{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,4]],"date-time":"2025-10-04T01:28:46Z","timestamp":1759541326988},"reference-count":30,"publisher":"Springer Science and Business Media LLC","issue":"3","license":[{"start":{"date-parts":[[2015,3,6]],"date-time":"2015-03-06T00:00:00Z","timestamp":1425600000000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/www.springer.com\/tdm"}],"content-domain":{"domain":["link.springer.com"],"crossmark-restriction":false},"short-container-title":["Arch Toxicol"],"published-print":{"date-parts":[[2016,3]]},"DOI":"10.1007\/s00204-015-1481-1","type":"journal-article","created":{"date-parts":[[2015,3,5]],"date-time":"2015-03-05T10:03:27Z","timestamp":1425549807000},"page":"603-616","update-policy":"http:\/\/dx.doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Resolving pathways of interaction of mipafox and a sarin analog with human acetylcholinesterase by kinetics, mass spectrometry and molecular modeling approaches"],"prefix":"10.1007","volume":"90","author":[{"given":"I.","family":"Mangas","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"P.","family":"Taylor","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"E.","family":"Vilanova","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"J.","family":"Est\u00e9vez","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"T. C. C.","family":"Fran\u00e7a","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"E.","family":"Komives","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Z.","family":"Radi\u0107","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"297","published-online":{"date-parts":[[2015,3,6]]},"reference":[{"issue":"1\u20133","key":"1481_CR1","doi-asserted-by":"crossref","first-page":"187","DOI":"10.1016\/j.tox.2006.09.020","volume":"233","author":"G Amitai","year":"2007","unstructured":"Amitai G, Adani R, Yacov G, Yishay S, Teitlboim S, Tveria L, Limanovich O, Kushnir M, Meshulam H (2007) Asymmetric fluorogenic organophosphates for the development of active organophosphate hydrolases with reversed stereoselectivity. Toxicology 233(1\u20133):187\u2013198","journal-title":"Toxicology"},{"key":"1481_CR3","doi-asserted-by":"crossref","first-page":"404","DOI":"10.1002\/(SICI)1096-987X(199803)19:4<404::AID-JCC3>3.0.CO;2-W","volume":"19","author":"V Barone","year":"1998","unstructured":"Barone V, Cossi M, Tomasi J (1998) Geometry optimization of molecular structures in solution by the polarizable continuum model. J Comp Chem 19:404\u2013417","journal-title":"J Comp Chem"},{"issue":"10","key":"1481_CR4","doi-asserted-by":"crossref","first-page":"4002","DOI":"10.1021\/jm901853b","volume":"53","author":"E Carletti","year":"2010","unstructured":"Carletti E, Colletier JP, Dupeux F, Trovaslet M, Masson P, Nachon F (2010) Structural evidence that human acetylcholinesterase inhibited by tabun ages through O-dealkylation. J Med Chem 53(10):4002\u20134008","journal-title":"J Med Chem"},{"issue":"34","key":"1481_CR5","doi-asserted-by":"crossref","first-page":"29718","DOI":"10.1074\/jbc.M111.264739","volume":"286","author":"R Cochran","year":"2011","unstructured":"Cochran R, Kalisiak J, K\u00fc\u00e7\u00fckkilin\u00e7 T, Radic Z, Garcia E, Zhang L, Ho KY, Amitai G, Kovarik Z, Fokin VV, Sharpless KB, Taylor P (2011) Oxime-assisted acetylcholinesterase catalytic scavengers of organophosphates that resist aging. J Biol Chem 286(34):29718\u201329724","journal-title":"J Biol Chem"},{"issue":"2","key":"1481_CR6","doi-asserted-by":"crossref","first-page":"73","DOI":"10.1006\/taap.2001.9279","volume":"176","author":"JA Doorn","year":"2001","unstructured":"Doorn JA, Schall