Superoxide dismutase mimetics: synthesis and structure-activity relationship study of MnTBAP analogues.
Carboxylic ester and amide-substituted analogues of [5,10,15,20-tetrakis(4-carboxyphenyl)-porphyrinato]manganese(III) chloride (MnTBAP) were synthesized and assayed as potential superoxide dismutase (SOD) mimetics. The tetraester analogues 4a and 4b were found to have comparable SOD activity to the known SOD mimetic MnTBAP, while amides 4c-4e exhibited reduced SOD activity. In the substituted methyl benzoate/acid and disubstituted porphyrin series, analogues 12c, 12f, and 12m were found to have comparable to improved SOD activity relative to MnTBAP and analogues 12j, 13a, and 13d exhibited improved activity in both the SOD and thiobarbituric acid reactive species (TBARS) assays relative to MnTBAP.
Gauuan
Polivina Jolicia F
PJ
Albany Molecular Research, Inc., 21 Corporate Circle, PO Box 15098, Albany, NY 12212-5098, USA. joli@ablmolecular.com
Trova
Michael P
MP
Gregor-Boros
Livia
L
Bocckino
Stephen B
SB
Crapo
James D
JD
Day
Brian J
BJ
D016166:Free Radical Scavengers / Q000138:chemical synthesis* / Q000737:chemistry; D008665:Metalloporphyrins / Q000138:chemical synthesis* / Q000737:chemistry; D018716:Molecular Mimicry; D013329:Structure-Activity Relationship; D013482:Superoxide Dismutase / Q000737:chemistry*; D017392:Thiobarbituric Acid Reactive Substances
D016166:Free Radical Scavengers; D008665:Metalloporphyrins; D017392:Thiobarbituric Acid Reactive Substances; C097284:manganese(III)-tetrakis(4-benzoic acid)porphyrin; D013482:Superoxide Dismutase