Design, synthesis, and study of novel phenethyl-based antitumor phospholipids downregulating p38 mitogen-activated protein kinase

References

• Hassan AHE, Cho MC, Kim HI, Yang JS, Park KT, Hwang JY, Jang C-G, Park KD, Lee YS. Synthesis of oxidative metabolites of CRA13 and their analogs: Identification of CRA13 active metabolites and analogs thereof with selective CB2R affinity. Bioorg Med Chem. 2018;26(18):5069–5078.
   PubMed Web of Science ®Google Scholar
• Hassan AHE, Park KT, Kim HJ, Lee HJ, Kwon YH, Hwang JY, Jang C-G, Chung JH, Park KD, Lee SJ, et al. Fluorinated CRA13 analogues: Synthesis, in vitro evaluation, radiosynthesis, in silico and in vivo PET study. Bioorg Chem. 2020;99:103834.
   PubMed Web of Science ®Google Scholar
• Hassan AHE, Park HR, Yoon YM, Kim HI, Yoo SY, Lee KW, Lee YS. Antiproliferative 3-deoxysphingomyelin analogs: Design, synthesis, biological evaluation and molecular docking of pyrrolidine-based 3-deoxysphingomyelin analogs as anticancer agents. Bioorg Chem. 2019;84:444–455.
   PubMed Web of Science ®Google Scholar
• Hassan AHE, Phan T-N, Yoon S, Lee CJ, Jeon HR, Kim S-H, No JH, Lee YS. Pyrrolidine-based 3-deoxysphingosylphosphorylcholine analogs as possible candidates against neglected tropical diseases (NTDs): identification of hit compounds towards development of potential treatment of Leishmania donovani. J Enzyme Inhib Med Chem. 2021;36(1):1922–1930.
   PubMed Web of Science ®Google Scholar
• Alam MM, Hassan AHE, Kwon YH, Lee HJ, Kim NY, Min KH, Lee S-Y, Kim D-H, Lee YS. Design, synthesis and evaluation of alkylphosphocholine-gefitinib conjugates as multitarget anticancer agents. Arch Pharm Res. 2018;41(1):35–45.
   PubMed Web of Science ®Google Scholar
• Alam MM, Hassan AHE, Lee KW, Cho MC, Yang JS, Song J, Min KH, Hong J, Kim D-H, Lee YS. Design, synthesis and cytotoxicity of chimeric erlotinib-alkylphospholipid hybrids. Bioorg Chem. 2019;84:51–62.
   PubMed Web of Science ®Google Scholar
• Koul HK, Pal M, Koul S. Role of p38 MAP Kinase Signal Transduction in Solid Tumors. Genes Cancer. 2013;4(9-10):342–359.
   PubMedGoogle Scholar
• Igea A, Nebreda AR. The Stress Kinase p38α as a Target for Cancer Therapy. Cancer Res. 2015;75(19):3997–4002.
   PubMed Web of Science ®Google Scholar
• Kudaravalli S, den Hollander P, Mani SA. Role of p38 MAP kinase in cancer stem cells and metastasis. Oncogene. 2022;41(23):3177–3185.
   PubMed Web of Science ®Google Scholar
• Fang Z, Grütter C, Rauh D. Strategies for the Selective Regulation of Kinases with Allosteric Modulators: exploiting exclusive structural features. ACS Chem Biol. 2013;8(1):58–70.
   PubMed Web of Science ®Google Scholar
• Elkamhawy A, Kim Ny, Hassan AHE, Park J-e, Yang J-E, Oh K-S, Lee BH, Lee MY, Shin KJ, Lee K-T, et al. Design, synthesis and biological evaluation of novel thiazolidinedione derivatives as irreversible allosteric IKK-β modulators. Eur J Med Chem. 2018;157:691–704.
   PubMed Web of Science ®Google Scholar
• Elkamhawy A, Kim Ny, Hassan AHE, Park J-e, Paik S, Yang J-E, Oh K-S, Lee BH, Lee MY, Shin KJ, et al. Thiazolidine-2,4-dione-based irreversible allosteric IKK-β kinase inhibitors: optimization into in vivo active anti-inflammatory agents. Eur J Med Chem. 2020;188:111955.
