Benzimidazole Derivatives as New Potential NLRP3 Inflammasome Inhibitors That Provide Neuroprotection in a Rodent Model of Neurodegeneration and Memory Impairment

References

• Heemels M-T. Neurodegenerative diseases. Nature. 2016;539(7628):179–180. doi:10.1038/539179a
   PubMed Web of Science ®Google Scholar
• Jinawath N, Bunbanjerdsuk S, Chayanupatkul M, et al. Bridging the gap between clinicians and systems biologists: from network biology to translational biomedical research. J Transl Med. 2016;14(1):1–13. doi:10.1186/s12967-016-1078-3
   PubMed Web of Science ®Google Scholar
• Mott M, Koroshetz W. Bridging the gap in neurotherapeutic discovery and development: the role of the National Institute of Neurological Disorders and Stroke in translational neuroscience. Neurotherapeutics. 2015;12(3):651–654. doi:10.1007/s13311-015-0366-6
   PubMed Web of Science ®Google Scholar
• Keri RS, Hiremathad A, Budagumpi S, et al. Comprehensive review in current developments of benzimidazole‐based medicinal chemistry. Chem Biol Drug Des. 2015;86(1):19–65. doi:10.1111/cbdd.12462
   PubMed Web of Science ®Google Scholar
• El-Feky SA, Abd El-Samii ZK, Osman NA, et al. Synthesis, molecular docking and anti-inflammatory screening of novel quinoline incorporated pyrazole derivatives using the Pfitzinger reaction II. Bioorg Chem. 2015;58:104–116. doi:10.1016/j.bioorg.2014.12.003
   PubMed Web of Science ®Google Scholar
• Evans CW, Atkins C, Pathak A, et al. Benzimidazole analogs inhibit respiratory syncytial virus G protein function. Antiviral Res. 2015;121:31–38. doi:10.1016/j.antiviral.2015.06.016
   PubMed Web of Science ®Google Scholar
• Hranjec M, Pavlović G, Karminski-Zamola G. Synthesis, crystal structure determination and antiproliferative activity of novel 2-amino-4-aryl-4, 10-dihydro [1, 3, 5] triazino [1, 2-a] benzimidazoles. J Mol Struct. 2012;1007:242–251. doi:10.1016/j.molstruc.2011.10.054
   Web of Science ®Google Scholar
• Anastassova N, Yancheva D, Hristova-Avakumova N, et al. New benzimidazole-aldehyde hybrids as neuroprotectors with hypochlorite and superoxide radical-scavenging activity. Pharmacol Rep. 2020;72(4):846–856. doi:10.1007/s43440-020-00077-3
   PubMed Web of Science ®Google Scholar
• Anastassova N, Argirova M, Yancheva D, et al. In vitro assessment of the neuroprotective and antioxidant properties of new benzimidazole derivatives as potential drug candidates for the treatment of Parkinson’s disease. Multidisciplin Digit Publ Instit Proc. 2019;22(1):54.
   Google Scholar
• Anastassova N, Aluani D, Kostadinov A, et al. Evaluation of the combined activity of benzimidazole arylhydrazones as new anti-Parkinsonian agents: monoamine oxidase-B inhibition, neuroprotection and oxidative stress modulation. Neural Regener Res. 2021;16(11):2299. doi:10.4103/1673-5374.309843
   PubMed Web of Science ®Google Scholar
• Gurjar AS, Solanki VS, Meshram AR, et al. Exploring beta amyloid cleavage enzyme‐1 inhibition and neuroprotective role of benzimidazole analogues as anti‐Alzheimer agents. J Chin Chem Soc. 2020;67(5):864–873. doi:10.1002/jccs.201900200
   Web of Science ®Google Scholar
• Gao C, Li B, Zhang B, et al. Synthesis and biological evaluation of benzimidazole acridine derivatives as potential DNA-binding and apoptosis-inducing agents. Bioorg Med Chem. 2015;23(8):1800–1807. doi:10.1016/j.bmc.2015.02.036
   PubMed Web of Science ®Google Scholar
• Imran M, Al Kury LT, Nadeem H, et al. Benzimidazole containing acetamide derivatives attenuate neuroinflammation and oxidative stress in ethanol-induced neurodegeneration. Biomolecules. 2020;10(1):108. doi:10.3390/biom10010108
   PubMed Web of Science ®Google Scholar
• Gulcan HO, Mavideniz A, Sahin MF, et al. Benzimidazole-derived compounds designed for different targets of Alzheimer’s disease. Curr Med Chem. 2019;26(18):3260–3278. doi:10.2174/0929867326666190124123208
   PubMed Web of Science ®Google Scholar
