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Analytical Chemistry
μL DMSO) and imaged after 20 min. (C-D) The mouse was given
(10) Clark, J.-E.; Naughton, P.; Shurey, S.; Green, C.-J.; Johnson, T.-
R.; Mann, B.-E.; Foresti, R.; Motterlini, R. Cardioprotective
actions by a water-soluble carbon monoxide-releasing molecule,
Circ. Res. 2003, 93, 2–8.
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an intraperitoneal injection of CORM3-green (50 μM, in 50 μL
DMSO), followed with injection of 50 μM CORM-3 (100 μL in
saline) and then imaged respectively after 5 and 20 min of
incubation. The red cycle shows the injection and the fluorescence
collection area. (E) A plot of fluorescent intensity of images A-D.
Excitation was set at 405 nm and emission was collected at 450-
(
11) Foresti, R.; Hammad, J.; Clark, J. E.; Johnson, T. R.; Mann, B.
E.; Friebe, A.; Green, C. J.; Motterlini, R. Vasoactive properties
of CORM-3, a novel water-soluble carbon monoxide-releasing
molecule, Br. J. Pharmaco. 2004, 142, 453–460.
5
50 nm
(12) Tinajero-Trejo, M.; Denby, K.-J.; Sedelnikova, S.-E.;
Hassoubah, S.-A.; Mann, B.-E.; Poole, R.-K. The carbon
CONCLUSION
monoxide-releasing
molecule,
CORM-3
In summary, we have developed a fluorescent ESIPT probe
for imaging of CORM-3 in living systems. This probe is water-
soluble and can be easily prepared from cheap reagents. More
importantly, this probe provided a fast responsive, highly
selective and sensitive fluorescent turn-on detection method for
CORM-3. Moreover, this probe exhibits great potential for
imaging of CORM-3 in living cells, zebrafishes and animals.
(Ru(CO) Cl(Glycinate)), targets respiration and oxidases in
3
campylobacter jejuni, generating hydrogen peroxide, J. Biol.
Chem. 2014, 289, 29471–29482.
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(
13) Song, H.; Bergstrasser, C.; Rafat, N.; Höger, S.; Schmidt, M.;
Endres, N.; Goebeler, M.; Hillebrands, J.-L.; Brigelius-Flohé, R.;
Banning, A.; Beck, G.; Loesel, R.; Yard, B.-A. The carbon
monoxide releasing molecule (CORM-3) inhibits expression of
vascular cell adhesion molecule-1 and E-selectin independently
of haem oxygenase-1 expression, Br. J. Pharmacol. 2009, 157,
769–780.
ASSOCIATED CONTENT
Supporting Information
(
14) Song, H.; Hoeger, S.; Hillebrands, J.-L.; Mandel, I.; Loesel, R.;
Beck, G.; Schilling, L.; Schnuelle, P.; Yard, B. CORMs protect
endothelial cells during cold preservation, resulting in inhibition
of intimal hyperplasia after aorta transplantation in rats,
Transplant International. 2010, 23, 1144–1153.
Structure characterizations for CORM3-green and PTI, data for
the mechanism of sensing, and additional data of UV-vis and
fluorescence studies. This material is available free of charge via
the Internet at http://pubs.acs.org.
(
15) Vadori, M.; Seveso, M.; Besenzon, F.; Bosio, E.; Tognato, E.;
Fante, F.; Boldrin, M.; Gavasso, S.; Ravarotto, L.; Mann, B.-E.;
Simioni, P.; Ancona, E.; Motterlini, R.; Cozzi, E. In vitro and in
vivo effects of the carbon monoxide-releasing molecule, CORM-
AUTHOR INFORMATION
3
,
in
the
xenogeneic
pig-to-primate
context,
Corresponding Author
Xenotransplantation. 2010, 16, 99–114.
(
(
(
16) Santos-Silva, T.; Mukhopadhyay, A.; Seixas, J.-D.; Bernardes,
G.-J.; Romão, C.-C.; Romão, M.-J. CORM-3 reactivity toward
proteins: the crystal structure of a Ru(II) dicarbonyl-lysozyme
complex, J. Am. Chem. Soc. 2011, 133, 1192–1195.
17) Long, R.; Salouage, I.; Berdeaux, A.; Motterlini, R.; Morin, D.
CORM-3, a water soluble CO-releasing molecule, uncouples
mitochondrial respiration via interaction with the phosphate
carrier, Biochim. Biophys. Acta. 2014, 1837, 201–209.
18) Michel, B. W.; Lippert, A. R.; Chang, C. A reaction-based
fluorescent probe for selective imaging of carbon monoxide in
living cells using a palladium-mediated carbonylation, J. Am.
Chem. Soc. 2012, 134, 15668–15671.
ACKNOWLEDGMENT
We gratefully thank the National Natural Science Foundation of
China (21672080 and 21472066) and Fundamental Research Funds
for the Central Universities (CCNU19TS007) for financial support.
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