Cytotoxicity-related effects of imidazolium and chlorinated bispyridinium oximes in SH-SY5Y cells

1Worek F, Wille T, Koller M, Thiermann H. Toxicology of organophosphorus compounds in view of an increasing terrorist threat. Arch Toxicol 2016;90:2131–45. doi: 10.1007/s00204-016-1772-1Worek F Wille T Koller M Thiermann H Toxicology of organophosphorus compounds in view of an increasing terrorist threat Arch Toxicol 2016902131 45 10.1007/s00204-016-1772-1Open DOISearch in Google Scholar

2Worek F, Thiermann H, Wille T. Oximes in organophosphate poisoning: 60 years of hope and despair. Chem Biol Interact 2016;259:93–8. doi: 10.1016/j.cbi.2016.04.032Worek F Thiermann H Wille T Oximes in organophosphate poisoning: 60 years of hope and despair Chem Biol Interact 201625993 8 10.1016/j.cbi.2016.04.032Open DOISearch in Google Scholar

3Katalinić M, Šinko G, Maček Hrvat N, Zorbaz T, Bosak A, Kovarik Z. Oxime-assisted reactivation of tabun-inhibited acetylcholinesterase analysed by active site mutations. Toxicology 2018;406–407:104–13. doi: 10.1016/j.tox.2018.05.008Katalinić M Šinko G Maček Hrvat N Zorbaz T Bosak A Kovarik Z Oxime-assisted reactivation of tabun-inhibited acetylcholinesterase analysed by active site mutations Toxicology 2018406–407104 13 10.1016/j.tox.2018.05.008Open DOISearch in Google Scholar

4Gašo-Sokač D, Katalinić M, Kovarik Z, Bušić V, Kovač S. Synthesis and evaluation of novel analogues of vitamin B6 as reactivators of tabun and paraoxon inhibited acetylcholinesterase. Chem Biol Interact 2010;187:234–7. doi: 10.1016/j.cbi.2010.02.004Gašo-Sokač D Katalinić M Kovarik Z Bušić V Kovač S Synthesis and evaluation of novel analogues of vitamin B6 as reactivators of tabun and paraoxon inhibited acetylcholinesterase Chem Biol Interact 2010187234 7 10.1016/j.cbi.2010.02.004Open DOISearch in Google Scholar

5Zorbaz T, Braïki A, Maraković N, Renou J, de la Mora E, Maček Hrvat N, Katalinić M, Silman I, Sussman JL, Mercey G, Gomez C, Mougeot R, Pérez B, Baati R, Nachon F, Weik M, Jean L, Kovarik Z, Renard PY. Potent 3-hydroxy-2-pyridine aldoxime reactivators of organophosphate-inhibited cholinesterases with predicted blood-brain barrier penetration. Chemistry 2018;24:9675–91. doi: 10.1002/chem.201801394Zorbaz T Braïki A Maraković N Renou J de la Mora E Maček Hrvat N Katalinić M Silman I Sussman JL Mercey G Gomez C Mougeot R Pérez B Baati R Nachon F Weik M Jean L Kovarik Z Renard PY Potent 3-hydroxy-2-pyridine aldoxime reactivators of organophosphate-inhibited cholinesterases with predicted blood-brain barrier penetration Chemistry 2018249675 91 10.1002/chem.201801394Open DOISearch in Google Scholar

6Zorbaz T, Malinak D, Maraković N, Maček Hrvat N, Zandona A, Novotny M, Skarka A, Andrys R, Benkova M, Soukup O, Katalinić M, Kuca K, Kovarik Z, Musilek K. Pyridinium oximes with ortho-positioned chlorine moiety exhibit improved physicochemical properties and efficient reactivation of human acetylcholinesterase inhibited by several nerve agents. J Med Chem 2018;61:10753–66. doi: 10.1021/acs.jmedchem.8b01398Zorbaz T Malinak D Maraković N Maček Hrvat N Zandona A Novotny M Skarka A Andrys R Benkova M Soukup O Katalinić M Kuca K Kovarik Z Musilek K Pyridinium oximes with ortho-positioned chlorine moiety exhibit improved physicochemical properties and efficient reactivation of human acetylcholinesterase inhibited by several nerve agents J Med Chem 20186110753 66 10.1021/acs.jmedchem.8b01398Open DOISearch in Google Scholar

