Contact Allergy to Oxidized Linalool and Oxidized Limonene is Over-represented in Individuals with Photocontact Allergy to Ketoprofen

Authors

  • Magnus Bruze
  • Victoria Marmgren Department of Dermatology, Sahlgrenska University Hospital, SE-413 45 Gothenburg, Sweden
  • Annarita Antelmi
  • Monica Hindsén Stenström
  • Cecilia Svedman
  • Erik Zimersson
  • Martin Mowitz

DOI:

https://doi.org/10.2340/00015555-3799

Keywords:

allergic contact dermatitis, photoallergic, delayed hypersensitivity, fragrance substance, oxidation, patch-testing, photopatch-testing, photosensitizer

Abstract

Simultaneous contact allergies are common in individuals with photocontact allergy to ketoprofen. The rate of contact allergy to the fragrance substances oxidized linalool and oxidized limonene in ketoprofen-photo­allergic individuals were investigated in comparison with the corresponding rates in individuals without photo­contact allergy to ketoprofen, using Fisher’s exact test. A total of 4,021 patients were routinely tested with oxidized linalool; of whom 190 (4.7%) tested positively. For oxidized limonene the numbers were 3,797 patients and 111 positive reactions (2.9%). A total of 19 contact allergic reactions to oxidized linalool were noted in 29 patients (65.5%) who also had photocontact allergy to ketoprofen (p < 0.0001). The corresponding figures for oxidized limonene were 10 positive reactions in 24 ketoprofen-photoallergic individuals (41.7%) (p < 0.0001). Contact allergy to oxidized linalool and/or oxidized limonene is common in routinely tested patients with dermatitis and, particularly, in those patients who are photoallergic to ketoprofen.

Downloads

Download data is not yet available.

References

Mozzanica N, Pigatto PD. Contact and photocontact allergy to ketoprofen: clinical and experimental study. Contact Dermatitis 1990; 23: 336-340.

DOI: https://doi.org/10.1111/j.1600-0536.1990.tb05168.x

Pigatto P, Bigardi A, Legori A, Valsecchi R, Picardo M. Cross-reactions in patch testing and photopatch testing with ketoprofen, thiaprophenic acid, and cinnamic aldehyde. Am J Contact Dermat 1996; 7: 220-223.

DOI: https://doi.org/10.1097/01206501-199612000-00004

Le Coz CJ, Bottlaender A, Scrivener JN, Santinelli F, Cribier BJ, Heid E, et al. Photocontact dermatitis from ketoprofen and tiaprofenic acid: cross-reactivity study in 12 consecutive patients. Contact Dermatitis 1998; 38: 245-252.

DOI: https://doi.org/10.1111/j.1600-0536.1998.tb05737.x

Sugiyama M, Nakada T, Hosaka H, Sucki H, Iijima M. Photocontact dermatitis to ketoprofen. Am J Contact Dermat 2001; 12: 180-181.

DOI: https://doi.org/10.1097/01206501-200109000-00010

Vigan M, Girardin P, Desprez P, Adessi B, Aubin F, Laurent R. Photocontact dermatitis due to ketoprofen and photosensitization to tetrachlorosalicylanide and to Fenticlor(R). Ann Dermatol Venereol 2002; 129: 1125-1127.

Durbize E, Vigan M, Puzenat E, Girardin P, Adessi B, Desprez PH, et al. Spectrum of cross-photosensitization in 18 consecutive patients with contact photoallergy to ketoprofen: associated photoallergies to non-benzophenone-containing molecules. Contact Dermatitis 2003; 48: 144.

DOI: https://doi.org/10.1034/j.1600-0536.2003.00066.x

Matthieu L, Meuleman L, Van Hecke E, Blondeel A, Dezfoulian B, Constandt L, et al. Contact and photocontact allergy to ketoprofen. The Belgian experience. Contact Dermatitis 2004; 50: 238-241.

DOI: https://doi.org/10.1111/j.0105-1873.2004.00323.x

Hindsén M, Zimerson E, Bruze M. Photoallergic contact dermatitis from ketoprofen in southern Sweden. Contact Dermatitis 2006; 54: 150-157.

DOI: https://doi.org/10.1111/j.0105-1873.2005.00778.x

Marmgren V, Hindsén M, Zimerson E, Bruze M. Successful photopatch testing with ketoprofen using one-hour occlusion. Acta Derm Venereol 2011; 91: 131-136.

DOI: https://doi.org/10.2340/00015555-1029

Karlsson I, Vanden Broecke K, Mårtensson J, Goossens A, Börje A. Clinical and experimental studies of octocrylene's allergenic potency. Contact Dermatitis 2011; 64: 343-352.

