Diverse Biological Activity of Benzofuroxan/Sterically Hindered Phenols Hybrids
Chugunova E. Gibadullina E. Matylitsky K. Bazarbayev B. Neganova M. Volcho K. Rogachev A. Akylbekov N. Nguyen H.B.T. Voloshina A. Lyubina A. Amerhanova S. Syakaev V. Burilov A. Appazov N. Zhanakov M. Kuhn L. Sinyashin O. Alabugin I.
April 2023Multidisciplinary Digital Publishing Institute (MDPI)
Pharmaceuticals
2023#16Issue 4
Combining two pharmacophores in a molecule can lead to useful synergistic effects. Herein, we show hybrid systems that combine sterically hindered phenols with dinitrobenzofuroxan fragments exhibit a broad range of biological activities. The modular assembly of such phenol/benzofuroxan hybrids allows variations in the phenol/benzofuroxan ratio. Interestingly, the antimicrobial activity only appears when at least two benzofuroxan moieties are introduced per phenol. The most potent of the synthesized compounds exhibit high cytotoxicity against human duodenal adenocarcinoma (HuTu 80), human breast adenocarcinoma (MCF-7), and human cervical carcinoma cell lines. This toxicity is associated with the induction of apoptosis via the internal mitochondrial pathway and an increase in ROS production. Encouragingly, the index of selectivity relative to healthy tissues exceeds that for the reference drugs Doxorubicin and Sorafenib. The biostability of the leading compounds in whole mice blood is sufficiently high for their future quantification in biological matrices.
anti-cancer activity , apoptosis , benzofuroxan , cytotoxicity , ROS production , sterically hindered phenol
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Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Akad. Arbuzov St. 8, Kazan, 420088, Russian Federation
The Department of General Organic and Petrochemical Synthesis Technology, The Kazan National Research Technological University, Karl Marx St., 68, Kazan, 420015, Russian Federation
Department of Medicinal Chemistry, Novosibirsk Institute of Organic Chemistry, Lavrentiev Av. 9, Novosibirsk, 630090, Russian Federation
Zelman Institute for Medicine and Psychology, Novosibirsk State University, Pirogov St. 2, Novosibirsk, 630090, Russian Federation
Laboratory of Engineering Profile “Physical and Chemical Methods of Analysis”, Korkyt Ata Kyzylorda University, Aitekebie Str. 29A, Kyzylorda, 120014, Kazakhstan
I. Zhakhaev Kazakh Scientific Research Institute of Rice Growing, Abay Av. 25B, Kyzylorda, 120008, Kazakhstan
Faculty of Natural Sciences, L.N. Gumilyov Eurasian National University, Satpayev Str. 2, Astana, 010000, Kazakhstan
Department of Chemistry and Biochemistry, Florida State University, 95 Chieftan Way, Tallahassee, 32306-4390, FL, United States
Arbuzov Institute of Organic and Physical Chemistry
The Department of General Organic and Petrochemical Synthesis Technology
Department of Medicinal Chemistry
Zelman Institute for Medicine and Psychology
Laboratory of Engineering Profile “Physical and Chemical Methods of Analysis”
I. Zhakhaev Kazakh Scientific Research Institute of Rice Growing
Faculty of Natural Sciences
Department of Chemistry and Biochemistry
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