Novel harmine derivatives as potent acetylcholinesterase and amyloid beta aggregation dual inhibitors for management of Alzheimer’s disease

References

• Goedert M, Spillantini MG. A century of Alzheimer’s disease. Science. 2006;314(5800):777–781.
   PubMed Web of Science ®Google Scholar
• Mendiola–Precoma J, Berumen LC, Padilla K, Garcia–Alcocer G. Therapies for prevention and treatment of Alzheimer’s disease. Biomed Res Int. 2016; 2016:2589276.
   PubMed Web of Science ®Google Scholar
• Alzheimer’s Disease International. World Alzheimer Report. 2016. https://www.alz.co.uk/research/WorldAlzheimerReport2016.pdf.
   Google Scholar
• Tan CC, Yu JT, Wang HF, Tan MS, Meng XF, Wang C, Jiang T, Zhu XC, Tan L. Efficacy and safety of donepezil, galantamine, rivastigmine, and memantine for the treatment of Alzheimer’s disease: a systematic review and meta–analysis. J Alzheimers Dis. 2014;41(2):615–631.
   PubMed Web of Science ®Google Scholar
• Dal–Re R. Approval of aducanumab for Alzheimer’s disease in the United States: the surrender of science. Rev Neurologia. 2021; 73(8):296–297.
   PubMed Web of Science ®Google Scholar
• Larkin HDD. Lecanemab gains FDA approval for early Alzheimer disease. Jama–J Am Med Associ. 2023;329(5):363.
   Web of Science ®Google Scholar
• Zissimopoulos J, Jacobson M, Chen Y, Borson S. Knowledge and attitudes concerning aducanumab among older americans after FDA approval for treatment of Alzheimer disease. JAMA Netw Open. 2022;5(2):e2148355.
   PubMed Web of Science ®Google Scholar
• Lythgoe MP, Jenei K, Prasad V. Regulatory decisions diverge over aducanumab for Alzheimer’s disease. BMJ. 2022; 376(8326):e069780.
   PubMedGoogle Scholar
• Bartus RT, Dean RL, Beer B, Lippa AS. The cholinergic hypothesis of geriatric memory dysfunction. Science. 1982;217(4558):408–414.
   PubMed Web of Science ®Google Scholar
• Selkoe DJ. Alzheimer’s disease: Genes, proteins, and therapy. Physiol Rev. 2001;81(2):741–766.
   PubMed Web of Science ®Google Scholar
• Querfurth HW, LaFerla FM. MECHANISMS OF DISEASE Alzheimer’s Disease. N Engl J Med. 2010;362(4):329–344. Review.
   PubMed Web of Science ®Google Scholar
• Nasb M, Tao W, Chen N. Alzheimer’s disease puzzle: delving into pathogenesis hypotheses. Aging Dis. 2023;15(1):0608. doi:10.14336/AD.2023.0608.
   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
• Ramesh M, Govindaraju T. Multipronged diagnostic and therapeutic strategies for Alzheimer’s disease. Chem Sci. 2022;13(46):13657–13689.
   PubMed 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
• Nakamura A, Kaneko N, Villemagne VL, Kato T, Doecke J, Doré V, Fowler C, Li Q-X, Martins R, Rowe C, et al. High performance plasma amyloid–beta biomarkers for Alzheimer’s disease. Nature. 2018;554(7691):249–254.
   PubMed Web of Science ®Google Scholar
• John A, Reddy PH. Synaptic basis of Alzheimer’s disease: Focus on synaptic amyloid beta, P–tau and mitochondria. Ageing Res Rev. 2021;65:101208.
   PubMed Web of Science ®Google Scholar
• Jeremic D, Jimenez–Diaz L, Navarro–Lopez JD. Past, present and future of therapeutic strategies against amyloid–beta peptides in Alzheimer’s disease: a systematic review. Ageing Res Rev. 2021;72:101496. doi:10.1016/j.arr.2021.101496.
   PubMed Web of Science ®Google Scholar
• Zhang Y, Chen H, Li R, Sterling K, Song W. Amyloid beta–based therapy for Alzheimer’s disease: challenges, successes and future. Sig Transduct Target Ther. 2023;8(1):248–248.
   PubMed Web of Science ®Google Scholar
• Marucci G, Buccioni M, Dal Ben D, Lambertucci C, Volpini R, Amenta F. Efficacy of acetylcholinesterase inhibitors in Alzheimer’s disease. Neuropharmacology. 2021;190:108352.
   PubMed Web of Science ®Google Scholar
• Tonelli M, Catto M, Sabaté R, Francesconi V, Laurini E, Pricl S, Pisani L, Miniero DV, Liuzzi GM, Gatta E, et al. Thioxanthenone–based derivatives as multitarget therapeutic leads for Alzheimer’s disease. Eur J Med Chem. 2023;250:115169.
   PubMed Web of Science ®Google Scholar
• Ahmed S, Khan ST, Zargaham MK, Khan AU, Khan S, Hussain A, Uddin J, Khan A, Al –, Harrasi A. Potential therapeutic natural products against Alzheimer’s disease with reference of acetylcholinesterase. Biomed Pharmacother. 2021;139:111609. doi:10.1016/j.biopha.2021.111609.
