Interactions of acetamide and acrylamide with heme models: Synthesis, infrared spectra, and solid state molecular structures of five- and six-coordinate ferric porphyrin derivatives
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Plewa, 2008, Occurrence, synthesis, and mammalian cell cytotoxicity and genotoxicity of haloacetamides: an emerging class of nitrogenous drinking water disinfection byproducts, Environ. Sci. Technol., 42, 955, 10.1021/es071754h
Ding, 2018, Formation and estimated toxicity of trihalomethanes, haloacetonitriles, and haloacetamides from the chlor(am)ination of acetaminophen, J. Haz. Mater., 341, 112, 10.1016/j.jhazmat.2017.07.049
Chu, 2016, Zero valent iron produces dichloroacetamide from chloramphenicol antibiotics in the absence of chlorine and chloramines, Water Res., 104, 254, 10.1016/j.watres.2016.08.021
Mucci, 2008, Acrylamide intake through diet and human cancer risk, J. Agric. Food Chem., 56, 6013, 10.1021/jf703747b
Tareke, 2000, Acrylamide: a cooking carcinogen?, Chem. Res. Toxicol., 13, 517, 10.1021/tx9901938
Adedipe, 2016, Development and validation of a near-infrared spectroscopy method for the prediction of acrylamide content in French-fried potato, J. Agric. Food Chem., 64, 1850, 10.1021/acs.jafc.5b04733
Girma, 2005, Coordination chemistry of acrylamide, Coord. Chem. Rev., 249, 1283, 10.1016/j.ccr.2005.01.028
Raptopoulou, 2006, Hexanuclear iron(III) salicylaldoximato complexes presenting the [Fe6(μ3-O)2(μ2-OR)2]12+ core: syntheses, crystal structures, and spectroscopic and magnetic characterization, Inorg. Chem., 45, 2317, 10.1021/ic051945q
Broring, 2011, Cationic palladium(II) complexes of the sterically hindered bis(4-methylthiazolyl)isoindoline (4-Mebti) with neutral group XVI donor ligands, Inorg. Chim. Acta, 374, 572, 10.1016/j.ica.2011.02.080
Girma, 2005, Coordination chemistry of acrylamide 2. Classical complexes of acrylamide with manganese(II), iron(II) and nickel(II) chlorides: syntheses and crystal structures, Z. Anorg. Allg. Chem., 631, 2763, 10.1002/zaac.200500132
Girma, 2006, Coordination chemistry of acrylamide. 5. Crystal structures of complexes of metal(II) perchlorates and tetrafluoroborates with acrylamide, Z. Anorg. Allg. Chem., 632, 1874, 10.1002/zaac.200600076
Girma, 2006, Coordination chemistry of acrylamide 3: synthesis, crystal structure and IR spectroscopic properties of dichloro-tetrakis(O-acrylamide)copper(II), [Cu(O-OC(NH2)CH=CH2)4Cl2], Inorg. Chim. Acta, 359, 364, 10.1016/j.ica.2005.07.009
Cini, 1998, Isomerism of amides coordinated to platinum; X-ray crystal structure of O-bonded acetamide in a platinum(II) complex, Eur. J. Inorg. Chem., 1305, 10.1002/(SICI)1099-0682(199809)1998:9<1305::AID-EJIC1305>3.0.CO;2-9
Cini, 1996, Isomerism of amides coordinated to platinum. X-ray crystal structure of dichloro-bisacetamide-platinum(II), Inorg. Chim. Acta, 251, 111, 10.1016/S0020-1693(96)05262-0
Schmuckler, 1977, Interaction of platinum chloride with a polyacrylamide-gel and its monomeric analogs, J. Inorg. Nucl. Chem., 39, 137, 10.1016/0022-1902(77)80448-X
Girma, 2008, Coordination chemistry of acrylamide 6: formation and structural characterization of [Fe(O-OC(NH2)CH=CH2)6][Fe2OCl6], Inorg. Chim. Acta, 361, 346, 10.1016/j.ica.2007.06.012
Fagard, 1983, The effect of hemin and of allyl isopropyl acetamide on protein-synthesis in rat hepatocytes, Biochem. Biophys. Res. Commun., 114, 612, 10.1016/0006-291X(83)90824-0
Matteis, 1971, Loss of haem in rat liver caused by porphyrogenic agent 2-allyl-2-isopropylacetamide, Biochem. J., 124, 767, 10.1042/bj1240767
Hashimoto, 1982, Anemia and porphyria caused by N,N'-methylene-bis-acrylamide (MBA) in mice and rats, Arch. Toxicol., 50, 47, 10.1007/BF00569236
Sumner, 1999, Role of cytochrome P450 2E1 in the metabolism of acrylamide and acrylonitrile in mice, Chem. Res. Toxicol., 12, 1110, 10.1021/tx990040k
Doroshyenko, 2009, In vivo role of cytochrome P450 2E1 and glutathione-S-transferase activity for acrylamide toxicokinetics in humans, Cancer Epidem. Biom. Prev., 18, 433, 10.1158/1055-9965.EPI-08-0832
Dawson, 1982, Spectroscopic investigations of ferric cytochrome P450-CAM ligand complexes. Identification of the ligand trans to cysteinate in the native enzyme, J. Biol. Chem., 257, 3606, 10.1016/S0021-9258(18)34823-3
