Discovery of novel dehydroabietic acid derivatives as DNA/BSA binding and anticancer agents

Lin-Ying Li; Bao-Li Fei; Pingping Wang; Ling-Yan Kong; Jian-Ying Long

doi:10.1016/j.saa.2020.118944

Discovery of novel dehydroabietic acid derivatives as DNA/BSA binding and anticancer agents

Spectrochim Acta A Mol Biomol Spectrosc. 2021 Feb 5:246:118944. doi: 10.1016/j.saa.2020.118944. Epub 2020 Sep 15.

Authors

Lin-Ying Li¹, Bao-Li Fei², Pingping Wang³, Ling-Yan Kong⁴, Jian-Ying Long⁵

Affiliations

¹ Jiangsu Key Lab of Biomass-based Green Fuels and Chemicals, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China; Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Nanjing Forestry University, Nanjing 210037, China.
² Jiangsu Key Lab of Biomass-based Green Fuels and Chemicals, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China; Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Nanjing Forestry University, Nanjing 210037, China; State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Guangxi Normal University, Guilin 541004, China. Electronic address: hgfbl@njfu.edu.cn.
³ Jiangsu Key Lab of Biomass-based Green Fuels and Chemicals, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China.
⁴ College of Food Science and Engineering, Nanjing University of Finance and Economics, Nanjing 210023, China.
⁵ College of Science, Nanjing Forestry University, Nanjing 210037, China.

PMID: 33007643
DOI: 10.1016/j.saa.2020.118944

Abstract

To explore the biological properties of rosin derivatives, two dehydroabietic acid derivatives N-(5-dehydroabietyl-1,3,4-thiadiazole)-yl-pyridine-2-carboxamide (DTPC) and di-N-(5-dehydroabietyl-1,3,4-thiadiazole)-yl-pyridine-2,6-carboxamide (DDTPC) with 1,3,4-thiadiazole, pyridine and amide moieties were designed and synthesized according to superposition principle of activity group. They interact with calf thymus DNA (CT DNA) via intercalation based on the results of circular dichroism (CD) and fluorescence spectroscopy, DNA denaturation and viscosity studies. Fluorescence and CD spectral experiments indicate that they might be transported and stored by protein like bovine serum albumin (BSA). MTT assay was further carried out to examine their cytotoxicity, they both showed selective cytotoxicity and DTPC exhibited better cytotoxicity. The antiproliferative effect of DTPC toward A431 cell line was stronger than that of clinically used cisplatin and oxaliplatin. In addition, the cytotoxicity of DTPC and DDTPC was closely related with their DNA binding ability.

Keywords: Amide; Anticancer; BSA; DNA; Rosin derivative.

MeSH terms

Abietanes
Animals
Antineoplastic Agents* / pharmacology
Cattle
Cisplatin
Coordination Complexes*
DNA / metabolism
Protein Binding
Serum Albumin, Bovine / metabolism

Substances

Abietanes
Antineoplastic Agents
Coordination Complexes
dehydroabietic acid
Serum Albumin, Bovine
DNA
Cisplatin