Mechanistic efficacy assessment of selected novel methanimine derivatives against vincristine induced Neuropathy: In-vivo, Ex-vivo and In-silico correlates

Starobova, 2017, Pathophysiology of chemotherapy-induced peripheral neuropathy, Front. Mol. Neurosci., 10, 174, 10.3389/fnmol.2017.00174 Seretny, 2014, Incidence, prevalence, and predictors of chemotherapy-induced peripheral neuropathy: a systematic review and meta-analysis, Pain®, 155, 2461, 10.1016/j.pain.2014.09.020 Dorsey, 2019, The national cancer institute clinical trials planning meeting for prevention and treatment of chemotherapy-induced peripheral neuropathy, J. Natl. Cancer. Inst., 111, 531, 10.1093/jnci/djz011 Cuozzo, 2021, Effects of chronic oral probiotic treatment in paclitaxel-induced neuropathic pain, Biomedicines, 9, 346, 10.3390/biomedicines9040346 Geisler, 2016, Prevention of vincristine-induced peripheral neuropathy by genetic deletion of SARM1 in mice, Brain, 139, 3092, 10.1093/brain/aww251 Park, 2010, Antinociceptive effect of memantine and morphine on vincristine-induced peripheral neuropathy in rats, Korean. J. Pain., 23, 179, 10.3344/kjp.2010.23.3.179 Higuera, 2004, 91 Diouf, 2019, Pharmacogenomics of vincristine-induced peripheral neuropathy: progress continues, Clin. Pharm. Therap., 105, 315, 10.1002/cpt.1209 Sisignano, 2014, Mechanism-based treatment for chemotherapy-induced peripheral neuropathic pain, Nat. Rev. Neurol., 10, 694, 10.1038/nrneurol.2014.211 Tanner, 1998, Microtubule disorientation and axonal swelling in unmyelinated sensory axons during vincristine-induced painful neuropathy in rat, J. Comp. Neurol., 395, 481, 10.1002/(SICI)1096-9861(19980615)395:4<481::AID-CNE5>3.0.CO;2-Y Yan, 2017, Research progress of mechanisms and drug therapy for neuropathic pain, Life Sci., 190, 68, 10.1016/j.lfs.2017.09.033 Tanner, 1998, Nociceptor hyper-responsiveness during vincristine-induced painful peripheral neuropathy in the rat, J. Neurosci., 18, 6480, 10.1523/JNEUROSCI.18-16-06480.1998 Gautam, 2019, Saponins of Tribulus terrestris attenuated neuropathic pain induced with vincristine through central and peripheral mechanism, Inflammopharmacology, 27, 761, 10.1007/s10787-018-0502-0 Kiguchi, 2008, Up-regulation of tumor necrosis factor-alpha in spinal cord contributes to vincristine-induced mechanical allodynia in mice, Neurosci. Lett., 445, 140, 10.1016/j.neulet.2008.09.009 Khalilzadeh, 2020, Aripiprazole prevents from development of vincristine-induced neuropathic nociception by limiting neural NOS overexpression and NF-kB hyperactivation, Cancer. Chemother. Pharmacol., 86, 393, 10.1007/s00280-020-04127-8 Zhou, 2018, Levo-corydalmine alleviates vincristine-induced neuropathic pain in mice by inhibiting an NF-kappa B-dependent CXCL1/CXCR2 signaling pathway, Neuropharmacology, 135, 34, 10.1016/j.neuropharm.2018.03.004 Khan, 2022, Ameliorative effect of two structurally divergent hydrazide derivatives against DSS-induced colitis by targeting Nrf2 and NF-κB signaling in mice, Naunyn Schmiedebergs Arch. Pharmacol., 1–22 Nasir, 2022, Datura stramonium Leaf Extract Exhibits Anti-inflammatory Activity in CCL4-induced hepatic injury model by modulating oxidative stress markers and iNOS/Nrf2 expression, Biomed Res. Int., 2022, 10.1155/2022/1382878 Khan, 2022 Sana, 2021, Topical delivery of curcumin-loaded transfersomes gel ameliorated rheumatoid arthritis by inhibiting NF-kappabeta pathway, Nanomedicine (Lond), 16, 819, 10.2217/nnm-2020-0316 Chen, 2020, Mitoquinone alleviates vincristine-induced neuropathic pain through inhibiting oxidative stress and apoptosis via the improvement of mitochondrial dysfunction, Biomed. Pharmacother., 125, 