Contact dermatitis to topical drugs is frequent in leg ulcer patients and a major factor contributing to delayed wound healing. Among the most common contact allergens are topical antibiotics, which should be avoided in these patients [1]. An alternative for the control of bacterial contaminations are disinfectants. Triphenylmethane dyes are traditionally used for this purpose. Among those, gentian violet and brilliant green – (4-[4-(diethylamino)benzhydrylene]cyclo-hexa-2,4-dien-1-ylidene)diethylammonium hydrogen sulphate; C.I. 42040 – are still popular because of the relatively broad range of antibacterial activity, low price, easy preparation and their availability in aqueous solutions [2]. Table 1. Open epicutaneous test reactions
{"title":"Contact Allergy to Brilliant Green in a Leg Ulcer Patient","authors":"U. Wollina, A. Koch, Iris-Sylvia Schulze","doi":"10.1159/000071934","DOIUrl":"https://doi.org/10.1159/000071934","url":null,"abstract":"Contact dermatitis to topical drugs is frequent in leg ulcer patients and a major factor contributing to delayed wound healing. Among the most common contact allergens are topical antibiotics, which should be avoided in these patients [1]. An alternative for the control of bacterial contaminations are disinfectants. Triphenylmethane dyes are traditionally used for this purpose. Among those, gentian violet and brilliant green – (4-[4-(diethylamino)benzhydrylene]cyclo-hexa-2,4-dien-1-ylidene)diethylammonium hydrogen sulphate; C.I. 42040 – are still popular because of the relatively broad range of antibacterial activity, low price, easy preparation and their availability in aqueous solutions [2]. Table 1. Open epicutaneous test reactions","PeriodicalId":12086,"journal":{"name":"Exogenous Dermatology","volume":"34 1","pages":"49 - 50"},"PeriodicalIF":0.0,"publicationDate":"2003-08-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"85121686","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
In vitro testing methods for the evaluation of potential skin hazards due to chemicals released from textiles or textile auxiliaries are presented and discussed in order to establish further focussed research.
{"title":"Surface of Textiles and the Human Skin","authors":"D. Knittel, K. Beermann, E. Schollmeyer","doi":"10.1159/000071929","DOIUrl":"https://doi.org/10.1159/000071929","url":null,"abstract":"In vitro testing methods for the evaluation of potential skin hazards due to chemicals released from textiles or textile auxiliaries are presented and discussed in order to establish further focussed research.","PeriodicalId":12086,"journal":{"name":"Exogenous Dermatology","volume":"60 1","pages":"17 - 22"},"PeriodicalIF":0.0,"publicationDate":"2003-08-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"89045495","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Background: For testing skin irritancy, many cytotoxicity tests have been carried out and evaluated. It is evident that human subjects cannot be used as the initial experimental subjects. Therefore, several models, including monolayer and three-dimensional cultures, have been tested to measure skin irritancy. Objective: This study was done to compare several alternative in vitro methods used for evaluating the irritancy of cosmetic constituents. Methods: Cytotoxicity was measured by checking ED50 values with the MTT assay. The irritancy ranking of the five irritants was analyzed using the ED50 values. Results: In terms of irritancy ranking, good correlations were obtained between the monolayer and three-dimensional culture systems, although the concentrations of irritants needed to obtain the ED50 values differed considerably. Conclusion: These findings suggest that caution is necessary in the evaluation of the results of such tests, because the concentration of irritants needed to obtain the ED50 values may differ depending on the culture model used.
