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Original Articles

Combined QSAR studies of inhibitor properties of O-phosphorylated oximes toward serine esterases involved in neurotoxicity, drug metabolism and Alzheimer's disease

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Pages 627-647 | Received 20 Dec 2011, Accepted 27 Feb 2012, Published online: 15 May 2012

References

  • Richardson , RJ , Worden , RM and Makhaeva , GF . 2009 . “ Biomarkers and biosensors of delayed neuropathic agents ” . In Handbook of Toxicology of Chemical Warfare Agents , Edited by: Gupta , RC . 859 – 876 . Amsterdam : Academic Press/Elsevier .
  • Sit , RK , Radić , Z , Gerardi , V , Zhang , L , Garcia , E , Katalinić , M , Amitai , G , Kovarik , Z , Fokin , VV , Sharpless , KB and Taylor , P . 2011 . New structural scaffolds for centrally acting oxime reactivators of phosphylated cholinesterases . J. Biol. Chem. , 286 : 19422 – 19430 .
  • Thompson , CM and Richardson , RJ . 2004 . “ Anticholinesterase insecticides ” . In Pesticide Toxicology and International Regulation , Edited by: Marrs , TC and Ballantyne , B . 89 – 127 . New York : Wiley .
  • Leader , H , Vincze , A , Manisterski , B , Rothschild , N , Dosoretz , C and Ashani , Y . 1999 . Characterization of O,O-diethylphosphoryl oximes as inhibitors of cholinesterases and substrates of phosphotriesterases . Biochem. Pharmacol. , 58 : 503 – 515 .
  • Luo , C , Saxena , A , Smith , M , Garcia , G , Radić , Z , Taylor , P and Doctor , BP . 1999 . Phosphoryl oxime inhibition of acetylcholinesterase during oxime reactivation is prevented by edrophonium . Biochemistry , 38 : 9937 – 9947 .
  • Becker , C , Worek , F and John , H . 2010 . Chromatographic analysis of toxic phosphylated oximes (POX): A brief overview . Drug Test. Anal. , 2 : 460 – 468 .
  • Radchenko , EV , Makhaeva , GF , Sokolov , VB , Palyulin , VA and Zefirov , NS . 2009 . Study of the structural determinants of acute and delayed neurotoxicity of O-phosphorylated oximes by molecular field topology analysis (MFTA) . Dokl. Biochem. Biophys. , 429 : 309 – 314 .
  • Makhaeva , G , Filonenko , I , Fomicheva , S and Malygin , V . 1996 . “Esterase profiles” of O,O-dialkyl-O-dimethyl-chloroformiminophosphates in prediction of their toxic effects . Toxicol. Lett. , 88 ( Suppl. 1 ) : 25
  • Makhaeva , GF , Serebryakova , OG , Boltneva , NP , Galenko , TG , Aksinenko , AY , Sokolov , VB and Martynov , IV . 2008 . Esterase profile and analysis of structure-inhibitor selectivity relationships for homologous phosphorylated 1-hydroperfluoroisopropanols . Dokl. Biochem. Biophys. , 423 : 352 – 357 .
  • Richardson , RJ . 2010 . “ Anticholinesterase insecticides ” . In Comprehensive Toxicology , Edited by: McQueen , CA . Vol. 13 , 433 – 444 . Oxford : Elsevier .
  • Wijeyesakere , SJ and Richardson , RJ . 2010 . “ Neuropathy target esterase ” . In in Hayes' Handbook of Pesticide Toxicology , Edited by: Krieger , R . 1435 – 1455 . New York : Academic Press/Elsevier .
  • Maxwell , DM and Brecht , KM . 2001 . Carboxylesterase: Specificity and spontaneous reactivation of an endogenous scavenger for organophosphorus compounds . J. Appl. Toxicol. , 21 : S103 – S107 .
  • Masson , P and Lockridge , O . 2010 . Butyrylcholinesterase for protection from organophosphorus poisons: Catalytic complexities and hysteretic behavior . Arch. Biochem. Biophys. , 494 : 107 – 120 .
  • Furukawa-Hibi , Y , Alkam , T , Nitta , A , Matsuyama , A , Mizoguchi , H , Suzuki , K , Moussaoui , S , Yu , QS , Greig , NH , Nagai , T and Yamada , K . 2011 . Butyrylcholinesterase inhibitors ameliorate cognitive dysfunction induced by amyloid-β peptide in mice . Behav. Brain Res. , 225 : 222 – 229 .
  • Lane , RM , Potkin , SG and Enz , A . 2006 . Targeting acetylcholinesterase and butyrylcholinesterase in dementia . Int. J. Neuropsychopharmacol. , 9 : 101 – 124 .