7Zandona A, Katalinić M, Šinko G, Radman Kastelic A, Primožič I, Kovarik Z. Targeting organophosphorus compounds poisoning by novel quinuclidine-3 oximes: development of butyrylcholinesterase-based bioscavengers. Arch Toxicol 2020;94:3157–71. doi: 10.1007/s00204-020-02811-5Zandona A Katalinić M Šinko G Radman Kastelic A Primožič I Kovarik Z Targeting organophosphorus compounds poisoning by novel quinuclidine-3 oximes: development of butyrylcholinesterase-based bioscavengers Arch Toxicol 2020943157 71 10.1007/s00204-020-02811-5Open DOISearch in Google Scholar

8Horn G, Wille T, Musilek K, Kuca K, Thiermann H, Worek F. Reactivation kinetics of 31 structurally different bispyridinium oximes with organophosphate-inhibited human butyrylcholinesterase. Arch Toxicol 2015;89:405–14. doi: 10.1007/s00204-014-1288-5Horn G Wille T Musilek K Kuca K Thiermann H Worek F Reactivation kinetics of 31 structurally different bispyridinium oximes with organophosphate-inhibited human butyrylcholinesterase Arch Toxicol 201589405 14 10.1007/s00204-014-1288-5Open DOISearch in Google Scholar

9Gorecki L, Junova L, Kucera T, Hepnarova V, Prchal L, Kobrlova T, Muckova L, Soukup O, Korabecny J. Tacroximes: novel unique compounds for the recovery of organophosphorus-inhibited acetylcholinesterase. Future Med Chem 2019;11:2625–34. doi: 10.4155/fmc-2019-0027Gorecki L Junova L Kucera T Hepnarova V Prchal L Kobrlova T Muckova L Soukup O Korabecny J Tacroximes: novel unique compounds for the recovery of organophosphorus-inhibited acetylcholinesterase Future Med Chem 2019112625 34 10.4155/fmc-2019-0027Open DOISearch in Google Scholar

10Taylor P, Yan-Jye S, Momper J, Hou W, Camacho-Hernandez GA, Radić Z, Rosenberg Y, Kovarik Z, Sit R, Sharpless KB. Assessment of ionizable, zwitterionic oximes as reactivating antidotal agents for organophosphate exposure. Chem Biol Interact 2019;308:194–7. doi: 10.1016/j.cbi.2019.05.015Taylor P Yan-Jye S Momper J Hou W Camacho-Hernandez GA Radić Z Rosenberg Y Kovarik Z Sit R Sharpless KB Assessment of ionizable, zwitterionic oximes as reactivating antidotal agents for organophosphate exposure Chem Biol Interact 2019308194 7 10.1016/j.cbi.2019.05.015Open DOISearch in Google Scholar

11Radman Kastelic A, Odžak R, Pezdirc I, Sović K, Hrenar T, Čipak Gašparović A, Skočibušić M, Primožič I. New and potent quinuclidine-based antimicrobial agents. Molecules 2019;24(14):2675. doi: 10.3390/molecules24142675Radman Kastelic A Odžak R Pezdirc I Sović K Hrenar T Čipak Gašparović A Skočibušić M Primožič I New and potent quinuclidine-based antimicrobial agents Molecules 201924142675 10.3390/molecules24142675Open DOISearch in Google Scholar

12Skočibušić M, Odžak R, Štefanić Z, Križić I, Krišto L, Jović O, Hrenar T, Primožič I, Jurašin D. Structure-property relationship of quinuclidinium surfactants - Towards multifunctional biologically active molecules. Colloids Surfaces B Biointerfaces 2016;140:548–59. 10.1016/j.colsurfb.2015.11.023Skočibušić M Odžak R Štefanić Z Križić I Krišto L Jović O Hrenar T Primožič I Jurašin D Structure-property relationship of quinuclidinium surfactants - Towards multifunctional biologically active molecules Colloids Surfaces B Biointerfaces 2016140548 59 10.1016/j.colsurfb.2015.11.023Open DOISearch in Google Scholar