{"title":"Application of in vitro Monolayer and Three-Dimensional Culture Systems to Evaluate the Irritancy of Cosmetic Constituents","authors":"D. Suh, J.H. Han, K. Park, H. Eun","doi":"10.1159/000071933","DOIUrl":"https://doi.org/10.1159/000071933","url":null,"abstract":"Background: For testing skin irritancy, many cytotoxicity tests have been carried out and evaluated. It is evident that human subjects cannot be used as the initial experimental subjects. Therefore, several models, including monolayer and three-dimensional cultures, have been tested to measure skin irritancy. Objective: This study was done to compare several alternative in vitro methods used for evaluating the irritancy of cosmetic constituents. Methods: Cytotoxicity was measured by checking ED50 values with the MTT assay. The irritancy ranking of the five irritants was analyzed using the ED50 values. Results: In terms of irritancy ranking, good correlations were obtained between the monolayer and three-dimensional culture systems, although the concentrations of irritants needed to obtain the ED50 values differed considerably. Conclusion: These findings suggest that caution is necessary in the evaluation of the results of such tests, because the concentration of irritants needed to obtain the ED50 values may differ depending on the culture model used.","PeriodicalId":12086,"journal":{"name":"Exogenous Dermatology","volume":"8 1","pages":"41 - 48"},"PeriodicalIF":0.0,"publicationDate":"2003-08-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"82223655","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Reports on contact sensitization to disperse dyes are increasing, although its true incidence is not known. In fact, the diagnosis of textile contact dermatitis may be difficult because of its clinical polymorphism, including unusual clinical patterns and unexpected localizations. This review summarizes literature data referring to clinical aspects of allergic dermatitis due to disperse dyes and presents our data on this issue. Based on our findings, two different clinical subtypes of disperse dye dermatitis can be identified: an ‘eczematous’ and an ‘oedematous plaque’ type. The former is characterized by eczematous lesions in patients sensitized to disperse dyes, but frequently to other haptens too. The ‘oedematous-plaque’ type, mainly associated with disperse blue sensitization, includes unusual clinical aspects. However, its localization to skin sites of friction or sweating may induce the suspicion of a textile dye dermatitis.
{"title":"Disperse Dye Dermatitis: Clinical Aspects and Sensitizing Agents","authors":"F. Giusti, S. Seidenari","doi":"10.1159/000071927","DOIUrl":"https://doi.org/10.1159/000071927","url":null,"abstract":"Reports on contact sensitization to disperse dyes are increasing, although its true incidence is not known. In fact, the diagnosis of textile contact dermatitis may be difficult because of its clinical polymorphism, including unusual clinical patterns and unexpected localizations. This review summarizes literature data referring to clinical aspects of allergic dermatitis due to disperse dyes and presents our data on this issue. Based on our findings, two different clinical subtypes of disperse dye dermatitis can be identified: an ‘eczematous’ and an ‘oedematous plaque’ type. The former is characterized by eczematous lesions in patients sensitized to disperse dyes, but frequently to other haptens too. The ‘oedematous-plaque’ type, mainly associated with disperse blue sensitization, includes unusual clinical aspects. However, its localization to skin sites of friction or sweating may induce the suspicion of a textile dye dermatitis.","PeriodicalId":12086,"journal":{"name":"Exogenous Dermatology","volume":"26 1","pages":"6 - 10"},"PeriodicalIF":0.0,"publicationDate":"2003-08-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"75121115","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The Draize test has long been used as a method to evaluate skin irritancy. However, alternative methods have since been developed, in response to pressure from the ever-increasing movement of animal protectionists. Cell culture represents the most promising alternative method, and many trials of various kinds are under way, for example the monolayer culture, skin explant culture and three-dimensional skin equivalent culture. It is quite likely that better-qualified three-dimensional culture systems constitute the final goal in the search for alternative methods to evaluate skin irritancy. However, its effective validation will require not only further large-scale studies, but also the development of superior artificial skin models, with properties more closely resembling those of normal skin. In this review, we focus mainly on the skin equivalent culture method for measuring skin irritancy. Its superiority to other models as well as its problems and limitations are discussed.