• Becaria A, Bondy SC, Campbell A. Aluminum and copper interact in the promotion of oxidative but not inflammatory events: implications for Alzheimer’s disease. J Alzheimers Dis. 2003;5(1):31–38. doi:10.3233/JAD-2003-5105
   PubMed Web of Science ®Google Scholar
• Qiao Y, Wang P, Qi J, et al. TLR-induced NF-κB activation regulates NLRP3 expression in murine macrophages. FEBS Lett. 2012;586(7):1022–1026. doi:10.1016/j.febslet.2012.02.045
   PubMed Web of Science ®Google Scholar
• Muñoz-Planillo R, Kuffa P, Martínez-Colón G, et al. K+ efflux is the common trigger of NLRP3 inflammasome activation by bacterial toxins and particulate matter. Immunity. 2013;38(6):1142–1153. doi:10.1016/j.immuni.2013.05.016
   PubMed Web of Science ®Google Scholar
• Jiang H, Yan Y, Jiang W, et al. NLRP3 inflammasome: activation, regulation, and role in diseases. SCIENTIA SINICA Vitae. 2017;47(1):125. doi:10.1360/N052016-00360
   Google Scholar
• Franchi L, Eigenbrod T, Muñoz-Planillo R, et al. The inflammasome: a caspase-1-activation platform that regulates immune responses and disease pathogenesis. Nat Immunol. 2009;10(3):241–247. doi:10.1038/ni.1703
   PubMed Web of Science ®Google Scholar
• Gong Z, Pan J, Shen Q, et al. Mitochondrial dysfunction induces NLRP3 inflammasome activation during cerebral ischemia/reperfusion injury. J Neuroinflammation. 2018;15(1):242. doi:10.1186/s12974-018-1282-6
   PubMed Web of Science ®Google Scholar
• Toma C, Higa N, Koizumi Y, et al. Pathogenic vibrio activate NLRP3 inflammasome via cytotoxins and TLR/nucleotide-binding oligomerization domain-mediated NF-κB signaling. J Immunol. 2010;184(9):5287–5297. doi:10.4049/jimmunol.0903536
   PubMed Web of Science ®Google Scholar
• Alaqeel SI. Synthetic approaches to benzimidazoles from o-phenylenediamine: a literature review. J Saudi Chem Soc. 2017;21(2):229–237. doi:10.1016/j.jscs.2016.08.001
   Web of Science ®Google Scholar
• Keerthi DS. Chlorosulfonation of acetanilide to obtain an intermediate for the preparation of a sulfa drug. Asian J Pharma. 2017;11(01). doi:10.22377/ajp.v11i01.1099
   Google Scholar
• Hay LA, Koenig TM, Ginah FO, et al. Palladium-catalyzed hydroarylation of propiolamides. A regio-and stereocontrolled method for preparing 3, 3-diarylacrylamides. J Org Chem. 1998;63(15):5050–5058. doi:10.1021/jo980235h
   Web of Science ®Google Scholar
• Bowers KJ, Chow DE, Xu H, et al. Scalable algorithms for molecular dynamics simulations on commodity clusters. In: SC’06: Proceedings of the 2006 ACM/IEEE Conference on Supercomputing. IEEE; 2006.
   Google Scholar
• Shah FA, Rashid S, Rashid S. Conformational ensembles of non-peptide ω-conotoxin mimetics and Ca+ 2 ion binding to human voltage-gated N-type calcium channel Cav2. 2. Comput Struct Biotechnol J. 2020;18:2357–2372. doi:10.1016/j.csbj.2020.08.027
   PubMed Web of Science ®Google Scholar
• Al Kury LT, Zeb A, Abidin ZU, et al. Neuroprotective effects of melatonin and celecoxib against ethanol-induced neurodegeneration: a computational and pharmacological approach. Drug Des Devel Ther. 2019;13:2715. doi:10.2147/DDDT.S207310
   PubMed Web of Science ®Google Scholar
• Iqbal S, Shah FA, Naeem K, et al. Succinamide derivatives ameliorate neuroinflammation and oxidative stress in scopolamine-induced neurodegeneration. Biomolecules. 2020;10(3):443. doi:10.3390/biom10030443
   PubMed Web of Science ®Google Scholar
• Khan A, Shal B, Naveed M, et al. Matrine ameliorates anxiety and depression-like behaviour by targeting hyperammonemia-induced neuroinflammation and oxidative stress in CCl4 model of liver injury. Neurotoxicology. 2019;72:38–50. doi:10.1016/j.neuro.2019.02.002
   PubMed Web of Science ®Google Scholar
• Kumar KS, Hsieh HW, Wang S-Y. Anti-inflammatory effect of lucidone in mice via inhibition of NF-κB/MAP kinase pathway. Int Immunopharmacol. 2010;10(4):385–392. doi:10.1016/j.intimp.2009.12.013
   PubMed Web of Science ®Google Scholar
