TRPA1 and TRPV1 activation is a novel adjuvant effect mechanism in contact hypersensitivity

Shiba, Tomoaki; Maruyama, Takashi; Kurohane, Kohta; Iwasaki, Yusaku; Watanabe, Tatsuo; Imai, Yumiko

doi:10.1016/j.jneuroim.2008.12.001

Cited by 32 publications

(45 citation statements)

References 43 publications

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“…For example, di-n-heptyl phthalate (DHPP) enhanced sensitization to FITC, but di(2-ethylhexyl)phthalate (DEHP) did not. 8,17) DEHP has a similar but slightly higher value in the octanol-water partition coefficient (log P ow ) than that of DHPP. 18,19) Another example is diethyl phthalate (DEP).…”

Section: Discussionmentioning

confidence: 96%

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Dibutyl Maleate and Dibutyl Fumarate Enhance Contact Sensitization to Fluorescein Isothiocyanate in Mice

Matsuoka

Kurohane

Suzuki

et al. 2016

Biological & Pharmaceutical Bulletin

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Di-n-butyl phthalate (DBP), a phthalate ester, has been shown to have an adjuvant effect on fluorescein isothiocyanate (FITC)-induced contact hypersensitivity (CHS) mouse models. Di-n-butyl maleate (DBM), widely used as a plasticizer for industrial application, has been reported to cause dermatitis in humans. DBM is a butyl alcohol ester of di-carboxylic acid that represents a part of the DBP structure, while di-nbutyl fumarate (DBF) is a trans isomer of DBM. We examined whether DBM or DBF exhibits an adjuvant effect like DBP does. When BALB/c mice were epicutaneously sensitized with FITC in the presence of DBM or DBF, the FITC-specific CHS response was enhanced, as we have observed for DBP. As to underlying mechanisms, DBM and DBF facilitated the trafficking of FITC-presenting CD11c dendritic cells (DCs) from skin to draining lymph nodes and increased the cytokine production by draining lymph nodes. In conclusion, DBM and DBF may have an effect that aggravates contact dermatitis through a skin sensitization process.Key words dibutyl maleate; dibutyl fumarate; adjuvant; contact hypersensitivity; dendritic cell trafficking; cytokine productionIn 1985, a dermatitis outbreak occurred in an envelopemaking factory where di-n-butyl maleate (DBM)-containing polyvinyl acetate glue was used. 1) In 2009, a case of allergic dermatitis due to occupational exposure to DBM was reported. 2) A 47-year-old woman working as a batch mixer in a factory producing gelcoats and specialty paints developed eczematous lesions until she was withdrawn from work. Interestingly, among the North American Contact Dermatitis Group standard series, plastics, glues, adhesives as well as products in the workplace, DBM was the only chemical that gave a positive reaction in the patch test. DBM is a colorless, clear, and oily liquid used for industrial applications. DBM consists of an alkenyl di-carboxylic acid with two butyl alcohol esters of cis configuration.Di-n-butyl fumarate (DBF) is an isomer of DBM with butyl alcohol esters of trans configuration. There has been no report on dermatitis caused by DBF. However, dimethyl fumarate (DMF) has been banned for the use in consumer products in the European Union (EU), because it caused an unprecedented large-scale dermatitis outbreak. 3) DBM and DBF have been used as plasticizers, raw materials for polymer syntheses, and preservatives for oils and fats, but the risk of their use for dermatitis development has not been established. 4) DBM represents a part of the structure of di-n-butyl phthalate (DBP), an aromatic dibutyl ester. DBP is widely used as a plasticizer for consumer products such as paints, varnishes, paper coatings and cosmetics. 5,6) Our previous studies demonstrated that DBP contributed to contact hypersensitivity (CHS) to isothiocyanate haptens as adjuvant chemicals. 7) Thus, we hypothesized that DBM might exhibit an enhancing effect through a similar mechanism as observed for DBP. We also examined whether or not DBF, an isomer of DBM, produced such an enhancing effect.In this study, we ...

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Section: Discussionmentioning

confidence: 96%

“…8,10) We have demonstrated a correlation of the adjuvant effect with the ability to activate transient receptor potential ankyrin 1 (TRPA1) cation channels. 10,17,20) We are currently under investigation whether DBM and DBF activate TRPA1.…”

Section: Discussionmentioning

confidence: 99%

Dibutyl Maleate and Dibutyl Fumarate Enhance Contact Sensitization to Fluorescein Isothiocyanate in Mice

Matsuoka

Kurohane

Suzuki

et al. 2016

Biological & Pharmaceutical Bulletin

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“…The immunological and nervous activation effects caused by phthalate esters were found to be well correlated. 11,12) In studies on reproductive toxicity, the role of monobutyl phthalate (MBP) as an active metabolite derived from DBP has been investigated. 13,14) Although studies on reproductive toxicity involve systemic administration of DBP, with which MBP is more likely to be produced in the body, topical application of DBP may yield MBP through esterase in the skin.…”