{"title":"Alternative Methods for Evaluating Skin Irritation Using Three-Dimensional Cultures","authors":"H. Eun, Chunja Nam","doi":"10.1159/000071926","DOIUrl":"https://doi.org/10.1159/000071926","url":null,"abstract":"The Draize test has long been used as a method to evaluate skin irritancy. However, alternative methods have since been developed, in response to pressure from the ever-increasing movement of animal protectionists. Cell culture represents the most promising alternative method, and many trials of various kinds are under way, for example the monolayer culture, skin explant culture and three-dimensional skin equivalent culture. It is quite likely that better-qualified three-dimensional culture systems constitute the final goal in the search for alternative methods to evaluate skin irritancy. However, its effective validation will require not only further large-scale studies, but also the development of superior artificial skin models, with properties more closely resembling those of normal skin. In this review, we focus mainly on the skin equivalent culture method for measuring skin irritancy. Its superiority to other models as well as its problems and limitations are discussed.","PeriodicalId":12086,"journal":{"name":"Exogenous Dermatology","volume":"27 1","pages":"1 - 5"},"PeriodicalIF":0.0,"publicationDate":"2003-08-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"87460952","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Background: The skin of patients with atopic dermatitis (AD) is known to have a defective barrier function of the stratum corneum (SC) that facilitates the induction of unique skin hypersensitivity to various environmental allergens and irritants. However, it has not been determined whether there are characteristics unique to AD, because an apparently similar dysfunction of the SC is also observable in other inflammatory dermatoses such as psoriasis. Objective: Our purpose was to analyze the SC functions of patients with AD in comparison with those with psoriasis, an endogenously induced immune-mediated dermatosis. Methods: We conducted functional analyses of the lesional and nonlesional skin of AD and psoriasis patients by using noninvasive biophysical methods. Results: When we classified their skin changes into several subtypes based on the clinical features, we found that a severity-dependent disruption in the barrier function as well as a decrease in the SC hydration occurred in both dermatoses and to a similar degree. The extent of their SC barrier damage on the skin of the trunk and limbs was almost comparable to that of normal facial skin of healthy individuals. We also found similarly small, immature corneocytes that are associated with epidermal hyperproliferation accompanied by poor differentiation in both dermatoses. Moreover, we found similar but much milder SC functional abnormalities in the nonlesional skin where the extent of the dysfunction was much closer to that of healthy skin than to that of lesional skin. Conclusion: From these data, we could not find any differences in the functional abnormalities of the SC of AD patients that would justify considering it to be a unique dermatosis at least in terms of barrier damage. Because the presence of smaller corneocytes reflects the active proliferation of the underlying epidermis, we think that the barrier impairment and deficient water-holding capacity of the SC develop as a result of the enhanced epidermal proliferation in both dermatoses that is caused by the underlying inflammation.
{"title":"Functional Analysis of the Stratum corneum of Patients with Atopic Dermatitis: Comparison with Psoriasis vulgaris","authors":"H. Kobayashi, H. Tagami","doi":"10.1159/000071932","DOIUrl":"https://doi.org/10.1159/000071932","url":null,"abstract":"Background: The skin of patients with atopic dermatitis (AD) is known to have a defective barrier function of the stratum corneum (SC) that facilitates the induction of unique skin hypersensitivity to various environmental allergens and irritants. However, it has not been determined whether there are characteristics unique to AD, because an apparently similar dysfunction of the SC is also observable in other inflammatory dermatoses such as psoriasis. Objective: Our purpose was to analyze the SC functions of patients with AD in comparison with those with psoriasis, an endogenously induced immune-mediated dermatosis. Methods: We conducted functional analyses of the lesional and nonlesional skin of AD and psoriasis patients by using noninvasive biophysical methods. Results: When we classified their skin changes into several subtypes based on the clinical features, we found that a severity-dependent disruption in the barrier function as well as a decrease in the SC hydration occurred in both dermatoses and to a similar degree. The extent of their SC barrier damage on the skin of the trunk and limbs was almost comparable to that of normal facial skin of healthy individuals. We also found similarly small, immature corneocytes that are associated with epidermal hyperproliferation accompanied by poor differentiation in both dermatoses. Moreover, we found similar but much milder SC functional abnormalities in the nonlesional skin where the extent of the dysfunction was much closer to that of healthy skin than to that of lesional skin. Conclusion: From these data, we could not find any differences in the functional abnormalities of the SC of AD patients that would justify considering it to be a unique dermatosis at least in terms of barrier damage. Because the presence of smaller corneocytes reflects the active proliferation of the underlying epidermis, we think that the barrier impairment and deficient water-holding capacity of the SC develop as a result of the enhanced epidermal proliferation in both dermatoses that is caused by the underlying inflammation.","PeriodicalId":12086,"journal":{"name":"Exogenous Dermatology","volume":"50 1","pages":"33 - 40"},"PeriodicalIF":0.0,"publicationDate":"2003-08-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"88448530","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Colour film developers based upon substituted phenylene diamines have been a known cause of occupational allergic contact dermatitis (ACD) and lichenoid eruptions. These reactions are well documented in patients involved in the developing of colour photography film. It has been suggested that lichenoid eruptions evolve from ACD. We describe a patient who presented with an eruption identical to lichen planus soon after commencing work as a technician in a motion-picture-film-processing facility. There was no history of a preceding ACD. Patch testing identified sensitivity to Kodak colour developer (CD-2) used for motion picture film, with which he worked on a daily basis.
