PMID- 38079418
OWN - NLM
STAT- MEDLINE
DCOM- 20240116
LR  - 20240325
IS  - 1520-5010 (Electronic)
IS  - 0893-228X (Print)
IS  - 0893-228X (Linking)
VI  - 37
IP  - 1
DP  - 2024 Jan 15
TI  - Electrophilic Reactivity of Sulfated Alcohols in the Context of Skin 
      Sensitization.
PG  - 16-19
LID - 10.1021/acs.chemrestox.3c00292 [doi]
AB  - 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.
FAU - Roberts, David W
AU  - Roberts DW
AUID- ORCID: 0000-0001-6112-5868
AD  - School of Pharmacy and Biomolecular Sciences, Liverpool John Moores University, 
      Liverpool L3 3AF, U.K.
LA  - eng
PT  - Journal Article
DEP - 20231211
PL  - United States
TA  - Chem Res Toxicol
JT  - Chemical research in toxicology
JID - 8807448
RN  - SS8YOP444F (cinnamyl alcohol)
RN  - 0 (Alcohols)
RN  - 0 (Sulfates)
RN  - 0 (Propanols)
RN  - 0 (Allergens)
SB  - IM
MH  - Humans
MH  - Animals
MH  - Mice
MH  - *Alcohols/metabolism
MH  - Sulfates/metabolism
MH  - Skin/metabolism
MH  - Propanols/metabolism
MH  - Local Lymph Node Assay
MH  - *Dermatitis, Allergic Contact/metabolism
MH  - Allergens/chemistry
PMC - PMC10792661
EDAT- 2023/12/11 18:42
MHDA- 2024/01/16 06:42
PMCR- 2024/01/17
CRDT- 2023/12/11 13:33
PHST- 2024/01/16 06:42 [medline]
PHST- 2023/12/11 18:42 [pubmed]
PHST- 2023/12/11 13:33 [entrez]
PHST- 2024/01/17 00:00 [pmc-release]
AID - 10.1021/acs.chemrestox.3c00292 [doi]
PST - ppublish
SO  - Chem Res Toxicol. 2024 Jan 15;37(1):16-19. doi: 10.1021/acs.chemrestox.3c00292. 
      Epub 2023 Dec 11.