Chemical Compounds as Trigger Factors of Immediate Contact Skin Reactions
Ana M. Giménez-Arnau, Howard I. Maibach in Contact Urticaria Syndrome, 2014
In the plastic industry, workers are in contact with highly reacting chemicals. Cyclic acid anhydrides are synthetic highly reactive LMW compounds widely used as curing agents for epoxy resins and in the production of polyester resins. Commonly used anhydrides are phthalic anhydride, tetrahydrophthalic anhydride, methyl tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyl hexahydrophthalic anhydride, maleic anhydride, and trimellitic anhydride. Cyclic acid anhydrides often cause allergic respiratory diseases, and in the literature only single case reports of CoU of a few patients were found. However, recently, occupational CoU has been described by a Finnish study as workers may be exposed in powder or liquid form during manufacturing processes.[64] Data are presented for 21 subjects who had been diagnosed with occupational CoU because of exposure to organic acid anhydrides and examined during 1990–2006. Prick tests with HSA-acid anhydrides conjugates, RAST determination of specific IgE and open application tests were used for the diagnosis. The majority of the patients had been exposed to an epoxy resin containing methyl hexahydrophthalic anhydride. Specific IgE results were in line with the prick tests and the large reaction was seen for the acid anhydride the patient had been exposed to. Phthalic anhydride IgE was positive in 19 of 20 patients. The authors concluded that CoU to these compounds may be more common than previously believed, as first shown by a previous Finnish study with two patients.[65]
Pseudo-Proteins and Related Synthetic Amino Acid-Based Polymers Promising for Constructing Artificial Vaccines
Mesut Karahan in Synthetic Peptide Vaccine Models, 2021
The BPs could be broken down in the physiological environment after their functions are fulfilled, resulting in small-sized debris which can be cleared from the body via metabolic means. To be fragmented into small-sized breakdown products, the BPs should contain chemical bonds in the backbones which are easily cleavable either enzymatically or chemically with reasonable rates. Normally these chemical bonds are cleaved via either hydrolysis or (rarely) a redox mechanism. The polymers degradable via a redox mechanism could contain suitable bonds (e.g. reduction-sensitive S-S disulfide links), whereas the BPs which degrade via a hydrolytic mechanism should contain hydrolytically labile bonds such as highly polarized C-C bonds (e.g. in polycyanoacrylates), ester, ortho-ester, and anhydride bonds, as well as amide, urethane, or urea bonds; the latter are also subjected to hydrolysis but with much lower rates. The BPs which contain only amide (peptide) bonds undergo mostly enzyme-catalyzed (specific) hydrolysis, e.g. hydrolytic degradation of collagen is catalyzed by collagenase. The anhydride bonds are cleaved predominantly via chemical (non-specific) hydrolysis whereas the ester bonds could be subjected to both enzymatic and chemical hydrolysis.
The Modification of Lysine
Roger L. Lundblad in Chemical Reagents for Protein Modification, 2020
Acylation of amino groups in proteins by reaction with carboxylic acid anhydrides has been extensively used. Riordan and Vallee21 have discussed the process of acetylation in some detail. Acetylation is generally carried out with acetic anhydride at alkaline pH in either a pH-stat or in saturated sodium acetate. Performing the modification reaction under these latter conditions (saturated sodium acetate) results in increased specificity since O-acetyl tyrosine is unstable in sodium acetate. Acetylation has been used to study calcitonin22 and a bacterial cytochrome.23 Acetic and maleic anhydride have been used to study elastase.24 In these studies, the reaction was carried out in a pH-stat to maintain alkaline pH. Reaction occurred at both lysyl and tyrosyl residues. It is relatively easy to differentiate between the two sites of modification since O-acyl tyrosyl residues are unstable at pH ≥9.0. Studies with maleic anhydride showed that the amino terminal valine was not available for modification at pH 8.0 to 9.0 but could be modified at pH 11.0. Modification of this residue could be achieved in the presence of urea at a lower pH.
