N-Methylprotoporphyrin IX: chemical synthesis and identification as the green pigment produced by 3,5-diethoxycarbonyl-1,4-dihydrocollidine treatment.
The hepatic pigment accumulated in 3,5-diethoxycarbonyl-1,4-dihydrocollidine-treated rats, which has been reported to inhibit ferrochelatase, has been isolated and purified. The pigment has been resolved into one major, one minor, and two trace components, all of which appear to be isomeric porphyrins. The major fraction has been unambiguously identified by spectroscopic methods as the isomer of N-methylprotoporphyrin IX (isolated as the dimethyl ester) in which vinyl-substituted pyrrole ring A is methylated. The minor product appears to be an isomer of the same porphyrin with the N-methyl group on propionic acid-substituted ring C, and the trace components have the same high-pressure liquid chromatography retention times as the other two possible isomers of the porphyrin. The four isomers of N-methylprotoporphyrin IX have been chemically synthesized, independently characterized, and used to confirm the structures of the biologically products.
D000818:Animals; D002851:Chromatography, High Pressure Liquid; D003997:Dicarbethoxydihydrocollidine / Q000494:pharmacology*; D008099:Liver / Q000187:drug effects / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D008722:Methods; D009587:Nitrogen Isotopes; D011166:Porphyrins / Q000138:chemical synthesis*; D011524:Protoporphyrins / Q000138:chemical synthesis* / Q000302:isolation & purification; D011725:Pyridines / Q000494:pharmacology*; D051381:Rats; D013053:Spectrophotometry
D009587:Nitrogen Isotopes; D011166:Porphyrins; D011524:Protoporphyrins; D011725:Pyridines; D003997:Dicarbethoxydihydrocollidine; C028842:N-methylprotoporphyrin IX