13Topcu S, Ozen T, Bal A, Tas M. Synthesis, characterization and antioxidant activities of some novel oxime derivatives. Pharm Pharmacol Int J 2021;9:176–92. doi: 10.15406/ppij.2021.09.00343Topcu S Ozen T Bal A Tas M Synthesis, characterization and antioxidant activities of some novel oxime derivatives Pharm Pharmacol Int J 20219176 92 10.15406/ppij.2021.09.00343Open DOISearch in Google Scholar

14Schepetkin IA, Plotnikov MB, Khlebnikov AI, Plotnikova TM, Quinn MT. Oximes: novel therapeutics with anticancer and anti-inflammatory potential. Biomolecules 2021;11(6):777. doi: 10.3390/biom11060777Schepetkin IA Plotnikov MB Khlebnikov AI Plotnikova TM Quinn MT Oximes: novel therapeutics with anticancer and anti-inflammatory potential Biomolecules 2021116777 10.3390/biom11060777Open DOISearch in Google Scholar

15Zandona A, Maraković N, Mišetić P, Madunić J, Miš K, Padovan J, Pirkmajer S, Katalinić M. Activation of (un)regulated cell death as a new perspective for bispyridinium and imidazolium oximes. Arch Toxicol 2021;95:2737–54. doi: 10.1007/s00204-021-03098-wZandona A Maraković N Mišetić P Madunić J Miš K Padovan J Pirkmajer S Katalinić M Activation of (un)regulated cell death as a new perspective for bispyridinium and imidazolium oximes Arch Toxicol 2021952737 54 10.1007/s00204-021-03098-wOpen DOISearch in Google Scholar

16Zorbaz T, Malinak D, Maraković N, Maček Hrvat N, Zandona A, Novotny M, Skarka A, Andrys R, Benkova M, Soukup O, Katalinić M, Kuca K, Kovarik Z, Musilek K. Pyridinium oximes with ortho-positioned chlorine moiety exhibit improved physicochemical properties and efficient reactivation of human acetylcholinesterase inhibited by several nerve agents. J Med Chem 2018;61:10753–66. doi: 10.1021/acs.jmedchem.8b01398Zorbaz T Malinak D Maraković N Maček Hrvat N Zandona A Novotny M Skarka A Andrys R Benkova M Soukup O Katalinić M Kuca K Kovarik Z Musilek K Pyridinium oximes with ortho-positioned chlorine moiety exhibit improved physicochemical properties and efficient reactivation of human acetylcholinesterase inhibited by several nerve agents J Med Chem 20186110753 66 10.1021/acs.jmedchem.8b01398Open DOISearch in Google Scholar

17Katalinić M, Maček Hrvat N, Baumann K, Morasi Piperčić S, Makarić S, Tomić S, Jović O, Hrenar T, Miličević A, Jelić D, Žunec S, Primožič I, Kovarik Z. A comprehensive evaluation of novel oximes in creation of butyrylcholinesterase-based nerve agent bioscavengers. Toxicol Appl Pharmacol 2016;310:195–204. doi: 10.1016/j.taap.2016.09.015Katalinić M Maček Hrvat N Baumann K Morasi Piperčić S Makarić S Tomić S Jović O Hrenar T Miličević A Jelić D Žunec S Primožič I Kovarik Z A comprehensive evaluation of novel oximes in creation of butyrylcholinesterase-based nerve agent bioscavengers Toxicol Appl Pharmacol 2016310195 204 10.1016/j.taap.2016.09.015Open DOISearch in Google Scholar