Bottomley, 1981, Counterion and solvent effects on the electrode-reactions of iron porphyrins, Inorg. Chem., 20, 1348, 10.1021/ic50219a003
Chaudhary, 2011, Synthesis, structure and properties of a high-spin Fe(III) porphyrin with non-equivalent axial ligands: implications for the hemoproteins, Indian J. Chem., Section A, 50, 432
Nakane, 2006, Acrylamide analog as a novel nitric oxide-independent soluble guanylyl cyclase activator, J. Pharmacol. Sci., 102, 231, 10.1254/jphs.FPJ06017X
Rosenberg, 2018, Coffee must carry cancer warning
Xu, 2017, Synthesis, characterization and solid state molecular structures of five- and six-coordinate primary amide manganese porphyrin complexes, Polyhedron, 127, 432, 10.1016/j.poly.2016.10.022
Chen, 1998, Synthesis, characterization, and molecular structures of diethylnitrosamine metalloporphyrin complexes of iron, ruthenium, and osmium, Inorg. Chem., 37, 4677, 10.1021/ic9801591
APEX2, 2007
SAINT, 2007
Sheldrick, 2015, Crystal structure refinement with SHELXL, Acta Cryst, C71, 3
Krause, 2015, Comparison of silver and molybdenum microfocus X-ray sources for single-crystal structure determination, J. Appl. Crystallogr., 48, 3, 10.1107/S1600576714022985
Spek, 2015, PLATON SQUEEZE: a tool for the calculation of the disordered solvent contribution to the calculated structure factors, Acta Cryst, C71, 9
Knudsen, 1994, A low-temperature matrix-isolation infrared study of acetamides.1: Acetamide and some deuterated derivatives, J. Mol. Struc., 321, 187, 10.1016/0022-2860(93)07964-X
Neville, 1961, The infrared and Raman spectra and structure of acrylamide, J. Mol. Spectrosc., 6, 205, 10.1016/0022-2852(61)90243-0
Sundaraganesan, 2001, Vibrational spectra, assignments and normal coordinate calculation of acrylamide, Talanta, 54, 233, 10.1016/S0039-9140(00)00585-3
Scheidt, 1981, Spin-state/stereochemical relationships in iron porphyrins: implications for the hemoproteins, Chem. Rev., 81, 543, 10.1021/cr00046a002
Sigel, 1982, Coordinating properties of the amide bond. Stability and structure of metal ion complexes of peptides and related ligands, Chem. Rev., 82, 385, 10.1021/cr00050a003
Bats, 2003, A new refinement of the orthorhombic polymorph of acetamide, Acta Cryst. E, 59, O1483, 10.1107/S1600536803019494
Stone, 1971, Crystal structures of dichlorotetrakis(acetaldoxime)nickel(II) and tetrakis(acetamide)bisaquonickel(II) dichloride, J. Chem. Soc. A, Inorg. Phys. Theor., 3632, 10.1039/j19710003632
Du, 1992, Structure and magnetic properties of monophenylphosphinate bridged chain polymers of manganese(II), [MnL2(HPhPO2)2]X (where L = HPhPO2H, CH3CONH2, H2O, HCONH(CH3), and C5H5N), Can. J. Chem., 70, 732, 10.1139/v92-098
Zhou, 2007, Acrylamide, Acta Cryst. E, 63, O3039, 10.1107/S1600536807024816
Xu, 2010, Five- and six-coordinate adducts of nitrosamines with ferric porphyrins: structural models for the type II interactions of nitrosamines with ferric cytochrome P450, Inorg. Chem., 49, 4405, 10.1021/ic901751z
Abucayon, 2016, Over or under: hydride attack at the metal versus the coordinated nitrosyl ligand in ferric nitrosyl porphyrins, Dalton Trans., 45, 18259, 10.1039/C6DT03860C
Ellison, 2000, Structural and electronic characterization of nitrosyl(octaethylporphinato)iron(III) perchlorate derivatives, Inorg. Chem., 39, 5102, 10.1021/ic000789e
Scheidt, 1987, Recent advances in the stereochemistry of metallotetrapyrroles, Struct. Bond., 64, 1, 10.1007/BFb0036789
Mu, 1988, In situ FTIR and UV-visible spectroelectrochemical studies of iron nitrosyl porphyrins in nonaqueous media, Inorg. Chem., 27, 4720, 10.1021/ic00299a009
Xu, 2011, Nitrosylation in a crystal: remarkable movements of iron porphyrins upon binding of nitric oxide, Angew. Chem. Int. Ed. Engl., 50, 9694, 10.1002/anie.201103329
Scheidt, 1984, Preparation and structural characterization of nitrosyl complexes of ferric porphyrinates. Molecular structure of aquonitrosyl(meso-tetraphenylporphinato)iron(III) perchlorate and nitrosyl(octaethylporphinato)iron(III) perchlorate, J. Am. Chem. Soc., 106, 3191, 10.1021/ja00323a022
Yi, 1997, Activation of thionitrites and isoamyl nitrite by group 8 metalloporphyrins and the subsequent generation of nitrosyl thiolates and alkoxides of ruthenium and osmium porphyrins, Inorg. Chem., 36, 3876, 10.1021/ic970282c