Biological Evaluation of 3-Aminoisoquinolin-1(2H)-one Derivatives as Potential Anticancer Agents
DOI:
https://doi.org/10.17721/fujcV9I2P52-63Keywords:
1-isoquinolinone, anticancer activity, growth inhibitor, cytostatic activity, selectivityAbstract
Anticancer activity of a series of 3-(hetaryl/aryl)amino substituted isoquinolin-1(2H)-ones has been studied within the international scientific program “NCI-60 Human Tumor Cell Lines Screen”. Screening was performed in vitro on 60 cell lines of lungs, kidneys, CNS, ovaries, prostate, and breast cancer, epithelial cancer, leukemia, and melanoma. The most effective compounds were those with thiazolyl or pyrazolyl substituent at 3-amino group and had no substituents at C(4) of the isoquinoline cycle. We identified a new lead compound, 3-(1,3-thiazol-2-ylamino)isoquinolin-1(2H)-one 12, which effectively prevents tumor cell growth (average lg GI50 = -5.18, lg TGI = -4.1, lg LC50 > -4.0) with good selectivity.
References
Cao B, Soerjomataram I, Bray F. The global cancer burden. In: Wild CP, Weiderpass E, Stewart BW, editors. World Cancer Report: Cancer Research for Cancer Prevention. Lyon, France: International Agency for Research on Cancer; 2020.
Aziz H, Zahoor A, Ahmad S. Pyrazole bearing molecules as bioactive scaffolds: A review. Journal of the Chilean Chemical Society 2020;65(1):4746-4753. https://doi.org/10.4067/s0717-97072020000104746
Kumari P, Mishra V, Narayana C, Khanna A, Chakrabarty A, Sagar R. Design and efficient synthesis of pyrazoline and isoxazole bridged indole C-glycoside hybrids as potential anticancer agents. Scientific Reports 2020;10(1):6660. https://doi.org/10.1038/s41598-020-63377-x
Guerrero-Pepinosa N, Cardona-Trujillo M, Garzón-Castaño S, Veloza L, Sepúlveda-Arias J. Antiproliferative activity of thiazole and oxazole derivatives: A systematic review of in vitro and in vivo studies. Biomedicine & Pharmacotherapy 2021;138:111495. https://doi.org/10.1016/j.biopha.2021.111495
Alizadeh S, Hashemi S. Development and therapeutic potential of 2-aminothiazole derivatives in anticancer drug discovery. Medicinal Chemistry Research 2021;30(4):771-806. https://doi.org/10.1007/s00044-020-02686-2
Ramos-Inza S, Aydillo C, Sanmartín C, Plano D. Thiazole Moiety: An Interesting Scaffold for Developing New Antitumoral Compounds. Heterocycles - Synthesis and Biological Activities 2019:1-21. https://doi.org/10.5772/intechopen.82741
Habartová K, Cahlíková L, Řezáčová M, Havelek R. The Biological Activity of Alkaloids from the Amaryllidaceae: From Cholinesterases Inhibition to Anticancer Activity. Natural Product Communications 2016;11(10):1587-1594. https://doi.org/10.1177/1934578x1601101038
Cheon S, Park J, Lee J, Lee Y, Yi H, Chung B, Choi B, Cho W, Choi S, Lee C. Structure-activity relationship studies of isoquinolinone type anticancer agent. Archives of Pharmacal Research 2001;24(4):276-280. https://doi.org/10.1007/bf02975091
Tang Z, Niu S, Liu F, Lao K, Miao J, Ji J, Wang X, Yan M, Zhang L, You Q, Xiao H, Xiang H. Synthesis and biological evaluation of 2,3-diaryl isoquinolinone derivatives as anti-breast cancer agents targeting ERα and VEGFR-2. Bioorganic & Medicinal Chemistry Letters 2014;24(9):2129-2133. https://doi.org/10.1016/j.bmcl.2014.03.042
Johnston P, Foster C, Tierno M, Shun T, Shinde S, Paquette W, Brummond K, Wipf P, Lazo J. Cdc25B Dual-Specificity Phosphatase Inhibitors Identified in a High-Throughput Screen of the NIH Compound Library. ASSAY and Drug Development Technologies 2009;7(3):250-265. https://doi.org/10.1089/adt.2008.186
George Rosenker K, Paquette W, Johnston P, Sharlow E, Vogt A, Bakan A, Lazo J, Wipf P. Synthesis and biological evaluation of 3-aminoisoquinolin-1(2H)-one based inhibitors of the dual-specificity phosphatase Cdc25B. Bioorganic & Medicinal Chemistry 2015;23(12):2810-2818. https://doi.org/10.1016/j.bmc.2015.01.043
Chen L, Georges G, Mertens A, Wu X, inventors; F. Hoff-Mann-La Roche AG, assignee. Isoquinoline aminopyrazole derivatives, their manufacture and use as pharmaceutical agents for the treatment of cancer. World Intellectual Property Organisation patent 2007/071348. 2007 June 28.
