Novel anti-neuroinflammatory pyranone-carbamate derivatives as selective butyrylcholinesterase inhibitors for treating Alzheimer’s disease

References

• Scheltens P, De Strooper B, Kivipelto M, Holstege H, Chételat G, Teunissen CE, Cummings J, van der Flier WM. Alzheimer’s disease. Lancet. 2021;397(10284):1–16.
   PubMed Web of Science ®Google Scholar
• Meyers EA, Sexton C, Snyder HM, Carrillo MC. Impact of Alzheimer’s association support and engagement in the AD/ADRD research community through the COVID-19 pandemic and beyond. Alzheimers Dement. 2023;19(7):3222–3225.
   PubMed Web of Science ®Google Scholar
• Giacobini E, Cuello AC, Fisher A. Reimagining cholinergic therapy for Alzheimer’s disease. Brain. 2022;145(7):2250–2275.
   PubMed Web of Science ®Google Scholar
• Srivastava S, Ahmad R, Khare SK. Alzheimer’s disease and its treatment by different approaches: a review. Eur J Med Chem. 2021;216:113320.
   PubMed Web of Science ®Google Scholar
• Wang Y, Xiong B, Lin H, Li Q, Yang H, Qiao Y, Li Q, Xu Z, Lyu W, Qu W, et al. Design, synthesis and evaluation of fused hybrids with acetylcholinesterase inhibiting and Nrf2 activating functions for Alzheimer’s disease. Eur J Med Chem. 2022;244:114806.
   PubMed Web of Science ®Google Scholar
• Padhi D, Govindaraju T. Mechanistic insights for drug repurposing and the design of hybrid drugs for Alzheimer’s disease. J Med Chem. 2022;65(10):7088–7105.
   PubMed Web of Science ®Google Scholar
• Jing L, Wu G, Kang D, Zhou Z, Song Y, Liu X, Zhan P. Contemporary medicinal-chemistry strategies for the discovery of selective butyrylcholinesterase inhibitors. Drug Discov Today. 2019;24(2):629–635.
   PubMed Web of Science ®Google Scholar
• Lane CA, Hardy J, Schott JM. Alzheimer’s disease. Eur J Neurol. 2018;25(1):59–70.
   PubMed Web of Science ®Google Scholar
• Ha ZY, Mathew S, Yeong KY. Butyrylcholinesterase: A multifaceted pharmacological target and tool. Curr Protein Pept Sci. 2020;21(1):99–109.
   PubMed Web of Science ®Google Scholar
• Xing S, Li Q, Xiong B, Chen Y, Feng F, Liu W, Sun H. Structure and therapeutic uses of butyrylcholinesterase: application in detoxification, Alzheimer’s disease, and fat metabolism. Med Res Rev. 2021;41(2):858–901.
   PubMed Web of Science ®Google Scholar
• Košak U, Brus B, Knez D, Šink R, Žakelj S, Trontelj J, Pišlar A, Šlenc J, Gobec M, Živin M, et al. Development of an in-vivo active reversible butyrylcholinesterase inhibitor. Sci Rep. 2016;6(1):39495.
   PubMedGoogle Scholar
• Košak U, Brus B, Knez D, Žakelj S, Trontelj J, Pišlar A, Šink R, Jukič M, Živin M, Podkowa A, et al. The magic of crystal structure-based inhibitor optimization: Development of a butyrylcholinesterase inhibitor with picomolar affinity and in vivo activity. J Med Chem. 2018;61(1):119–139.
   PubMed Web of Science ®Google Scholar
• Panek D, Pasieka A, Latacz G, Zaręba P, Szczęch M, Godyń J, Chantegreil F, Nachon F, Brazzolotto X, Skrzypczak-Wiercioch A, et al. Discovery of new, highly potent and selective inhibitors of BuChE - design, synthesis, in vitro and in vivo evaluation and crystallography studies. Eur J Med Chem. 2023;249:115135.
   PubMed Web of Science ®Google Scholar
• Pereira CF, Santos AE, Moreira PI, Pereira AC, Sousa FJ, Cardoso SM, Cruz MT. Is Alzheimer’s disease an inflammasomopathy? Ageing Res Rev. 2019;56:100966.
