دورية أكاديمية

Design and Synthesis of Novel β-Carboline-Bisindole Hybrids as Potential Anticancer Agents.

التفاصيل البيبلوغرافية
العنوان: Design and Synthesis of Novel β-Carboline-Bisindole Hybrids as Potential Anticancer Agents.
المؤلفون: Huyen NTT; Faculty of Chemistry, VNU-Ha Noi University of Science, 19 Le Thanh Tong, Phan Chu Trinh, Hoan Kiem, Hanoi, Vietnam., Phuc BV; Institute of Chemistry, Vietnamese Academy of Science and Technology (VAST), 18 Hoang Quoc Viet, Hanoi, Vietnam., Huyen TT; Faculty of Chemistry, VNU-Ha Noi University of Science, 19 Le Thanh Tong, Phan Chu Trinh, Hoan Kiem, Hanoi, Vietnam., Hong TT; Faculty of Chemistry, VNU-Ha Noi University of Science, 19 Le Thanh Tong, Phan Chu Trinh, Hoan Kiem, Hanoi, Vietnam., Nguyen H; Faculty of Chemistry, Hanoi National University of Education (HNUE), Vietnam., Nguyen VH; Faculty of Chemistry, VNU-Ha Noi University of Science, 19 Le Thanh Tong, Phan Chu Trinh, Hoan Kiem, Hanoi, Vietnam., Nguyen MT; Faculty of Applied Technology, School of Technology, Van Lang University, Ho Chi Minh City, 70000, Vietnam., Hung TQ; Institute of Chemistry, Vietnamese Academy of Science and Technology (VAST), 18 Hoang Quoc Viet, Hanoi, Vietnam.; Graduate University of Science and Technology, Vietnam Academy of Science and Technology, Vietnam., Dinh CP; NuChem Sciences, a Sygnature Discovery Business, 480 rue Perreault, Lévis, QC, G6 W 7 V6, Canada., Dang TT; Faculty of Chemistry, VNU-Ha Noi University of Science, 19 Le Thanh Tong, Phan Chu Trinh, Hoan Kiem, Hanoi, Vietnam.
المصدر: ChemMedChem [ChemMedChem] 2024 Jun 10, pp. e202400316. Date of Electronic Publication: 2024 Jun 10.
Publication Model: Ahead of Print
نوع المنشور: Journal Article
اللغة: English
بيانات الدورية: Publisher: Wiley-VCH Country of Publication: Germany NLM ID: 101259013 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1860-7187 (Electronic) Linking ISSN: 18607179 NLM ISO Abbreviation: ChemMedChem Subsets: MEDLINE
أسماء مطبوعة: Original Publication: Weinheim, Germany : Wiley-VCH, c2006-
مستخلص: We are reporting a short and convenient pathway for the synthesis of novel β-carboline-bisindole hybrid compounds from relatively cheap and commercially available chemicals such as tryptamine, dialdehydes and indoles. These newly designed compounds can also be prepared in high yields with the tolerance of many functional groups under mild conditions. Notably, these β-carboline-bisindole hybrid compounds exhibited some promising applications as anticancer agents against the three common cancer cell lines MCF-7 (breast cancer), SK-LU-1 (lung cancer), and HepG2 (liver cancer). The two best compounds 5 b and 5 g inhibited the aforementioned cell lines with the same IC 50 range of the reference Ellipticine at less than 2 μM. A molecular docking study to gain more information about the interactions between the synthesized molecules and the kinase domain of the EGFR was performed. Therefore, this finding can have significant impacts on the development of future research in medicinal chemistry and drug discovery.
(© 2024 Wiley-VCH GmbH.)
References: “Cancer,” can be found under https://www.who.int/news-room/fact-sheets/detail/cancer.
M. Zoeller, in Encyclopedia of Cancer (Ed.: M. Schwab), Springer Berlin Heidelberg, Berlin, Heidelberg, 2011, pp. 2998–3001.
