UZH-Logo

Maintenance Infos

Iron Dienylphosphate Tricarbonyl complexes as water-soluble enzyme-triggered CO-releasing molecules (ET-CORMs)


Romanski, Steffen; Ruecker, Hannelore; Stamellou, Eleni; Guttentag, Miguel; Neudoerfl, Joerg-Martin; Alberto, Roger; Amslinger, Sabine; Yard, Benito; Schmalz, Hans-Guenther (2012). Iron Dienylphosphate Tricarbonyl complexes as water-soluble enzyme-triggered CO-releasing molecules (ET-CORMs). Organometallics, 31(16):5800-5809.

Abstract

A series of racemic phosphoryloxy-substituted (eta(4)-cyclohexadiene)Fe(CO)(3) complexes was synthesized by exploiting the O-phosphorylation of (dienol)Fe(CO)(3) intermediates generated in situ from the corresponding triisopropylsiloxy-protected complexes. The phosphorylated products were fully characterized by spectroscopic methods, including single-crystal X-ray diffraction in four cases. Monodeprotection of two dimethyl phosphate derivatives with trimethylamine led to the tetramethylammonium salts of the (cyclohexadienyl methyl phosphate)Fe(CO)(3) complexes. These compounds are the first water-soluble enzyme-trigged CO-releasing molecules (ET-CORMs). The phosphatase-induced CO release was monitored by means of GC. The biological activity was assessed in different cellular assays. The compounds were shown to be only slightly toxic, and a moderate anti-inflammatory potential was determined in an assay based on the inhibition of inducible NO synthase (iNOS)-induced NO production.

Abstract

A series of racemic phosphoryloxy-substituted (eta(4)-cyclohexadiene)Fe(CO)(3) complexes was synthesized by exploiting the O-phosphorylation of (dienol)Fe(CO)(3) intermediates generated in situ from the corresponding triisopropylsiloxy-protected complexes. The phosphorylated products were fully characterized by spectroscopic methods, including single-crystal X-ray diffraction in four cases. Monodeprotection of two dimethyl phosphate derivatives with trimethylamine led to the tetramethylammonium salts of the (cyclohexadienyl methyl phosphate)Fe(CO)(3) complexes. These compounds are the first water-soluble enzyme-trigged CO-releasing molecules (ET-CORMs). The phosphatase-induced CO release was monitored by means of GC. The biological activity was assessed in different cellular assays. The compounds were shown to be only slightly toxic, and a moderate anti-inflammatory potential was determined in an assay based on the inhibition of inducible NO synthase (iNOS)-induced NO production.

Citations

29 citations in Web of Science®
28 citations in Scopus®
Google Scholar™

Altmetrics

Downloads

0 downloads since deposited on 01 Mar 2013
0 downloads since 12 months

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:01 Mar 2013 10:17
Last Modified:05 Apr 2016 16:34
Publisher:American Chemical Society
ISSN:0276-7333
Publisher DOI:https://doi.org/10.1021/om300359a

Download

[img]
Content: Published Version
Filetype: PDF - Registered users only
Size: 2MB
View at publisher

TrendTerms

TrendTerms displays relevant terms of the abstract of this publication and related documents on a map. The terms and their relations were extracted from ZORA using word statistics. Their timelines are taken from ZORA as well. The bubble size of a term is proportional to the number of documents where the term occurs. Red, orange, yellow and green colors are used for terms that occur in the current document; red indicates high interlinkedness of a term with other terms, orange, yellow and green decreasing interlinkedness. Blue is used for terms that have a relation with the terms in this document, but occur in other documents.
You can navigate and zoom the map. Mouse-hovering a term displays its timeline, clicking it yields the associated documents.

Author Collaborations