Electrophilic Reactivity of Sulfated Alcohols in the Context of Skin Sensitization

Roberts, DW (2023) Electrophilic Reactivity of Sulfated Alcohols in the Context of Skin Sensitization. Chemical Research in Toxicology, 37 (1). pp. 16-19. ISSN 0893-228X

Preview

Text Electrophilic Reactivity of Sulfated Alcohols in the Context of Skin Sensitization.pdf - Published Version Available under License Creative Commons Attribution. Download (1MB) | Preview

Abstract

The surfactant sodium lauryl sulfate (SLS), although consistently positive in the murine local lymph node assay (LLNA) for skin sensitization, shows no evidence of being a human sensitizer and is often described as a false positive, lacking structural alerts for sensitization. However, there is evidence of the cinnamyl sulfate anion being the metabolite responsible for the sensitization potential of cinnamyl alcohol to humans and in animal tests. Here, manufacturing chemistry data and physical organic chemistry principles are applied to confirm that SLS is not reactive enough to sensitize, whereas sensitization to cinnamyl alcohol via cinnamyl sulfate is plausible. Sensitization data for several other primary alcohols, including geraniol, farnesol, and possibly hydrocortisone, are also consistent with this mechanism. It seems possible that biosulfation may play a wider role than has previously been recognized in skin sensitization.

Item Type:	Article
Uncontrolled Keywords:	Skin; Animals; Humans; Mice; Dermatitis, Allergic Contact; Sulfates; Alcohols; Propanols; Allergens; Local Lymph Node Assay; Humans; Animals; Mice; Alcohols; Sulfates; Skin; Propanols; Local Lymph Node Assay; Dermatitis, Allergic Contact; Allergens; 0302 Inorganic Chemistry; 0304 Medicinal and Biomolecular Chemistry; 0305 Organic Chemistry; Toxicology
Subjects:	Q Science > QD Chemistry Q Science > QH Natural history > QH301 Biology
Divisions:	Pharmacy and Biomolecular Sciences
Publisher:	American Chemical Society (ACS)
Date of acceptance:	6 December 2023
Date of first compliant Open Access:	17 September 2024
Date Deposited:	17 Sep 2024 13:52
Last Modified:	17 Sep 2024 14:00
DOI or ID number:	10.1021/acs.chemrestox.3c00292
URI:	https://ljmu-9.eprints-hosting.org/id/eprint/24162

View Item