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Effective Synthesis and Cytotoxic Activity of Methyl Maleopimarate Imides

[ Vol. 15 , Issue. 10 ]

Author(s):

Ilshat Maratovich Sakhautdinov*, Rauilya Nadirovna Malikova, Diana Valievna Khasanova, Liana Fanzilevna Zainullina, Vener Absatarovich Vakhitov, Alexander Nikolaevich Lobov, Yuliya Venerovna Vakhitova and Marat Sabirovich Yunusov   Pages 854 - 862 ( 9 )

Abstract:


An ongoing problem of modern biochemistry is the search for ways of synthesizing new hybrid compounds based on available natural adducts with various pharmacophore groups with anticancer activity and, at the same time, with a small effect on normal cells of the organism as a whole.

Methyl maleopimarate MMP, obtained from rosin was treated with different amines in DMSO to give maleopimarimides by thermal condensation during 60 min and condensation with ultrasonic (US) treatment during 30 min. All the synthesized compounds including parent compounds – maleopimaric acid and MMP) were subjected to in vitro cytotoxicity MTT assay in HEK293 (human embryonic kidney cells) and Jurkat cells (human T- cell lymphoblast-like cell line). By the developed method а series of new maleopimarimides were obtained. It was found that the use of two-fold excess of amines and ultrasonic influence increased yield of target products and reduced reaction time. The structures of the products were proved by two-dimensional correlation spectra of HSQC, HMBC, COSY, NOESY.

A new efficient method for the synthesis of a large group of hybrid potentially biologically active compounds by condensation of methyl maleopimarate with various amines (glycine, β-alanine, γ- aminobutyric acid, aminocaproic acid, α-alanine, β-phenyl-α-alanine, hydrazine, phenylhydrazine, aminoguanidine, 9-aminonacridine, glycyl methionine) under ultrasonic influence in dimethylsulfoxide (DMSO) was developed. Screening of new methyl maleopimarate derivatives afforded to identify a compound with moderate cytotoxicity and establish a selective towards different cells mechanism of its cytotoxic action.

Keywords:

Amino acids, apoptosis, caspase 3/7, cytotoxicity, maleopimaric acid, N-maleopimarimides, terpenes, ultrasonic influence.

Affiliation:

Department of Bioorganic Chemistry and Catalysis, Ufa Institute of Chemistry, Russian Academy of Sciences, Ufa, Department of Bioorganic Chemistry and Catalysis, Ufa Institute of Chemistry, Russian Academy of Sciences, Ufa, Institute of Biochemistry and Genetics, Ufa Science Centre of the Russian Academy of Sciences, Ufa, Institute of Biochemistry and Genetics, Ufa Science Centre of the Russian Academy of Sciences, Ufa, Institute of Biochemistry and Genetics, Ufa Science Centre of the Russian Academy of Sciences, Ufa, Department of Bioorganic Chemistry and Catalysis, Ufa Institute of Chemistry, Russian Academy of Sciences, Ufa, Institute of Biochemistry and Genetics, Ufa Science Centre of the Russian Academy of Sciences, Ufa, Department of Bioorganic Chemistry and Catalysis, Ufa Institute of Chemistry, Russian Academy of Sciences, Ufa



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