18Pirkmajer S, Bezjak K, Matkovič U, Dolinar K, Jiang LQ, Miš K, Gros K, Milovanova K, Pirkmajer KP, Marš T, Kapilevich L, Chibalin AV. Ouabain suppresses IL-6/STAT3 signaling and promotes cytokine secretion in cultured skeletal muscle cells. Front Physiol 2020;11:566584. doi: 10.3389/fphys.2020.566584Pirkmajer S Bezjak K Matkovič U Dolinar K Jiang LQ Miš K Gros K Milovanova K Pirkmajer KP Marš T Kapilevich L Chibalin AV Ouabain suppresses IL-6/STAT3 signaling and promotes cytokine secretion in cultured skeletal muscle cells Front Physiol 202011566584 10.3389/fphys.2020.566584Open DOISearch in Google Scholar

19Zandona A, Lihtar G, Maraković N, Miš K, Bušić V, Gašo-Sokač D, Pirkmajer S, Katalinić M. Vitamin B3-based biologically active compounds as inhibitors of human cholinesterases. Int J Mol Sci 2020;21(21):8088. doi: 10.3390/ijms21218088Zandona A Lihtar G Maraković N Miš K Bušić V Gašo-Sokač D Pirkmajer S Katalinić M Vitamin B3-based biologically active compounds as inhibitors of human cholinesterases Int J Mol Sci 202021218088 10.3390/ijms21218088Open DOISearch in Google Scholar

20Gros K, Matkovič U, Parato G, Miš K, Luin E, Bernareggi A, Sciancalepore M, Marš T, Lorenzon P, Pirkmajer S. Neuronal agrin promotes proliferation of primary human myoblasts in an age-dependent manner. Int J Mol Sci 2022;23:11784. doi: 10.3390/ijms231911784Gros K Matkovič U Parato G Miš K Luin E Bernareggi A Sciancalepore M Marš T Lorenzon P Pirkmajer S Neuronal agrin promotes proliferation of primary human myoblasts in an age-dependent manner Int J Mol Sci 20222311784 10.3390/ijms231911784Open DOISearch in Google Scholar

21Martínez M, Martínez N, Silva W. Measurement of the intracellular calcium concentration with Fura-2 AM using a fluorescence plate reader. Bio Protoc 2017;7(14):e2411. doi: 10.21769/BioProtoc.2411Martínez M Martínez N Silva W Measurement of the intracellular calcium concentration with Fura-2 AM using a fluorescence plate reader Bio Protoc 2017714e2411 10.21769/BioProtoc.2411Open DOISearch in Google Scholar

22Daina A, Michielin O, Zoete V. SwissTargetPrediction: updated data and new features for efficient prediction of protein targets of small molecules. Nucleic Acids Res 2019;47:W357–64. doi: 10.1093/nar/gkz382Daina A Michielin O Zoete V SwissTargetPrediction: updated data and new features for efficient prediction of protein targets of small molecules Nucleic Acids Res 201947W357 64 10.1093/nar/gkz382Open DOISearch in Google Scholar

23Gfeller D, Michielin O, Zoete V. Shaping the interaction landscape of bioactive molecules. Bioinformatics 2013;29:3073–9. doi: 10.1093/bioinformatics/btt540Gfeller D Michielin O Zoete V Shaping the interaction landscape of bioactive molecules Bioinformatics 2013293073 9 10.1093/bioinformatics/btt540Open DOISearch in Google Scholar

24Chaban Y, Boekema EJ, Dudkina NV. Structures of mitochondrial oxidative phosphorylation supercomplexes and mechanisms for their stabilisation. Biochim Biophys Acta 2014;1837:418–26. doi: 10.1016/j.bbabio.2013.10.004Chaban Y Boekema EJ Dudkina NV Structures of mitochondrial oxidative phosphorylation supercomplexes and mechanisms for their stabilisation Biochim Biophys Acta 20141837418 26 10.1016/j.bbabio.2013.10.004Open DOISearch in Google Scholar

25Leist M, Single B, Castoldi AF, Kühnle S, Nicotera P. Intracellular adenosine triphosphate (ATP) concentration: a switch in the decision between apoptosis and necrosis. J Exp Med 1997;185:1481–6. doi: 10.1084/jem.185.8.1481Leist M Single B Castoldi AF Kühnle S Nicotera P Intracellular adenosine triphosphate (ATP) concentration: a switch in the decision between apoptosis and necrosis J Exp Med 19971851481 6 10.1084/jem.185.8.1481Open DOISearch in Google Scholar