   PubMed Web of Science ®Google Scholar
• Elkamhawy A, Youn Kim N, Hassan AHE, Park J-e, Yang J-E, Elsherbeny MH, Paik S, Oh K-S, Lee BH, Lee MY, et al. Optimization study towards more potent thiazolidine-2,4-dione IKK-β modulator: synthesis, biological evaluation and in silico docking simulation. Bioorg Chem. 2019;92:103261.
   PubMed Web of Science ®Google Scholar
• Diskin R, Engelberg D, Livnah O. A Novel Lipid Binding Site Formed by the MAP Kinase Insert in p38α. J Mol Biol. 2008;375(1):70–79.
   PubMed Web of Science ®Google Scholar
• Kumar GS, Clarkson MW, Kunze MBA, Granata D, Wand AJ, Lindorff-Larsen K, Page R, Peti W. Dynamic activation and regulation of the mitogen-activated protein kinase p38. Proc Natl Acad Sci U S A. 2018;115(18):4655–4660.
   PubMed Web of Science ®Google Scholar
• Perry JJP, Harris RM, Moiani D, Olson AJ, Tainer JA. p38α MAP Kinase C-Terminal Domain Binding Pocket Characterized by Crystallographic and Computational Analyses. J Mol Biol. 2009;391(1):1–11.
   PubMed Web of Science ®Google Scholar
• Comess KM, Sun C, Abad-Zapatero C, Goedken ER, Gum RJ, Borhani DW, Argiriadi M, Groebe DR, Jia Y, Clampit JE, et al. Discovery and Characterization of Non-ATP Site Inhibitors of the Mitogen Activated Protein (MAP) Kinases. ACS Chem Biol. 2011;6(3):234–244.
   PubMed Web of Science ®Google Scholar
• Bührmann M, Wiedemann BM, Müller MP, Hardick J, Ecke M, Rauh D. Structure-based design, synthesis and crystallization of 2-arylquinazolines as lipid pocket ligands of p38α MAPK. PLOS One. 2017;12(9):e0184627.
   PubMed Web of Science ®Google Scholar
• Zhang XH, Chen C-H, Li H, Hsiang J, Wu X, Hu W, Horne D, Nam S, Shively J, Rosen ST. Targeting the non-ATP-binding pocket of the MAP kinase p38γ mediates a novel mechanism of cytotoxicity in cutaneous T-cell lymphoma (CTCL). FEBS Lett. 2021;595(20):2570–2592.
   PubMed Web of Science ®Google Scholar
• Boshkow J, Fischer S, Bailey AM, Wolfrum S, Carreira EM. Stereochemistry and biological activity of chlorinated lipids: a study of danicalipin A and selected diastereomers. Chem Sci. 2017;8(10):6904–6910.
   PubMed Web of Science ®Google Scholar
• Gaich T, Baran PS. Aiming for the Ideal Synthesis. J Org Chem. 2010;75(14):4657–4673.
   PubMed Web of Science ®Google Scholar
• Jo H, Hassan AHE, Jung SY, Lee JK, Cho YS, Min S-J. Construction of 8-Azabicyclo[3.2.1]octanes via Sequential DDQ-Mediated Oxidative Mannich Reactions of N-Aryl Pyrrolidines. Org Lett. 2018;20(4):1175–1178.
   PubMed Web of Science ®Google Scholar
• Seo JM, Hassan AHE, Lee YS. An expeditious entry to rare tetrahydroimidazo[1,5-c]pyrrolo[1,2-a]pyrimidin-7(8H)-ones: a single-step gateway synthesis of glochidine congeners. Tetrahedron. 2019;75(51):130760.
   Web of Science ®Google Scholar
• Lue H-w, Derrick DS, Rao S, Van Gaest A, Cheng L, Podolak J, Lawson S, Xue C, Garg D, White R, et al. Cabozantinib and dasatinib synergize to induce tumor regression in non-clear cell renal cell carcinoma. Cell Rep Med. 2021;2(5):100267.
   PubMedGoogle Scholar
• Liu AY. Differential Expression of Cell Surface Molecules in Prostate Cancer Cells. Cancer Res. 2000;60:3429–3434.
