PORPHYRIN-FLAVONOL HYBRID MOLECULES FOR EFFICIENT
DELIVERY OF CO
Andrea Ramundo,1 Lucie Muchová,2 Libor Vítek,2 and Petr Klán1
1
Department of Chemistry and RECETOX, Masaryk University, Kamenice 5, 62500, Brno,
Czech Republic; 2
Institute of Medical Biochemistry and Laboratory Diagnostics, Charles
University, Na Bojišti 3, 12108, Praha 2, Czech Republic
e-mail: andre.ramundo@gmail.com; klan@sci.muni.cz
Carbon monoxide (CO) is known to be a toxic gas for mammals, yet it has been
recognized as a signaling molecule with anti-inflammatory and cell-protective
properties, with possible applications in clinical treatments.1, 2
Light-activated COreleasing
molecules (photoCORMs) can provide a high spatial and temporal control,
allowing the drug to be delivered only into the targeted tissues when required. However,
many of well-known photoCORMs show poor water solubility, require short irradiation
wavelengths, or suffer of low quantum efficiencies, with evidently limited use under a
clinical scenario. Herein, we present a platform that combines the excellent
photoproperties of porphyrins, which act as antennas and sensitizers, with the CO
releasing abilities of four flavonol-based appendices.3
CO proved to be released upon
irradiation in the range of 440-670 nm in both organic and aqueous solutions with high
chemical yield (up to 3.4 equiv) and excellent quantum yield (up to 4%). A facile metal
insertion was used to fine-tune the compound photoproperties and allowed for an
unprecedented uncaging cross-section (ΦCOεmax) exceeding 104
M-1
cm-1
.
Figure 1. Structure of the porphyrin-flavonol hybrids molecules.
References
1. Verma, A.; Hirsch, D.; Glatt, C.; Ronnett, G. Science 1993, 259, 381-384.
2. Motterlini, R.; Otterbein, L. E. Nat. Rev. Drug Discov. 2010, 9, 728-743.
3. Studer, L. S.; Brewer W. E.; Martinez, M. L.; Chou, P. J. Am. Chem. Soc. 1989, 111, 7643-
7644.
N
N N
N
O
O
OH
N
O
O
OH
N
O
O
OH
N
O
O
HO
N
M
M = Zn, Pd, Cu
N
NH N
HN
O
O
HO
O
OHO
O
O OH
O
O
OH