Heterocyclic Schiff bases as non toxic antioxidants: Solvent effect, structure activity relationship and mechanism of action

Phenolic heterocyclic imine based Schiff bases from Thiophene-2-carboxaldehyde and Pyrrole-2-carboxaldehyde were synthesized and characterized as novel antioxidants. The solvent effects of these Schiff bases were determined and compared with standard antioxidants, BHA employing DPPH assay and ABTS a...

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Bibliographic Details
Published inSpectrochimica acta. Part A, Molecular and biomolecular spectroscopy Vol. 192; pp. 181 - 187
Main Authors Shanty, Angamaly Antony, Mohanan, Puzhavoorparambil Velayudhan
Format Journal Article
LanguageEnglish
Published England Elsevier B.V 05.03.2018
Subjects
3T3-L1 Cells
ABTS
Animals
Antioxidant activity
Antioxidants - chemistry
Antioxidants - pharmacology
Benzothiazoles - chemistry
Biphenyl Compounds - chemistry
Cell Death - drug effects
Cell Survival - drug effects
DPPH
Free Radical Scavengers - chemistry
Heterocyclic Compounds - chemistry
Heterocyclic Compounds - pharmacology
Kinetics
Mice
Picrates - chemistry
Schiff base
Schiff Bases - chemistry
Schiff Bases - pharmacology
Solvent effect
Solvents - chemistry
Structure activity relationship
Sulfonic Acids - chemistry
Schiff base
Solvent effect
Structure activity relationship
DPPH
Antioxidant activity
ABTS
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Summary:Phenolic heterocyclic imine based Schiff bases from Thiophene-2-carboxaldehyde and Pyrrole-2-carboxaldehyde were synthesized and characterized as novel antioxidants. The solvent effects of these Schiff bases were determined and compared with standard antioxidants, BHA employing DPPH assay and ABTS assay. Fixed reaction time and Steady state measurement were used for study. IC50 and EC50 were calculated. Structure–activity relationship revealed that the electron donating group in the phenolic ring increases the activity where as the electron withdrawing moiety decreases the activity. The Schiff base derivatives showed antioxidant property by two different pathways namely SPLET and HAT mechanisms in DPPH assay. While in ABTS method, the reaction between ABTS radical and Schiff bases involves electron transfer followed by proton transfer (ET–PT) mechanism. The cytotoxicity of these compounds has been evaluated by MTT assay. The results showed that all these compounds are non toxic in nature. [Display omitted] •Antioxidant activities of heterocyclic Schiff bases•Solvent effect•Mechanism of action•Structure activity relationship•Cytotoxicity
ISSN:1386-1425
1873-3557
DOI:10.1016/j.saa.2017.11.019