DOI: https://doi.org/10.1111/j.1600-0536.2011.01899.x

Foti C, Bonamonte D, Conserva A, Stingeni L, Lisi P, Lionetti N, et al. Allergic and photoallergic contact dermatitis from ketoprofen: evaluation of cross-reactivities by a combination of photopatch testing and computerized conformational analysis. Curr Pharm Des 2008; 14: 2833-2839.

DOI: https://doi.org/10.2174/138161208786369696

Karlsson I, Persson E, Ekebergh A, Mårtensson J, Börje A. Ketoprofen-induced formation of amino acid photoadducts: possible explanation for photocontact allergy to ketoprofen. Chem Res Toxicol 2014; 27: 1294-1303.

DOI: https://doi.org/10.1021/tx5001656

Gonçalo M, Ferguson J, Bonevalle A, Bruynzeel DP, Gimenez-Arnau A, Goossens A, et al. Photopatch testing: recommendations for a European photopatch test baseline series. Contact Dermatitis 2013; 68: 239-243.

DOI: https://doi.org/10.1111/cod.12037

Thune P, Jansén C, Wennersten G, Rystedt I, Brodthagen H, McFadden N. The Scandinavian multicenter photopatch study 1980-1985: final report. Photodermatol 1988; 5: 261-269.

DOI: https://doi.org/10.1007/978-3-642-74299-6_97

Bråred Christensson J, Andersen KE, Bruze M, Johansen JD, Garcia-Bravo B, Gimenez-Arnau A, et al. Air-oxidized linalool: a frequent cause of fragrance contact allergy. Contact Dermatitis 2012; 67: 247-259.

DOI: https://doi.org/10.1111/j.1600-0536.2012.02134.x

Bråred Christensson J, Matura M, Gruvberger B, Bruze M, Karlberg AT. Linalool - a significant contact sensitizer after air exposure. Contact Dermatitis 2010; 62: 32-41.

DOI: https://doi.org/10.1111/j.1600-0536.2009.01657.x

Christensson J, Karlberg AT, Andersen KE, Bruze M, Johansen JD, Garcia-Bravo B, et al. Oxidized limonene and oxidized linalool?-?concomitant contact allergy to common fragrance terpenes. Contact Dermatitis 2016; 74: 273-280.

DOI: https://doi.org/10.1111/cod.12545

Bråred Christensson J, Andersen KE, Bruze M, Johansen JD, Garcia-Bravo B, Gimenez-Arnau A, et al. An international multicentre study on the allergenic activity of air-oxidized R-limonene. Contact Dermatitis 2013; 68: 214-223.

DOI: https://doi.org/10.1111/cod.12036

Bråred Christensson J, Andersen KE, Bruze M, Johansen JD, Garcia-Bravo B, Gimenez-Arnau A, et al. Positive patch test reactions to oxidized limonene: exposure and relevance. Contact Dermatitis 2014; 71: 264-272.

DOI: https://doi.org/10.1111/cod.12285

Bruze M, Isaksson M, Gruvberger B, Frick-Engfeldt M. Recommendation of appropriate amounts of petrolatum preparation to be applied at patch testing. Contact Dermatitis 2007; 56: 281-285.

DOI: https://doi.org/10.1111/j.1600-0536.2007.01098.x

Mowitz M, Zimerson E, Svedman C, Bruze M. Stability of fragrance patch test preparations applied in test chambers. Br J Dermatol 2012; 167: 822-827.

DOI: https://doi.org/10.1111/j.1365-2133.2012.11143.x

Fregert S. Manual of contact dermatitis. 2nd edition. Copenhagen: Munksgaard, 1981.

Johansen JD, Aalto-Korte K, Agner T, Andersen KE, Bircher A, Bruze M, et al. European Society of Contact Dermatitis guideline for diagnostic patch testing - recommendations on best practice. Contact Dermatitis 2015; 73: 195-221.

DOI: https://doi.org/10.1111/cod.12432

Bruynzeel DP, Ferguson J, Andersen K, Gonçalo M, English J, Goossens A, et al. Photopatch testing: a consensus methodology for Europe. The European Taskforce for Photopatch Testing. J Eur Acad Dermatol Venereol 2004; 18: 679-682.

DOI: https://doi.org/10.1111/j.1468-3083.2004.01053.x

Bäckström P, Okecha S, De Sliva N, Wijekoon D, Norin T. Photooxidation with simultaneous reduction of hydroperoxides with tetrabutylammonium borohydride. Synthesis of perillenal from myrcene. Acta Chem Scand 1982; 36b: 31-36.

DOI: https://doi.org/10.3891/acta.chem.scand.36b-0031

Sköld M, Börje A, Harambasic E, Karlberg AT. Contact allergens formed on air exposure of linalool. Identification and quantification of primary and secondary oxidation products and the effect on skin sensitization. Chem Res Toxicol 2004; 17: 1697-1705.

