Identification of covalent binding sites of ethyl 2-cyanoacrylate, methyl methacrylate and 2-hydroxyethyl methacrylate in human hemoglobin using LC/MS/MS techniques

A systematic characterization of the factors influencing polymerization and dynamic behavior of n-butyl cyanoacrylate

“…It is known that amine groups from proteins can act as electron donors to initiate polymerization via a zwitterionic mechanism 29. Cyanoacrylates have also been shown to form covalent bonds with proteins (ie, protein adducts) on exposure to biologic tissue 33. Cell membrane components and charge probably do not fully explain this as both endothelium and platelets contain cell membranes and neither substrate showed polymerization times that were as rapid.…”

Methemoglobin Formation and Characterization of Hemoglobin Adducts of Carcinogenic Aromatic Amines and Heterocyclic Aromatic Amines

“…84 The β-Cys 93 also binds low molecular weight alkylating agents such as styrene oxide, 85 benzene oxide, 25 nitric oxide, 86 and acrylate contact allergens present in paint. 87 The induced-fit docking program of MOE 2013.08 (Chemical Computing Group, Inc.) allowed only the active site residue side chains to be included in the final minimization stage of docking. 58,59 On the basis of these docking results (Figure 10 and Table 3), variations in side chain configuration were too small to allow any of the five AA and HAA substrates to approach the oxy-heme complex closely enough to engage in hydrogen bonding and/or electron donation.…”

“…In the native form of tetrameric Hb, the two β-Cys 93 residues are accessible to solvent and can react with low molecular weight electrophiles, whereas the α-Cys 104 and β-Cys 112 are shielded, and their reactivity with electrophiles is minor. , However, under high concentrations of PMB and prolonged incubation, a partial disassembly of the Hb subunits occurs, and the α-Cys 104 and β-Cys 112 become more accessible to solvent and can react with PMB and other electrophiles. ,, The reactivity of β-Cys 93 with sulfhydryl agents has been employed to separate the Hb tetramer into separate monomer chains . The β-Cys 93 also binds low molecular weight alkylating agents such as styrene oxide, benzene oxide, nitric oxide, and acrylate contact allergens present in paint . The induced-fit docking program of MOE 2013.08 (Chemical Computing Group, Inc.) allowed only the active site residue side chains to be included in the final minimization stage of docking. , On the basis of these docking results (Figure and Table ), variations in side chain configuration were too small to allow any of the five AA and HAA substrates to approach the oxy-heme complex closely enough to engage in hydrogen bonding and/or electron donation.…”