   PubMed Web of Science ®Google Scholar
• Wang C, Zong S, Cui X, Wang X, Wu S, Wang L, Liu Y, Lu Z. The effects of microglia-associated neuroinflammation on Alzheimer’s disease. Front Immunol. 2023;14:1117172.
   PubMed Web of Science ®Google Scholar
• Ozben T, Ozben S. Neuro-inflammation and anti-inflammatory treatment options for Alzheimer’s disease. Clin Biochem. 2019;72:87–89.
   PubMed Web of Science ®Google Scholar
• Twarowski B, Herbet M. Inflammatory processes in Alzheimer’s disease – pathomechanism, diagnosis and treatment: A review. Int J Mol Sci. 2023;24(7):6518.
   PubMed Web of Science ®Google Scholar
• Kumari S, Dhapola R, Sharma P, Singh SK, Reddy DH. Implicative role of cytokines in neuroinflammation mediated AD and associated signaling pathways: Current progress in molecular signaling and therapeutics. Ageing Res Rev. 2023;92:102098.
   Web of Science ®Google Scholar
• Choi S-B, Kwon S, Kim J-H, Ahn N-H, Lee J-H, Yang S-H. The molecular mechanisms of neuroinflammation in Alzheimer’s disease, the consequence of neural cell death. Int J Mol Sci. 2023;24(14):11757.
   PubMed Web of Science ®Google Scholar
• Savelieff MG, Nam G, Kang J, Lee HJ, Lee M, Lim MH. Development of multifunctional molecules as potential therapeutic candidates for Alzheimer’s disease, Parkinson’s disease, and amyotrophic lateral sclerosis in the last decade. Chem Rev. 2019;119(2):1221–1322.
   PubMed Web of Science ®Google Scholar
• Chen H, Mi J, Li S, Liu Z, Yang J, Chen R, Wang Y, Ban Y, Zhou Y, Dong W, et al. Design, synthesis and evaluation of quinoline-O-carbamate derivatives as multifunctional agents for the treatment of Alzheimer’s disease. J Enzyme Inhib Med Chem. 2023;38(1):2169682.
   PubMedGoogle Scholar
• Zaręba P, Łątka K, Mazur G, Gryzło B, Pasieka A, Godyń J, Panek D, Skrzypczak-Wiercioch A, Höfner GC, Latacz G, et al. Discovery of novel multifunctional ligands targeting GABA transporters, butyrylcholinesterase, β-secretase, and amyloid β aggregation as potential treatment of Alzheimer’s disease. Eur J Med Chem. 2023;261:115832.
   PubMed Web of Science ®Google Scholar
• He M, Fan M, Peng Z, Wang G. An overview of hydroxypyranone and hydroxypyridinone as privileged scaffolds for novel drug discovery. Eur J Med Chem. 2021;221:113546.
   PubMed Web of Science ®Google Scholar
• Liu X, Yu C, Yao Y, Lai H, Ye X, Xu J, Guo J, Xiao X, Lin C, Huang Z, et al. Novel neuroprotective pyromeconic acid derivatives with concurrent anti-Aβ deposition, anti-inflammatory, and anti-oxidation properties for treatment of Alzheimer’s disease. Eur J Med Chem. 2023;248:115120.
   PubMed Web of Science ®Google Scholar
• Ghosh AK, Brindisi M. Organic carbamates in drug design and medicinal chemistry. J Med Chem. 2015;58(7):2895–2940.
   PubMed Web of Science ®Google Scholar
• Zhang H, Wang Y, Wang Y, Li X, Wang S, Wang Z. Recent advance on carbamate-based cholinesterase inhibitors as potential multifunctional agents against Alzheimer’s disease. Eur J Med Chem. 2022;240:114606.
   PubMed Web of Science ®Google Scholar
• Bar-On P, Millard CB, Harel M, Dvir H, Enz A, Sussman JL, Silman I. Kinetic and structural studies on the interaction of cholinesterases with the anti-Alzheimer drug rivastigmine. Biochemistry. 2002;41(11):3555–3564.
   PubMed Web of Science ®Google Scholar
• Ellman GL, Courtney KD, Andres V, Feather-Stone RM. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol. 1961;7(2):88–95.
