Methods for synthesizing metal mesoporphyrins

Abstract

Embodiments describe methods of synthesizing metal mesoporphyrin compounds. In embodiments, a metal mesoporphyrin compound may be formed by hemin transmetallation and subsequent hydrogenation of the tin protoporphyrin IX to form a metal mesoporphyrin. In other embodiments, a method of synthesizing a metal mesoporphyrin compound comprises forming a protoporphyrin methyl ester from hemin and converting the protoporphyrin methyl ester intermediate to a metal mesoporphyrin compound through metal insertion and hydrogenation. In other embodiments, a metal mesoporphyrin compound may be formed from hemin by a hydrogen-free hydrogenation method to form a mesoporphyrin IX intermediate followed by metal insertion and hydrogenation. In embodiments, a method of synthesizing a metal mesoporphyrin compound comprises forming a mesoporphyrin IX dihydrochloride intermediate compound and converting the mesoporphyrin IX intermediate to a metal mesoporphyrin compound through metal insertion. In embodiments, a metal mesoporphyrin compound may be formed directly from hemin without isolation of any intermediates.

1 . A method of synthesizing a metal mesoporphyrin compound comprising:
 hydrogenating hemin to form a mesoporphyrin IX dihydrochloride intermediate compound;   isolating the mesoporphyrin IX dihydrochloride intermediate compound; and   inserting a metal into the mesoporphyrin IX dihydrochloride intermediate.   
     
     
         2 . The method of  claim 1 , wherein the metal may be selected from tin, iron, zinc, chromium, manganese, copper, nickel, magnesium, cobalt, platinum, gold, silver, arsenic, antimony, cadmium, gallium, germanium, and palladium. 
     
     
         3 . The method of  claim 2 , wherein the metal is tin. 
     
     
         4 . The method of  claim 3 , wherein the tin is inserted using tin oxide, tin chloride, tin sulfate, tin bromide, tin oxalate, tin pyrophosphate hydrate, tin 2-ethylhexanoate, tin methanesulfonic acid, or tin trifluromethanesulfonate. 
     
     
         5 . The method of  claim 1 , wherein the metal mesoporphyrin compound is stannsoporfin. 
     
     
         6 . A method of synthesizing a metal mesoporphyrin compound comprising:
 hydrogenating hemin in formic acid to form a formic acid solution; and   inserting a metal into the formic acid solution, wherein the metal mesoporphyrin compound is synthesized without isolating an intermediate compound.   
     
     
         7 . The method of  claim 6 , wherein the metal may be selected from tin, iron, zinc, chromium, manganese, copper, nickel, magnesium, cobalt, platinum, gold, silver, arsenic, antimony, cadmium, gallium, germanium, and palladium. 
     
     
         8 . The method of  claim 7 , wherein the metal is tin. 
     
     
         9 . The method of  claim 8 , wherein the tin is inserted using tin oxide, tin chloride, tin sulfate, tin bromide, tin oxalate, tin pyrophosphate hydrate, tin 2-ethylhexanoate, tin methanesulfonic acid, or tin trifluromethanesulfonate. 
     
     
         10 . The method of  claim 9 , wherein the metal mesoporphyrin compound is stannsoporfin.