The Reactions of Formaldehyde with Amino Acids and Proteins

French, Dexter; Edsall, John T.

doi:10.1016/s0065-3233(08)60627-0

Cited by 337 publications

(129 citation statements)

References 96 publications

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“…The reactions that occur during the treatment of proteins with formaldehyde have been investigated in detail (28,30,31). Among all protein amino acid residues, the side chains of cysteine, lysine, histidine, and tyrosine possess the highest reactivity toward formaldehyde (28).…”

Section: Resultsmentioning

confidence: 99%

Stabilization of tetanus and diphtheria toxoids against moisture-induced aggregation.

Schwendeman

Costantino

Gupta

et al. 1995

Proc. Natl. Acad. Sci. U.S.A.

102

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The progress toward single-dose vaccines has been limited by the poor solid-state stability of vaccine antigens within controlled-release polymers, such as poly(lactide-co-glycolide). For example, herein we report that lyophilized tetanus toxoid aggregates during incubation at 37°C and elevated humidity-i.e., conditions relevant to its release from such systems. The mechanism and extent of this aggregation are dependent on the moisture level in the solid protein, with maximum aggregation observed at intermediate moisture contents. The main aggregation pathway is consistent with formaldehyde-mediated cross-linking, where reactive electrophiles created and stored in the vaccine upon formalinization (exposure to formaldehyde during vaccine preparation) react with nucleophiles of a second vaccine molecule to form intermolecular cross-links. This process is inhibited by the following: (i) succinylating the vaccine to block reactive amino groups; (ii) treating the vaccine with sodium cyanoborohydride, which presumably reduces Schiff bases and some other electrophiles created upon formalinization; and (iii) addition of low-molecular-weight excipients, particularly sorbitol. The moisture-induced aggregation of another formalinized vaccine, diphtheria toxoid, is also retarded by succinylation, suggesting the generality of this mechanism for formalinized vaccines. Hence, mechanistic stability studies of the type described herein may be important for the development of effective single-dose vaccines.

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Section: Resultsmentioning

confidence: 99%

Stabilization of tetanus and diphtheria toxoids against moisture-induced aggregation.

Schwendeman

Costantino

Gupta

et al. 1995

Proc. Natl. Acad. Sci. U.S.A.

102

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“…gonorrhoeae (Table I) reveals that, like other bacteria, they are negatively charged at physiological pH (Gittens & James, I 963). Treatment with formaldehyde increased the negative charge by blocking the free protonated amino groups (French & Edsall, 1945), resulting in a decrease in PI to 4.0. This PI value reflects the overall pK of the carboxyl groups on the cell surface and shows that acidic phosphate groups, like those present on lipopolysaccharides, do not make a significant contribution to the surface charge for, if they were present, the PI value of the formaldehyde-treated cells would be less than 3.0 (Sherbet & Lakshmi, 1973).…”

Section: Results a N D Discussionmentioning

confidence: 99%

The Influence of Surface Charge on the Attachment of Neisseria gonorrhoeae to Human Cells

Heckels

Blackett

Everson

et al. 1976

Journal of General Microbiology

100

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“…Before formaldehyde can directly affect the underlining epithelium they must penetrate this superficial layer [41]. Due to their low K ow value formaldehyde binds readily to mucous proteins [18] and polysaccharides [23] thereafter, diffuse through the underlining periciliary fluid and altered the normal functioning of the cell. But, the exact mechanisms and their metabolic fate are still unknown.…”

Section: Pyridine and Formaldehyde Toxicitymentioning

confidence: 99%

Effect of Pyridine and Formaldehyde on a Macrophyte ( Lemna Minor L.) and a Sludge Worm ( Tubifex Tubifex Müller) in Fresh Water Microcosms

Singh¹

2008

Appl Ecol Env Res

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Singh et al.: Effect of pyridine and formaldehyd on Lemna minor L and Tubifex tubifex Müller in freshwater microcosmsAbstract. Pyridine, a suspected genotoxic and formaldehyde, a potent carcinogen, are present in several industrial wastewater including commercial solvent, resin and pesticide manufacturing industries. The extent of pyridine and formaldehyde toxicity in aquatic organisms is unknown. Therefore, in present study the toxicity of pyridine and formaldehyde were investigated in artificial aquatic ecosystem (microcosm) using two freshwater organisms of different trophic levels i.e. a common duckweed; Lemna minor L. and an oligochaete; Tubifex tubifex Müller. In microcosm, formaldehyde was found to be more toxic to chlorophyll (21 days IC50 = 0.08±0.02 mgL-1), protein (21 days IC50 = 0.15±0.02 mgL-1) and biomass (21 days IC50 = 0.18±0.02 mgL-1) contents of L. minor than pyridine. In addition, pyridine was found growth supportive to L. minor at concentration of 0.1-0.3 mgL-1. Formaldehyde was found more toxic than pyridine for T. tubifex. Lethal concentrations for formaldehyde were 0.08±0.004 (LC10-21 days), 0.2±0.03 (LC25-21 days) and 0.39±0.05 mgL-1 (LC50-21 days). For pyridine, lethal concentrations were 0.85±0.08 (LC10-21 days), 2.14±0.2 (LC25-21days) and 4.27±0.3 mgL-1 (LC50-21days). The concentration and time dependent decrease in growth rate, soluble protein and glycogen content was observed. To overcome the stress situation, high-energy requirement of worms lead to protein and glycogen catabolism. The results of present study might be an important consideration while assessing the hazards of materials to aquatic organisms or when deriving water quality criteria for aquatic organisms.

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The Reactions of Formaldehyde with Amino Acids and Proteins

Cited by 337 publications

References 96 publications

Stabilization of tetanus and diphtheria toxoids against moisture-induced aggregation.

Stabilization of tetanus and diphtheria toxoids against moisture-induced aggregation.

The Influence of Surface Charge on the Attachment of Neisseria gonorrhoeae to Human Cells

Effect of Pyridine and Formaldehyde on a Macrophyte ( Lemna Minor L.) and a Sludge Worm ( Tubifex Tubifex Müller) in Fresh Water Microcosms

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