M, Gage DA, Talley TT, Thompson CM, Richardson RJ (2001) Identification of butyrylcholinesterase adducts after inhibition with isomalathion using mass spectrometry: difference in mechanism between (1R)- and(1S)-stereoisomers. Toxicol Appl Pharmacol 176(2):73\u201380","journal-title":"Toxicol Appl Pharmacol"},{"key":"1481_CR7","doi-asserted-by":"crossref","first-page":"88","DOI":"10.1016\/0006-2952(61)90145-9","volume":"7","author":"GL Ellman","year":"1961","unstructured":"Ellman GL, Courtney KD, Andres V Jr, Feather-Stone RM (1961) A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 7:88\u201395","journal-title":"Biochem Pharmacol"},{"key":"1481_CR8","unstructured":"Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill P. MW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2004) Gaussian 03, Revision C.02. Gaussian, Inc., Wallingford, CT"},{"key":"1481_CR9","doi-asserted-by":"crossref","first-page":"2154","DOI":"10.1063\/1.456010","volume":"90","author":"C Gonzalez","year":"1989","unstructured":"Gonzalez C, Schlegel CB (1989) An improved algorithm for reaction path following. J Chem Phys 90:2154\u20132159","journal-title":"J Chem Phys"},{"issue":"2","key":"1481_CR10","doi-asserted-by":"crossref","first-page":"149","DOI":"10.1016\/j.taap.2009.07.020","volume":"240","author":"H Grigoryan","year":"2009","unstructured":"Grigoryan H, Schopfer LM, Peeples ES, Duysen EG, Grigoryan M, Thompson CM, Lockridge O (2009) Mass spectrometry identifies multiple organophosphorylated sites on tubulin. Toxicol Appl Pharmacol 240(2):149\u2013158","journal-title":"Toxicol Appl Pharmacol"},{"issue":"3747","key":"1481_CR11","doi-asserted-by":"crossref","first-page":"404","DOI":"10.1126\/science.154.3747.404","volume":"154","author":"LW Harris","year":"1966","unstructured":"Harris LW, Fleisher JH, Clark J, Cliff WJ (1966) Dealkylation and loss of capacity for reactivation of cholinesterase inhibited by sarin. Science 154(3747):404\u2013407","journal-title":"Science"},{"key":"1481_CR12","volume-title":"PC spartan pro","author":"WJ Hehre","year":"1999","unstructured":"Hehre WJ, Deppmeier BJ, Klunzinger PE (1999) PC spartan pro. Wavefunction Inc., Irvine"},{"key":"1481_CR13","unstructured":"Hobbiger F (1963) Cholinesterases and anticholinesterase agents. In: Koelle GB (ed) Handbuch der Experimentellen Pharmakologie, Erganzungswerk, vol 15. Springer, Berlin, pp 799\u2013832"},{"issue":"37","key":"1481_CR14","doi-asserted-by":"crossref","first-page":"11083","DOI":"10.1021\/bi034756x","volume":"42","author":"LL Jennings","year":"2003","unstructured":"Jennings LL, Malecki M, Komives EA, Taylor P (2003) Direct analysis of the kinetic profiles of organophosphate-acetylcholinesterase adducts by MALDI-TOF mass spectrometry. Biochemistry 42(37):11083\u201311091","journal-title":"Biochemistry"},{"key":"1481_CR15","doi-asserted-by":"crossref","first-page":"334","DOI":"10.1021\/tx050342o","volume":"19","author":"TJ Kropp","year":"2006","unstructured":"Kropp TJ, Richardson RJ (2006) Aging of mipafox-inhibited human acetylcholinesterase proceeds by displacement of both isopropylamine groups to yield a phosphate adduct. Chem Res Toxicol. 19:334\u2013339","journal-title":"Chem Res Toxicol."