Examination of Michael addition reactivity towards glutathione by transition-state calculations

References

• Aptula , AO and Roberts , DW . 2006 . Mechanistic applicability domains for non-animal-based prediction of toxicological end points: General principles and application to reactive toxicity . Chem. Res. Toxicol. , 19 : 1097 – 1105 .
   PubMed Web of Science ®Google Scholar
• Schultz , TW , Carlson , RE , Cronin , MTD , Hermens , JLM , Johnson , R , O’Brien , PJ , Roberts , DW , Siraki , A , Wallace , KD and Veith , GD . 2006 . A conceptual framework for predicting toxicity of reactive chemicals: Models for soft electrophilicity . SAR QSAR Environ. Res. , 17 : 413 – 428 .
   PubMed Web of Science ®Google Scholar
• Roberts , DW , Aptula , AO and Patlewicz , G . 2007 . Electrophilic chemistry related to skin sensitization. Reaction mechanistic applicability domain classification for a published data set of 106 chemicals tested in the mouse local lymph node assay . Chem. Res. Toxicol. , 20 : 40 – 60 .
   Google Scholar
• Roberts , DW , Patlewicz , G , Kern , PS , Gerberick , F , Kimber , I , Dearman , RJ , Ryan , CA , Basketter , DA and Aptula , AO . 2007 . Mechanistic applicability domain classification of a local lymph node assay dataset for skin sensitization . Chem. Res. Toxicol. , 20 : 1019 – 1030 .
   PubMed Web of Science ®Google Scholar
• von der Ohe , PC , Kühne , R , Ebert , R-U , Altenburger , R , Liess , M and Schüürmann , G . 2005 . Structural alerts – A new classification model to discriminate excess toxicity from narcotic effect levels of organic compounds in the acute daphnid assay . Chem. Res. Toxicol. , 18 : 536 – 555 .
   PubMed Web of Science ®Google Scholar
• Cronin , MTD , Dearden , JC , Duffy , JC , Edwards , R , Manga , N , Worth , AP and Worgan , ADP . 2002 . The importance of hydrophobicity and electrophilicity descriptors in mechanistically-based QSARs for toxicological endpoints . SAR QSAR Environ. Res. , 13 : 167 – 176 .
   PubMed Web of Science ®Google Scholar
• Enoch , SJ , Roberts , DW and Cronin , MTD . 2009 . Electrophilic reaction chemistry of low molecular weight respiratory sensitizers . Chem. Res. Toxicol. , 22 : 1447 – 1453 .
   PubMed Web of Science ®Google Scholar
• Tanii , H and Hashimoto , K . 1982 . Structure–toxicity relationship of acrylates and methacrylates . Toxicol. Lett. , 11 : 125 – 129 .
   PubMed Web of Science ®Google Scholar
• Potter , DW and Tran , T-B . 1992 . Rates of ethyl acrylate binding to glutathione and protein . Toxicol. Lett. , 62 : 275 – 285 .
   PubMedGoogle Scholar
• Schultz , TW , Yarbrough , JW , Hunter , RS and Aptula , AO . 2007 . Verification of the structural alerts for Michael acceptors . Chem. Res. Toxicol. , 20 : 1359 – 1363 .
   PubMed Web of Science ®Google Scholar
• Koleva , YK , Madden , JC and Cronin , MTD . 2008 . Formation of categories from structure-activity relationships to allow read-across for risk assessment: Toxicity of α, β-unsaturated carbonyl compounds . Chem. Res. Toxicol. , 21 : 2300 – 2313 .
   PubMedGoogle Scholar
• Schwöbel , JAH , Koleva , YK , Enoch , SJ , Bajot , F , Hewitt , M , Madden , JC , Roberts , DW , Schultz , TW and Cronin , MTD . 2010 . Measurement and estimation of electrophilic reactivity for predictive toxicology . Chem. Rev. , in press
   Google Scholar
• Aptula , AO , Patlewicz , G , Roberts , DW and Schultz , TW . 2006 . Non-enzymatic glutathione reactivity and in vitro toxicity: A non-animal approach to skin sensitization . Toxicol. Vitro , 20 : 239 – 247 .
