Copper-induced dealkylation studies of biologically N-alkylated porphyrins by fast atom bombardment mass spectrometry

Gibbs, Anthony H.; Naylor, Stephen; Lamb, John H.; Frater, Yvonne; Matteis, Federico De

doi:10.1016/s0003-2670(00)83651-x

Cited by 5 publications

(2 citation statements)

References 16 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…m.s. By using this technique, transfer of a methyl group to the amine could be demonstrated, starting either from synthetic N-methylprotoporphyrin or from the minor griseofulvin pigment (Gibbs et al, 1990), confirming the identification of the latter pigment as Nmethylprotoporphyrin.…”

Section: Ms Studiesmentioning

confidence: 60%

“…Additional evidence that the minor griseofulvin pigment is Nmethylprotoporphyrin was obtained by direct identification of the N-methyl group. In a recently developed technique (Gibbs et al, 1990) the N-alkyl group released during copper-dependent dealkylation of N-alkylporphyrins is trapped by dodecylamine and the amine adduct is identified by f.a.b. m.s.…”

Section: Ms Studiesmentioning

confidence: 99%

See 1 more Smart Citation

Isolation of two N-monosubstituted protoporphyrins, bearing either the whole drug or a methyl group on the pyrrole nitrogen atom, from liver of mice given griseofulvin

Holley

Frater

Gibbs

et al. 1991

Biochemical Journal

View full text Add to dashboard Cite

1. A hepatic green pigment with inhibitory properties towards the enzyme ferrochelatase has been isolated from the liver of mice treated with griseofulvin and identified as N-methylprotoporphyrin. 2. All four structural isomers of N-methylprotoporphyrin have been demonstrated to be present, NA, where ring A of protoporphyrin IX is N-methylated, being the predominant isomer. 3. In addition to N-methylprotoporphyrin, a second green pigment, present in far greater amounts, was also isolated from the liver of griseofulvin-treated mice. This second green pigment is also an N-monosubstituted protoporphyrin, but in this case the substituent on the pyrrole nitrogen atom appears to be intact griseofulvin rather than a methyl group. 4. The fragmentation of this adduct in tandem m.s. studies suggests that griseofulvin is bound to the pyrrole nitrogen through one of its carbon atoms and further suggests that N-methylprotoporphyrin may arise as a secondary product from the major griseofulvin pigment.

show abstract

Section: Ms Studiesmentioning

confidence: 60%

Section: Ms Studiesmentioning

confidence: 99%