S. Bogdan, C. Klämbt, Curr. Biology 2001, 11, R292–R295.
R. S. Herbst, M. Fukuoka, J. Baselga, Nat. Rev. Cancer 2004, 4, 956–965.
B. Debnath, W. S. Singh, M. Das, S. Goswami, M. K. Singh, D. Maiti, K. Manna, Mater. Today Chem. 2018, 9, 56–72.
F. de Sa Alves, E. Barreiro, C. M. Fraga, Mini-Rev. Med. Chem. 2009, 9, 782–793.
Y. Wan, Y. Li, C. Yan, M. Yan, Z. Tang, Eur. J. Med. Chem. 2019, 183, 111691.
R. Cao, W. Peng, Z. Wang, A. Xu, Curr. Med. Chem. 2007, 14, 479–500.
F. Zhao, Z. Gao, W. Jiao, L. Chen, L. Chen, X. Yao, Planta Med. 2012, 78, 1906–1911.
A. Beato, A. Gori, B. Boucherle, M. Peuchmaur, R. Haudecoeur, J. Med. Chem. 2021, 64, 1392–1422.
P. Ashok, S. Ganguly, S. Murugesan, Drug. Discov. Today 2014, 19, 1781–1791.
S.-F. Li, Y.-Y. Cheng, Y. Zhang, S.-L. Li, H.-P. He, X.-J. Hao, Nat. Prod. Bioprospect. 2012, 2, 126–129.
M. Hassani, W. Cai, K. H. Koelsch, D. C. Holley, A. S. Rose, F. Olang, J. P. Lineswala, W. G. Holloway, J. M. Gerdes, M. Behforouz, H. D. Beall, J. Med. Chem. 2008, 51, 3104–3115.
Z. Taira, S. Kanzawa, C. Dohara, S. Ishida, M. Matsutomo, Y. Sakiya, Eisei Kagaku 1997, 43, 83–91.
R. Cao, W. Peng, H. Chen, Y. Ma, X. Liu, X. Hou, H. Guan, A. Xu, Biochem. Biophys. Res. Commun. 2005, 338, 1557–1563.
Y. Song, J. Wang, S. F. Teng, D. Kesuma, Y. Deng, J. Duan, J. H. Wang, R. Z. Qi, M. M. Sim, Bioorg. Med. Chem. Lett. 2002, 12, 1129–1132.
J. I. Trujillo, M. J. Meyers, D. R. Anderson, S. Hegde, M. W. Mahoney, W. F. Vernier, I. P. Buchler, K. K. Wu, S. Yang, S. J. Hartmann, D. B. Reitz, Bioorg. Med. Chem. Lett. 2007, 17, 4657–4663.
J. Zhang, Y. Li, L. Guo, R. Cao, P. Zhao, W. Jiang, Q. Ma, H. Yi, Z. Li, J. Jiang, J. Wu, Y. Wang, S. Si, Cancer Biol. Ther. 2009, 8, 2374–2383.
P. A. Barsanti, W. Wang, Z. J. Ni, D. Duhl, N. Brammeier, E. Martin, D. Bussiere, A. O. Walter, Bioorg. Med. Chem. Lett. 2010, 20, 157–160.
S. Hotha, J. C. Yarrow, J. G. Yang, S. Garrett, K. V. Renduchintala, T. U. Mayer, T. M. Kapoor, Angew. Chem. Int. Ed. 2003, 42, 2379–2382.
A. Spindler, K. Stefan, M. Wiese, J. Med. Chem. 2016, 59, 6121–6135.
S. Kumar, A. Singh, K. Kumar, V. Kumar, Eur. J. Med. Chem. 2017, 142, 48–73.
J. Dai, W. Dan, U. Schneider, J. Wang, Eur. J. Med. Chem. 2018, 157, 622–656.
B. Luo, X. Song, Eur. J. Med. Chem. 2021, 224, 113688, DOI 10.1016/j.ejmech.2021.113688.
S. Aaghaz, K. Sharma, R. Jain, A. Kamal, Eur. J. Med. Chem. 2021, 216, 113321, DOI 10.1016/j.ejmech.2021.113321.
S. Imran, M. Taha, N. Ismail, Curr. Med. Chem. 2015, 22, 4412–4433.
J. Poornima, S. Mirunalini, Mol. Cell. Biochem. 2014, 385, 7–15.
Y. Gong, H. Sohn, L. Xue, G. L. Firestone, L. F. Bjeldanes, Cancer Res. 2006, 66, 4880–4887.
C. Hong, H.-A. Kim, G. L. Firestone, L. F. Bjeldanes, 3,3-Diindolylmethane (DIM) Induces a G 1 Cell Cycle Arrest in Human Breast Cancer Cells That Is Accompanied by Sp1-Mediated Activation of P21 WAF1/CIP1 Expression, 2002.
