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


Romanski, Steffen; Kraus, Birgit; Guttentag, Miguel; Schlundt, Waldemar; Ruecker, Hannelore; Adler, Andreas; Neudoerfl, Joerg-Martin; Alberto, Roger; Amslinger, Sabine; 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):13862-13875.

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.

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.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2012
Deposited On:04 Mar 2013 13:41
Last Modified:05 Apr 2016 16:34
Publisher:RSC Publishing
ISSN:1477-9226
Publisher DOI:https://doi.org/10.1039/C2DT30662J

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