DOI: https://doi.org/10.1021/tx049831z

Hagvall L, Bråred Christensson J. Patch-testing with main sensitizers does not detect all cases of contact allergy to oxidized lavender oil. Acta Derm Venereol 2016; 96: 679-684.

DOI: https://doi.org/10.2340/00015555-2319

Hagvall L, Sköld M, Bråred-Christensson J, Börje A, Karlberg AT. Lavender oil lacks natural protection against autoxidation, forming strong contact allergens on air exposure. Contact Dermatitis 2008; 59: 143-150.

DOI: https://doi.org/10.1111/j.1600-0536.2008.01402.x

Karlberg AT, Börje A, Duus Johansen J, Lidén C, Rastogi S, Roberts D, et al. Activation of non-sensitizing or low-sensitizing fragrance substances into potent sensitizers - prehaptens and prohaptens. Contact Dermatitis 2013; 69: 323-334.

DOI: https://doi.org/10.1111/cod.12127

Kern S, Dkhil H, Hendarsa P, Ellis G, Natsch A. Detection of potentially skin sensitizing hydroperoxides of linalool in fragranced products. Anal Bioanal Chem 2014; 40625: 6165-6178.

DOI: https://doi.org/10.1007/s00216-014-8066-3

Foti C, Romita P, Antelmi A. Sunscreen allergy due to cinnamyl alcohol in a ketoprofen-sensitized patient. Eur J Dermatol 2011; 21: 295.

DOI: https://doi.org/10.1684/ejd.2011.1256

Sköld M, Börje A, Matura M, Karlberg AT. Studies on the autoxidation and sensitizing capacity of the fragrance chemical linalool, identifying a linalool hydroperoxide. Contact Dermatitis 2002; 46: 267-272.

DOI: https://doi.org/10.1034/j.1600-0536.2002.460504.x

Bråred Christensson J, Matura M, Bäcktorp C, Börje A, Nilsson JL, Karlberg AT. Hydroperoxides form specific antigens in contact allergy. Contact Dermatitis 2006; 55: 230-237.

DOI: https://doi.org/10.1111/j.1600-0536.2006.00913.x

Christensson JB, Hellsén S, Börje A, Karlberg AT. Limonene hydroperoxide analogues show specific patch test reactions. Contact Dermatitis 2014; 70: 291-299.

DOI: https://doi.org/10.1111/cod.12195

Natsch A, Emter R, Badertscher RP, Brunner G, Granier T, Kern S, et al. Oxidative tryptophan modification by terpene- and squalene-hydroperoxides and a possible link to cross-reactions in diagnostic tests. Chem Res Toxicol 2015; 28: 1205-1208.

DOI: https://doi.org/10.1021/acs.chemrestox.5b00039

Bennike NH, Lepoittevin JP, Johansen JD. Can contact allergy to p-phenylenediamine explain the high rates of terpene hydroperoxide allergy??-?An epidemiological study based on consecutive patch test results. Contact Dermatitis 2017; 76: 67-73.

DOI: https://doi.org/10.1111/cod.12618

Karlberg AT, Börje A, Lepoittevin JP, Gimenez-Arnau E, Bråred Christensson J, Hagvall L. Letter to the editor regarding the article by Natsch, et al. Chem Res Toxicol 2015; 28: 2079-2081.

DOI: https://doi.org/10.1021/acs.chemrestox.5b00306

Raffalli C, Clouet E, Kuresepi S, Damiens MH, Lepoittevin JP, Pallardy M, et al. Fragrance allergens linalool and limonene allylic hydroperoxides in skin allergy: mechanisms of action focusing on transcription factor Nrf2. Toxicol Sci 2018; 161: 139-148.

DOI: https://doi.org/10.1093/toxsci/kfx207

Deza G, García-Bravo B, Silvestre JF, Pastor-Nieto MA, González-Pérez R, Heras-Mendaza F, et al. Contact sensitization to limonene and linalool hydroperoxides in Spain: a GEIDAC* prospective study. Contact Dermatitis 2017; 76: 74-80.

DOI: https://doi.org/10.1111/cod.12714

Audrain H, Kenward C, Lovell CR, Green C, Ormerod AD, Sansom J, et al. Allergy to oxidized limonene and linalool is frequent in the U.K. Br J Dermatol 2014; 171: 292-297.

DOI: https://doi.org/10.1111/bjd.13037

Matura M, Goossens A, Bordalo O, Garcia-Bravo B, Magnusson K, Wrangsjö K, et al. Oxidized citrus oil (R-limonene): a frequent skin sensitizer in Europe. J Am Acad Dermatol 2002; 47: 709-714.

