Conjugation of 7-oxodehydroabietic acid to lysine, a haptenation mechanism for an oxidized resin acid with dermal sensitizing properties

Applied Occupational and Environmental Hygiene

Volumn 14, Issue 3, 1999, Pages 171-176

  Smith, Philip A ^a   Bowerbank, Christopher R ^b   Savage, Paul B ^b   Drown, David B ^c   Lee, Milton L ^b   Alexander, William ^d   Jederberg, Warren W ^e   Still, Kenneth ^c  

^a Uniformed Services of the Health Sciences   (United States)

^b Brigham Young University   (United States)

^c UTAH STATE UNIVERSITY   (United States)

^d NAVAL MEDICAL RESEARCH CENTER   (United States)

^e US Pacific Fleet   (United States)

Author keywords

7 Oxodehydroabietic Acid; Colophony; Dehydroabietic Acid; Haptenation; Oxidation; Rosin; Sensitization

Indexed keywords

ALCOHOL; ANTIBODY; BENZENE; DEHYDROABIETIC ACID; IMINE; LYSINE; MEMBRANE PROTEIN; ROSIN;

ANTIBODY PRODUCTION; ARTICLE; CATALYST; CELL MEMBRANE; CONJUGATION; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; OCCUPATIONAL ASTHMA; OXIDATION; PRIORITY JOURNAL; SKIN ALLERGY; SKIN SENSITIZATION;

ASTHMA; DERMATITIS, ALLERGIC CONTACT; DITERPENES; DITERPENES, ABIETANE; HAPTENS; HUMANS; LYSINE; OCCUPATIONAL DISEASES; OCCUPATIONAL EXPOSURE; PHENANTHRENES; RESINS, PLANT;

EID: 0033037990     PISSN: 1047322X     EISSN: None     Source Type: Journal    
DOI: 10.1080/104732299303133     Document Type: Article

References (39)