• Firdous A, Sarwar S, Shah FA, et al. Contribution of attenuation of TNF-α and NF-κB in the anti-epileptic, anti-apoptotic and neuroprotective potential of Rosa webbiana fruit and its chitosan encapsulation. Molecules. 2021;26(8):2347. doi:10.3390/molecules26082347
   PubMed Web of Science ®Google Scholar
• Ullah U, Badshah H, Malik Z, et al. Hepatoprotective effects of melatonin and celecoxib against ethanol-induced hepatotoxicity in rats. Immunopharmacol Immunotoxicol. 2020;42(3):255–263. doi:10.1080/08923973.2020.1746802
   PubMed Web of Science ®Google Scholar
• Al Kury LT, Dayyan F, Ali Shah F, et al. Ginkgo biloba extract protects against methotrexate-induced hepatotoxicity: a computational and pharmacological approach. Molecules. 2020;25(11):2540. doi:10.3390/molecules25112540
   PubMed Web of Science ®Google Scholar
• Shah FA, Zeb A, Ali T, et al. Identification of proteins differentially expressed in the striatum by melatonin in a middle cerebral artery occlusion rat model—a proteomic and in silico approach. Front Neurosci. 2018;12:888. doi:10.3389/fnins.2018.00888
   PubMed Web of Science ®Google Scholar
• Akhtar W, Khan MF, Verma G, et al. Therapeutic evolution of benzimidazole derivatives in the last quinquennial period. Eur J Med Chem. 2017;126:705–753. doi:10.1016/j.ejmech.2016.12.010
   PubMed Web of Science ®Google Scholar
• Tahlan S, Kumar S, Ramasamy K, et al. Design, synthesis and biological profile of heterocyclic benzimidazole analogues as prospective antimicrobial and antiproliferative agents. BMC Chem. 2019;13(1):1–15.
   PubMed Web of Science ®Google Scholar
• Harada R, Okamura N, Furumoto S, et al. Use of a benzimidazole derivative BF-188 in fluorescence multispectral imaging for selective visualization of tau protein fibrils in the Alzheimer’s disease brain. Mol Imaging Biol. 2014;16(1):19–27. doi:10.1007/s11307-013-0667-2
   PubMed Web of Science ®Google Scholar
• Ortiz-Guerrero G, Amador-Muñoz D, Calderón-Ospina CA, et al. Proton pump inhibitors and dementia: physiopathological mechanisms and clinical consequences. Neural Plast. 2018;2018:1–9. doi:10.1155/2018/5257285
   Web of Science ®Google Scholar
• Brown SA, Tapert SF, Granholm E, et al. Neurocognitive functioning of adolescents: effects of protracted alcohol use. Alcohol Clin Exp Res. 2000;24(2):164–171. doi:10.1111/j.1530-0277.2000.tb04586.x
   PubMed Web of Science ®Google Scholar
• Ridley NJ, Draper B, Withall A. Alcohol-related dementia: an update of the evidence. Alzheimers Res Ther. 2013;5(1):3. doi:10.1186/alzrt157
   PubMed Web of Science ®Google Scholar
• Pfefferbaum A, Sullivan EV, Mathalon DH, et al. Frontal lobe volume loss observed with magnetic resonance imaging in older chronic alcoholics. Alcohol Clin Exp Res. 1997;21(3):521–529. doi:10.1111/j.1530-0277.1997.tb03798.x
   PubMed Web of Science ®Google Scholar
• Harper C. The neuropathology of alcohol-specific brain damage, or does alcohol damage the brain? J Neuropathol Exp Neurol. 1998;57(2):101–110. doi:10.1097/00005072-199802000-00001
   PubMed Web of Science ®Google Scholar
• White CS, Lawrence CB, Brough D, et al. Inflammasomes as therapeutic targets for A lzheimer’s disease. Brain Pathol. 2017;27(2):223–234. doi:10.1111/bpa.12478
   PubMed Web of Science ®Google Scholar
• Carugo O. How root-mean-square distance (rmsd) values depend on the resolution of protein structures that are compared. J Appl Crystallogr. 2003;36(1):125–128. doi:10.1107/S0021889802020502
   Web of Science ®Google Scholar
• Qin L, Crews FT. NADPH oxidase and reactive oxygen species contribute to alcohol-induced microglial activation and neurodegeneration. J Neuroinflammation. 2012;9(1):1–19. doi:10.1186/1742-2094-9-5
   PubMed Web of Science ®Google Scholar
• Yin J, Valin KL, Dixon ML, Leavenworth JW. The role of microglia and macrophages in CNS homeostasis, autoimmunity, and cancer. J Immunol Res. 2017;2017:5150678.