DOI: https://doi.org/10.1067/mjd.2002.124817

Matura M, Goossens A, Bordalo O, Garcia-Bravo B, Magnusson K, Wrangsjö K, et al. Patch testing with oxidized R-(+)-limonene and its hydroperoxide fraction. Contact Dermatitis 2003; 49: 15-21.

DOI: https://doi.org/10.1111/j.0105-1873.2003.00135.x

Matura M, Sköld M, Börje A, Andersen KE, Bruze M, Frosch P, et al. Not only oxidized R-(+)- but also S-(-)-limonene is a common cause of contact allergy in dermatitis patients in Europe. Contact Dermatitis 2006; 55: 274-279

DOI: https://doi.org/10.1111/j.1600-0536.2006.00939.x

Karlberg AT, Dooms-Goossens A. Contact allergy to oxidized d-limonene among dermatitis patients. Contact Dermatitis 1997; 36: 201-206.

DOI: https://doi.org/10.1111/j.1600-0536.1997.tb00270.x

Bruze M, Condé-Salazar L, Goossens A, Kanerva R, White IR. Thoughts on sensitizers in a standard patch test series. The European Society of Contact Dermatitis. Contact Dermatitis 1999; 41: 241-250.

DOI: https://doi.org/10.1111/j.1600-0536.1999.tb06154.x

Elliott JF, Ramzy A, Nilsson U, Moffat W, Suzuki K. Severe intractable eyelid dermatitis probably caused by exposure to hydroperoxides of linalool in a heavily fragranced shampoo. Contact Dermatitis 2017; 76: 114-115.

DOI: https://doi.org/10.1111/cod.12738

Gatica-Ortega ME, Pastor-Nieto MA, Schoendorff-Ortega C, Mollejo-Villanueva M, Giménez-Arnau A. Lymphomatoid contact dermatitis caused by limonene hydroperoxides confirmed by an exposure provocation test with the involved personal hygiene products. Contact Dermatitis 2018; 78: 230-233.

DOI: https://doi.org/10.1111/cod.12908

Isaksson M, Karlberg AT, Nilsson U. Allergic contact dermatitis caused by oxidized linalool in a deodorant. Contact Dermatitis 2019; 81: 213-214.

DOI: https://doi.org/10.1111/cod.13276

Ramzi A, Ahmadi H, Sadiktsis I, Nilsson U. A two-dimensional non-comprehensive reversed/normal phase high-performance liquid chromatography/tandem mass spectrometry system for determination of limonene and linalool hydroperoxides. J Chromatogr A 2018; 1566: 102-110.

DOI: https://doi.org/10.1016/j.chroma.2018.06.056

Natsch A, Nägelin M, Leijs H, van Strien M, Giménez-Arnau E, Vey M, et al. Exposure source for skin sensitizing hydroperoxides of limonene and linalool remains elusive: an analytical market surveillance. Food Chem Toxicol 2019; 127: 156-162.

DOI: https://doi.org/10.1016/j.fct.2019.03.028

Wlodek C, Penfold CM, Bourke JF, Chowdhury MM, Cooper SM, Ghaffar S, et al. Recommendation to test limonene hydroperoxides 0·3% and linalool hydroperoxides 1·0% in the British baseline patch test series. Br J Dermatol 2017; 177: 1708-1715.

DOI: https://doi.org/10.1111/bjd.15648

Wilkinson M, Gallo R, Goossens, A, Johansen JD, Rustemeyer T, Sánchez-Pérez J, et al. A proposal to create an extension to the European baseline series. Contact Dermatitis 2018; 78: 101-108.

DOI: https://doi.org/10.1111/cod.12918

Andersch Björkman Y, Hagvall L, Siwmark C, Niklasson B, Karlberg AT, Bråred Christensson J. Air-oxidized linalool elicits eczema in allergic patients?-?a repeated open application test study. Contact Dermatitis 2014; 70: 129-138.

DOI: https://doi.org/10.1111/cod.12163

Bennike NH, Palangi L, Christensson JB, Nilsson U, Zachariae C, Johansen JD, et al. Allergic contact dermatitis caused by hydroperoxides of limonene and dose-response relationship - a repeated open application test (ROAT) study. Contact Dermatitis 2019; 80: 208-216.

DOI: https://doi.org/10.1111/cod.13168

Published

2021-05-19

How to Cite

Bruze, M., Marmgren, V., Antelmi, A., Hindsén Stenström, M., Svedman, C., Zimersson, E., & Mowitz, M. (2021). Contact Allergy to Oxidized Linalool and Oxidized Limonene is Over-represented in Individuals with Photocontact Allergy to Ketoprofen. Acta Dermato-Venereologica, 101(5), adv00454. https://doi.org/10.2340/00015555-3799