Mercaptobenzothiazole allergenicity - Role of the thiol group

Cutaneous and Ocular Toxicology

Volumn 27, Issue 2, 2008, Pages 103-116

  Chipinda, Itai ^a,b   Zhang, Xing Dong ^a   Simoyi, Reuben H ^b   Siegel, Paul D ^a  

^a NATIONAL INSTITUTE FOR OCCUPATIONAL SAFETY AND HEALTH   (United States)

^b PORTLAND STATE UNIVERSITY   (United States)

Author keywords

Allergenicity; Contact dermatitis; Mercaptobenzothiazole; Thiol; Vulcanization accelerator

Indexed keywords

2 (METHYLTHIO)BENZOTHIAZOLE; 2 HYDROXYBENZOTHIAZOLE; BENZOTHIAZOLE; GLUTATHIONE REDUCTASE; MERCAPTOBENZOTHIAZOLE; THIOREDOXIN REDUCTASE;

ALLERGENICITY; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CONTACT DERMATITIS; CONTROLLED STUDY; DIAGNOSTIC TEST; DISULFIDE BOND; FEMALE; GUINEA PIG; GUINEA PIG MAXIMIZATION TEST; HUMAN; HUMAN CELL; NONHUMAN; OCCUPATIONAL SKIN DISEASE; REDUCTION KINETICS; RUBBER INDUSTRY; SKIN ALLERGY;

ANALYSIS OF VARIANCE; ANIMALS; BENZOTHIAZOLES; CROSS REACTIONS; DERMATITIS, ALLERGIC CONTACT; DISULFIDES; DOSE-RESPONSE RELATIONSHIP, DRUG; FEMALE; GLUTATHIONE REDUCTASE; GUINEA PIGS; HAPTENS; IMMUNIZATION; OXIDATION-REDUCTION; RUBBER; SKIN; SULFHYDRYL COMPOUNDS; THIOREDOXIN-DISULFIDE REDUCTASE;

ANIMALIA; CAVIA;

EID: 45849094747     PISSN: 15569527     EISSN: 15569535     Source Type: Journal    
DOI: 10.1080/15569520701713008     Document Type: Article

References (22)

1. Reddy CM, Quinn JG. Environmental chemistry of benzothiazoles derived from rubber. Environ Sci Technol 1997; 31:2847-2853.
2. Adams AK, Warshaw EM. Allergic contact dermatitis from mercapto compounds. Dermatitis 2006; 17:56-70.
3. Kaniwa M, Isama K, Nakamura A, Kantoh H, Hosono K, Itoh M, Shibata K, Usuda T, Asahi K, Osada T, Matsunaga K, Ueda H. Identification of causative chemicals of allergic contact dermatitis using a combination of patch testing in patients and chemical analysis. Application to cases from rubber gloves. Contact Dermatitis 1994; 31:65-71.
4. Landsteiner K, Jacobs J. Studies on the sensitization of animals with simple chemical compounds. J Exp Med 1936; 64:625-639.
5. Divkovic M, Pease CK, Gerberick GF, Basketter DA. Hapten-protein binding: from theory to practical application in the in vitro prediction of skin sensitization. Contact Dermatitis 2005; 53:189-200.
6. Gerberick GF, Vassallo JD, Bailey RE, Chaney JG, Morrall SW, Lepoittevin JP. Development of a peptide reactivity assay for screening contact allergens. Toxicol Sci 2004; 81:332-343.
7. Haneke KE, Tice RR, Carson BL, Margolin BH, Stokes WS. ICCVAM evaluation of the murine local lymph node assay. Data analyses completed by the National Toxicology Program Interagency Center for the Evaluation of Alternative Toxicological Methods. Regul Toxicol Pharmacol 2001; 34:274-286.
8. Magnusson B, Kligman AM. The identification of contact allergens by animal assay. The guinea pig maximization test. J Invest Dermatol 1969; 52:268-276.
9. Rosenkranz HS, Klopman G, Zhang YP, Graham C, Karol MH. Relationship between allergic contact dermatitis and electrophilicity. Environ Health Perspect 1999; 107:129-132.
10. Chipinda I, Hettick JM, Simoyi RH, Siegel PD. Oxidation of 2-mercaptobenzothiazole in latex gloves and its possible haptenation pathway. Chem Res Toxicol 2007; 20:1084-1092.
11. Worthington DJ, Rosemeyer MA. Glutathione reductase from human erythrocytes. Catalytic properties and aggregation. Eur J Biochem 1976; 67:231-238.
12. American Society for Testing and Materials. Standard Practice for Testing Guinea Pigs for Contact Allergens: Guinea Pig Maximization Test. F 720-81; West Conshohocken, PA: American Society for Testing and Materials. 2002; Ref Type: Catalog.
13. Sapan CV, Lundblad RL, Price NC. Colorimetric protein assay techniques. Biotechnol Appl Biochem 1999; 29(pt. 2):99-108.
14. Arner ES, Zhong L, Holmgren A. Preparation and assay of mammalian thioredoxin and thioredoxin reductase. Methods Enzymol 1999; 300:226-239.
15. Sjogren F, Anderson C. The spectrum of inflammatory cell response to dimethyl sulfoxide. Contact Dermatitis 2000; 42:216-221.
16. Moore KG, Dannenberg AM, Jr. Immediate and delayed (late-phase) dermal contact sensitivity reactions in guinea pigs. Passive transfer by IgG1 antibodies, initiation by mast cell degranulation, and suppression by soybean proteinase inhibitor. Int Arch Allergy Immunol 1993; 101:72-81.
17. Sjogren F, Anderson C, Groth O. The cellular dermal infiltrate in experimental immediate type cutaneous hypersensitivity. Acta Derm Venereol 1995; 75:417-421.
18. Dupuis G, Benezra C, Schlewer G, Stampf JL. Allergic contact dermatitis to alpha-methylene-gamma-butyrolactones. Preparation of alantolactone-protein conjugates and induction of contact sensitivity in the guinea pig by an alantolactone-skin protein conjugate. Mol Immunol 1980; 17:1045-1051.
19. Fedorowicz A, Singh H, Soderholm S, Demchuk E. Structure-activity models for contact sensitization. Chem Res Toxicol 2005; 18:954-969.
20. Hansson C, Agrup G. Stability of the mercaptobenzothiazole compounds. Contact Dermatitis 1993; 28:29-34.
21. Wang XS, Tabor MW. Studies of the reactivity of morpholine, 2-mercaptobenzothiazole and 2 of their derivatives with selected amino acids. Contact Dermatitis 1988; 19:16-21.
22. Fregert S, Skog E. Allergic contact dermatitis from mercaptobenzothiazole in cutting oil. Acta Derm Venereol 1962; 42:235-238.