Benzothiazole carbamates and amides as antiproliferative species

Milica Videnović; Marija Mojsin; Milena Stevanović; Igor Opsenica; Tatjana Srdić-Rajić; Bogdan Šolaja

doi:10.1016/j.ejmech.2018.08.067

Benzothiazole carbamates and amides as antiproliferative species

Eur J Med Chem. 2018 Sep 5:157:1096-1114. doi: 10.1016/j.ejmech.2018.08.067. Epub 2018 Aug 29.

Authors

Milica Videnović¹, Marija Mojsin², Milena Stevanović³, Igor Opsenica⁴, Tatjana Srdić-Rajić⁵, Bogdan Šolaja⁶

Affiliations

¹ Faculty of Chemistry Innovative Centre, Studentski Trg 12-16, 11158 Belgrade, Serbia.
² Institute of Molecular Genetics and Genetic Engineering, University of Belgrade, Vojvode Stepe 444a, 11010 Belgrade, Serbia.
³ Institute of Molecular Genetics and Genetic Engineering, University of Belgrade, Vojvode Stepe 444a, 11010 Belgrade, Serbia; University of Belgrade, Faculty of Biology, Studentski Trg 16, 11158 Belgrade, Serbia; Serbian Academy of Sciences and Arts, Knez Mihailova 35, 11158 Belgrade, Serbia.
⁴ University of Belgrade, Faculty of Chemistry, Studentski Trg 16, P.O. Box 51, 11158 Belgrade, Serbia.
⁵ Institute for Oncology and Radiology of Serbia, Pasterova 14, 11000 Belgrade, Serbia.
⁶ Serbian Academy of Sciences and Arts, Knez Mihailova 35, 11158 Belgrade, Serbia; University of Belgrade, Faculty of Chemistry, Studentski Trg 16, P.O. Box 51, 11158 Belgrade, Serbia. Electronic address: bsolaja@chem.bg.ac.rs.

PMID: 30179747
DOI: 10.1016/j.ejmech.2018.08.067

Abstract

A series of new benzothiazole-based carbamates and amides were synthesized and their antiproliferative activity was determined. Derivatives with profound activity were identified and further investigated for their possible mechanism of action. It was found that these compounds induce specific apoptosis, G2/M cell cycle arrest and decrease ROS level in MCF-7 human breast cancer cell line. Moreover, submicromolar antiproliferative activity of examined carbamates against NT2/D1 testicular embryonal carcinoma was shown. The most potent derivatives strongly inhibited NT2/D1 cell migration and invasiveness.

Keywords: Anoikis; Antiproliferative; Benzothiazoles; MCF-7; NT2/D1.

MeSH terms

Amides / chemical synthesis
Amides / chemistry
Amides / pharmacology*
Animals
Antineoplastic Agents / chemical synthesis
Antineoplastic Agents / chemistry
Antineoplastic Agents / pharmacology*
Apoptosis / drug effects
Benzothiazoles / chemical synthesis
Benzothiazoles / chemistry
Benzothiazoles / pharmacology*
Carbamates / chemical synthesis
Carbamates / chemistry
Carbamates / pharmacology*
Cell Line
Cell Proliferation / drug effects
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Female
Humans
Mice
Mice, Nude
Molecular Structure
Reactive Oxygen Species / analysis
Reactive Oxygen Species / metabolism
Structure-Activity Relationship

Substances

Amides
Antineoplastic Agents
Benzothiazoles
Carbamates
Reactive Oxygen Species
benzothiazole