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Research Article

Imparting aromaticity to 2-pyridone derivatives by O-alkylation resulted in new competitive and non-competitive PIM-1 kinase inhibitors with caspase-activated apoptosis

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Article: 2304044 | Received 17 Jul 2023, Accepted 07 Jan 2024, Published online: 17 Jan 2024

References

  • Wang BW, Huang CH, Liu LC, Cheng FJ, Wei YL, Lin YM, Wang YF, Wei CT, Chen Y, Chen YJ, et al. PIM1 kinase inhibitors exert anti-cancer activity against HER2-positive breast cancer cells through downregulation of HER2. Front Pharmacol. 2021;12:614673.
  • Puente-Moncada N, Costales P, Antolín I, Núñez L-E, Oro P, Hermosilla MA, Pérez-Escuredo J, Ríos-Lombardía N, Sanchez-Sanchez AM, Luño E, et al. Inhibition of FLT3 and PIM kinases by EC-70124 exerts potent activity in preclinical models of acute myeloid leukemia. Mol Cancer Ther. 2018;17(3):614–624.
  • Ogawa N, Yuki H, Tanaka A. Insights from PIM1 structure for anti-cancer drug design. Expert Opin Drug Discov. 2012;7(12):1177–1192.
  • Schenone S, Tintori C, Botta M. Using insights into PIM1 structure to design new anticancer drugs. Curr Pharm Des. 2010;16(35):3964–3978.
  • Blanco-Aparicio C, Carnero A. Pim kinases in cancer: diagnostic, prognostic and treatment opportunities. Biochem Pharmacol. 2013;85(5):629–643.
  • Mohamed EA, Ismail NSM, Hagras M, Refaat H. Medicinal attributes of pyridine scaffold as anticancer targeting agents. Futur J Pharm Sci. 2021;7(1):24.
  • Ye C, Zhang C, Huang H, Yang B, Xiao G, Kong D, Tian Q, Song Q, Song Y, Tan H, et al. The natural compound myricetin effectively represses the malignant progression of prostate cancer by inhibiting PIM1 and disrupting the PIM1/CXCR4 interaction. Cell Physiol Biochem. 2018;48(3):1230–1244.
  • Liu K, Gao H, Wang Q, Wang L, Zhang B, Han Z, Chen X, Han M, Gao M. Hispidulin suppresses cell growth and metastasis by targeting PIM1 through JAK2/STAT3 signaling in colorectal cancer. Cancer Sci. 2018;109(5):1369–1381.
  • Stafman LL, Mruthyunjayappa S, Waters AM, Garner EF, Aye JM, Stewart JE, Yoon KJ, Whelan K, Mroczek-Musulman E, Beierle EA. Targeting PIM kinase as a therapeutic strategy in human hepatoblastoma. Oncotarget. 2018;9(32):22665–22679.
  • Brasó-Maristany F, Filosto S, Catchpole S, Marlow R, Quist J, Francesch-Domenech E, Plumb DA, Zakka L, Gazinska P, Liccardi G, et al. PIM1 kinase regulates cell death, tumor growth and chemotherapy response in triple-negative breast cancer. Nat Med. 2016;22(11):1303–1313.
  • Kronschnabl P, Grünweller A, Hartmann RK, Aigner A, Weirauch U. Inhibition of PIM2 in liver cancer decreases tumor cell proliferation in vitro and in vivo primarily through the modulation of cell cycle progression. Int J Oncol. 2020;56(2):448–459.
  • Zhang M, Liu T, Sun H, Weng W, Zhang Q, Liu C, Han Y, Sheng W. PIM1 supports human colorectal cancer growth during glucose deprivation by enhancing the Warburg effect. Cancer Sci. 2018;109(5):1468–1479.
  • Hu XF, Li J, Vandervalk S, Wang Z, Magnuson NS, Xing PX. PIM-1-specific mAb suppresses human and mouse tumor growth by decreasing PIM-1 levels, reducing Akt phosphorylation, and activating apoptosis. J Clin Invest. 2009;119(2):362–375.
  • Li J, Hu XF, Loveland BE, Xing PX. PIM-1 expression and monoclonal antibody targeting in human leukemia cell lines. Exp Hematol. 2009;37(11):1284–1294.
  • Liu Z, Zhang Y, Guo Y, Wang H, Fu R. An overview of PIM kinase as a target in multiple myeloma. Cancer Med. 2023;12(10):11746–11759.
  • Abnous K, Manavi H, Mehri S, Alibolandi M, Kamali H, Ghandadi M, Hadizadeh F. In vitro evaluation of dihydropyridine-3-carbonitriles as potential cytotoxic agents through PIM-1 protein kinase inhibition. Res Pharm Sci. 2017;12(3):196–203.