F. A. Wati, M. Santoso, Z. Moussa, S. Fatmawati, A. Fadlan, Z. M. A. Judeh, RSC Adv. 2021, 11, 25381–25421.
C. H. Lee, C. F. Yao, S. M. Huang, S. Ko, Y. H. Tan, G. J. Lee-Chen, Y. C. Wang, Cancer 2008, 113, 815–825.
W. S. Li, C. H. Wang, S. Ko, T. T. Chang, Y. C. Jen, C. F. Yao, S. V. More, S. C. Jao, J. Med. Chem. 2012, 55, 1583–1592.
S. M. Huang, P. C. Hsu, M. Y. Chen, W. S. Li, S. V. More, K. T. Lu, Y. C. Wang, Int. J. Cancer 2012, 131, 722–732.
M. Shiri, M. A. Zolfigol, H. G. Kruger, Z. Tanbakouchian, Chem. Rev. 2010, 110, 2250–2293.
P. J. Praveen, P. S. Parameswaran, M. S. Majik, Synthesis 2015, 47, 1827–1837.
S. Whitneys, R. Grigg, A. Derrick, A. Keep, Org. Lett. 2007, 9, 3299–3302.
A. E. Putra, K. Takigawa, H. Tanaka, Y. Ito, Y. Oe, T. Ohta, Eur. J. Org. Chem. 2013, 28, 6344–6354.
N. Biswas, R. Sharma, D. Srimani, Adv. Synth. Catal. 2020, 362, 2902–2910.
N. K. Nguyen, M. T. Ha, H. Y. Bui, Q. T. Trinh, B. N. Tran, V. T. Nguyen, T. Q. Hung, T. T. Dang, X. H. Vu, Catal. Commun. 2021, 149, 106240.
N. K. Nguyen, D. L. Tran, T. Q. Hung, T. M. Le, N. T. Son, Q. T. Trinh, T. T. Dang, P. Langer, Tetrahedron Lett. 2021, 68, 152936.
C. W. Murray, D. C. Rees, Nat. Chem. 2009, 1, 187–192.
P. J. Hajduk, J. Greer, Nat. Rev. Drug Discovery 2007, 6, 211–219.
D. A. Erlanson, S. W. Fesik, R. E. Hubbard, W. Jahnke, H. Jhoti, Nat. Rev. Drug Discovery 2016, 15, 605–619.
J. D. St Denis, R. J. Hall, C. W. Murray, T. D. Heightman, D. C. Rees, RSC Med. Chem. 2021, 12, 321–329.
S. W. Youn, Org. Prep. Proced. Int. 2006, 38, 505–591.
E. D. Cox, J. M. Cook, The Pictet-Spengler Condensation: A New Direction for an Old Reaction, 1995.
M. Stiborová, J. Poljaková, E. Martínková, L. Bořek-Dohalská, T. Eckschlager, R. Kizek, E. Frei, Interdiscip. Toxicol. 2011, 4, 98–105.
A. Daina, O. Michielin, V. Zoete, Sci. Rep. 2017, 7, 42717.
C. A. Lipinski, F. Lombardo, B. W. Dominy, P. J. Feeney, Adv. Drug Delivery Rev. 1997, 23, 3–25.
S. Prasanna, R. J. Doerksen, Topological Polar Surface Area: A Useful Descriptor in 2D-QSAR, 2009.
J. B. Baell, G. A. Holloway, J. Med. Chem. 2010, 53, 2719–2740.
L. R. Vidler, I. A. Watson, B. J. Margolis, D. J. Cummins, M. Brunavs, ACS Med. Chem. Lett. 2018, 9, 792–796.
A. Daina, O. Michielin, V. Zoete, Nucleic Acids Res. 2019, 47, W357–W3664.
A. Grosdidier, V. Zoete, O. Michielin, Nucleic Acids Res. 2011, 39, W270–W277.
Y. Yosaatmadja, S. Silva, J. M. Dickson, A. V. Patterson, J. B. Smaill, J. U. Flanagan, M. J. McKeage, C. J. Squire, J. Struct. Biol. 2015, 192, 539–544.