10.1016/j.biopha.2020.110003 Singh, 2019, Bergapten ameliorates vincristine-induced peripheral neuropathy by inhibition of inflammatory cytokines and NFκB Signaling, ACS Chem. Neurosci., 10, 3008, 10.1021/acschemneuro.9b00206 Dworkin, 2010, Recommendations for the pharmacological management of neuropathic pain: an overview and literature update, Mayo Clinic Proceedings, Elsevier, S3, 10.4065/mcp.2009.0649 Kajal, 2013, Schiff bases: a versatile pharmacophore, J. Catal., 10.1155/2013/893512 Vashi, 2004, Synthesis of novel Schiff base and azetidinone derivatives and their antibacterial activity, Eur. J. Chem., 1, 272 Goleij, 2021, Induction of anxiolytic, antidepressant and analgesic effects by Shiff base of (E)-3-(1H-imidazol-4-yl)-2-((2-oxoindolin-3-ylidene) amino) propanoic acid derivatives in diabetic rats, J. Diabetes Metab. Disord., 20, 31, 10.1007/s40200-020-00689-9 Bano, 2017, Aminoquinoline Schiff Bases as Non-Acidic, Non-Steroidal, Anti-Inflammatory Agents, Chem. Select, 2, 10050 Chioua, 2019, New quinolylnitrones for stroke therapy: Antioxidant and neuroprotective (Z)-N-tert-Butyl-1-(2-chloro-6-methoxyquinolin-3-yl) methanimine oxide as a new lead-compound for ischemic stroke treatment, J. Med. Chem., 62, 2184, 10.1021/acs.jmedchem.8b01987 Nilkanth, 2020, Synthesis and evaluation of anticonvulsant activity of some schiff bases of 7-Amino-1, 3-dihydro-2H-1, 4-benzodiazepin-2-one, Chem. Biodivers., 17, 10.1002/cbdv.202000342 Sadia, 2021, Schiff base ligand L synthesis and its evaluation as anticancer and antidepressant agent, J. King Saud Univ. Sci., 33, 10.1016/j.jksus.2020.101331 Boulguemh, 2020, Monomeric and dimeric copper (II) complexes based on bidentate Nʹ-(propan-2-ylidene) thiophene carbohydrazide Schiff base ligand: Synthesis, structure, magnetic properties, antioxidant and anti-Alzheimer activities, Inorganica Chim. Acta., 507, 10.1016/j.ica.2020.119519 Kamga, 2021, Synthesis, Characterization and Biological Activities of Binuclear Metal Complexes of 2-Benzoylpyridine and Phenyl (Pyridin-2-yl) Methanediol Derived from 1-Phenyl-1-(Pyridin-2-yl)-N-(Pyrimidin-2-yl) Methanimine Dihydrate Schiff Base, Open J. Inorg. Chem., 11, 20, 10.4236/ojic.2021.111002 Khan, 2021, Mechanistic evaluation of a novel cyclohexenone derivative’s functionality against nociception and inflammation: An in-vitro, in-vivo and in-silico approach, Eur. J. Pharmacol, 902, 10.1016/j.ejphar.2021.174091 Akbar, 2016, 6-Methoxyflavanone attenuates mechanical allodynia and vulvodynia in the streptozotocin-induced diabetic neuropathic pain, Biomed. Pharmacother, 84, 962, 10.1016/j.biopha.2016.10.017 Weng, 2003, Changes in sensory processing in the spinal dorsal horn accompany vincristine-induced hyperalgesia and allodynia, PAIN®, 103, 131, 10.1016/S0304-3959(02)00445-1 Ullah, 2022, The 7-Hydroxyflavone attenuates chemotherapy-induced neuropathic pain by targeting inflammatory pathway, Int. Immunopharmacol., 107, 10.1016/j.intimp.2022.108674 Khan, 2019, Attenuation of vincristine-induced neuropathy by synthetic cyclohexenone-functionalized derivative in mice model, Neurol. Sci., 40, 1799, 10.1007/s10072-019-03884-6 Thibault, 2008, Antinociceptive and anti-allodynic effects of oral PL37, a complete inhibitor of enkephalin-catabolizing enzymes, in a rat model of peripheral neuropathic pain induced by vincristine, Eur. J. Pharmacol., 600, 71, 10.1016/j.ejphar.2008.10.004 Yoon, 1994, Behavioral signs of ongoing pain and cold allodynia in a rat model of neuropathic pain, Pain, 59, 369, 10.1016/0304-3959(94)90023-X Necker, 1977, Noxious thermal input from the rat tail: modulation by descending inhibitory influences, Pain, 4, 231, 