26Rahaman SO, Harbor PC, Chernova O, Barnett GH, Vogelbaum MA, Haque SJ. Inhibition of constitutively active Stat3 suppresses proliferation and induces apoptosis in glioblastoma multiforme cells. Oncogene 2002;21:8404–13. doi: 10.1038/sj.onc.1206047Rahaman SO Harbor PC Chernova O Barnett GH Vogelbaum MA Haque SJ Inhibition of constitutively active Stat3 suppresses proliferation and induces apoptosis in glioblastoma multiforme cells Oncogene 2002218404 13 10.1038/sj.onc.1206047Open DOISearch in Google Scholar

27Theivendren P, Kunjiappan S, Mariappa Hegde Y, Vellaichamy S, Gopal M, Rajan Dhramalingam S, Kumar S. Importance of protein kinase and its inhibitor: a review. In: Singh RK, editor. Protein kinases - promis. Targets anticancer drug research. IntechOpen Series Biochemistry. Vol 24, 2021. p. 75–100. doi: 10.5772/intechopen.98552Theivendren P Kunjiappan S Mariappa Hegde Y Vellaichamy S Gopal M Rajan Dhramalingam S Kumar S Importance of protein kinase and its inhibitor: a review. In: Singh RK, editor. Protein kinases - promis. Targets anticancer drug research IntechOpen Series Biochemistry Vol 24 2021 p 75 100 10.5772/intechopen.98552Open DOISearch in Google Scholar

28Roskoski R. ERK1/2 MAP kinases: structure, function, and regulation. Pharmacol Res 2012;66:105–43. doi: 10.1016/j.phrs.2012.04.005Roskoski R ERK1/2 MAP kinases: structure, function, and regulation Pharmacol Res 201266105 43 10.1016/j.phrs.2012.04.005Open DOISearch in Google Scholar

29John P Konhilas YL. AMP-activated protein kinase signalling in cancer and cardiac hypertrophy. Cardiovasc Pharm Open Access 2015;4(3):154. doi: 10.4172/2329-6607.1000154John P Konhilas YL AMP-activated protein kinase signalling in cancer and cardiac hypertrophy Cardiovasc Pharm Open Access 201543154 10.4172/2329-6607.1000154Open DOISearch in Google Scholar

30Soukup O, Korabecny J, Malinak D, Nepovimova E, Pham NL, Musílek K, Hrabinova M, Hepnarova V, Dolezal R, Pavek P, Kobrlova T, Jankockova J, Gorecki L, Psotka M, Thuy D, Box K, Outhwaite B, Ceckova M, Sorf A, Jun D, Kuca K. In vitro and in silico evaluation of non-quaternary reactivators of AChE as antidotes of organophosphorus poisoning - a new hope or a blind alley? Med Chem (Los Angeles) 2018;14:281–92. doi: 10.2174/1573406414666180112105657Soukup O Korabecny J Malinak D Nepovimova E Pham NL Musílek K Hrabinova M Hepnarova V Dolezal R Pavek P Kobrlova T Jankockova J Gorecki L Psotka M Thuy D Box K Outhwaite B Ceckova M Sorf A Jun D Kuca K In vitro and in silico evaluation of non-quaternary reactivators of AChE as antidotes of organophosphorus poisoning - a new hope or a blind alley? Med Chem (Los Angeles) 201814281 92 10.2174/1573406414666180112105657Open DOISearch in Google Scholar

31Bong AHL, Monteith GR. Calcium signaling and the therapeutic targeting of cancer cells. Biochim Biophys Acta Mol Cell Res 2018;1865:1786–94. doi: 10.1016/j.bbamcr.2018.05.015Bong AHL Monteith GR Calcium signaling and the therapeutic targeting of cancer cells Biochim Biophys Acta Mol Cell Res 201818651786 94 10.1016/j.bbamcr.2018.05.015Open DOISearch in Google Scholar