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

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Chemical Compound Review:

NSC-15 anthracene-9-carbaldehyde

Synonyms: NSC15, CCRIS 3165, NSC 15, AC1Q6QDA, AC-13621, ...

Watanabe, K. et al., Watanabe, K. et al., Marini, S. et al., Wang, C. et al.

Watanabe, Matsunaga, Kimura, Funahashi, Funae, Ohshima, Yamamoto,

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High impact information on anthracene-9-carbaldehyde

Initial N-alkylation via reductive amination with anthracene-9-carbaldehyde provided the secondary amines in good yield [1].
P450 MUT-2 exhibited aldehyde oxygenase activity for 11-oxo-delta 8-TH, 11-oxo-delta 9-THC, 11-oxo-cannabinol (11-oxo-CBN) and 9-anthraldehyde together with high activity for the hydroxylation of cannabinoids at the 11-position [2].
Antibody against P450 MUT-2 significantly inhibited the microsomal formation of delta 8-THC-11-oic acid from 11-oxo-delta 8-THC, but not that of 9-anthracene carboxylic acid from 9-anthraldehyde [2].
4-Biphenylaldehyde and 9-anthraldehyde: two fluorescent substrates for determining P450 enzyme activities in rat and human [3].
1. 4-Biphenylaldehyde (4-BA) and 9-anthraldehyde (9-AA) were examined as substrates for cytochrome P450 (CYPs) enzymes in rat and human [3].

Anatomical context of anthracene-9-carbaldehyde

Hepatic microsomes from human liver catalyzed oxidation of the allyl aldehydes such as 11-oxo-Delta(8)-tetrahydrocannabinol and 9-anthraldehyde to the corresponding carboxylic acid metabolites [4].

Gene context of anthracene-9-carbaldehyde

These results indicate that CYP2C9 and CYP3A4 are major enzymes responsible for the MALDO activity in human liver for 11-oxo-Delta(8)-tetrahydrocannabinol and 9-anthraldehyde, respectively [4].

References

Synthesis and characterization of N(1)-(4-toluenesulfonyl)-N(1)- (9-anthracenemethyl)triamines. Wang, C., Abboud, K.A., Phanstiel IV, O. J. Org. Chem. (2002) [Pubmed]
A cytochrome P450 isozyme having aldehyde oxygenase activity plays a major role in metabolizing cannabinoids by mouse hepatic microsomes. Watanabe, K., Narimatsu, S., Matsunaga, T., Yamamoto, I., Yoshimura, H. Biochem. Pharmacol. (1993) [Pubmed]
4-Biphenylaldehyde and 9-anthraldehyde: two fluorescent substrates for determining P450 enzyme activities in rat and human. Marini, S., Grasso, E., Longo, V., Puccini, P., Riccardi, B., Gervasi, P.G. Xenobiotica (2003) [Pubmed]
Major cytochrome P450 enzymes responsible for microsomal aldehyde oxygenation of 11-oxo-Delta8-tetrahydrocannabinol and 9-anthraldehyde in human liver. Watanabe, K., Matsunaga, T., Kimura, T., Funahashi, T., Funae, Y., Ohshima, T., Yamamoto, I. Drug Metab. Pharmacokinet. (2002) [Pubmed]

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