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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.

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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:01 Mar 2013 10:17
Last Modified:21 Nov 2017 16:34
Publisher:American Chemical Society
ISSN:0276-7333
Publisher DOI:https://doi.org/10.1021/om300359a

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