Quantifying cellular protrusion in alginate capsules with covalently crosslinked shells
Published in Journal of Microencapsulation, 2019
Mitchell A. Johnson, Rachelle Kleinberger, Ali Abu Helal, Nicole Latchminarine, Ahmed Ayyash, Shanna Shi, Nicholas A. D. Burke, Alison C. Holloway, Harald D. H. Stöver
Poly(methylvinylether-alt-maleic anhydride) (MW 80 kDa, Sigma Aldrich) was heated under vacuum for 96 h at 110 °C to ensure any hydrolysed anhydride units are dehydrated back to the anhydride form. Poly-l-lysine HBr (15–30 kDa) was obtained from Polysciences. UP-MVG sodium alginate BP-1603–09 was obtained from FMC Biosciences. Deuterated acetonitrile 99.96% D was obtained from Cambridge Isotope Laboratories. Fluorescent LIVE/DEAD assay kits based on Calcein AM/Ethidium homodimer and 20 mM Hoechst 3342 was obtained from Thermo Fisher Scientific. Deuterium dioxide 99.9% D, Rhodamine isothiocyanate (RITC), Trypan blue stain 0.4%, Phosphate buffered saline, Trypsin EDTA 0.25%, HEPES sodium salt, RPMI-1640, HEPES 1 M, 100 mM Sodium Pyruvate, 55 mM β-mercaptoethanol, 200 mM Glutamine, foetal bovine serum, Gibco, heat-inactivated at 56 °C for 30 min prior to use, Dextran-FITC 2000 kDa were purchased from (Sigma Aldrich, Oakville, ON). All reagents and chemicals were used as received. Calcium Chloride dihydrate and Sodium Chloride were purchased from (Caledon Laboratories Ltd, ON), Sodium Hydroxide was purchased from Labchem INC, (Tri)sodium citrate dihydrate was purchased from EMD chemicals. All reagents and chemicals were used as received.
Framework for sensitization assessment of extractables and leachables in pharmaceuticals
Published in Critical Reviews in Toxicology, 2022
Patricia Parris, Geraldine Whelan, Anders Burild, Jessica Whritenour, Uma Bruen, Joel Bercu, Courtney Callis, Jessica Graham, Esther Johann, Troy Griffin, Martin Kohan, Elizabeth A. Martin, Melisa Masuda-Herrera, Brad Stanard, Eric Tien, Maureen Cruz, Lee Nagao
For the purposes of E&L sensitization assessment, ELSIE recommends a conservative and precautionary approach that any chemical identified (or predicted using in silico methods) to be a skin sensitizer provides an indication that the chemical can activate T cells (or activate the immune system). Therefore, the chemical is assumed to have the potential to be a respiratory sensitizer and is evaluated accordingly. A literature search was conducted to identify if there are any human case reports of induction of sensitization associated with known respiratory sensitizers as E&Ls. No case studies or clinical reports were found suggesting there is little evidence of a safety concern thus far. However, measurement of IgE levels is not routinely conducted on clinical studies with novel pharmaceuticals, let alone for E&Ls. Occupational case reports were identified associated with phthalic anhydride (CAS No. 85-44-9) which is a known respiratory sensitizer, and a chemical intermediate in the plastics industry. Phthalic anhydride is reported in the ELSIE database however, based on feedback from ELSIE consortium members, it is generally observed as an extractable and not a leachable substance.
Alveolar hemorrhage due to marijuana smoking using water pipe made with plastic bottle: case report and narrative review of the literature
Published in Inhalation Toxicology, 2021
Ségolène Toquet, Joël Cousson, Nathalie Choiselle, Claire Gozalo, Delphine Giusti, Firouze Bani-Sadr, Yohan N’Guyen
The main explanation suggested by Grassin and the authors of these cases (Klotz and Martin 2009; Grassin et al. 2011; Moatemri et al. 2016; Caviedes et al. 2019), almost all described before the e-cigarette, or vaping, product use-associated lung injury (EVALI) epidemics, was the potential concomitant inhalation of acid anhydrides derived from heated plastic bottle. This was suggested by the implication of acid anhydrides, such as phtalic anhydride or trimellitic anhydrides (TMA) in two former occupational diseases associated with resins or plastics vapors, namely ‘meat’s wrapper asthma’ and ‘pulmonary disease- anemia syndrome’ (Herbert and Orford 1979; Zeiss et al. 1988; Venables 1989; Kaplan et al. 1993). AH could occur in ‘pulmonary disease- anemia syndrome’ but not in meat’s wrapper asthma. ‘Meat’s wrapper’ asthma is immune mediated and more frequently due to phtalic anhydride, whereas ‘pulmonary disease- anemia syndrome’ is due to TMA and either toxic or immune mediated (Zeiss et al. 1988; Venables 1989). Indeed, specific antibodies against TMA were inconsistently detected in serum of workers exposed to epoxy resin vapors (Herbert and Orford 1979; Kaplan et al. 1993), but they appeared correlated with the number of hemorragic foci in lungs of Sprague Dawley rats (Zeiss et al. 1988). Lastly, a case very similar to ‘pulmonary disease- anemia syndrome’ had been described without any professional exposure but after smoking marijuana adulterated with benzene (Mémain et al. 2001). We therefore tried to confirm the role of acid anhydrides in our case using available means.
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