10.1016/0304-3959(77)90135-X Ginski, 1994, Sensitive and rapid behavioral differentiation of N-methyl-D-aspartate receptor antagonists, Psychopharmacology, 114, 573, 10.1007/BF02244987 Nouri, 2012, Antinociceptive effect of Matricaria chamomilla on vincristine-induced peripheral neuropathy in mice, Afr. J. Pharmacy. Pharmacol., 6, 24, 10.5897/AJPP11.340 Sajid, 2016, Proficiencies of Artemisia scoparia against CCl4 induced DNA damages and renal toxicity in rat, BMC. Complement. Altern. Med., 16, 1, 10.1186/s12906-016-1137-6 Habig, 1974, Glutathione S-transferases: the first enzymatic step in mercapturic acid formation, J. Biol. Chem., 249, 7130, 10.1016/S0021-9258(19)42083-8 Khan, 2021, Suppression of TRPV1/TRPM8/P2Y nociceptors by withametelin via downregulating MAPK signaling in mouse model of vincristine-induced neuropathic pain, Int. J. Mol. Sci., 22, 6084, 10.3390/ijms22116084 Khan, 2020, The newly synthesized compounds (NCHDH and NTHDH) attenuates LPS-induced septicemia and multi-organ failure via Nrf2/HO1 and HSP/TRVP1 signaling in mice, Chem. Biol. Interact., 329, 10.1016/j.cbi.2020.109220 Ali, 2021, Cadmium, an environmental contaminant exacerbates alzheimer’s pathology in the Aged Mice’s Brain, Front. Aging. Neurosci., 13, 237, 10.3389/fnagi.2021.650930 Khan, 2013, Molecular mechanism of capillarisin-mediated inhibition of MyD88/TIRAP inflammatory signaling in in vitro and in vivo experimental models, J. Ethnopharmacol., 145, 626, 10.1016/j.jep.2012.12.001 de Oliveira, 2011, Antinociceptive properties of bergenin, J. Nat. Prod., 74, 2062, 10.1021/np200232s Khan, 2021, Inhibition of NF-κB signaling and HSP70/HSP90 proteins by newly synthesized hydrazide derivatives in arthritis model, Naunyn Schmiedebergs Arch. Pharmacol., 394, 1497, 10.1007/s00210-021-02075-5 Lee, 2015, Silibinin suppresses astroglial activation in a mouse model of acute Parkinson׳ s disease by modulating the ERK and JNK signaling pathways, Brain. Res., 1627, 233, 10.1016/j.brainres.2015.09.029 Shah, 2014, Novel osmotin attenuates glutamate-induced synaptic dysfunction and neurodegeneration via the JNK/PI3K/Akt pathway in postnatal rat brain, Cell Death. Dis., 5, e1026, 10.1038/cddis.2013.538 Sussman, 1998, Protein Data Bank (PDB): database of three-dimensional structural information of biological macromolecules, Acta. Crystallogr. D. Biol. Crystallogr., 54, 1078, 10.1107/S0907444998009378 Pettersen, 2004, UCSF Chimera—a visualization system for exploratory research and analysis, J. Comput. Chem., 25, 1605, 10.1002/jcc.20084 Maier, 2015, ff14SB: improving the accuracy of protein side chain and backbone parameters from ff99SB, J. Chem. Theory Comput., 11, 3696, 10.1021/acs.jctc.5b00255 Cousins, 2011, Computer review of ChemDraw ultra 12.0, ACS Publications Trott, 2010, AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading, J. Comput. Chem., 31, 455, 10.1002/jcc.21334 Abro, 2016, Binding free energy based analysis of arsenic (+ 3 oxidation state) methyltransferase with S-adenosylmethionine, J. Mol. Liq., 220, 375, 10.1016/j.molliq.2016.04.109 Wang, 2004, Development and testing of a general amber force field, J. Comput. Chem., 25, 1157, 10.1002/jcc.20035 Case, 2014, The FF14SB force field, Amber, 14, 29 Kräutler, 2001, A fast SHAKE algorithm to solve distance constraint equations for small molecules in molecular dynamics simulations, J. Comput. Chem., 22, 501, 10.1002/1096-987X(20010415)22:5<501::AID-JCC1021>3.0.CO;2-V Izaguirre, 2001, Langevin stabilization of molecular dynamics, J. Chem. Phys., 114, 2090, 10.1063/1.1332996 Roe, 2013, PTRAJ and CPPTRAJ: software for processing and analysis of molecular dynamics trajectory