   PubMed Web of Science ®Google Scholar
• Rao J, Rapoport S, Kim H. Altered neuroinflammatory, arachidonic acid cascade and synaptic markers in postmortem Alzheimer’s disease brain. Transl Psychiatry. 2011;1(8):e31–e31. doi:10.1038/tp.2011.27
   PubMed Web of Science ®Google Scholar
• Dean B, Tawadros N, Scarr E, et al. Regionally-specific changes in levels of tumour necrosis factor in the dorsolateral prefrontal cortex obtained postmortem from subjects with major depressive disorder. J Affect Disord. 2010;120(1–3):245–248. doi:10.1016/j.jad.2009.04.027
   PubMed Web of Science ®Google Scholar
• Maes M, Stevens WJ, Declerck LS, et al. Significantly increased expression of T-cell activation markers (interleukin-2 and HLA-DR) in depression: further evidence for an inflammatory process during that illness. Prog Neuropsychopharmacol Biol Psychiatry. 1993;17(2):241–255. doi:10.1016/0278-5846(93)90045-T
   PubMed Web of Science ®Google Scholar
• Freitas R. Investigation of oxidative stress involvement in hippocampus in epilepsy model induced by pilocarpine. Neurosci Lett. 2009;462(3):225–229. doi:10.1016/j.neulet.2009.07.037
   PubMed Web of Science ®Google Scholar
• Pascual M, Blanco AM, Cauli O, et al. Intermittent ethanol exposure induces inflammatory brain damage and causes long‐term behavioural alterations in adolescent rats. Eur J Neurosci. 2007;25(2):541–550. doi:10.1111/j.1460-9568.2006.05298.x
   PubMed Web of Science ®Google Scholar
• Halle A, Hornung V, Petzold GC, et al. The NALP3 inflammasome is involved in the innate immune response to amyloid-β. Nat Immunol. 2008;9(8):857–865. doi:10.1038/ni.1636
   PubMed Web of Science ®Google Scholar
• Lee H-M, Kim -J-J, Kim HJ, et al. Upregulated NLRP3 inflammasome activation in patients with type 2 diabetes. Diabetes. 2013;62(1):194–204. doi:10.2337/db12-0420
   PubMed Web of Science ®Google Scholar
• Mittal M, Siddiqui MR, Tran K, et al. Reactive oxygen species in inflammation and tissue injury. Antioxid Redox Signal. 2014;20(7):1126–1167. doi:10.1089/ars.2012.5149
   PubMed Web of Science ®Google Scholar
• Bortolato B, Carvalho A, Soczynska J, et al. The involvement of TNF-α in cognitive dysfunction associated with major depressive disorder: an opportunity for domain specific treatments. Curr Neuropharmacol. 2015;13(5):558–576. doi:10.2174/1570159X13666150630171433
   PubMed Web of Science ®Google Scholar
• Ting JP-Y, Lovering RC, Alnemri ES, et al. The NLR gene family: a standard nomenclature. Immunity. 2008;28(3):285–287. doi:10.1016/j.immuni.2008.02.005
   PubMed Web of Science ®Google Scholar
• Martinon F, Burns K, Tschopp J. The inflammasome: a molecular platform triggering activation of inflammatory caspases and processing of proIL-β. Mol Cell. 2002;10(2):417–426. doi:10.1016/S1097-2765(02)00599-3
   PubMed Web of Science ®Google Scholar
• Fann DY-W, Lee S-Y, Manzanero S, et al. Intravenous immunoglobulin suppresses NLRP1 and NLRP3 inflammasome-mediated neuronal death in ischemic stroke. Cell Death Dis. 2013;4(9):e790–e790. doi:10.1038/cddis.2013.326
   PubMed Web of Science ®Google Scholar
• Hernández JA, López-Sánchez RC, Rendón-Ramírez A. Lipids and oxidative stress associated with ethanol-induced neurological damage. Oxid Med Cell Longev. 2016;2016:1–15. doi:10.1155/2016/1543809
   Web of Science ®Google Scholar
• Tanner CM. Is the cause of Parkinson’s disease environmental or hereditary? Evidence from twin studies. Adv Neurol. 2003;91:133–142.
   PubMed Web of Science ®Google Scholar
• DeLegge M, Smoke A. Neurodegeneration and Inflammation. Nutr Clin Pract. 2008;23:35–41. doi:10.1177/011542650802300135
   PubMed Web of Science ®Google Scholar
• Dembo G, Park SB, Kharasch ED. Central nervous system concentrations of cyclooxygenase-2 inhibitors in humans. Anesthesiology. 2005;102(2):409–415. doi:10.1097/00000542-200502000-00026
   PubMed Web of Science ®Google Scholar
• McCoy MK, Tansey MG. TNF signaling inhibition in the CNS: implications for normal brain function and neurodegenerative disease. J Neuroinflammation. 2008;5(1):1–13. doi:10.1186/1742-2094-5-45
   PubMed Web of Science ®Google Scholar