TỔNG HỢP VÀ ĐÁNH GIÁ HOẠT TÍNH GÂY ĐỘC TẾ BÀO MỘT SỐ DẪN XUẤT MỚI CỦA MURRAYAFOLINE A
Nội dung chính của bài viết
Tóm tắt
SYNTHESIS AND CYTOTOXIC ACTIVITY EVALUATION OF NOVEL DERIVATIVES OF MURRAYAFOLINE A
In this research, we presented a method for preparation of four new derivatives of murrayafoline A. They were synthesized via Claisen-Schmidt reaction from two consecutive O-alkylation and N -alkylation reactions. Four derivatives including compounds 15-18 were tested for cytotoxic activity. The result showed that these four derivatives exhibited cytotoxic activity against to cancer cell P388 with IC50 value ranging from 22,7 to 46,96 μg/mL, however they had no cytotoxicity against to other four human cancer cells LU-1, Hep-G2, MCF7 and SW480.
Từ khóa
Murrayafoline A, Claisen-Schmidt, N-alkyl, O-alkyl, cytotoxic activity
Chi tiết bài viết
Tài liệu tham khảo
1. Lê Đức Anh, Trương Ngọc Hùng, Nguyễn Thị Nga, Lê Mai Hương, Nguyễn Mạnh Cường, Vũ Thị Hà, Lưu Văn Chính, Tổng hợp và đánh giá hoạt tính kháng khuẩn của một số dẫn xuất mới của murrayafoline A, Tạp chí Hóa học, 2015, 53(5e1):162-167.
2. Bringmann G., Ledermann A.,Franc-ois G., Dimeric murrayafoline A, a potential bis-carbazole alkaloid: biomimetic synthesis, atropoisomer separation, and antimalarial activity, Heterocycles, 1995, 40:293-300.
3. Carsten Bӧrger, Olga Kataeva, Hans-Joachim Knӧlker, Novel approach to biscarbazole alkaloid via Ullmann coupling-synthesis of murrastifoline-A and bismurrayafoline A, Org. Biomol. Chem., 2012, 10:7269-7273.
4. Chakraborty D.P., Chowdhury B.K., Synthesis of murrayanine, J. Org. Chem., 1968, 33:1265-1268.
5. Chihiro Ito, Masataka Itoigawa, Keisuke Nakao, Tomiyasu Murata, Norio Kaneda, Hiroshi Furukawa, Apoptosis of HL-60 leukemia cells induced by carbazole alkaloids isolated from Murraya euchrestifolia, J. Nat. Med., 2012, 66:357-361.
6. C. Ma, R.J. Case, Y. Wang, H.J. Zhang, G.T. Tan, N.V. Hung, N.M. Cuong, S.G. Franzblau, D.D. Soejarto, H.H. S. Fong, G.F. Pauli, Anti-Tuberculosis Constituents from the Stem Bark of Micromelum hirsutum, Planta Med., 2005, 71:261-267
7. Furukawa H., Wu T.S., Ohta T., Kuoh C.S., Chemical constituents of murraya euchrestifolia hayata. Structure of novel carbazolequinones and other carbazole alkaloids, Chem. Pharm. Bull., 1985, 33:4132-4138.
8. Gerhard Bringmann, Stefan Tasler, Synthesis of methylene-brdidgede binary carbazole alkaloids and related tricarbazole, Tetrahedron, 2001, 57:2337-2343.
9. Gerhard Bringmann, Stefan Tasler, Heike Endress, Jūrgen Kraus, Kim Messer, Micheal Wohlfarth, Wolfram Lobin, Murrastifoline-F: First Total Synthsis, Astrpo-Enantiomer Resolution and Stereoanalysis of an Axially Chiral N,C-coupled Biaryl Alkaloid, J. Am. Chem. Soc., 2001, 123:2703-2711.
10. Guoqiang L., Aimin Z., Synthesis of Optically Pure Biscarbazole and Determination of Their Absolute Configurations, Tetrahedron Letters,1999, 40:341-344.
11. Hyuk Choi, Jungsug Gwak, Munju Cho, Min-Jung Ryu, Jee-Hyun Lee, Sang Kyum Kim, Young Ho Kim, Gye Won Lee, Mi-Young Yun, Nguyen Manh Cuong, Jae-Gook Shin, Gyu-Yong Song, Sangtaek Oh., Murrayafoline A attenuates the Wnt/β-catenin pathway by promoting the degradation of intracellular β-catenin proteins, Biochemical and Biophysical Research Communications, 2010, 391:915-920.
12. Ian A. Cree, Cancer Cell Culture:Methods and Protocols, Second Edition, Methods in Molecular Biology, 2011,731, DOI 10.1007/978-1-61779-080-5_20, @ Springer Science+Business Media, LLC.