},{"issue":"3","key":"1481_CR16","doi-asserted-by":"crossref","first-page":"504","DOI":"10.1021\/tx600310y","volume":"20","author":"TJ Kropp","year":"2007","unstructured":"Kropp TJ, Richardson RJ (2007) Mechanism of aging of mipafox-inhibited butyrylcholinesterase. Chem Res Toxicol 20(3):504\u2013510","journal-title":"Chem Res Toxicol"},{"issue":"12","key":"1481_CR17","doi-asserted-by":"crossref","first-page":"3716","DOI":"10.1021\/bi049960e","volume":"43","author":"TJ Kropp","year":"2004","unstructured":"Kropp TJ, Glynn P, Richardson RJ (2004) The mipafox-inhibited catalytic domain of human neuropathy target esterase ages by reversible proton loss. Biochemistry 43(12):3716\u20133722","journal-title":"Biochemistry"},{"issue":"Pt 1","key":"1481_CR18","doi-asserted-by":"crossref","first-page":"53","DOI":"10.1042\/bj3250053","volume":"325","author":"P Masson","year":"1997","unstructured":"Masson P, Froment MT, Bartels CF, Lockridge O (1997) Importance of aspartate-70 in organophosphate inhibition, oxime re-activation and aging of human butyrylcholinesterase. Biochem J 325(Pt 1):53\u201361","journal-title":"Biochem J"},{"issue":"1\u20133","key":"1481_CR19","doi-asserted-by":"crossref","first-page":"157","DOI":"10.1016\/j.cbi.2010.03.027","volume":"187","author":"P Masson","year":"2010","unstructured":"Masson P, Nachon F, Lockridge O (2010) Structural approach to the aging of phosphylated cholinesterases. Chem Biol Interact 187(1\u20133):157\u2013162","journal-title":"Chem Biol Interact"},{"issue":"1\u20133","key":"1481_CR20","doi-asserted-by":"crossref","first-page":"425","DOI":"10.1016\/0009-2797(93)90070-F","volume":"87","author":"D Milatovic","year":"1993","unstructured":"Milatovic D, Johnson MK (1993) Reactivation of phosphorodiamidated acetylcholinesterase and neuropathy target esterase by treatment of inhibited enzyme with potassium fluoride. Chem Biol Interact 87(1\u20133):425\u2013430","journal-title":"Chem Biol Interact"},{"issue":"22","key":"1481_CR21","doi-asserted-by":"crossref","first-page":"7032","DOI":"10.1021\/bi982678l","volume":"38","author":"CB Millard","year":"1999","unstructured":"Millard CB, Kryger G, Ordentlich A, Greenblatt HM, Harel M, Raves ML, Segall Y, Barak D, Shafferman A, Silman I, Sussman JL (1999) Crystal structures of aged phosphonylated acetylcholinesterase: nerve agent reaction products at the atomic level. Biochemistry 38(22):7032\u20137039","journal-title":"Biochemistry"},{"issue":"15","key":"1481_CR22","doi-asserted-by":"crossref","first-page":"11798","DOI":"10.1074\/jbc.M111.333732","volume":"287","author":"Z Radi\u0107","year":"2012","unstructured":"Radi\u0107 Z, Sit RK, Kovarik Z, Berend S, Garcia E, Zhang L, Amitai G, Green C, Radi\u0107 B, Fokin VV, Sharpless KB, Taylor P (2012) Refinement of structural leads for centrally acting oxime reactivators of phosphylated cholinesterases. J Biol Chem 287(15):11798\u201311809","journal-title":"J Biol Chem"},{"issue":"1","key":"1481_CR23","doi-asserted-by":"crossref","first-page":"67","DOI":"10.1016\/j.cbi.2012.08.014","volume":"203","author":"Z Radi\u0107","year":"2013","unstructured":"Radi\u0107 Z, Sit RK, Garcia E, Zhang L, Berend S, Kovarik Z, Amitai G, Fokin VV, Sharpless BK, Taylor P (2013) Mechanism of interaction of novel uncharged, centrally active reactivators with OP-hAChE conjugates. Chem Biol Interact 203(1):67\u201371","journal-title":"Chem Biol Interact"},{"key":"1481_CR24","doi-asserted-by":"crossref","first-page":"0543191","DOI":"10.1063\/1.1996577","volume":"123","author":"TC Ramalho","year":"2005","unstructured":"Ramalho TC, Taft CA (2005) Thermal and solvent effects on the NMR and UV parameters of some bioreductive drugs. J Chem Phys 123:0543191\u20130543197","journal-title":"J Chem Phys"},{"key":"1481_CR25","doi-asserted-by":"crossref","first-page":"37","DOI":"10.1142\/S0219633608003575","volume":"7","author":"TC Ramalho","year":"2008","unstructured":"Ramalho TC, da Cunha EFF, Figueroa-Villar JD, Peixoto FC (2008) Computational NMR investigation of Radiosensitizer in solution. J Theor