   PubMed Web of Science ®Google Scholar
• Blair , IA . 2006 . Endogenous glutathione adducts . Curr. Drug Metab. , 7 : 853 – 872 .
   PubMed Web of Science ®Google Scholar
• Freidig , AP , Verhaar , HJM and Hermens , JLM . 1999 . Comparing the potency of chemicals with multiple modes of action in aquatic toxicology: Acute toxicity due to narcosis versus reactive toxicity of acrylic compounds . Environ. Sci. Technol. , 33 : 3038 – 3043 .
   Google Scholar
• Böhme , A , Thaens , D , Paschke , A and Schüürmann , G . 2009 . Kinetic glutathione chemoassay to quantify thiol reactivity of organic electrophiles – Application to α, β-unsaturated ketones, acrylates, and propiolates . Chem. Res. Toxicol. , 22 : 742 – 750 .
   PubMed Web of Science ®Google Scholar
• Cronin , MTD , Bajot , F , Enoch , SJ , Madden , JC , Roberts , DW and Schwöbel , J . 2009 . The in chemico–in silico interface: Challenges for integrating experimental and computational chemistry to identify toxicity . ATLA , 37 : 513 – 521 .
   Google Scholar
• Schaafsma , G , Kroese , ED , Tielemans , ELJP , van de Sandt , JJM and van Leeuwen , CJ . 2009 . REACH, non-testing approaches and the urgent need for a change in mind set . Regul. Toxicol. Pharmacol. , 53 : 70 – 80 .
   PubMed Web of Science ®Google Scholar
• Schwöbel , J , Wondrousch , D , Koleva , YK , Madden , JC , Cronin , MTD and Schüürmann , G . 2010 . Prediction of Michael type acceptor reactivity toward glutathione . Chem. Res. Toxicol. , 23 : 1576 – 1585 .
   PubMed Web of Science ®Google Scholar
• Esterbauer , H , Zollner , H and Scholz , N . 1975 . Reaction of glutathione with conjugated carbonyls . Z. Naturforsch. , 30c : 466 – 473 .
   Google Scholar
• McCarthy , TJ and Witz , G . 1997 . Structure–activity relationships in the hydrolysis of acrylate and methacrylate esters by carboxylesterase in vitro . Toxicology , 116 : 153 – 158 .
   PubMed Web of Science ®Google Scholar
• Freidig , AP , Verhaar , HJM and Hermens , JLM . 1999 . Quantitative structure–property relationships for the chemical reactivity of acrylates and methacrylates . Environ. Toxicol. Chem. , 18 : 1133 – 1139 .
   Web of Science ®Google Scholar
• Laidler , KJ and King , MC . 1983 . Development of transition-state theory . J. Phys. Chem. , 87 : 2657 – 2664 .
   Web of Science ®Google Scholar
• Truhlar , DG , Garrett , BC and Klippenstein , SJ . 1996 . Current status of transition-state theory . J. Phys. Chem. , 100 : 12771 – 12800 .
   Web of Science ®Google Scholar
• Kostin , MD . 1997 . Transition state theory and grand canonical partition functions . J. Chem. Phys. , 107 : 5811 – 5814 .
   Google Scholar
• Ju , L-P , Han , K-L and Zhang , JZH . 2009 . Global dynamics and transition state theories: Comparative study of reaction rate constants for gas-phase chemical reactions . J. Comput. Chem. , 30 : 305 – 316 .
   PubMed Web of Science ®Google Scholar
• Osman , R , Namboodiri , K , Weinstein , H and Rabinowitz , JR . 1988 . Reactivities of acrylic and methacrylic acids in a nucleophilic addition model of their biological activity . J. Am. Chem. Soc. , 110 : 1701 – 1707 .
