Acyloxybutadiene tricarbonyl iron complexes as enzyme-triggered CO-releasing molecules (ET-CORMs): a structure-activity relationship study

Romanski, Steffen and Kraus, Birgit and Guttentag, Miguel and Schlundt, Waldemar and Ruecker, Hannelore and Adler, Andreas and Neudoerfl, Joerg-Martin and Alberto, Roger and Amslinger, Sabine and Schmalz, Hans-Guenther (2012) Acyloxybutadiene tricarbonyl iron complexes as enzyme-triggered CO-releasing molecules (ET-CORMs): a structure-activity relationship study. DALTON TRANSACTIONS, 41 (45). pp. 13862-13875. ISSN 1477-9226, 1477-9234

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Abstract

A series of eta(4)-acyloxycyclohexadiene-Fe(CO)(3) complexes was prepared and fully characterized by spectroscopic methods including single crystal X-ray diffraction. For this purpose a new synthetic access to differently acylated 1,3- and 1,5-dienol-Fe(CO)(3) complexes was developed. The enzymatically triggered CO release from these compounds was monitored (detection of CO through GC and/or by means of a myoglobin assay) and the anti-inflammatory effect of the compounds was assessed by a cellular assay based on the inhibition of NO-production by inducible NO synthase (iNOS). It was demonstrated that the properties (rate of esterase-triggered CO release, iNOS inhibition, cytotoxicity) of the complexes strongly depend on the substitution pattern of the pi-ligand and the nature of the acyloxy substituent.

Item Type: Article
Uncontrolled Keywords: NITRIC-OXIDE SYNTHASE; CARBON-MONOXIDE; HEME; TRANSCRIPTION; CARCINOGENS; EXPRESSION; INDUCTION; PROTECT;
Subjects: 500 Science > 540 Chemistry & allied sciences
600 Technology > 615 Pharmacy
Divisions: Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical Biology (Prof. Heilmann)
Chemistry and Pharmacy > Institut für Organische Chemie > Arbeitskreis Dr. Sabine Amslinger
Depositing User: Dr. Gernot Deinzer
Date Deposited: 26 May 2020 04:57
Last Modified: 26 May 2020 04:57
URI: https://pred.uni-regensburg.de/id/eprint/19427

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