Comput Chem 7:37\u201352","journal-title":"J Theor Comput Chem"},{"issue":"13","key":"1481_CR26","doi-asserted-by":"crossref","first-page":"3590","DOI":"10.1021\/ac0497104","volume":"76","author":"MJ Schroeder","year":"2004","unstructured":"Schroeder MJ, Shabanowitz J, Schwartz JC, Hunt DF, Coon JJ (2004) A neutral loss activation method for improved phosphopeptide sequence analysis by quadrupole ion trap mass spectrometry. Anal Chem 76(13):3590\u20133598","journal-title":"Anal Chem"},{"issue":"49","key":"1481_CR27","doi-asserted-by":"crossref","first-page":"13441","DOI":"10.1021\/bi00212a009","volume":"32","author":"Y Segall","year":"1993","unstructured":"Segall Y, Waysbort D, Barak D, Ariel N, Doctor BP, Grunwald J, Ashani Y (1993) Direct observation and elucidation of the structures of aged and nonaged phosphorylated cholinesterases by 31P NMR spectroscopy. Biochemistry 32(49):13441\u201313450","journal-title":"Biochemistry"},{"issue":"22","key":"1481_CR28","doi-asserted-by":"crossref","first-page":"19422","DOI":"10.1074\/jbc.M111.230656","volume":"286","author":"RK Sit","year":"2011","unstructured":"Sit RK, Radi\u0107 Z, Gerardi V, Zhang L, Garcia E, Katalini\u0107 M, Amitai G, Kovarik Z, Fokin VV, Sharpless KB, Taylor P (2011) New structural scaffolds for centrally acting oxime reactivators of phosphylated cholinesterases. J Biol Chem 286(22):19422\u201319430","journal-title":"J Biol Chem"},{"issue":"4","key":"1481_CR29","doi-asserted-by":"crossref","first-page":"1378","DOI":"10.1021\/jm401650z","volume":"57","author":"RK Sit","year":"2014","unstructured":"Sit RK, Fokin VV, Amitai G, Sharpless KB, Taylor P, Radi\u0107 Z (2014) Imidazole aldoximes effective in assisting butyrylcholinesterase catalysis of organophosphate detoxification. J Med Chem 57(4):1378\u20131389","journal-title":"J Med Chem"},{"issue":"3","key":"1481_CR30","doi-asserted-by":"crossref","first-page":"271","DOI":"10.1080\/15287399409531921","volume":"43","author":"LG Sultatos","year":"1994","unstructured":"Sultatos LG (1994) Mammalian toxicology of organophosphorus pesticides. J Toxicol Environ Health 43(3):271\u2013289","journal-title":"J Toxicol Environ Health"},{"key":"1481_CR32","doi-asserted-by":"crossref","first-page":"281","DOI":"10.1146\/annurev.pa.34.040194.001433","volume":"34","author":"P Taylor","year":"1994","unstructured":"Taylor P, Radi\u0107 Z (1994) The cholinesterases: from genes to proteins. Annu Rev Pharmacol Toxicol 34:281\u2013320","journal-title":"Annu Rev Pharmacol Toxicol"}],"container-title":["Archives of Toxicology"],"original-title":[],"language":"en","link":[{"URL":"http:\/\/link.springer.com\/content\/pdf\/10.1007\/s00204-015-1481-1.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"http:\/\/link.springer.com\/article\/10.1007\/s00204-015-1481-1\/fulltext.html","content-type":"text\/html","content-version":"vor","intended-application":"text-mining"},{"URL":"http:\/\/link.springer.com\/content\/pdf\/10.1007\/s00204-015-1481-1","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2019,5,23]],"date-time":"2019-05-23T19:17:08Z","timestamp":1558639028000},"score":1,"resource":{"primary":{"URL":"http:\/\/link.springer.com\/10.1007\/s00204-015-1481-1"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2015,3,6]]},"references-count":30,"journal-issue":{"issue":"3","published-print":{"date-parts":[[2016,3]]}},"alternative-id":["1481"],"URL":"https:\/\/doi.org\/10.1007\/s00204-015-1481-1","relation":{},"ISSN":["0340-5761","1432-0738"],"issn-type":[{"value":"0340-5761","type":"print"},{"value":"1432-0738","type":"electronic"}],"subject":[],"published":{"date-parts":[[2015,3,6]]}}}