Chen H, He L, Li S, Zhang Y, Huang J, Qin H, Wang J, Li Q, Yang D. A Derivate of Benzimidazole-Isoquinolinone Induces SKP2 Transcriptional Inhibition to Exert Anti-Tumor Activity in Glioblastoma Cells. Molecules 2019;24(15):2722. https://doi.org/10.3390/molecules24152722
He L, Yang D, Li S, Zhang Y, Tang Y, Lei J, Frett B, Lin H, Li H, Chen Z, Xu Z. Facile construction of fused benzimidazole-isoquinolinones that induce cell-cycle arrest and apoptosis in colorectal cancer cells. Bioorganic & Medicinal Chemistry 2018;26(14):3899-3908. https://doi.org/10.1016/j.bmc.2018.06.010
Sondhi S, Rani R, Singh J, Roy P, Agrawal S, Saxena A. Solvent free synthesis, anti-inflammatory and anticancer activity evaluation of tricyclic and tetracyclic benzimidazole derivatives. Bioorganic & Medicinal Chemistry Letters 2010;20(7):2306-2310. https://doi.org/10.1016/j.bmcl.2010.01.147
Potikha L, Gutsul R, Kovtunenko V, Tolmachev A. 3-(Hetarylamino)- and 3-[(hetarylmethyl)amino]-isoquinolin-1(2H)-ones. Chemistry of Heterocyclic Compounds 2010;46(4):457-467. https://doi.org/10.1007/s10593-010-0531-0
Potikha L, Gutsul R, Kovtunenko V, Turov A. Study of acylation reactions in 3-aminocarbostyril derivatives. Chemistry of Heterocyclic Compounds 2010;46(5):569-580. https://doi.org/10.1007/s10593-010-0547-5
NCI-60 Human Tumor Cell Lines Screen. DTP Developmental Therapeutics Program, NIH website [Internet]. 2020 [updated 20 March 2020]. https://dtp.cancer.gov/discovery_development/nci-60/default.htm
Alley MC, Scudiero DS, Monks PA, Hursey ML, Czerwinski MJ, Fine DL, Abbott BJ, Mayo JG, Shoemaker RH, Boyd MR. Feasibility of Drug Screening with Panels of Human Tumor Cell Lines Using a Microculture Tetrazolium Assay. Cancer Res. 1988;48(3):589-601. https://cancerres.aacrjournals.org/content/48/3/589.full-text.pdf
Grever MR, Schepartz SA, Chabner BA. The National Cancer Institute: cancer drug discovery and development program. Semin Oncol. 1992;19(6):622-638.
Boyd M, Paull K. Some practical considerations and applications of the national cancer institute in vitro anticancer drug discovery screen. Drug Development Research 1995;34(2):91-109. https://doi.org/10.1002/ddr.430340203
Shoemaker R. The NCI60 human tumour cell line anticancer drug screen. Nature Reviews Cancer 2006;6(10):813-823. https://doi.org/10.1038/nrc1951
Arias J. Novel Strategies to Improve the Anticancer Action of 5-Fluorouracil by Using Drug Delivery Systems. Molecules 2008;13(10):2340-2369. https://doi.org/10.3390/molecules13102340
Bunz F. Thymidylate synthase and 5-fluorouracil: a cautionary tale. Cancer Biology & Therapy 2008;7(7):995-996. https://doi.org/10.4161/cbt.7.7.6414
Luzina E, Popov A. Synthesis and anticancer activity of N-bis(trifluoromethyl)alkyl-N′-thiazolyl and N-bis(trifluoromethyl)alkyl-N′-benzothiazolyl ureas. European Journal of Medicinal Chemistry 2009;44(12):4944-4953. https://doi.org/10.1016/j.ejmech.2009.08.007
Paull K, Shoemaker R, Hodes L, Monks A, Scudiero D, Rubinstein L, Plowman J, Boyd M. Display and Analysis of Patterns of Differential Activity of Drugs Against Human Tumor Cell Lines: Development of Mean Graph and COMPARE Algorithm. JNCI Journal of the National Cancer Institute 1989;81(14):1088-1092. https://doi.org/10.1093/jnci/81.14.1088
COMPARE Analysis. DTP Developmental Therapeutics Program, NIH website [Internet]. US National Cancer Institute; 2021 [updated 26 February 2021]. https://dtp.cancer.gov/databases_tools/compare.htm
Mukaka MM. Statistics corner: A guide to appropriate use of correlation coefficient in medical research. Malawi Med J. 2012;24(3):69-71.
Kim D, Sun M, He L, Zhou Q, Chen J, Sun X, Bepler G, Sebti S, Cheng J. A Small Molecule Inhibits Akt through Direct Binding to Akt and Preventing Akt Membrane Translocation. Journal of Biological Chemistry 2010;285(11):8383-8394. https://doi.org/10.1074/jbc.m109.094060
Berndt N, Yang H, Trinczek B, Betzi S, Zhang Z, Wu B, Lawrence N, Pellecchia M, Schönbrunn E, Cheng J, Sebti S. The Akt activation inhibitor TCN-P inhibits Akt phosphorylation by binding to the PH domain of Akt and blocking its recruitment to the plasma membrane. Cell Death & Differentiation 2010;17(11):1795-1804. https://doi.org/10.1038/cdd.2010.63
Garrett C, Coppola D, Wenham R, Cubitt C, Neuger A, Frost T, Lush R, Sullivan D, Cheng J, Sebti S. Phase I pharmacokinetic and pharmacodynamic study of triciribine phosphate monohydrate, a small-molecule inhibitor of AKT phosphorylation, in adult subjects with solid tumors containing activated AKT. Investigational New Drugs 2010;29(6):1381-1389. https://doi.org/10.1007/s10637-010-9479-2
Brown T, Ettinger D, Donehower R. A phase I trial of spirohydantoin mustard (NSC 172112) in patients with advanced cancer.. Journal of Clinical Oncology 1986;4(8):1270-1276. https://doi.org/10.1200/jco.1986.4.8.1270
Downloads
Published
Issue
Section
License
Copyright (c) 2021 French-Ukrainian Journal of Chemistry
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
Authors who publish with this journal agree to the following terms:
Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.
Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (See The Effect of Open Access).