   Google Scholar
• Nakamura , E , Mori , S and Morokuma , K . 1997 . Reaction pathway of the conjugate addition of lithium organocuprate clusters to acrolein . J. Am. Chem. Soc. , 119 : 4900 – 4910 .
   Google Scholar
• Mori , S and Nakamura , E . 1999 . Density functional studies on conjugate addition of (Me2CuLi)2 to cyclohexenone: Stereoselectivity and rate-determining step . Chem. Eur. J. , 5 : 1534 – 1543 .
   Google Scholar
• Hemmateenejad , B , Sanchooli , M and Mehdipour , A . 2009 . Quantitative structure-reactivity relationship studies on the catalyzed Michael addition reactions . J. Phys. Org. Chem. , 22 : 613 – 618 .
   Google Scholar
• Paton , RS , Goodman , JM and Pellegrinet , SC . 2008 . Theoretical study of the asymmetric conjugate alkenylation of enones catalyzed by binaphthols . J. Org. Chem. , 73 : 5078 – 5089 .
   PubMedGoogle Scholar
• Um , I-H , Hwang , S-J and Lee , E-J . 2008 . A kinetic study on Michael-type reactions of 1-(X-substituted phenyl)-2-propyn-1-ones with amines: Effect of amine nature on reactivity and mechanism . Bull. Korean Chem. Soc. , 29 : 767 – 771 .
   Google Scholar
• Um , I-H , Lee , E-J , Seok , J-A and Kim , K-H . 2005 . The a-effect in reactions of sp-hybridized carbon atom: Michael-type reactions of 1-aryl-2-propyn-1-ones with primary amines . J. Org. Chem. , 70 : 7530 – 7536 .
   PubMed Web of Science ®Google Scholar
• Frisch , MJ , Trucks , GW , Schlegel , HB , Scuseria , GE , Robb , MA , Cheeseman , JR , Montgomery , JA , 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 , Adamo , C , Jaramillo , J , Gomperts , R , Stratmann , RE , Yazyev , O , Austin , AJ , Cammi , R , Pompelli , 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 , Raghavavachari , 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 , PMW , Johnson , B , Chen , W , Wong , MW , Gonzalez , C and Pople , JA . 2003 . Gaussian 03, Revision C.02 , Pittsburgh, PA, , USA : Gaussian, Inc. .
   Google Scholar
• Cossi , M , Rega , N , Scalmani , G and Barone , V . 2003 . Energies, structures, and electronic properties of molecules in solution with the C-PCM solvation model . J. Comput. Chem. , 24 : 669 – 681 .
   PubMed Web of Science ®Google Scholar
• M. Sanner, MSMS, Molecular Graphics Laboratory, La Jolla, CA, USA, 1996
   Google Scholar
• Connolly , ML . 1992 . The molecular surface package . J. Mol. Graphics , 11 : 139 – 141 .
   Google Scholar
• Céspedes-Camacho , IF , Manso , JA , Pérez-Prior , MT , Gómez-Bombarelli , R , González-Pérez , M , Calle , E and Casado , J . 2009 . Reactivity of acrylamide as an alkylating agent: A kinetic approach . J. Phys. Org. Chem. , 23 : 171 – 175 .
   Google Scholar
• Wang , X and Ashby , MT . 2008 . Reactive sulfur species: Kinetics and mechanism of the reaction of thiocarbamate-S-oxide with cysteine . Chem. Res. Toxicol. , 21 : 2120 – 2126 .
   PubMed Web of Science ®Google Scholar
• Cai , J , Bhatnagar , A and Pierce , WM Jr . 2009 . Protein modification by acrolein: Formation and stability of cysteine adducts . Chem. Res. Toxicol. , 22 : 708 – 716 .
   PubMed Web of Science ®Google Scholar
• Bernasconi , CF and Killion , RB Jr . 1988 . Nucleophilic addition to olefins. Part 23. High intrinsic rate constant and large imbalances in the thiolate ion addition to substituted a-nitrostilbenes . J. Am. Chem. Soc. , 110 : 7506 – 7512 .
   Google Scholar