  • Chen J, Kobayashi M, Darmanin S, Qiao Y, Gully C, Zhao R, Kondo S, Wang H, Wang H, Yeung S-CJ, et al. Hypoxia-mediated up-regulation of PIM-1 contributes to solid tumor formation. Am J Pathol. 2009;175(1):400–411.
  • Walhekar V, Bagul C, Kumar D, Muthal A, Achaiah G, Kulkarni R. Topical advances in PIM kinases and their inhibitors: medicinal chemistry perspectives. Biochim Biophys Acta Rev Cancer. 2022;1877(3):188725.
  • Mori M, Tintori C, Christopher RSA, Radi M, Schenone S, Musumeci F, Brullo C, Sanità P, Delle Monache S, Angelucci A, et al. A combination strategy to inhibit PIM-1: synergism between noncompetitive and ATP-competitive inhibitors. ChemMedChem. 2013;8(3):484–496.
  • Morwick T. PIM kinase inhibitors: a survey of the patent literature. Expert Opin Ther Pat. 2010;20(2):193–212.
  • Nair JR, Caserta J, Belko K, Howell T, Fetterly G, Baldino C, Lee KP. Novel inhibition of PIM2 kinase has significant anti-tumor efficacy in multiple myeloma. Leukemia. 2017;31(8):1715–1726.
  • Wähler K, Kräling K, Steuber H, Meggers E. Non-ATP-mimetic organometallic protein kinase inhibitor. ChemistryOpen. 2013;2(5–6):180–185.
  • Lee SJ, Han B-G, Cho J-W, Choi J-S, Lee J, Song H-J, Koh JS, Lee BI. Crystal structure of PIM1 kinase in complex with a pyrido[4,3-d]pyrimidine derivative suggests a unique binding mode. PLOS One. 2013;8(7):e70358.
  • El-Miligy MMM, Abdelaziz ME, Fahmy SM, Ibrahim TM, Abu-Serie MM, Mahran MA, Hazzaa AA. Discovery of new pyridine–quinoline hybrids as competitive and non-competitive PIM-1 kinase inhibitors with apoptosis induction and caspase 3/7 activation capabilities. J Enzyme Inhib Med Chem. 2023;38(1):2152810.
  • Ethics Committee. Faculty of Medicine, Alexandria University, Member of ICLAS, IRB No.: 00018699, SN: 0201797(9-4-2023); 2023.
  • Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods. 1983;65(1–2):55–63.
  • Xu T, Niu C, Zhang X, Dong M. B-ecdysterone protects SH-SY5Y cells against β-amyloid-induced apoptosis via c-Jun N-terminal kinase- and Akt-associated complementary pathways. Lab Invest. 2018;98(4):489–499.
  • Brown AM. A new software for carrying out one-way ANOVA post hoc tests. Comput Methods Prog Biomed. 2005;79(1):89–95.
  • Promega; 2023. Available from: https://www.promega.com/-/media/files/resources/protocols/kinase-enzyme, appnotes/pim1-kinase-assay.pdf?la=en
  • Arrouchi H, Lakhlili W, Ibrahimi A. A review on PIM kinases in tumors. Bioinformation. 2019;15(1):40–45.
  • Hassan AS, Hafez TS, Osman SA. Synthesis, characterization, and cytotoxicity of some new 5-aminopyrazole and pyrazolo[1,5-a]pyrimidine derivatives. Sci Pharm. 2015;83(1):27–39.
  • Riccardi C, Nicoletti I. Analysis of apoptosis by propidium iodide staining and flow cytometry. Nat Protoc. 2006;1(3):1458–1461.
  • Cheney IW, Yan S, Appleby T, Walker H, Vo T, Yao N, Hamatake R, Hong Z, Wu JZ. Identification and structure–activity relationships of substituted pyridones as inhibitors of PIM-1 kinase. Bioorg Med Chem Lett. 2007;17(6):1679–1683.
  • Sotriffer Accounting AC. For induced-fit effects in docking: what is possible and what is not? Curr Top Med Chem. 2011;11(2):179–191.
  • Barreca ML, Iraci N, De Luca L, Chimirri A. Induced‐fit docking approach provides insight into the binding mode and mechanism of action of HIV‐1 integrase inhibitors. ChemMedChem. 2009;4(9):1446–1456.
  • Nirwan S, Chahal V, Kakkar R. A comparative study of different docking methodologies to assess the protein–ligand interaction for the E. coli murb enzyme. J Biomol Struct Dyn. 2022;40(21):11229–11238.
  • Molinspiration; 2023. Available from: http://www.molinspiration.com/
  • Molsoft; 2023. Available from: http://molsoft.com/mprop/
  • Preadmet; 2023. Available from: http://preadmet.bmdrc.org/
  • Hopkins AL, Keserü GM, Leeson PD, Rees DC, Reynolds CH. The role of ligand efficiency metrics in drug discovery. Nat Rev Drug Discov. 2014;13(2):105–121.