Sàng lọc các dẫn xuất 2‒mercaptoimidazole sử dụng làm thuốc trong điều trị ung thư vú
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Author
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Tran Viet AnhThe University of Danang - University of Technology and Education, Danang, VietnamHuynh Thi Diem UyenThe University of Danang - University of Technology and Education, Danang, VietnamLe Thi Dieu HuongThe University of Danang - University of Technology and Education, Danang, VietnamNguyen Quang TrungThe University of Danang ‒ University of Science and Education; Quality Assurance and Testing Center 2, Danang, VietnamQuan V. VoThe University of Danang - University of Technology and Education, Danang, Vietnam
Từ khóa:
2‒Mecaptoimidazole
ung thư vú
chống oxy hoá
Erα
Aromatase
Tóm tắt
2‒Mecaptoimidazole (2MC), hợp chất tautomer của nó (2MI) và các dẫn xuất được sàng lọc để đánh giá tiềm năng chống oxy hoá và điều trị ung thư vú. Khảo sát 14 nhóm thế trên vòng ovothiol cho thấy, 2MC, 2MI và các dẫn xuất 5‒NH2‒2MC, 5‒NMe2‒2MC, 5‒NH2‒2MI và 5‒NMe2‒2MI có giá trị BDE thấp hơn các hợp chất chống oxy hoá như viniferifuran, resveratrol và puerarin, dự đoán phản ứng bắt gốc tự do trong pha khí có thể xảy ra theo cơ chế FHT. Các hợp chất nghiên cứu đều có năng lượng tương tác âm với ERα (1HVY) và Aromatase (1DNU), các thông số dược động học ADME đều tuân thủ quy tắt Lipinsky, trong đó 4‒COOH‒2MC, 4‒C₆H₅‒2MC, 5‒COOH‒2MC, 5‒C₆H₅‒2MC, 5‒NH₂‒2MC, 1‒C₆H₅‒2MI, 5‒COOH‒2MI, 5‒CH≡C‒2MI và 5‒C₆H₅‒2MI là các dẫn xuất có tiềm năng để phát triển thuốc điều trị ung thư vú tương tự như doxorubicin.
Tài liệu tham khảo
-
[1] Verma, S. Joshi, and D. Singh, "Imidazole: having versatile biological activities”, Journal of Chemistry, vol. 2013, no. 2, 329412, 2013. DOI:10.1155/2013/329412
[2] Yildiz, "Antioxidant and DNA damage protecting activities of newly synthesized thiol bridged bis‐benzimidazole derivative and its dicationic analogue”, Journal of Heterocyclic Chemistry, vol. 57, no. 11, pp. 4007-4012, 2020.
[3] Zhang, X. M. Peng, G. L. Damu, R. X. Geng, and C. H. Zhou, "Comprehensive review in current developments of imidazole‐based medicinal chemistry”, Medicinal research reviews, vol. 34, no. 2, pp. 340-437, 2014.
[4] Bensasson, J. Frederiksen, M. Rougée, D. Lexa, and N. Harrit, "Correlations between the rate constant of singlet oxygen quenching by imidazole derivatives and anti-inflammatory activity in rats”, Molecular pharmacology, vol. 42, no. 4, pp. 718-722, 1992.
[5] M. Shapiro, "The control of oxidant stress at fertilization”, Science, vol. 252, no. 5005, pp. 533-536, 1991.
[6] V. Vo, N. T. Hoa, and A. Mechler, "Study of the Mechanism and Kinetics of the Radical Scavenging Activity of 2-Mercaptoimidazole”, The Journal of Physical Chemistry A, vol. 127, no. 23, pp. 4934, 4939, 2023.
[7] V. Vo, N. T. Hoa, P. C. Nam, T. Q. Duong, and A. Mechler, "The radical scavenging activity of 4-mercaptoimidazole: theoretical insights into the mechanism, kinetics and solvent effects”, New Journal of Chemistry, vol. 47, no. 21, pp. 10381-10390, 2023.
[8] Álvarez-Bustamante et al., "Electrochemical study of 2-mercaptoimidazole as a novel corrosion inhibitor for steels”, Electrochimica Acta, vol. 54, no. 23, pp. 5393-5399, 2009.
[9] S. Chernov’yants, T. S. Kolesnikova, and A. O. Karginova, "Thioamides as radical scavenging compounds: Methods for screening antioxidant activity and detection”, Talanta, vol. 149, pp. 319-325, 2016.
[10] -L. Chen et al., "2-Mercaptoimidazole selectively etching and thiol-functionalized ZIF-8 metal–organic framework to serve as a multifaceted platform for radical scavenging and Au loading”, Materials Today Chemistry, vol. 27, p. 101259, 2023.