Section: )mentioning

confidence: 99%

“…ity and the adjuvant effect on FITC-CHS. 11,12) We first investigated whether MBP activates TRPA1. DBP, a positive control, induced an intracellular Ca 2+ increase in TRPA1-CHO cells, while no effect on T-REx CHO cells was observed without TRPA1 expression (Fig.…”

Section: Fig 1 Structures Of Chemicals Under Testmentioning

confidence: 99%

“…10) We also demonstrated that DBP had the ability to stimulate transient receptor potential ankyrin 1 (TRPA1) cation channels, which are expressed on sensory neurons. 11) We then compared several types of phthalate esters regarding adjuvant effects and TRPA1 stimulation. The immunological and nervous activation effects caused by phthalate esters were found to be well correlated.…”

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Dibutyl Phthalate Rather than Monobutyl Phthalate Facilitates Contact Hypersensitivity to Fluorescein Isothiocyanate in a Mouse Model

Kurohane

Sekiguchi

Ogawa

et al. 2017

Biological & Pharmaceutical Bulletin

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Dibutyl phthalate (DBP) is a plasticizer used for many consumer products including cosmetics. Potential health concerns regarding DBP include reproductive and developmental toxicity, endocrine disruption and neurotoxicity. DBP is a high priority chemical as to reduction of exposure of children to it. Through reproductive toxicity studies, monobutyl phthalate (MBP) has been proposed to be the active metabolite derived from DBP. We previously demonstrated that DBP activates transient receptor potential ankyrin 1 (TRPA1) cation channels expressed on sensory neurons. We have also shown that DBP enhanced skin sensitization in a fluorescein isothiocyanate (FITC)-induced contact hypersensitivity (CHS) mouse model. Through MBP formation by esterase in the skin, it is possible that MBP exerts a major effect on the biological activity we observed. To test this possibility, we directly compared DBP and MBP. A more than 40-fold higher concentration of MBP as compared with DBP was required for activation of TRPA1 in vitro. Unlike DBP, MBP did not enhance skin sensitization to FITC. These results demonstrated that DBP directly, i.e., not through its metabolite MBP, activates TRPA1 and enhances FITC-CHS. It is noteworthy that butyl benzoate, a related compound, activated TRPA1 and enhanced FITC-CHS.Key words adjuvant; contact hypersensitivity; phthalate; skin; transient receptor potential ankyrin 1; mouse Di-n-butyl phthalate (DBP) is widely used as a plasticizer for consumer products such as paint, adhesives, paper coatings, printing ink and cosmetics.1-5) Regarding children's health concerns, DBP has become one of the highest priority chemicals as to reduction of exposure of children to it in consumer products.6) The health concerns include reproductive and developmental toxicity, endocrine disruption and neurotoxicity. [6][7][8] We have been studying DBP from an immuno-toxicological perspective. We employ a fluorescein isothiocyanate (FITC)-induced contact hypersensitivity (CHS) mouse model, in which DBP is empirically added to the solvent for FITC. 9) We found that DBP acts as an adjuvant during skin sensitization to FITC. 10) We also demonstrated that DBP had the ability to stimulate transient receptor potential ankyrin 1 (TRPA1) cation channels, which are expressed on sensory neurons. 11)We then compared several types of phthalate esters regarding adjuvant effects and TRPA1 stimulation. The immunological and nervous activation effects caused by phthalate esters were found to be well correlated. 11,12) In studies on reproductive toxicity, the role of monobutyl phthalate (MBP) as an active metabolite derived from DBP has been investigated. 13,14) Although studies on reproductive toxicity involve systemic administration of DBP, with which MBP is more likely to be produced in the body, topical application of DBP may yield MBP through esterase in the skin. Thus, there is a possibility that MBP has biological effects as an active metabolite. To examine this idea, we investigated whether MBP is more active than DBP regarding TR...

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Acute exposure to bis(2-ethylhexyl)phthalate disrupts calcium homeostasis, energy metabolism and induces oxidative stress in the testis of Danio rerio

et al. 2020

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TRPA1 and TRPV1 activation is a novel adjuvant effect mechanism in contact hypersensitivity

Cited by 32 publications

References 43 publications

Dibutyl Maleate and Dibutyl Fumarate Enhance Contact Sensitization to Fluorescein Isothiocyanate in Mice

Dibutyl Maleate and Dibutyl Fumarate Enhance Contact Sensitization to Fluorescein Isothiocyanate in Mice

Dibutyl Phthalate Rather than Monobutyl Phthalate Facilitates Contact Hypersensitivity to Fluorescein Isothiocyanate in a Mouse Model

Acute exposure to bis(2-ethylhexyl)phthalate disrupts calcium homeostasis, energy metabolism and induces oxidative stress in the testis of Danio rerio

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