{"title":"Hypertrophic Lichenoid Eruption Caused by Exposure to Colour Film Developer Used for Motion Picture Film","authors":"K. Thai, S. Freeman","doi":"10.1159/000076802","DOIUrl":"https://doi.org/10.1159/000076802","url":null,"abstract":"Colour film developers based upon substituted phenylene diamines have been a known cause of occupational allergic contact dermatitis (ACD) and lichenoid eruptions. These reactions are well documented in patients involved in the developing of colour photography film. It has been suggested that lichenoid eruptions evolve from ACD. We describe a patient who presented with an eruption identical to lichen planus soon after commencing work as a technician in a motion-picture-film-processing facility. There was no history of a preceding ACD. Patch testing identified sensitivity to Kodak colour developer (CD-2) used for motion picture film, with which he worked on a daily basis.","PeriodicalId":12086,"journal":{"name":"Exogenous Dermatology","volume":"7 1","pages":"201 - 205"},"PeriodicalIF":0.0,"publicationDate":"2003-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"86535730","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Background: Xerosis, a well-known problem in the elderly part of the population, is often exacerbated in winter with negative effects on daily life. Objective: To describe differences in stratum corneum function of the lower legs in winter compared to summer using objective biometric methods. Methods: The following techniques were utilized: colorimetry, evaporimetry, laser Doppler perfusion imaging, sticky slides (D-Squames®) and corneometry. The reaction to a 24-hour patch test with sodium lauryl sulfate, burning to chloroform:methanol and the whealing response to dimethylsulfoxide were also studied. Results: In winter, the stratum corneum had a looser structure and a diminished barrier function with an increased neurosensory reactivity. Conclusion: The results suggest that the exacerbation of xerosis in the winter is accompanied by structural changes in the stratum corneum, making it looser and more permeable to chemical irritants with a heightened response to neurosensory stimuli.
{"title":"Xerotic Skin of the Elderly: A Summer versus Winter Comparison Based on Biophysical Measurements","authors":"F. Andersen, K. H. Andersen, A. Kligman","doi":"10.1159/000076800","DOIUrl":"https://doi.org/10.1159/000076800","url":null,"abstract":"Background: Xerosis, a well-known problem in the elderly part of the population, is often exacerbated in winter with negative effects on daily life. Objective: To describe differences in stratum corneum function of the lower legs in winter compared to summer using objective biometric methods. Methods: The following techniques were utilized: colorimetry, evaporimetry, laser Doppler perfusion imaging, sticky slides (D-Squames®) and corneometry. The reaction to a 24-hour patch test with sodium lauryl sulfate, burning to chloroform:methanol and the whealing response to dimethylsulfoxide were also studied. Results: In winter, the stratum corneum had a looser structure and a diminished barrier function with an increased neurosensory reactivity. Conclusion: The results suggest that the exacerbation of xerosis in the winter is accompanied by structural changes in the stratum corneum, making it looser and more permeable to chemical irritants with a heightened response to neurosensory stimuli.","PeriodicalId":12086,"journal":{"name":"Exogenous Dermatology","volume":"117 1","pages":"190 - 194"},"PeriodicalIF":0.0,"publicationDate":"2003-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"80385040","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Contact dermatitis is a common cause of eczematous cheilitis. In a Singapore series, allergic contact dermatitis is commoner than irritant contact dermatitis. More females are affected than males. Eczematous cheilitis usually presents in the 3rd and 4th decades of life. Eczematous cheilitis tends to occur among office workers and professionals (50.5%). This is probably due to the more frequent use of cosmetics and lip preparations among office workers compared to ‘blue collar’ workers. Irritant