Development of novel salicylic acid–donepezil–rivastigmine hybrids as multifunctional agents for the treatment of 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):1577–1590.
   PubMed Web of Science ®Google Scholar
• World Alzheimer Report 2019: attitudes to dementia. Alzheimer’s Disease International; 2019. p. 1–13. https://www.alz.co.uk/research/world-report-2019.
   Google Scholar
• Cummings J, Lee G, Zhong K, Fonseca J, Taghva K. Alzheimer’s disease drug development pipeline: 2021. Alzheimers Dement. 2021;7(1):e12179.
   Web of Science ®Google Scholar
• Sang Z, Wang K, Dong J, Tang L. Alzheimer’s disease: updated multi-targets therapeutics are in clinical and in progress. Eur J Med Chem. 2022;238:114464.
   PubMed Web of Science ®Google Scholar
• Zhang P, Xu S, Zhu Z, Xu J. Multi-target design strategies for the improved treatment of Alzheimer’s disease. Eur J Med Chem. 2019;176:228–247.
   PubMed Web of Science ®Google Scholar
• de Freitas Silva M, Dias KST, Gontijo VS, Ortiz CJC, Viegas C Jr. Multi-target directed drugs as a modern approach for drug design towards Alzheimer’s disease: an update. Curr Med Chem. 2018;25(29):3491–3525.
   PubMed Web of Science ®Google Scholar
• Anand P, Singh B. A review on cholinesterase inhibitors for Alzheimer’s disease. Arch Pharm Res. 2013;36(4):375–399.
   PubMed Web of Science ®Google Scholar
• Li Q, Yang H, Chen Y, Sun H. Recent progress in the identification of selective butyrylcholinesterase inhibitors for Alzheimer’s disease. Eur J Med Chem. 2017;132:294–309.
   PubMed Web of Science ®Google Scholar
• Hardy J, Selkoe DJ. The amyloid hypothesis of Alzheimer’s disease: progress and problems on the road to therapeutics. Science. 2002;297(5580):353–356.
   PubMed Web of Science ®Google Scholar
• Cheignon C, Tomas M, Bonnefont-Rousselot D, Faller P, Hureau C, Collin F. Oxidative stress and the amyloid beta peptide in Alzheimer’s disease. Redox Biol. 2018;14:450–464.
   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
• Liu P, Wang Y, Sun Y, Peng G. Neuroinflammation as a potential therapeutic target in Alzheimer’s disease. Clin Interv Aging. 2022;17:665–674.
   PubMed Web of Science ®Google Scholar
• Blacklock CJ, Lawrence JR, Wiles D, Malcolm EA, Gibson IH, Kelly CJ, Paterson JR. Salicylic acid in the serum of subjects not taking aspirin. Comparison of salicylic acid concentrations in the serum of vegetarians, non-vegetarians, and patients taking low dose aspirin. J Clin Pathol. 2001;54(7):553–555.
   PubMed Web of Science ®Google Scholar
• Li Q, He S, Chen Y, Feng F, Qu W, Sun H. Donepezil-based multi-functional cholinesterase inhibitors for treatment of Alzheimer’s disease. Eur J Med Chem. 2018;158:463–477.
   PubMed Web of Science ®Google Scholar
• He Y, Rao Z, Liu Z, Mi J, Yang J, Zhou Y, Yin Z, Chen P, Liu W, Zeng N, et al. Design, synthesis and evaluation of salicylic acid–donepezil hybrids as functional agents for the treatment of Alzheimer’s disease. Med Chem Res. 2023;32(2):355–368.
   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
• Sang Z, Wang K, Bai P, Wu A, Shi J, Liu W, Zhu G, Wang Y, Lan Y, Chen Z, et al. Design, synthesis and biological evaluation of novel O-carbamoyl ferulamide derivatives as multi-target-directed ligands for the treatment of Alzheimer’s disease. Eur J Med Chem. 2020;194:112265.
   PubMed Web of Science ®Google Scholar
• Bajda M, Łątka K, Hebda M, Jończyk J, Malawska B. Novel carbamate derivatives as selective butyrylcholinesterase inhibitors. Bioorg Chem. 2018;78:29–38.
   PubMed Web of Science ®Google Scholar
• Yamazaki DAS, Rozada AMF, Baréa P, Reis EC, Basso EA, Sarragiotto MH, Seixas FAV, Gauze GF. Novel arylcarbamate-N-acylhydrazones derivatives as promising BuChE inhibitors: design, synthesis, molecular modeling and biological evaluation. Bioorg Med Chem. 2021;32:115991.
   PubMed Web of Science ®Google Scholar
• Sang Z, Wang K, Han X, Cao M, Tan Z, Liu W. Design, synthesis, and evaluation of novel ferulic acid derivatives as multi-target-directed ligands for the treatment of Alzheimer’s disease. ACS Chem Neurosci. 2019;10(2):1008–1024.
   PubMed Web of Science ®Google Scholar
• Sang Z, Qiang X, Li Y, Yuan W, Liu Q, Shi Y, Ang W, Luo Y, Tan Z, Deng Y. Design, synthesis and evaluation of scutellarein-O-alkylamines as multifunctional agents for the treatment of Alzheimer’s disease. Eur J Med Chem. 2015;94:348–366.
   PubMed Web of Science ®Google Scholar
• Sang Z, Wang K, Shi J, Cheng X, Zhu G, Wei R, Ma Q, Yu L, Zhao Y, Tan Z, et al. Apigenin-rivastigmine hybrids as multi-target-directed ligands for the treatment of Alzheimer’s disease. Eur J Med Chem. 2020;187:111958.
   PubMed Web of Science ®Google Scholar
• Dighe SN, Deora GS, De la Mora E, Nachon F, Chan S, Parat M-O, Brazzolotto X, Ross BP. Discovery and structure–activity relationships of a highly selective butyrylcholinesterase inhibitor by structure-based virtual screening. J Med Chem. 2016;59(16):7683–7689.
   PubMed Web of Science ®Google 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
• Tian C, Qiang X, Song Q, Cao Z, Ye C, He Y, Deng Y, Zhang L. Flurbiprofen-chalcone hybrid Mannich base derivatives as balanced multifunctional agents against Alzheimer’s disease: design, synthesis and biological evaluation. Bioorg Chem. 2020;94:103477.
   PubMed Web of Science ®Google Scholar
• Yang Z, Song Q, Cao Z, Yu G, Liu Z, Tan Z, Deng Y. Design, synthesis and evaluation of flurbiprofen–clioquinol hybrids as multitarget-directed ligands against Alzheimer’s disease. Bioorg Med Chem. 2020;28(7):115374.
   PubMed Web of Science ®Google Scholar
• Xu P, Wang H, Li Z, Yang Z. Triptolide attenuated injury via inhibiting oxidative stress in Amyloid-Beta25-35-treated differentiated PC12 cells. Life Sci. 2016;145:19–26.
   PubMed Web of Science ®Google Scholar
• Xie X, Wang HT, Li CL, Gao XH, Ding JL, Zhao HH, Lu YL. Ginsenoside Rb1 protects PC12 cells against β-amyloid-induced cell injury. Mol Med Rep. 2010;3(4):635–639.
   PubMed Web of Science ®Google Scholar
• Sang Z, Bai P, Ban Y, Wang K, Wu A, Mi J, Hu J, Xu R, Zhu G, Wang J, et al. Novel donepezil–chalcone–rivastigmine hybrids as potential multifunctional anti-Alzheimer’s agents: design, synthesis, in vitro biological evaluation, in vivo and in silico studies. Bioorg Chem. 2022;127:106007.
   PubMed Web of Science ®Google Scholar