F. Solca, G. Dahl, A. Zoephel, G. Bader, M. Sanderson, C. Klein, O. Kraemer, F. Himmelsbach, E. Haaksma, G. R. Adolf, J. Pharmacol. Exper. Ther. 2012, 343, 342–350.
J. H. Park, Y. Liu, M. A. Lemmon, R. Radhakrishnan, Biochem. J. 2012, 448, 417–423.
S. K. Burley, H. M. Berman, C. Bhikadiya, C. Bi, L. Chen, L. Di Costanzo, C. Christie, K. Dalenberg, J. M. Duarte, S. Dutta, Z. Feng, S. Ghosh, D. S. Goodsell, R. K. Green, V. Guranović, D. Guzenko, B. P. Hudson, T. Kalro, Y. Liang, R. Lowe, H. Namkoong, E. Peisach, I. Periskova, A. Prlić, C. Randle, A. Rose, P. Rose, R. Sala, M. Sekharan, C. Shao, L. Tan, Y. P. Tao, Y. Valasatava, M. Voigt, J. Westbrook, J. Woo, H. Yang, J. Young, M. Zhuravleva, C. Zardecki, Nucleic Acids Res. 2019, 47, D464–D474.
G. M. Morris, H. Ruth, W. Lindstrom, M. F. Sanner, R. K. Belew, D. S. Goodsell, A. J. Olson, J. Comput. Chem. 2009, 30, 2785–2791.
PyMOL, Version 1.8, Schrodinger LLC, New York, NY, 2022.
Chemdraw Professional, Version 16.0, PerkinElmer, Cambridge, MA, 2017.
M. D. Hanwell, D. E. Curtis, D. C. Lonie, T. Vandermeersch, E. Zurek, G. R. Hutchison, J. Cheminf. 2012, 4, 17.
N. M. O'Boyle, M. Banck, C. A. James, C. Morley, T. Vandermeersch, G. R. Hutchison, J. Cheminf. 2011, 3, 33.
S. Forli, R. Huey, M. E. Pique, M. F. Sanner, D. S. Goodsell, A. J. Olson, Nat. Protoc. 2016, 11, 905–919.
P. Skehan, R. Storeng, D. Scudiero, A. Monks, J. Mcmahon, D. Vistica, J. T. Warren, H. Bokesch, S. Kenney, M. R. Boyd, New Colorimetric Cytotoxicity Assay for Anticancer-Drug Screening, 1990.
Systat, TableCurve 2D, Systat, Palo Alto, CA, 2021.
J. Hughes, S. Rees, S. Kalindjian, K. Philpott, Br. J. Pharmacol. 2011, 162, 1239–1249.
R. Mahato, C. K. Hazra, Chem. Eur. J. 2023, 29, e202203924.
S. Samundeeswari, B. Chougala, M. Holiyachi, L. Shastri, M. Kulkarni, S. Dodamani, S. Jalalpur, S. Joshi, S. Dixit, V. Sunagar, R. Hunnur, Eur. J. Med. Chem. 2017, 128, 123–139.
معلومات مُعتمدة: Vingroup Joint Stock Company; VINIF.2021.DA00203 Vingroup Innovation Foundation (VINIF)
فهرسة مساهمة: Keywords: anticancer agents; antiproliferative activity; bis(3-indolyl)methanes; molecular docking; β-carbolines
تواريخ الأحداث: Date Created: 20240610 Latest Revision: 20240808
رمز التحديث: 20240808
DOI: 10.1002/cmdc.202400316
PMID: 38856518
قاعدة البيانات: MEDLINE