   PubMed Web of Science ®Google Scholar
• Ruan BF, Ge WW, Cheng HJ, Xu HJ, Li QS, Liu XH. Resveratrol-based cinnamic ester hybrids: Synthesis, characterization, and anti-inflammatory activity. J Enzyme Inhib Med Chem. 2017;32(1):1282–1290.
   PubMed Web of Science ®Google Scholar
• Fu WY, Wang X, Ip NY. Targeting neuroinflammation as a therapeutic strategy for Alzheimer’s disease: mechanisms, drug candidates, and new opportunities. ACS Chem Neurosci. 2019;10(2):872–879.
   PubMed Web of Science ®Google Scholar
• Kulkarni B, Cruz-Martins N, Kumar D. Microglia in Alzheimer’s disease: An unprecedented opportunity as prospective drug target. Mol Neurobiol. 2022;59(5):2678–2693.
   PubMed Web of Science ®Google Scholar
• Morris GM, Huey R, Lindstrom W, Sanner MF, Belew RK, Goodsell DS, Olson AJ. Autodock4 and autodocktools4: automated docking with selective receptor flexibility. J Comput Chem. 2009;30(16):2785–2791.
   PubMed Web of Science ®Google Scholar
• Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev. 1997;23(1-3):3–25.
   Web of Science ®Google Scholar
• Xiong B, Wang Y, Chen Y, Xing S, Liao Q, Chen Y, Li Q, Li W, Sun H. Strategies for structural modification of small molecules to improve blood-brain barrier penetration: a recent perspective. J Med Chem. 2021;64(18):13152–13173.
   PubMed Web of Science ®Google Scholar
• Di L, Kerns EH, Fan K, McConnell OJ, Carter GT. High throughput artificial membrane permeability assay for blood–brain barrier. Eur J Med Chem. 2003;38(3):223–232.
   PubMed Web of Science ®Google Scholar
• Guo J, Zhang Y, Zhang C, Yao C, Zhang J, Jiang X, Zhong Z, Ge J, Zhou T, Bai R, et al. N-propargylamine-hydroxypyridinone hybrids as multitarget agents for the treatment of Alzheimer’s disease. Bioorg Chem. 2021;113:105013.
   PubMed Web of Science ®Google Scholar
• Lazarova M, Tancheva L, Alexandrova A, Tsvetanova E, Georgieva A, Stefanova M, Tsekova D, Vezenkov L, Kalfin R, Uzunova D, et al. Effects of new galantamine derivatives in a scopolamine model of dementia in mice. J Alzheimers Dis. 2021;84(2):671–690.
   PubMed Web of Science ®Google Scholar
• Du C, Wang L, Guan Q, Yang H, Chen T, Liu Y, Li Q, Lyu W, Lu X, Chen Y, et al. N-benzyl benzamide derivatives as selective sub-nanomolar butyrylcholinesterase inhibitors for possible treatment in advanced Alzheimer’s disease. J Med Chem. 2022;65(16):11365–11387.
   PubMed Web of Science ®Google Scholar
• Tang KS. The cellular and molecular processes associated with scopolamine-induced memory deficit: a model of Alzheimer’s biomarkers. Life Sci. 2019;233:116695.
   PubMed Web of Science ®Google Scholar
• Liu X, Yu C, Su B, Zha D. Synthesis and properties of the Kojic acid dimer and its potential for the treatment of Alzheimer’s disease. RSC Med Chem. 2023;14(2):268–276.
   PubMedGoogle Scholar
• Cornish-Bowden A. A simple graphical method for determining the inhibition constants of mixed, uncompetitive and non-competitive inhibitors. Biochem J. 1974;137(1):143–144.
   PubMed Web of Science ®Google Scholar
• Nicolet Y, Lockridge O, Masson P, Fontecilla-Camps JC, Nachon F. Crystal structure of human butyrylcholinesterase and of its complexes with substrate and products. J Biol Chem. 2003;278(42):41141–41147.
   PubMed Web of Science ®Google Scholar
• Cheung J, Rudolph MJ, Burshteyn F, Cassidy MS, Gary EN, Love J, Franklin MC, Height JJ. Structures of human acetylcholinesterase in complex with pharmacologically important ligands. J Med Chem. 2012;55(22):10282–10286.
   PubMed Web of Science ®Google Scholar