ISSN 2410-7751 (Print)
ISSN 2410-776X (Online)
"Biotechnologia Acta" v. 6, no. 2, 2013
https://doi.org/10.15407/biotech6.02.080
Р. 80-84, Bibliography 14, Russian.
Universal Decimal classification: 577.152.311/547.8/548.73
Bogatsky’s Physico-Chemical Institute of National Academy of Sciences of Ukraine, Odesa
The synthesis of new series of 7-bromo-5-aryl-1,2-dihydro-3H-1,4-benzdiazepine-2-one derivatives, containing in the tree position phthalimidoacyl and hexylacyl fragments was accomplished. The structure of new compounds was proved by mass-spectrometry and PMRspectroscopy methods. For the first time, hydrolysis of the earlier synthesized 3-hydroxy-7-bromo-5-aryl-1,2-dihydro-3H-1,4-benzdiazepine-2-one esters, potential anxiolytic and hypnotic means, catalyzed by carboxyl esterase in composition of pig liver microsomal fraction was studied. The quantitative inhibition of pig liver microsomal fraction esterase activity in the presence of carboxyl esterase selective inhibitor di-(pnitrophenyl)-phosphate was shown. The nonlinear dependence both of hydrolysis degree with acyl moiety length in 3-acyloxy-7-bromo-5-aryl-1,2-dihydro-3H-1,4-benzdiazepine-2-ones and decreased substrate transformation degree after substituent introduction in the first position of molecule was established. For the derivatives with phthalimidoacyl and hexylacyl-mo ie ties in the molecule 3 position it was shown, that increasing of CH2-groups number in this substituents and incorporation of chlorine atom in o-position of phenyl ring bring to increasing of hydrolysis degree.
Key words: 3-hydroxy-1,4-benzdiazepine-2-one esters, carboxyl esterase, microsomal fraction.
© Palladin Institute of Biochemistry of National Academy of Sciences of Ukraine, 2013
References
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9. Grinshtein Dzh.,Vinyts M. Chemistry of amino acids and peptides. M.: Myr. 1965, 815 P. (In Russian).
10. Andronati S., Semenishyna E., Pavlovsky V., Simonov Y. Synthesis, structure and affinity of novel 3-alkoxy-1,2-dihydro-3H-1,4-benzodiazepin-2-ones for CNS central and peripheral benzodiazepine receptors. Eur. J. Med. Chem. 2010, 45(4), 1346-1351.
https://doi.org/10.1016/j.ejmech.2009.12.027
11. Eriksson L. С. Preparation of liver microsomes with high recovery of endoplasmic reticulum and a low grade of contamination. Biochim. Biophys. Acta. 1978, 508(1), 155-164.
12. Hartree E. F. Determination of protein: a modification of the Lowry method, that gives a linear photometric response. Anal. Biochem. 1972, 48(2), 422-427.
13. Yang S., Liu K., Guengerich P. Enantioselective hydrolysis of oxazepam 3-acetate by esterases in human and rat liver microsomes and rat brain S9 fraction. Chyrality. 1990, V. 2, P. 150-155.
https://doi.org/10.1002/chir.530020305
14. Balls A. K., Wood H. N. Acetyl chymotrypsin and its reaction with ethanol. J. Biol. Chem. 1956, 219(1), 245-256.
{/spoiler}
1. Hosokawa M. Structure and catalytic properties of carboxylesterase isozymes involved in metabolic activation of prodrugs. Molecules. 2008, 13(2), 412-431.
2. Bornscheuer U. T., Kazlauskas R. J. Hydrolases in оrganic synthesis. Wienheim: Wiley-VCH. 2006, 368 p.
3. Imai T., Hosokawa M. Prodrug approach using carboxylesterases activity: catalytic properties and gene regulation of carboxylesterase in mammalian tissue. J. Pesticide Sci. 2010, 35(3), 229-239.
4. Shesterenko E. A., Romanovskaya I. I., Andronati S. A. et al. Stereoselective hydrolysis of 1-metil-5-phenil-3-atsetoxi-7-brom-1,2-dihydro-3Н-1,4-benzdiazepin-2-on using free and immobilized pig liver microsomal fraction. Dop. NANU. 2011, N 2, P. 166-172. (In Russian).
5. Sivko G. I., Kirichenko I. M., Maltsev G. V. et al. Anticonvulsant activity esters 3 hydroxyphenazepam in their oral administration. Odes. med. zhurn. 2006, 96(4), 27-29. (In Ukrainian).
6. Semenishina E. A., Pavlovskiy V. I., Andronati S. A. et al. Synthesis, structure, properties anticonvulsants 7-bromo-5- (2 chlor) phenyl-1,2-dihydro-3H-1,4-benzodiazepine-2-on. Visn. ONU, Ser. Khimiia. 2010, 14(3), 44-57. (In Ukrainian).
7. Zhu L. M. Applications of pig liver esterases (PLE) in asymmetric synthesis. Tetrahedron. 1990, 46(19), 6587-6611.
8. Andronati S. A., Shesterenko E. A., Sevastianov O. B. et al. Hydrolysis of esters 7- bromo -3-hydro-5- phenyl -1,2- dihydro -3Н-1,4- benzodiazepine -2-on pig liver microsomal fraction. Visn. ONU, Ser. Khimiia. 2008, 13(11), 37-45. (In Russian).
9. Grinshtein Dzh.,Vinyts M. Chemistry of amino acids and peptides. M.: Myr. 1965, 815 P. (In Russian).
10. Andronati S., Semenishyna E., Pavlovsky V., Simonov Y. et al. Synthesis, structure and affinity of novel 3-alkoxy-1,2-dihydro-3H-1,4-benzodiazepin-2-ones for CNS central and peripheral benzodiazepine receptors. Eur. J. Med. Chem. 2010, 45(4), 1346-1351.
11. Eriksson L. С. Preparation of liver microsomes with high recovery of endoplasmic reticulum and a low grade of contamination. Biochim. Biophys. Acta. 1978, 508(1), 155-164.
12. Hartree E. F. Determination of protein: a modification of the Lowry method, that gives a linear photometric response. Anal. Biochem. 1972, 48(2), 422-427.
13. Yang S., Liu K., Guengerich P. Enantioselective hydrolysis of oxazepam 3-acetate by esterases in human and rat liver microsomes and rat brain S9 fraction. Chyrality. 1990, V. 2, P. 150-155.
14. Balls A. K., Wood H. N. Acetyl chymotrypsin and its reaction with ethanol. J. Biol. Chem. 1956, 219(1), 245-256.