data, J. Chem. Theory. Comput., 9, 3084, 10.1021/ct400341p Genheden, 2015, The MM/PBSA and MM/GBSA methods to estimate ligand-binding affinities, Expert. Opin. Drug. Discov., 10, 449, 10.1517/17460441.2015.1032936 Miller, 2012, py: an efficient program for end-state free energy calculations, J. Chem. Theory Comput., 8, 3314, 10.1021/ct300418h Pignataro, 2010, Chemotherapy induced peripheral neuropathy: risk factors, pathophysiology, assessment, and potential physical therapy interventions, Rehabil. Oncol., 28, 10, 10.1097/01893697-201028020-00002 D, Tiwari, M, Tiwari, Vincristine: Beyond on anticancer treatment, Int. J. Pharmacognosy. Life Sci. Jaggi, 2012, Mechanisms in cancer-chemotherapeutic drugs-induced peripheral neuropathy, Toxicology, 291, 1, 10.1016/j.tox.2011.10.019 Shim, 2019, Peripheral and central oxidative stress in chemotherapy-induced neuropathic pain, Mol. Pain., 15, 10.1177/1744806919840098 Siau, 2006, Dysregulation of cellular calcium homeostasis in chemotherapy-evoked painful peripheral neuropathy, Anesth. Analg., 102, 1485, 10.1213/01.ane.0000204318.35194.ed Bhalla, 2015, Dose-related neuropathic and anti-neuropathic effects of simvastatin in vincristine-induced neuropathic pain in rats, Food. Chem. Toxicol., 80, 32, 10.1016/j.fct.2015.02.016 Xiao, 2008, Chemotherapy-evoked neuropathic pain: Abnormal spontaneous discharge in A-fiber and C-fiber primary afferent neurons and its suppression by acetyl-L-carnitine, Pain, 135, 262, 10.1016/j.pain.2007.06.001 Geis, 2011, Lacosamide has protective disease modifying properties in experimental vincristine neuropathy, Neuropharmacology, 61, 600, 10.1016/j.neuropharm.2011.05.001 Mika, 2013, Importance of glial activation in neuropathic pain, Eur. J. Pharmacol., 716, 106, 10.1016/j.ejphar.2013.01.072 Ji, 2013, Spinal astrocytic activation contributes to mechanical allodynia in a rat chemotherapy-induced neuropathic pain model, PloS one, 8, 10.1371/journal.pone.0060733 Pop-Busui, 2006, Diabetic neuropathy and oxidative stress, Diabetes Metab. Res. Rev., 22, 257, 10.1002/dmrr.625 Murtaza, 2017, Synthesis and biological evaluation of schiff bases of 4-aminophenazone as an anti-inflammatory, analgesic and antipyretic agent, J. Saudi Chem. Soc., 21, S359, 10.1016/j.jscs.2014.04.003 Fareed, 2017, Schiff bases derived from 1-aminoanthraquinone: a new class of analgesic compounds, Pak. J. Sci. Ind. Res. A: Phys. Sci., 60, 122, 10.52763/PJSIR.PHYS.SCI.60.3.2017.122.127 Lopes, 2009, Antinociceptive effect of topiramate in models of acute pain and diabetic neuropathy in rodents, Life Sci., 84, 105, 10.1016/j.lfs.2008.11.005 Shibata, 1989, Modified formalin test: characteristic biphasic pain response, Pain, 38, 347, 10.1016/0304-3959(89)90222-4 Le Bars, 2001, Animal models of nociception, Pharmacol. Rev., 53, 597 Zhang, 2020, Suppressing BRD4 exhibits protective effects against vincristine-induced peripheral neuropathy by alleviating inflammation and oxidative stress, Biochem. Biophys. Res. Comm., 532, 271, 10.1016/j.bbrc.2020.06.142 Srivastava, 2019, Design and development of some phenyl benzoxazole derivatives as a potent acetylcholinesterase inhibitor with antioxidant property to enhance learning and memory, Eur. J. Med. Chem., 163, 116, 10.1016/j.ejmech.2018.11.049 Mermer, 2019, Synthesis of novel Schiff bases using green chemistry techniques; antimicrobial, antioxidant, antiurease activity screening and molecular docking studies, J. Mol. Struct., 1181, 412, 10.1016/j.molstruc.2018.12.114 Raweh, 2013, Antioxidant properties of phenolic Schiff bases: structure–activity relationship and mechanism of action, J. Comput. Aided Mol. Des., 27, 951, 10.1007/s10822-013-9692-0