[11] Acharya, S. Chacko, P. Bose, A. Lapenna, and S. P. Pattanayak, "Structure based multitargeted molecular docking analysis of selected furanocoumarins against breast cancer”, Scientific reports, vol. 9, no. 1, p. 15743, 2019.
[12] Galano and J. R. Alvarez‐Idaboy, "Kinetics of radical‐molecule reactions in aqueous solution: A benchmark study of the performance of density functional methods”, Journal of computational chemistry, vol. 35, no. 28, pp. 2019-2026, 2014.
[13] Q. Huong, T. Duong, and P. C. Nam, "An experimental and computational study of antioxidant activity of N‐phenylthiourea and N‐phenylselenourea analogues”, Vietnam Journal of Chemistry, vol. 57, no. 4, pp. 469-479, 2019.
[14] Tanko, "Reaction mechanisms Part (i) Radical and radical ion reactions”, Annual Reports Section" B"(Organic Chemistry), vol. 102, pp. 247-268, 2006.
[15] S. Wright, E. R. Johnson, and G. A. DiLabio, "Predicting the activity of phenolic antioxidants: theoretical method, analysis of substituent effects, and application to major families of antioxidants”, Journal of the American Chemical Society, vol. 123, no. 6, pp. 1173-1183, 2001.
[16] Zhao, N. E. Schultz, and D. G. Truhlar, "Design of density functionals by combining the method of constraint satisfaction with parametrization for thermochemistry, thermochemical kinetics, and noncovalent interactions”, Journal of chemical theory and computation, vol. 2, no. 2, pp. 364-382, 2006.
[17] Zhao and D. G. Truhlar, "How well can new-generation density functionals describe the energetics of bond-dissociation reactions producing radicals?”, The Journal of Physical Chemistry A, vol. 112, no. 6, pp. 1095-1099, 2008.
[18] Zhao and D. G. Truhlar, "The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals”, Theoretical chemistry accounts, vol. 120, pp. 215-241, 2008.
[19] Carreon‐Gonzalez, A. Vivier‐Bunge, and J. R. Alvarez‐Idaboy, "Thiophenols, promising scavengers of peroxyl radicals: mechanisms and kinetics”, Journal of Computational Chemistry, vol. 40, no. 24, pp. 2103-2110, 2019.
[20] Boulebd, I. A. Khodja, M. V. Bay, N. T. Hoa, A. Mechler, and Q. V. Vo, "Thermodynamic and kinetic studies of the radical scavenging behavior of hydralazine and dihydralazine: theoretical insights”, The Journal of Physical Chemistry B, vol. 124, no. 20, pp. 4123-4131, 2020.
[21] Trott and A. J. Olson, "AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading”, Journal of computational chemistry, vol. 31, no. 2, pp. 455-461, 2010.
[22] Xiong et al., "ADMETlab 2.0: an integrated online platform for accurate and comprehensive predictions of ADMET properties”, Nucleic Acids Research, vol. 49, no. W1, pp. W5-W14, 2021.
[23] V. Vo et al., "A thermodynamic and kinetic study of the antioxidant activity of natural hydroanthraquinones”, RSC advances, vol. 10, no. 34, pp. 20089-20097, 2020.
[24] Shang, H. Zhou, X. Li, J. Zhou, and K. Chen, "Theoretical studies on the antioxidant activity of viniferifuran”, New Journal of Chemistry, vol. 43, no. 39, pp. 15736-15742, 2019.
[25] Zhou, X. Li, Y. Shang, and K. Chen, "Radical scavenging activity of puerarin: a theoretical study”, Antioxidants, vol. 8, no. 12, p. 590, 2019.
[26] N. Thompson, "Early ADME in support of drug discovery: the role of metabolic stability studies”, Current drug metabolism, vol. 1, no. 3, pp. 215-241, 2000.
[27] Ivanović, M. Rančić, B. Arsić, and A. Pavlović, "Lipinski’s rule of five, famous extensions and famous exceptions”, Popular Scientific Article, vol. 3, no. 1, pp. 171-177, 2020.
[28] T. Brogyányi et al., "Azulene hydrazide-hydrazones for selective targeting of pancreatic cancer cells”, Biomedicine & Pharmacotherapy, vol. 155, p. 113736, 2022.
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Nov 30, 2023
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Tran Viet Anh, Huynh Thi Diem Uyen, Le Thi Dieu Huong, Nguyen Quang Trung, và Quan V. Vo. “Sàng lọc các dẫn xuất 2‒mercaptoimidazole sử dụng làm thuốc Trong điều trị Ung Thư Vú”. Tạp Chí Khoa học Và Công nghệ - Đại học Đà Nẵng, vol 21, số p.h 11.2, Tháng Mười-Một 2023, tr 95-100, https://jst-ud.vn/jst-ud/article/view/8738.
