this research was to determine the antioxidant of ß-glucans from an edible mushroom, Schizophyllum commune in Thailand.Methods: The antioxidant activity of ß-glucans was measured in terms of hydrogen donating or radical scavenging ability by 2, 2-diphenyl-1-picrylhydrazyl (DPPH) method,2,2´-azinobis-(3-ethyl-benzothiazoline-6-sulfonic acid (ABTS) radical scavenging activity analysis, and total phenoliccompounds. The ß-glucans structure was analyzed using Fourier-transform infrared spectrophotometer.Results: The ß-glucans were extracted from S. commune and tested biological activities. Using the Folin–Ciocalteu Reactive method, we found thatthe phenolic compound contents of ethanol extracts of the mushroom sample were 284.41±1.22 mgGAE/g extract. The IC50 radical scavenging ability(DPPH) and IC50 radical scavenging activity (ABTS) of ß-glucans were 0.829±0.006 and 0.724±0.021 mg/mL, respectively.Conclusion: The ß-glucans from S. commune in Thailand showed a potent antioxidant activity and it will be able to apply in pharmaceutical cosmetics.


2015 ◽  
Author(s):  
Maité Sylla-Iyarreta Veitía ◽  
Elizabeth Goya Jorge ◽  
Anita Maria Rayar ◽  
Stephen Jones Barigye ◽  
María Elisa Jorge Rodríguez

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