   PubMed Web of Science ®Google Scholar
• Farag AK, Hassan AHE, Chung K-S, Lee J-H, Gil H-S, Lee K-T, Roh EJ. Diarylurea derivatives comprising 2,4-diarylpyrimidines: discovery of novel potential anticancer agents via combined failed-ligands repurposing and molecular hybridization approaches. Bioorg Chem. 2020;103:104121.
   PubMed Web of Science ®Google Scholar
• Hassan AHE, Lee K-T, Lee YS. Flavone-based arylamides as potential anticancers: design, synthesis and in vitro cell-based/cell-free evaluations. Eur J Med Chem. 2020;187:111965.
   PubMed Web of Science ®Google Scholar
• Farag AK, Hassan AHE, Ahn BS, Park KD, Roh EJ. Reprofiling of pyrimidine-based DAPK1/CSF1R dual inhibitors: identification of 2,5-diamino-4-pyrimidinol derivatives as novel potential anticancer lead compounds. J Enzyme Inhib Med Chem. 2020;35(1):311–324.
   PubMed Web of Science ®Google Scholar
• Hassan AHE, Choi E, Yoon YM, Lee KW, Yoo SY, Cho MC, Yang JS, Kim HI, Hong JY, Shin J-S, et al. Natural products hybrids: 3,5,4′-Trimethoxystilbene-5,6,7-trimethoxyflavone chimeric analogs as potential cytotoxic agents against diverse human cancer cells. Eur J Med Chem. 2019;161:559–580.
   PubMed Web of Science ®Google Scholar
• Elkamhawy A, Paik S, Hassan AHE, Lee YS, Roh EJ. Hit discovery of 4-amino-N-(4-(3-(trifluoromethyl)phenoxy)pyrimidin-5-yl)benzamide: a novel EGFR inhibitor from a designed small library. Bioorg Chem. 2017;75:393–405.
   PubMed Web of Science ®Google Scholar
• Hassan AHE, Yoo SY, Lee KW, Yoon YM, Ryu HW, Jeong Y, Shin J-S, Kang S-Y, Kim S-Y, Lee H-H, et al. Repurposing mosloflavone/5,6,7-trimethoxyflavone-resveratrol hybrids: discovery of novel p38-α MAPK inhibitors as potent interceptors of macrophage-dependent production of proinflammatory mediators. Eur J Med Chem. 2019;180:253–267.
   PubMed Web of Science ®Google Scholar
• Hassan AHE, Phan T-N, Choi Y, Moon S, No JH, Lee YS. Design, Rational Repurposing, Synthesis, In Vitro Evaluation, Homology Modeling and In Silico Study of Sulfuretin Analogs as Potential Antileishmanial Hit Compounds. Pharmaceuticals. 2022;15(9):1058.
   Web of Science ®Google Scholar
• Lee J-H, Lee H-H, Ryu KD, Kim M, Ko D, Chung K-S, Hassan AHE, Lee SH, Lee JY, Lee K-T. KCP10043F Represses the Proliferation of Human Non-Small Cell Lung Cancer Cells by Caspase-Mediated Apoptosis via STAT3 Inactivation. JCM. 2020;9(3):704.
   Google Scholar
• Hong JY, Chung K-S, Shin J-S, Lee J-H, Gil H-S, Lee H-H, Choi E, Choi J-H, Hassan AHE, Lee YS, et al. The Anti-Proliferative Activity of the Hybrid TMS-TMF-4f Compound Against Human Cervical Cancer Involves Apoptosis Mediated by STAT3 Inactivation. Cancers. 2019;11(12):1927.
   PubMed Web of Science ®Google Scholar
• Hassan AHE, Mahmoud K, Phan T-N, Shaldam MA, Lee CH, Kim YJ, Cho SB, Bayoumi WA, El-Sayed SM, Choi Y, et al. Bestatin analogs-4-quinolinone hybrids as antileishmanial hits: design, repurposing rational, synthesis, in vitro and in silico studies. Eur J Med Chem. 2023;250:115211.
   PubMed Web of Science ®Google Scholar
• Hassan AHE, Phan T-N, Moon S, Lee CH, Kim YJ, Cho SB, El-Sayed SM, Choi Y, No JH, Lee YS. Design, synthesis, and repurposing of O6-aminoalkyl-sulfuretin analogs towards discovery of potential lead compounds as antileishmanial agents. Eur J Med Chem. 2023;251:115256.
   PubMed Web of Science ®Google Scholar