2,020
Views
6
CrossRef citations to date
0
Altmetric
Research Paper

Discovery of new pyridine-quinoline hybrids as competitive and non-competitive PIM-1 kinase inhibitors with apoptosis induction and caspase 3/7 activation capabilities

ORCID Icon, , , , , & show all
Article: 2152810 | Received 25 Oct 2022, Accepted 24 Nov 2022, Published online: 11 Jan 2023

References

  • Puente-Moncada N, Costales P, Antolin I, Nunez LE, Oro P, Hermosilla MA, Perez-Escuredo J, Rios-Lombardia N, Sanchez-Sanchez AM, Luno 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.
  • 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.
  • 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 RS, Radi M, Schenone S, Musumeci F, Brullo C, Sanita 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):1–7.
  • 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.
  • 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.
  • Li K, Li Y, Zhou D, Fan Y, Guo H, Ma T, Wen J, Liu D, Zhao L. Synthesis and biological evaluation of quinoline derivatives as potential anti-prostate cancer agents and PIM-1 kinase inhibitors. Bioorg Med Chem. 2016;24(8):1889–1897.
  • Swellmeen L, Shahin R, Al-Hiari Y, Alamiri A, Hasan A, Shaheen O. Structure based drug design of PIM-1 kinase followed by pharmacophore guided synthesis of quinolone-based inhibitors. Bioorg Med Chem. 2017;25(17):4855–4875.
  • Abdelaziz ME, El-Miligy MMM, Fahmy SM, Mahran MA, Hazzaa AA. Design, synthesis and docking study of pyridine and thieno[2,3-b] pyridine derivatives as anticancer PIM-1 kinase inhibitors. Bioorg Chem. 2018;(80):674–692.
  • Howard JC. 2-amino-3-nitrotoluene. Org Synth. 1955:42–44.
  • JJaS B. Synthesis of novel substituted quinoline derivatives with 2-amino-5-methylthiophene-3-carbonitrile. Indo Am J Pharm Res. 2014; 45(5):2496–2502.
  • Hamama WS, Ibrahim ME, Gooda AA, Zoorob HH. Recent advances in the chemistry of 2-chloroquinoline-3-carbaldehyde and related analogs. RSC Adv. 2018;8(16):8484–8515.
  • Abdel-Wahab BF, Khidre RE. 2-chloroquinoline-3-carbaldehyde II: synthesis, reactions, and applications. J Chem. 2013;2013:1–13.
  • 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. β-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 Programs Biomed. 2005;79(1):89–95.
  • Available from: www.promega.com
  • Ishchenko A, Zhang L, Le Brazidec J-Y, Fan J, Chong JH, Hingway A, Raditsis A, Singh L, Elenbaas B, Hong VS, et al. Structure-based design of low-nanomolar PIM kinase inhibitors. Bioorg Med Chem Lett. 2015;25(3):474–480.
  • McGann M. Fred pose prediction and virtual screening accuracy. J Chem Inf Model. 2011;51(3):578–596.
  • McGann M. Fred and hybrid docking performance on standardized datasets. J Comput Aided Mol Des. 2012;26(8):897–906.
  • Andre CM, Hausman J-F, Guerriero G. Cannabis sativa: the plant of the thousand and one molecules. Front Plant Sci. 2016;7:19.
  • Hawkins PC, Skillman AG, Warren GL, Ellingson BA, Stahl MT. Conformer generation with omega: algorithm and validation using high quality structures from the protein databank and Cambridge structural database. J Chem Inf Model. 2010;50(4):572–584.
  • Pazouki L, Niinemets Ü. Multi-substrate terpene synthases: their occurrence and physiological significance. Front Plant Sci. 2016;7:1019.
  • Daina A, Michielin O, Zoete V. Swissadme: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Sci Rep. 2017;7:42717.
  • Riccardi C, Nicoletti I. Analysis of apoptosis by propidium iodide staining and flow cytometry. Nat Protoc. 2006;1(3):1458–1461.
  • Hopkins AL, Keseru 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.
  • Daina A, Zoete V. A boiled-egg to predict gastrointestinal absorption and brain penetration of small molecules. ChemMedChem. 2016;11(11):1117–1121.
  • Szakacs G, Varadi A, Ozvegy-Laczka C, Sarkadi B. The role of ABC transporters in drug absorption, distribution, metabolism, excretion and toxicity (ADME-Tox). Drug Discov Today. 2008;13(9-10):379–393.
  • Cheng T, Zhao Y, Li X, Lin F, Xu Y, Zhang X, Li Y, Wang R, Lai L. Computation of octanol-water partition coefficients by guiding an additive model with knowledge. J Chem Inf Model. 2007;47(6):2140–2148.
  • Farghaly A-R. Synthesis, reactions and antimicrobial activity of some new indolyl-1,3,4-oxadiazole, triazole and pyrazole derivatives. J Chin Chem Soc. 2004;51(1):147–156.
  • Di L. The role of drug metabolizing enzymes in clearance. Expert Opin Drug Metab Toxicol. 2014;10(3):379–393.
  • Hollenberg PF. Characteristics and common properties of inhibitors, inducers, and activators of CYP enzymes. Drug Metab Rev. 2002;34(1-2):17–35.
  • Huang SM, Strong JM, Zhang L, Reynolds KS, Nallani S, Temple R, Abraham S, Habet SA, Baweja RK, Burckart GJ, et al. New era in drug interaction evaluation: US Food and Drug Administration update on CYP enzymes, transporters, and the guidance process. J Clin Pharmacol. 2008;48(6):662–670.
  • Baell JB, Holloway GA. New substructure filters for removal of pan assay interference compounds (pains) from screening libraries and for their exclusion in bioassays. J Med Chem. 2010;53(7):2719–2740.
  • Veber DF, Johnson SR, Cheng HY, Smith BR, Ward KW, Kopple KD. Molecular properties that influence the oral bioavailability of drug candidates. J Med Chem. 2002;45(12):2615–2623.