13. Itoigawa M., Kashiwada Y., Ito C., Furukawa H., Tachibana Y., Bastow K.F., Lee K.H., Antitumor Agents 203. Carbazole Alkaloid Murrayaquinone A and Related Synthetic Carbazolequinones as Cytotoxyc Agents, J. Nat. Prod., 2000, 63:893-897.
14. Joon-Chul Kim, Nguyen Manh Cuong, Sun-Hee Woo, Enhancement of Ca2+Spark Occurrence by Murrayafoline-A in Rat Ventricular Myocytes, Yakhak Hoeji, 2014, 58(4):245-249.
15. Le Duc Anh, Truong Ngoc Hung, Nguyen Thi Nga, Le Mai Huong, Tran Thi Hong Ha, Tran Thi Thu Thuy, Nguyen Manh Cuong, Le Thi Thoa, Tran Minh Cong, Nguyen Trong Dan, Luu Van Chinh, Synthesis and biological activity of novel derivatives of murrayafoline A, The Academic conference on natural science for young scientists, master and PhD. student from Asean countries, Proceedings, 2015, tr.223-229.
16. Le Duc Anh, Nguyen Thi Hai Ly, Truong Ngoc Hung, Nguyen Thi Nga, Nguyen Manh Cuong, Le Mai Huong, Le Phong, Luu Van Chinh, Synthesis and cytotoxic activity evaluation novel deriveatives of murrayafoline A, Journal of Science and Technology, 2016, 54(2C):507-514.
17. Cuong N.M., Hung T.Q., Sung T.V., Taylor W.C., A New Dimeric Carbazole Alkaloid from Glycosmis stenocarpa Roots, Chem. Pharm. Bull., 2004, 52:1175-1178.
18. Song Gyu Yong, Myung Chang Seon, Kim Yeong Ho, Pharmaceutical composition comprising murrayafoline A derivatives for treating or preventing vascular diseases, Patent 2013, KR 2013026081 A 20130313.
19. Sunthitikawinsakul A., Kongkathip N., Kongkathip B., Phonnakhu S., Daly J.W., Spande T.F., Nimit Y., Rochanaruangrai S., Coumarins and Carbazoles from Clausena excavata Exhibited Antimycobacterial and Antifungal Activities. Planta Med., 2003, 69:155-157.
20. Tian-Shung Wu, Yu-Yi Chan, Meei-Jen Liou, Ful-Wen Lin, Li-Shian Shi and Kuo-Tung Chen,Platelet Aggregation Inhibitor fromMurraya euchrestifolia, Phytotherapy Research, 1998, 12:80-82.
21. Thuy T.T.T., Cuong N.M., Toan T.Q., Thang N.N., Tai B.H., Nhiem N.X., Hong H.J., KimS., Legoupy S., Koh Y.S., Kim Y.H., Synthesis of novel derivatives of murrayafoline A and their inhibitory effect on LPS-stimulated production of proinflammatory cytokines in bone marrow-derived dendritic cells, Arch. Pharmacal. Res., 2013, 36:832-839.
22. Truong V.V., Nam T.D., Hung T.N., Nga N.T., Quan P.M., Chinh L.V., Jung S.H., Synthesis and anti-proliferative activity of novel azazerumbone conjugates with chalcones, Bioorg Med Chem Lett., 2015, 25(22):5182-5185.
2. Bringmann G., Ledermann A.,Franc-ois G., Dimeric murrayafoline A, a potential bis-carbazole alkaloid: biomimetic synthesis, atropoisomer separation, and antimalarial activity, Heterocycles, 1995, 40:293-300.
3. Carsten Bӧrger, Olga Kataeva, Hans-Joachim Knӧlker, Novel approach to biscarbazole alkaloid via Ullmann coupling-synthesis of murrastifoline-A and bismurrayafoline A, Org. Biomol. Chem., 2012, 10:7269-7273.
4. Chakraborty D.P., Chowdhury B.K., Synthesis of murrayanine, J. Org. Chem., 1968, 33:1265-1268.
5. Chihiro Ito, Masataka Itoigawa, Keisuke Nakao, Tomiyasu Murata, Norio Kaneda, Hiroshi Furukawa, Apoptosis of HL-60 leukemia cells induced by carbazole alkaloids isolated from Murraya euchrestifolia, J. Nat. Med., 2012, 66:357-361.
6. C. Ma, R.J. Case, Y. Wang, H.J. Zhang, G.T. Tan, N.V. Hung, N.M. Cuong, S.G. Franzblau, D.D. Soejarto, H.H. S. Fong, G.F. Pauli, Anti-Tuberculosis Constituents from the Stem Bark of Micromelum hirsutum, Planta Med., 2005, 71:261-267
7. Furukawa H., Wu T.S., Ohta T., Kuoh C.S., Chemical constituents of murraya euchrestifolia hayata. Structure of novel carbazolequinones and other carbazole alkaloids, Chem. Pharm. Bull., 1985, 33:4132-4138.