contact cheilitis is often seen in individuals with an underlying endogenous tendency to eczema, e.g. atopic dermatitis. Contact irritants include lip cosmetics, toothpastes and dentrifices. In the early 1990s, tartar control (pyrophosphates) toothpastes were reported to cause outbreaks of irritant contact dermatitis on the lips and peri-oral skin. Other irritants include traditional Chinese medicines. Allergic contact cheilitis occurs from lip cosmetics, toothpastes and medicaments. Allergic contact cheilitis accounted for 35% of eczematous cheilitis presenting at the Singapore clinic. The commonest cause of allergic contact cheilitis was lip cosmetics. They include lipsticks, lip balms and other cosmetic preparations. In Singapore, ricinoleic acid present in lipsticks accounted for about 10% of all cases of allergic contact dermatitis. Other allergens include other lipstick ingredients, sunscreen agents, toothpaste ingredients, colophony in dental floss and toothpicks, nail varnish, cosmetics and nickel in the mouthpiece of a flute. Recently sunscreens have become a common sensitizer in lip cosmetics. Other allergens include fragrance, balsam of Peru, lanolin and flavourings (strawberry and vanilla). Toothpastes are the next most common cause of allergic contact cheilitis. Dentrifices and dental prostheses have been reported to cause allergic contact dermatitis. Diagnostic clues have to be obtained from a careful history which includes a review of oral rinses, toothpastes, cleansers, mouthwashes, dentrifices, denture materials, chewing gum and lipsticks used by the patient. Patch testing with these products is essential for investigating the possible cause of allergic contact cheilitis. However, there is a group of patients with troublesome cheilitis, who are often severely affected, but in whom the cause of the cheilitis remains obscure. This group may represent patients with endogenous cheilitis or factitious cheilitis.
{"title":"Contact Cheilitis – A Review","authors":"C. Goh","doi":"10.1159/000076797","DOIUrl":"https://doi.org/10.1159/000076797","url":null,"abstract":"Contact dermatitis is a common cause of eczematous cheilitis. In a Singapore series, allergic contact dermatitis is commoner than irritant contact dermatitis. More females are affected than males. Eczematous cheilitis usually presents in the 3rd and 4th decades of life. Eczematous cheilitis tends to occur among office workers and professionals (50.5%). This is probably due to the more frequent use of cosmetics and lip preparations among office workers compared to ‘blue collar’ workers. Irritant contact cheilitis is often seen in individuals with an underlying endogenous tendency to eczema, e.g. atopic dermatitis. Contact irritants include lip cosmetics, toothpastes and dentrifices. In the early 1990s, tartar control (pyrophosphates) toothpastes were reported to cause outbreaks of irritant contact dermatitis on the lips and peri-oral skin. Other irritants include traditional Chinese medicines. Allergic contact cheilitis occurs from lip cosmetics, toothpastes and medicaments. Allergic contact cheilitis accounted for 35% of eczematous cheilitis presenting at the Singapore clinic. The commonest cause of allergic contact cheilitis was lip cosmetics. They include lipsticks, lip balms and other cosmetic preparations. In Singapore, ricinoleic acid present in lipsticks accounted for about 10% of all cases of allergic contact dermatitis. Other allergens include other lipstick ingredients, sunscreen agents, toothpaste ingredients, colophony in dental floss and toothpicks, nail varnish, cosmetics and nickel in the mouthpiece of a flute. Recently sunscreens have become a common sensitizer in lip cosmetics. Other allergens include fragrance, balsam of Peru, lanolin and flavourings (strawberry and vanilla). Toothpastes are the next most common cause of allergic contact cheilitis. Dentrifices and dental prostheses have been reported to cause allergic contact dermatitis. Diagnostic clues have to be obtained from a careful history which includes a review of oral rinses, toothpastes, cleansers, mouthwashes, dentrifices, denture materials, chewing gum and lipsticks used