  • Radchenko , EV , Makhaeva , GF , Malygin , VV , Sokolov , VB , Palyulin , VA and Zefirov , NS . 2008 . Modeling of the relationships between the structure of O-phosphorylated oximes and their anticholinesterase activity and selectivity using molecular field topology analysis (MFTA) . Dokl. Biochem. Biophys. , 418 : 47 – 51 .
  • Lotti , M and Johnson , MK . 1978 . Neurotoxicity of organophosphorus pesticides: Predictions can be based on in vitro studies with hen and human enzymes . Arch. Toxicol. , 41 : 215 – 221 .
  • Malygin , VV , Sokolov , VB , Richardson , RJ and Makhaeva , GF . 2003 . Quantitative structure-activity relationships predict the delayed neurotoxicity potential of a series of O-alkyl-O-methylchloroformimino phenylphosphonates . J. Toxicol. Environ. Health, Part A , 66 : 611 – 625 .
  • Sokolov , VB , Ivanov , AN , Epishina , TA and Martynov , IV . 1987 . Reaction of alkyl hydrogen methylphosphonites with 1,1-dichloro-1-nitrosopropane . J. Gen. Chem. USSR (Engl. Transl.) , 57 : 845 – 846 .
  • Sokolov , VB , Ivanov , AN , Goreva , TV , Epishina , TA and Martynov , IV . 1988 . O-Alkylchloroformimino-O-alkylmethylphosphonates . Rus. Chem. Bull. , 37 : 989 – 991 .
  • Ivanov , AN , Epishina , TA , Goreva , TV , Sokolov , VB and Martynov , IV . 1987 . Reaction of dialkyl phosphites with 1,1-dichloronitrosoalkanes . Rus. Chem. Bull. , 36 : 204 – 205 .
  • Martynov , IV , Ivanov , AN , Epishina , TA and Sokolov , VB . 1987 . Reaction of polychloronitrosoethanes with phosphorous acid derivatives . Rus. Chem. Bull. , 36 : 1001 – 1003 .
  • Chepakova , LA , Brel , VK , Makhaeva , GF , Yankovskaya , VL , Beznosko , BK , Malygin , VV and Martynov , IV . 1988 . Synthesis and antiesterase activity of sulfur containing O-phosphorylated oximes . Pharm. Chem. J. , 22 : 143 – 146 .
  • Makhaeva , GF , Kononova , IV , Malygin , VV , Liashenko , IuE , Sokolov , VB and Martynov , IV . 1991 . O-alkyl-O-methylchlorformiminophenylphosphonates – effective inhibitors of hen brain neurotoxic esterase . Dokl. Akad. Nauk SSSR. , 317 : 1009 – 1012 . (Russ.)
  • Makhaeva , GF and Malygin , VV . 1999 . A stable preparation of hen brain neuropathy target esterase for rapid biochemical assessment of neurotoxic potential of organophosphates . Chem. Biol. Interact. , 119–120 : 551 – 557 .
  • Makhaeva , GF , Filonenko , IV , Yankovskaya , VL , Fomicheva , SB and Malygin , VV . 1998 . Comparative studies of O,O-dialkyl-O-chloromethylchloroformiminophosphates: Interaction with neuropathy target esterase and acetylcholinesterase . Neurotoxicology , 19 : 623 – 628 .
  • Makhaeva , GF , Aksinenko , AY , Sokolov , VB , Baskin , II , Palyulin , VA , Zefirov , NS , Hein , ND , Kampf , JW , Wijeyesakere , SJ and Richardson , RJ . 2010 . Kinetics and mechanism of inhibition of serine esterases by fluorinated aminophosphonates . Chem. Biol. Interact. , 187 : 177 – 184 .
  • Aldridge , WN and Reiner , E . 1972 . Enzyme Inhibitors as Substrates , 37 – 52 . Amsterdam : North Holland Publishing .
  • OriginPro 6.1, OriginLab, Northampton, MA, 2000; software available at http://www.originlab.com
  • Makhaeva , GF , Malygin , VV , Yakubov , ShM and Gorbunov , SM . 1994 . Investigation of the relationship between structure and antiesterase activity in the series of O-phosphorylated oximes. 1. Methylphosphonates . Pharm. Chem. J. , 28 : 367 – 371 .
  • Makhaeva , GF , Malygin , VV , Yakubov , ShM and Gorbunov , SM . 1994 . Investigation of the relationship between structure and antiesterase activity in the series of O-phosphorylated oximes. II. Dialkylphosphates and methylphosphonates . Pharm. Chem. J. , 28 : 620 – 625 .
  • Makhaeva , GF , Malygin , VV and Martynov , IV . 2001 . Assessment of the neurotoxic potential of some methyl- and phenylphosphonates using a stable preparation of neuropathy target esterase from chicken brain . Dokl. Biochem. Biophys. , 377 : 68 – 71 .
