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Polymerization of hexamethylene diisocyanate in solution and a 260.23 m/z [M+H]+ ion in exposed human cells
- Source :
- Analytical Biochemistry. 543:21-29
- Publication Year :
- 2018
- Publisher :
- Elsevier BV, 2018.
-
Abstract
- Hexamethylene diisocyanate (HDI) is an important industrial chemical that can cause asthma, however pathogenic mechanisms remain unclear. Upon entry into the respiratory tract, HDI's N=C=O groups may undergo nucleophilic addition (conjugate) to host molecules (e.g. proteins), or instead react with water (hydrolyze), releasing CO2 and leaving a primary amine in place of the original N=C=O. We hypothesized that (primary amine groups present on) hydrolyzed or partially hydrolyzed HDI may compete with proteins and water as a reaction target for HDI in solution, resulting in polymers that could be identified and characterized using LC-MS and LC-MS/MS. Analysis of the reaction products formed when HDI was mixed with a pH buffered, isotonic, protein containing solution identified multiple [M+H]+ ions with m/z's and collision-induced dissociation (CID) fragmentation patterns consistent with those expected for dimers (259.25/285.23 m/z), and trimers (401.36/427.35 m/z) of partially hydrolyzed HDI (e.g. ureas/oligoureas). Human peripheral blood mononuclear cells (PBMCs) and monocyte-like U937, but not airway epithelial NCI-H292 cell lines cultured with these HDI ureas contained a novel 260.23 m/z [M+H]+ ion. LC-MS/MS analysis of the 260.23 m/z [M+H]+ ion suggest the formula C13H29N3O2 and a structure containing partially hydrolyzed HDI, however definitive characterization will require further orthogonal analyses.
- Subjects :
- 0301 basic medicine
Nucleophilic addition
Chemistry
010401 analytical chemistry
Biophysics
Cell Biology
01 natural sciences
Biochemistry
Medicinal chemistry
Dissociation (chemistry)
0104 chemical sciences
03 medical and health sciences
chemistry.chemical_compound
030104 developmental biology
Polymerization
Diamine
Amine gas treating
Hexamethylene diisocyanate
Lewis acids and bases
Molecular Biology
Conjugate
Subjects
Details
- ISSN :
- 00032697
- Volume :
- 543
- Database :
- OpenAIRE
- Journal :
- Analytical Biochemistry
- Accession number :
- edsair.doi...........f7ba1bb67fc27c0114979f384f477afd