1. Widstrom, L.: Contact allergy to colophony in soldering flux. Contact Dermat., 9(3):205-207 (1983).
2. Mathias, C.G.T.; Adams, R.M.: Allergic contact dermatitis from rosin used as a soldering flux. J. Am. Acad. Dermatol., 10(3):454-456 (1984).
3. Goh, C.I.; Ng, S.K.: Airborne contact dermatitis to colophony in soldering flux. Contact Dermat., 17(2).89-91 (1978).
4. Fawcett, I.W.; Newman, T.A.J.; Pepys, J.: Asthma due to inhaled chemical agents-fumes from 'multicore' soldering flux and colophony resin. Clin. Allergy, 6(6):577-85 (1976).
5. Burge, P.S.; Harries, M.G.; O'Brien, I.M.; et al.: Respiratory disease in workers exposed to solder flux fumes containing colophony (pine resin). Clin Allergy, 8(1):1-14 (1978).
6. Burge, P.S.; Perks, W.; O'Brien; et al.: Occupational asthma in an electronics factory. Thorax, 34(1):13-18 (1979).
7. Burge, P.S.; Perks, W.H.; O'Brien, I.M. et al.: Occupational asthma in an electronics factory: a case control study to evaluate aetoiological factors. Thorax, 34(3):300-307 (1979).
8. Perks, W.; Burge, P.; Rehahn, M.; et al.: Work-related respiratory disease in employees leaving an electronics factory. Thorax, 34(1):19-22 (1979).
9. Burge, P.S.; Harries, M.G.; O'Brien, I.; et al.: Bronchial provocation studies in workers exposed to the fumes of electronic soldering fluxes. Clin Allergy, 10(2):137-149 (1980).
10. Burge, P.S.; Edge, G.; Hawkins, R.: et al.: Occupational asthma in a factory making flux-cored solder containing colophony. Thorax, 36(11):828-834 (1981).
11. Burge, P.S.: Occupational asthma due to soft soldering fluxes containing colophony (rosin, pine resin). Eur. J. Respir. Dis., 63(suppl. 123):65-77 (1982).
12. Burge, P.S.: Occupational asthma in electronics workers caused by colophony fumes: follow-up of affected workers. Thorax, 37(5):348-353 (1982).
13. Burge, P.S : Occupational asthma, rhinitis, and alveolitis due to colophony. Clin. Immunol. Allergy, 4(1):55-81 (1984).
14. Burge, P.S.; Wieland, A.; Robertson, A.S.; et al.: Occupational asthma due to unheated colophony. Br. J. hid. Med., 43(8):559-560 (1986).
15. Hendy, M S ; Beatttie, B.E.; Burge, P.S.: Occupational asthma due to an emulsified oil mist. Br J. Ind. Med., 42(1):51-54 (1985).
16. Karlberg, A.T.; Bergstedt, E.; Boman, A.; et al.: Is abietic acid the allergenic component of colophony? Contact Dermat., 13(4):209-215 (1985).
17. Karlberg, A.T.; Bohlinder, K.; Boman, A.; et al.: Identification of 15-hydroperoxyabietic acid as a contact allergen in Portuguese colophony. J. Pharm. Pharmacol, 40(1):42-47 (1987).
18. Karlberg, A.T.; Boman, A.; Hacksell, U.: et al: Contact allergy to dehydroabietic acid derivatives isolated from Portuguese colophony. Contact Dermat., 19(3):166-174 (1988).
19. Hausen, B.M.; Krohn, K.; Budianto, E.: Contact allergy due to colophony (VII). Sensitizing studies with oxidation products of abietic and related acids. Contact Dermat., 23(5):352-358 (1990).
20. Karlberg, A.T.: Air oxidation increases the allergenic potential of tall-oil rosin. Colophony contact allergens also identified in tall-oil rosin. Am. J. Contact Dermat., 2(1):43-49 (1991).
21. Gafvert, E.; Nilsson, U.; Karlberg, A.T.; et al.: Rosin allergy: identification of a dehydroabietic acid peroxide with allergenic properties. Arch. Dermatol. Res., 284(7):409-413 (1992).
22. Hausen, B.M.; Borries, M.; Budianto, E.; et al.: Contact allergy due to colophony (IX). Sensitization studies with further products isolated after oxidative degradation of resin acids and colophony. Contact Dermat., 29(5):234-240 (1993).
23. Gafvert, E.; Shao, L.P.: Karlberg, A.T.; et al.: Contact allergy to resin acid hydroperoxides. Hapten binding via free radicals and epoxides. Chem. Res. Toxicol., 7(2):260-266 (1994).
24. Shao, L.P.; Gafvert, E.; Nilsson, U.: et al: 15-Hydroperoxydehydroabietic acid-a contact allergen in colophony from Pinus species. Photochemistry, 38(4):853-857 (1995).
25. Karlberg, A.T.; Boman, A.; Nilsson, J.L.G.: Hydrogenation reduces the allergenicity of colophony (rosin). Contact Dermat., 19(1):22-29 (1988).
26. Sadhra, S.; Foulds, I.S.: Gray, C.N.: Identification of contact allergens in unmodified rosin using a combination of patch testing and analytical chemistry techniques. Br. J. Dermatol , 134(4):662-668 (1996).
27. Smith, P.A.: Gardner, D.R.; Drown, D.B.; et al.; Detection of resin acid compounds found in airborne particulate generated from rosin used as a soldering flux. Am. Ind. Hyg. Assoc. J., 58(12):000-000 (1997).
28. Smith, P.A.; Gardner, D.R.; Drown, D.; et al.: Oxidized Resin Acids in Aerosol Derived from Rosin Core Solder. Submitted to Am. Ind. Hyg. Assoc. J.,August,1997.
29. Cullen., R.T.; Cherrie, B.; Soutar, C.A.: Immune responses to colophony, an agent causing occupational asthma. Thorax, 47(12):1050-1055 (1992).
30. Rivers, J.K.; Rycroft, R.J.G.: Occupational contact urticaria from colophony. Contact Dermat., 17(3):181 (1987).
31. Lahti, A.: Immediate Contact Reactions. In: Textbook of Contact Dermatitis. pp.62-74. Rycroft, R.J.G.; Menne, T.; Frosch, P.J.; et al. eds. Springer-Verlag. Berlin (1992).
32. Dupuis G.; Benezra, C.: Chapter 6, Chemically reactive functions in haptens and in proteins. In: Allergic Contact Dermatitis to Simple Chemicals, a Molecular Approach, pp.47-85. Marcel Dekker, New York (1982).
33. Dayagi, S.; Degani, Y.: Methods of formation of the carbon-nitrogen double bond. In: The Chemistry of the Carbon-Nitrogen Double Bond, pp.64-68. Patai, S. ed. Wiley, New York (1970).
34. March, J.: In: Advanced Organic Chemistry, pp.896-897. Wiley, New York (1992).
35. Benezra, C.; Sigman, C.C.; Bagheri, D.; et al.: Molecular aspects of allergic contact dermatitis. In: Textbook of Contact Dermatitis, pp.105-119. Rycroft, R.J.G.; Menne, T.; Frosch, P.J.; et al. eds. Springer-Verlag, Berlin (1992).
36. Toivola, D M.; Isomaa, B.: Effects of dehydroabietic acid on the erythrocyte membrane. Chem. -Biol. Interactions, 79(1):65-78 (1991).
37. Butterfield, D.A.; Trad, C.H.; Hall, N.C.: Effects of dehydroabietic acid on the physical state of cytoskeletal proteins and the lipid bilayer of erythrocyte membranes. Biochim. et Biophys. Acta., 1192(2):185-189 (1994).
38. Villalain, J.: Location of the toxic molecule abietic acid in model membranes by MAS-NMR. Biochim. et Biophys. Acta, 1328(2):281-289 (1997).
39. Littlechild, J.; Watson, H.C.: A data-based reaction mechanism for type I fructose bisphosphate aldolase. Trends Biochem. Sci., 18(2):36-39 (1993).