  • Plyamovaty , AKh , Vandyukova , II , Shagidullin , RR , Makhaeva , GF , Malygin , VV and Gorbunov , SM . 1997 . Studies of the relationships between three-dimensional structure and anti-cholinesterase activity for O-phosphorylated oximes . Pharm. Chem. J. , 31 : 199 – 204 .
  • Baskin , I and Varnek , A . 2008 . “ Fragment descriptors in SAR/QSAR/QSPR studies, molecular similarity analysis and in virtual screening ” . In Chemoinformatics Approaches to Virtual Screening , Edited by: Varnek , A and Tropsha , A . 1 – 43 . Cambridge : RSC .
  • Zhokhova , NI , Baskin , II , Palyulin , VA , Zefirov , AN and Zefirov , NS . 2007 . Fragmental descriptors with labeled atoms and their application in QSAR/QSPR studies . Dokl. Chem. , 417 : 282 – 284 .
  • Artemenko , NV , Baskin , II , Palyulin , VA and Zefirov , NS . 2001 . Prediction of physical properties of organic compounds using artificial neural networks within the substructure approach . Dokl. Chem. , 381 : 317 – 320 .
  • Baskin , II , Halberstam , NM , Artemenko , NV , Palyulin , VA and Zefirov , NS . 2003 . “ NASAWIN – a universal software for QSPR/QSAR studies ” . In EuroQSAR 2002 Designing Drugs and Crop Protectants: Processes, Problems and Solutions , Edited by: Ford , M , Livingstone , D , Dearden , J and Waterbeemd , H . 260 – 263 . Malden : Blackwell .
  • Palyulin , VA , Radchenko , EV and Zefirov , NS . 2000 . Molecular Field Topology Analysis method in QSAR studies of organic compounds . J. Chem. Inf. Comp. Sci. , 40 : 659 – 667 .
  • Radchenko , EV , Palyulin , VA and Zefirov , NS . 2008 . “ Molecular Field Topology Analysis in drug design and virtual screening ” . In Chemoinformatics Approaches to Virtual Screening , Edited by: Varnek , A and Tropsha , A . 150 – 181 . Cambridge : RSC .
  • Radchenko , EV , Palyulin , VA and Zefirov , NS . September 10–17 2006 . QSAR validation, descriptor selection, and the quest for the best models , September 10–17 , 207 Italy : in XVI Eur. Symp. on Quantitative Structure–Activity Relationships and Molecular Modelling .
  • Klebe , G , Abraham , U and Mietzner , T . 1994 . Molecular similarity indices in a comparative analysis (CoMSIA) of drug molecules to correlate and predict their biological activity . J. Med. Chem. , 37 : 4130 – 4146 .
  • SYBYL 8.0, Tripos International, 1699 South Hanley Rd., St. Louis, Missouri, 63144, USA, 2008; software available at http://www.tripos.com
  • Concord, R.S. Pearlman, distributed by Tripos International, St. Louis, Missouri, 63144, USA, 2008; software available at http://www.tripos.com
  • Bourne , Y , Radic , Z , Sulzenbacher , G , Kim , E , Taylor , P and Marchot , P . 2006 . Substrate and product trafficking through the active center gorge of acetylcholinesterase analyzed by crystallography and equilibrium binding . J. Biol. Chem. , 281 : 29256 – 29267 .
  • Nicolet , Y , Lockridge , O , Masson , P , Fontecilla-Camps , JC and Nachon , F . 2003 . Crystal structure of human butyrylcholinesterase and of its complexes with substrate and products . J. Biol. Chem. , 278 : 41141 – 41147 .
  • Wijeyesakere , SJ , Richardson , RJ and Stuckey , JA . 2007 . Modeling the tertiary structure of the patatin domain of neuropathy target esterase . Protein J. , 26 : 165 – 172 .
  • Morris , GM , Huey , R , Lindstrom , W , Sanner , MF , Belew , RK , Goodsell , DS and Olson , AJ . 2009 . AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility . J. Comput. Chem. , 30 : 2785 – 2791 .
  • SYBYL-X 1.2, Tripos International, 1699 South Hanley Rd., St. Louis, Missouri, 63144, USA, 2010; software available at http://www.tripos.com
  • Radchenko , EV , Melnikov , AA , Makhaeva , GF , Palyulin , VA and Zefirov , NS . 2012 . Molecular design of O-phosphorylated oximes – selective butyrylcholinesterase inhibitors . Dokl. Biochem. Biophys. , 443 : 91 – 95 .
  • Melnikov , AA , Palyulin , VA , Radchenko , EV and Zefirov , NS . 2007 . Generation of chemical structures on the basis of QSAR Models of Molecular Field Topology Analysis . Dokl. Chem. , 415 : 196 – 199 .

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