Anti-inflammatory and antioxidant activity of coumarins designed as potential fluorescent zinc sensors.
A series of coumarin analogs, designed and synthesised as potential fluorescent zinc probes were evaluated for their biological activity as anti-inflammatory and antioxidant agents. The effect of the synthesised compounds on inflammation, using the carrageenin-induced rat paw oedema model, was studied. In general, the compounds were found to be potent anti-inflammatory agents (26.5-64%). Compound 5 was found to interact significantly with 1,1-diphenyl-2-picryl-hydrazyl stable free radical (DPPH) whereas the remainder were inactive in this assay. The compounds inhibit in general the soybean lipoxygenase and scavenge superoxide anion radicals. The anti-inflammatory activity seems to be connected with their reducing activity. Their RM values were determined as an expression of their lipophilicity. Theoretical calculations of their lipophilicity as clog P were performed indicating that only a poor relationship exists between their lipophilicity and anti-inflammatory activity.
Department of Pharmaceutical Chemistry, School of Pharmacy, Aristotle University of Thessaloniki, Thessaloniki 54124, Greece. hadjpav@pharm.auth.gr
Dimitra
D
Hadjipavlou-Litina
Christos
C
Kontogiorgis
Eleni
E
Pontiki
Marianna
M
Dakanali
Antonia
A
Akoumianaki
Haralambos E
HE
Katerinopoulos
D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry* / Q000494:pharmacology*; D000975:Antioxidants / Q000737:chemistry* / Q000494:pharmacology*; D001713:Biphenyl Compounds; D002351:Carrageenan / Q000633:toxicity; D003374:Coumarins / Q000737:chemistry* / Q000494:pharmacology*; D004353:Drug Evaluation, Preclinical; D004487:Edema / Q000139:chemically induced / Q000188:drug therapy; D005260:Female; D005456:Fluorescent Dyes; D016166:Free Radical Scavengers / Q000737:chemistry / Q000494:pharmacology; D006834:Hydrazines; D008084:Lipoxygenase / Q000187:drug effects; D008297:Male; D010851:Picrates; D051381:Rats; D011916:Rats, Inbred F344; D013025:Glycine max / Q000201:enzymology; D013329:Structure-Activity Relationship; D015032:Zinc
D000894:Anti-Inflammatory Agents, Non-Steroidal; D000975:Antioxidants; D001713:Biphenyl Compounds; D003374:Coumarins; D005456:Fluorescent Dyes; D016166:Free Radical Scavengers; D006834:Hydrazines; D010851:Picrates; D002351:Carrageenan; C004931:1,1-diphenyl-2-picrylhydrazyl; C101084:lipoxygenase L-1; D008084:Lipoxygenase; D015032:Zinc