by the patient. Patch testing with these products is essential for investigating the possible cause of allergic contact cheilitis. However, there is a group of patients with troublesome cheilitis, who are often severely affected, but in whom the cause of the cheilitis remains obscure. This group may represent patients with endogenous cheilitis or factitious cheilitis.","PeriodicalId":12086,"journal":{"name":"Exogenous Dermatology","volume":"37 1","pages":"173 - 177"},"PeriodicalIF":0.0,"publicationDate":"2003-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"74652159","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The binding of low-molecular-weight compounds to nucleophilic side-chains of amino acids bound within a protein, resulting in a hapten-modified macromolecule, is discussed to represent the very first step within the development of allergic contact dermatitis. For one of the best-known occupational dermatoses in the field of plant breeding, the so-called tulip fingers, α-methylene-γ-butyrolactone (tulipalin A) was proved to be the causative agent. In this paper, the reaction of tulipalin A with Nα-hippuryl-L-lysine as a model for peptide-bound lysine was studied. After the incubation of the α-methylene-γ-butyrolactone with the dipeptide in varying molar ratios in methanolic solution at 37°C up to 3 weeks, the reaction was monitored using reversed-phase high-performance liquid chromatography with UV detection. Tulipalin A was found to react with the Ε-amino group, resulting in the formation of one characteristic reaction product. After isolation, the structure of this addition product was unambiguously characterised by nuclear magnetic resonance spectroscopy as 2-(2-benzoylamino-acetylamino)-6-[(2-oxo-tetrahydro-furan-3-ylmethyl)amino] hexanoic acid (Hip-LysTu). After incubation of bovine serum albumin with tulipalin A, followed by acid hydrolysis and amino acid analysis, LysTu was found as addition product, thus representing the first known amino acid derivative resulting from the conjugation of the electrophilic α-methylene-γ-butyrolactone to protein.
{"title":"Studies on the Mechanism of Allergic Contact Dermatitis: The Reaction of α-Methylene-γ-Butyrolactone with Peptide-Bound Lysine","authors":"J. Pickert, C. Hartert, H. Raddatz, T. Henle","doi":"10.1159/000076804","DOIUrl":"https://doi.org/10.1159/000076804","url":null,"abstract":"The binding of low-molecular-weight compounds to nucleophilic side-chains of amino acids bound within a protein, resulting in a hapten-modified macromolecule, is discussed to represent the very first step within the development of allergic contact dermatitis. For one of the best-known occupational dermatoses in the field of plant breeding, the so-called tulip fingers, α-methylene-γ-butyrolactone (tulipalin A) was proved to be the causative agent. In this paper, the reaction of tulipalin A with Nα-hippuryl-L-lysine as a model for peptide-bound lysine was studied. After the incubation of the α-methylene-γ-butyrolactone with the dipeptide in varying molar ratios in methanolic solution at 37°C up to 3 weeks, the reaction was monitored using reversed-phase high-performance liquid chromatography with UV detection. Tulipalin A was found to react with the Ε-amino group, resulting in the formation of one characteristic reaction product. After isolation, the structure of this addition product was unambiguously characterised by nuclear magnetic resonance spectroscopy as 2-(2-benzoylamino-acetylamino)-6-[(2-oxo-tetrahydro-furan-3-ylmethyl)amino] hexanoic acid (Hip-LysTu). After incubation of bovine serum albumin with tulipalin A, followed by acid hydrolysis and amino acid analysis, LysTu was found as addition product, thus representing the first known amino acid derivative resulting from the conjugation of the electrophilic α-methylene-γ-butyrolactone to protein.","PeriodicalId":12086,"journal":{"name":"Exogenous Dermatology","volume":"24 1","pages":"210 - 215"},"PeriodicalIF":0.0,"publicationDate":"2003-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"77876891","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
京公网安备 11010802042870号
京ICP备2023020795号-1
扫码关注我们
求助内容：
应助结果提醒方式：