Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

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Chemical Compound Review:

AG-F-00711 12-anthracen-9- ylcarbonyloxyoctadecanoic acid

Synonyms: CTK4G5381, AR-1H5440, AC1L3TJ7, AC1Q5W8K, 12-AS Cpd, ...

Kamp, F. et al., Kumazawa, T. et al., Araya, H. et al., Ohyashiki, T. et al.

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High impact information on 12-AS Cpd

The three FA analogues [12-(9-anthroyloxy)stearic acid, 5-doxylstearic acid, and 1-pyrenenonanoic acid] moved across PC bilayers via the un-ionized form; except for the anthroyloxy FA (kappa FAH = 4.8 x 10(-3) s-1), the rates were too fast to measure (t 1/2 < 1 s) [1].
Acetaminophen, with or without NADPH, was also found to change the fluorescence polarization of lipid-soluble fluorescent probes, 2- and 12-(9-anthroyloxy)stearic acid labeled to microsomes, indicating its action on microsomal membrane lipids [2].
On the other hand, the kq value of the reaction of 12-(9-anthroyloxy)stearic acid with Cu2+ or I- was unaffected by lipid peroxidation [3].
The membrane fluidity of the N-18 cell monitored with 2-(9-anthroyloxy)stearic acid was changed in response to the bitter substances, while the fluidity monitored with 12-(9-anthroyloxy)stearic acid or 1,6-diphenyl-1,3,5-hexatriene was unchanged [4].

References

Movement of fatty acids, fatty acid analogues, and bile acids across phospholipid bilayers. Kamp, F., Hamilton, J.A., Kamp, F., Westerhoff, H.V., Hamilton, J.A. Biochemistry (1993) [Pubmed]
Alteration in rat liver microsomal membranes induced by acetaminophen. Araya, H., Horie, T., Hayashi, M., Awazu, S. J. Pharmacobio-dyn. (1987) [Pubmed]
A change in the lipid fluidity of the porcine intestinal brush-border membranes by lipid peroxidation. Studies using pyrene and fluorescent stearic acid derivatives. Ohyashiki, T., Ohtsuka, T., Mohri, T. Biochim. Biophys. Acta (1986) [Pubmed]
Contribution of electrostatic and hydrophobic interactions of bitter substances with taste receptor membranes to generation of receptor potentials. Kumazawa, T., Kashiwayanagi, M., Kurihara, K. Biochim. Biophys. Acta (1986) [Pubmed]

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