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@ARTICLE{Jaladanki:892139,
      author       = {Jaladanki, Chaitanya K. and Khatun, Samima and Gohlke,
                      Holger and Bharatam, Prasad V.},
      title        = {{R}eactive {M}etabolites from {T}hiazole-{C}ontaining
                      {D}rugs: {Q}uantum {C}hemical {I}nsights into
                      {B}iotransformation and {T}oxicity},
      journal      = {Chemical research in toxicology},
      volume       = {34},
      number       = {6},
      issn         = {1520-5010},
      address      = {New York, NY},
      publisher    = {ACS Publ.},
      reportid     = {FZJ-2021-01973},
      pages        = {1503–1517},
      year         = {2021},
      abstract     = {Drugs containing thiazole and aminothiazole groups are
                      known to generate reactive metabolites (RMs) catalyzed by
                      cytochrome P450s (CYPs). These RMs can covalently modify
                      essential cellular macromolecules and lead to toxicity and
                      induce idiosyncratic adverse drug reactions. Molecular
                      docking and quantum chemical hybrid DFT study were carried
                      out to explore the molecular mechanisms involved in the
                      biotransformation of thiazole (TZ) and aminothiazole (ATZ)
                      groups leading to RM epoxide, S-oxide, N-oxide, and
                      oxaziridine. The energy barrier required for the epoxidation
                      is 13.63 kcal/mol, that is lower than that of S-oxidation,
                      N-oxidation, and oxaziridine formation (14.56, 17.90, and
                      20.20, kcal/mol respectively). The presence of the amino
                      group in ATZ further facilitates all the metabolic pathways,
                      for example, the barrier for the epoxidation reaction is
                      reduced by ∼2.5 kcal/mol. Some of the RMs/their isomers
                      are highly electrophilic and tend to form covalent bonds
                      with nucleophilic amino acids, finally leading to the
                      formation of metabolic intermediate complexes (MICs). The
                      energy profiles of these competitive pathways have also been
                      explored},
      cin          = {JSC / NIC / IBI-7 / IBG-4},
      ddc          = {610},
      cid          = {I:(DE-Juel1)JSC-20090406 / I:(DE-Juel1)NIC-20090406 /
                      I:(DE-Juel1)IBI-7-20200312 / I:(DE-Juel1)IBG-4-20200403},
      pnm          = {217 - Für eine nachhaltige Bio-Ökonomie – von
                      Ressourcen zu Produkten (POF4-217) / 5111 - Domain-Specific
                      Simulation $\&$ Data Life Cycle Labs (SDLs) and Research
                      Groups (POF4-511) / Forschergruppe Gohlke $(hkf7_20200501)$},
      pid          = {G:(DE-HGF)POF4-217 / G:(DE-HGF)POF4-5111 /
                      $G:(DE-Juel1)hkf7_20200501$},
      typ          = {PUB:(DE-HGF)16},
      pubmed       = {33900062},
      UT           = {WOS:000664624800013},
      doi          = {10.1021/acs.chemrestox.0c00450},
      url          = {https://juser.fz-juelich.de/record/892139},
}