8. Gerhard Bringmann, Stefan Tasler, Synthesis of methylene-brdidgede binary carbazole alkaloids and related tricarbazole, Tetrahedron, 2001, 57:2337-2343.
9. Gerhard Bringmann, Stefan Tasler, Heike Endress, Jūrgen Kraus, Kim Messer, Micheal Wohlfarth, Wolfram Lobin, Murrastifoline-F: First Total Synthsis, Astrpo-Enantiomer Resolution and Stereoanalysis of an Axially Chiral N,C-coupled Biaryl Alkaloid, J. Am. Chem. Soc., 2001, 123:2703-2711.
10. Guoqiang L., Aimin Z., Synthesis of Optically Pure Biscarbazole and Determination of Their Absolute Configurations, Tetrahedron Letters,1999, 40:341-344.
11. Hyuk Choi, Jungsug Gwak, Munju Cho, Min-Jung Ryu, Jee-Hyun Lee, Sang Kyum Kim, Young Ho Kim, Gye Won Lee, Mi-Young Yun, Nguyen Manh Cuong, Jae-Gook Shin, Gyu-Yong Song, Sangtaek Oh., Murrayafoline A attenuates the Wnt/β-catenin pathway by promoting the degradation of intracellular β-catenin proteins, Biochemical and Biophysical Research Communications, 2010, 391:915-920.
12. Ian A. Cree, Cancer Cell Culture:Methods and Protocols, Second Edition, Methods in Molecular Biology, 2011,731, DOI 10.1007/978-1-61779-080-5_20, @ Springer Science+Business Media, LLC.
13. Itoigawa M., Kashiwada Y., Ito C., Furukawa H., Tachibana Y., Bastow K.F., Lee K.H., Antitumor Agents 203. Carbazole Alkaloid Murrayaquinone A and Related Synthetic Carbazolequinones as Cytotoxyc Agents, J. Nat. Prod., 2000, 63:893-897.
14. Joon-Chul Kim, Nguyen Manh Cuong, Sun-Hee Woo, Enhancement of Ca2+Spark Occurrence by Murrayafoline-A in Rat Ventricular Myocytes, Yakhak Hoeji, 2014, 58(4):245-249.
15. Le Duc Anh, Truong Ngoc Hung, Nguyen Thi Nga, Le Mai Huong, Tran Thi Hong Ha, Tran Thi Thu Thuy, Nguyen Manh Cuong, Le Thi Thoa, Tran Minh Cong, Nguyen Trong Dan, Luu Van Chinh, Synthesis and biological activity of novel derivatives of murrayafoline A, The Academic conference on natural science for young scientists, master and PhD. student from Asean countries, Proceedings, 2015, tr.223-229.
16. Le Duc Anh, Nguyen Thi Hai Ly, Truong Ngoc Hung, Nguyen Thi Nga, Nguyen Manh Cuong, Le Mai Huong, Le Phong, Luu Van Chinh, Synthesis and cytotoxic activity evaluation novel deriveatives of murrayafoline A, Journal of Science and Technology, 2016, 54(2C):507-514.
17. Cuong N.M., Hung T.Q., Sung T.V., Taylor W.C., A New Dimeric Carbazole Alkaloid from Glycosmis stenocarpa Roots, Chem. Pharm. Bull., 2004, 52:1175-1178.
18. Song Gyu Yong, Myung Chang Seon, Kim Yeong Ho, Pharmaceutical composition comprising murrayafoline A derivatives for treating or preventing vascular diseases, Patent 2013, KR 2013026081 A 20130313.
19. Sunthitikawinsakul A., Kongkathip N., Kongkathip B., Phonnakhu S., Daly J.W., Spande T.F., Nimit Y., Rochanaruangrai S., Coumarins and Carbazoles from Clausena excavata Exhibited Antimycobacterial and Antifungal Activities. Planta Med., 2003, 69:155-157.
20. Tian-Shung Wu, Yu-Yi Chan, Meei-Jen Liou, Ful-Wen Lin, Li-Shian Shi and Kuo-Tung Chen,Platelet Aggregation Inhibitor fromMurraya euchrestifolia, Phytotherapy Research, 1998, 12:80-82.
21. Thuy T.T.T., Cuong N.M., Toan T.Q., Thang N.N., Tai B.H., Nhiem N.X., Hong H.J., KimS., Legoupy S., Koh Y.S., Kim Y.H., Synthesis of novel derivatives of murrayafoline A and their inhibitory effect on LPS-stimulated production of proinflammatory cytokines in bone marrow-derived dendritic cells, Arch. Pharmacal. Res., 2013, 36:832-839.
22. Truong V.V., Nam T.D., Hung T.N., Nga N.T., Quan P.M., Chinh L.V., Jung S.H., Synthesis and anti-proliferative activity of novel azazerumbone conjugates with chalcones, Bioorg Med Chem Lett., 2015, 25(22):5182-5185.