These tools will no longer be maintained as of December 31, 2024. Archived website can be found here. PubMed4Hh GitHub repository can be found here. Contact NLM Customer Service if you have questions.


Pubmed for Handhelds

PUBMED FOR HANDHELDS

Search MEDLINE/PubMed

  • Title: The allylisopropylacetamide and novonal prosthetic heme adducts.
    Author: Ortiz de Montellano PR, Stearns RA, Langry KC.
    Journal: Mol Pharmacol; 1984 Mar; 25(2):310-7. PubMed ID: 6700576.
    Abstract:
    Administration of 2-isopropyl-4-pentenamide (AIA) and 2,2-diethyl-4-pentenamide (novonal) to phenobarbital-pretreated rats gives rise to abnormal porphyrins derived from the prosthetic heme group of inactivated cytochrome P-450. The abnormal porphyrins, identified by NMR and other spectroscopic methods, are N-alkylated protoporphyrin IX derivatives in which the N-alkyl moiety is derived from the parent drug by addition of a hydroxyl group to the internal carbon and of a porphyrin nitrogen to the terminal carbon of the pi-bond. A secondary reaction of the hydroxyl with the amide group converts the N-alkyl moiety into a lactone. The indicated alkylation-lactonization sequence is supported by the fact that the AIA adduct formed under an atmosphere of 18O2 incorporates one labeled oxygen atom. The regiochemistry of heme alkylation is consistent with a previously postulated active site topology [J. Biol. Chem. 258:4202-4207 (1983)].
    [Abstract] [Full Text] [Related] [New Search]