Structure activity relationship, cytotoxicity and evaluation of antioxidant activity of curcumin derivatives

Pramod K Sahu; Praveen K Sahu; Puran L Sahu; Dau D Agarwal

doi:10.1016/j.bmcl.2015.12.013

Structure activity relationship, cytotoxicity and evaluation of antioxidant activity of curcumin derivatives

Bioorg Med Chem Lett. 2016 Feb 15;26(4):1342-7. doi: 10.1016/j.bmcl.2015.12.013. Epub 2015 Dec 7.

Authors

Pramod K Sahu¹, Praveen K Sahu², Puran L Sahu³, Dau D Agarwal⁴

Affiliations

¹ School of Studies in Chemistry, Jiwaji University, Gwalior 474011, Madhya Pradesh, India; Department of Industrial Chemistry, Jiwaji University, Gwalior 474011, Madhya Pradesh, India. Electronic address: sahu.chemistry@gmail.com.
² Department of Industrial Chemistry, Jiwaji University, Gwalior 474011, Madhya Pradesh, India.
³ Indian Pharmacopoeia Commission Ministry of Health and Family Welfare, Sector-23, Raj Nagar, Ghaziabad 201002, India.
⁴ School of Studies in Chemistry, Jiwaji University, Gwalior 474011, Madhya Pradesh, India; Department of Industrial Chemistry, Jiwaji University, Gwalior 474011, Madhya Pradesh, India.

PMID: 26810315
DOI: 10.1016/j.bmcl.2015.12.013

Abstract

Series of curcumin derivatives/analogues were designed and efficient method for synthesis thereof is described. All the synthesized compounds have been screened for their cytotoxicity and evaluated their antioxidant activity. Cytotoxicity effect has been evaluated against three cell lines Hep-G2, HCT-116 and QG-56 by MTT assay method. Structure activity relationship has revealed that particularly, compound 3c, (IC50 value 6.25 μM) has shown better cytotoxicity effect against three cell lines. According to results of SAR study, it was found that 4H-pyrimido[2,1-b]benzothiazole derivatives (2e and 2f), pyrazoles (3a, 3b, 3c and 3d) benzylidenes (4d) exhibited better antioxidant activity than curcumin. A correlation of structure and activities relationship of these compounds with respect to drug score profiles and other physico-chemical properties of drugs are described and verified experimentally.

Keywords: Antioxidant activity; Curcumin derivatives/analogues; Cytotoxicity; Structure–activity relationship.

MeSH terms

Antioxidants / chemical synthesis
Antioxidants / chemistry*
Antioxidants / pharmacology
Cell Line, Tumor
Cell Survival / drug effects
Curcumin / chemical synthesis
Curcumin / chemistry*
Curcumin / pharmacology
Drug Screening Assays, Antitumor
HCT116 Cells
Hep G2 Cells
Humans
Oxidation-Reduction
Structure-Activity Relationship

Substances

Antioxidants
Curcumin