   PubMed Web of Science ®Google Scholar
• Patel K, Gadewar M, Tripathi R, Prasad SK, Patel DK. A review on medicinal importance, pharmacological activity and bioanalytical aspects of beta–carboline alkaloid ''Harmine. Asian Pac J Trop Biomed. 2012;2(8):660–664.
   PubMedGoogle Scholar
• Zhang L, Li D, Yu S. Pharmacological effects of harmine and its derivatives: a review. Arch Pharm Res. 2020;43(12):1259–1275.
   PubMed Web of Science ®Google Scholar
• Brito–da–Costa AM, Dias–da–Silva D, Gomes NGM, Dinis–Oliveira RJ, Madureira–Carvalho A. Toxicokinetics and toxicodynamics of ayahuasca alkaloids N,N–dimethyltryptamine (DMT), harmine, harmaline and tetrahydroharmine: Clinical and forensic impact. Pharmaceuticals. 2020;13(11):334.
   Web of Science ®Google Scholar
• Javeed M, Rasul A, Hussain G, Jabeen F, Rasool B, Shafiq N, Riaz A, Kaukab G, Ali M. Harmine and its derivatives: Biological activities and therapeutic potential in human diseases. Bangladesh J Pharmacol. 2018;13(3):203–213.
   Web of Science ®Google Scholar
• Beato A, Gori A, Boucherle B, Peuchmaur M, Haudecoeur R. Beta–carboline as a privileged scaffold for multitarget strategies in Alzheimer’s disease therapy. J Med Chem. 2021;64(3):1392–1422.
   PubMed Web of Science ®Google Scholar
• Mennenga SE, Gerson JE, Dunckley T, Bimonte–Nelson HA. Harmine treatment enhances short–term memory in old rats: Dissociation of cognition and the ability to perform the procedural requirements of maze testing. Physiol Behav. 2015;138:260–265.
   PubMed Web of Science ®Google Scholar
• He D, Wu H, Wei Y, Liu W, Huang F, Shi H, Zhang B, Wu X, Wang C. Effects of harmine, an acetylcholinesterase inhibitor, on spatial learning and memory of APP/PS1 transgenic mice and scopolamine–induced memory impairment mice. Eur J Pharmacol. 2015;768:96–107.
   PubMed Web of Science ®Google Scholar
• Li S-P, Wang Y-W, Qi S-L, Zhang Y-P, Deng G, Ding W-Z, Ma C, Lin Q-Y, Guan H-D, Liu W, et al. Analogous beta–carboline alkaloids harmaline and harmine ameliorate scopolamine–induced cognition dysfunction by attenuating acetylcholinesterase activity, oxidative stress, and inflammation in mice. Front Pharmacol. 2018;9:346.
   PubMed Web of Science ®Google Scholar
• Iraji A, Firuzi O, Khoshneviszadeh M, Tavakkoli M, Mahdavi M, Nadri H, Edraki N, Miri R. Multifunctional iminochromene–2H–carboxamide derivatives containing different aminomethylene triazole with BACE1 inhibitory, neuroprotective and metal chelating properties targeting Alzheimer’s disease. Eur J Med Chem. 2017;141:690–702.
   PubMed Web of Science ®Google Scholar
• Zhao YF, Ye F, Xu J, Liao QH, Chen L, Zhang WJ, Sun HP, Liu WY, Feng F, Qu W. Design, synthesis and evaluation of novel bivalent β -carboline derivatives as multifunctional agents for the treatment of Alzheimer’s disease. Bioorg Med Chem. 2018;26(13):3812–3824.
   PubMed Web of Science ®Google Scholar
• Lamie PF, Abdel-Fattah MM, Philoppes JN. Design and synthesis of new indole drug candidates to treat Alzheimer’s disease and targeting neuro-inflammation using a multi-target-directed ligand (MTDL) strategy. J Enzyme Inhib Med Chem. 2022;37(1):2660–2678.
   PubMed Web of Science ®Google Scholar
• Xiong GL, Wu ZX, Yi JC, Fu L, Yang ZJ, Hsieh CY, Yin MZ, Zeng XX, Wu CK, Chen X, et al. ADMETlab 2.0: an integrated online platform for accurate and comprehensive predictions of ADMET properties. Nucleic Acids Res. 2021;49(W1):W5–W14.
   PubMed Web of Science ®Google Scholar
• Banerjee P, Eckert OA, Schrey AK, Preissner R. ProTox-II: a webserver for the prediction of toxicity of chemicals. Nucleic Acids Res. 2018;46(W1):W257–W263.
   PubMed Web of Science ®Google Scholar
• Liu Y, Uras G, Onuwaje I, Li W, Yao H, Xu S, Li X, Li X, Phillips J, Allen S, et al. Novel inhibitors of AChE and Aβ aggregation with neuroprotective properties as lead compounds for the treatment of Alzheimer’s disease. Eur J Med Chem. 2022;235:114305.
   PubMed Web of Science ®Google Scholar
• Vaaland IC, López Ó, Puerta A, Fernandes MX, Padrón JM, Fernández-Bolaños JG, Sydnes MO, Lindbäck E. Investigation of the enantioselectivity of acetylcholinesterase and butyrylcholinesterase upon inhibition by tacrine-iminosugar heterodimers. J Enzyme Inhib Med Chem. 2023;38(1):349–360.
   PubMed Web of Science ®Google Scholar