Unusual Photophysics of a Rhenium(I) Dipyridophenazine Complex in Homogeneous Solution and Bound to DNA

Stoeffler, Heather D.; Thornton, Nancy B.; Temkin, Stacy L.; Schanze, Kirk S.

doi:10.1021/ja00132a012

Cited by 215 publications

(234 citation statements)

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“…In Table S1 (supporting material) are reported the proton chemical shifts of phendione and the corresponding Re(I) complex, and are compatible with those of the literature [8,18,33,34]. The deshielding of the diimine protons can attributed to the electron density's removal from phendione towards [Re(CO) 3 Cl] core after complexation [40].…”

supporting

confidence: 79%

“…The complex 1 was synthesized based on the following report by Stoeffler [8] with some modifications [18]. A mixture of Re(CO) 5 Cl (0.1211 g, 0.33 mmol) and phendione (0.1040 g, 0.50 mmol) were suspended in 5 mL toluene and refluxed under N 2 atmosphere for 4 h. Then, the mixture was allowed to cool to room temperature and the solid was collected by filtration under vacuum.…”

Section: Synthesis Of Fac-[re(co)3(phendione)cl] (1)mentioning

confidence: 99%

“…4 complexes with an intercalative ligand (such as dppz) [8,16,20], due to the non-intercalative mode of the phendione ligand.…”

Section: Absorption Titrationmentioning

confidence: 99%

“…In this context, transition metal complexes are studied for their efficient DNA binding ability [2][3][4][5][6] and it is well documented that they can be used as probes capable to utilize nucleic acid structures [2][3][4][5][6], DNA-molecular light switches [7,8], oxidative cleaving agents for DNA [4][5][6]8], and potential anti-cancer drugs [9][10][11]. Rhenium belonging in the same period as platinum have attracted researchers attention not only due to the 188-Re beneficial radiopharmaceutical activities but also because several Re(I) complexes were found to be very active against suspended cancer cell lines (as MOLT-4 and HL-60) and solid tumors like MCF-7 and SK2 [12].…”

Section: Introductionmentioning

confidence: 99%

“…Rhenium belonging in the same period as platinum have attracted researchers attention not only due to the 188-Re beneficial radiopharmaceutical activities but also because several Re(I) complexes were found to be very active against suspended cancer cell lines (as MOLT-4 and HL-60) and solid tumors like MCF-7 and SK2 [12]. Moreover, significant cancer cell cytotoxicity has been reported for rhenium (I) tricarbonyl complexes [13,14] whereas a plenty of Re(I) polypyridine complexes have been designed not only for targeting biomolecules, such as DNA [8,[15][16][17][18][19][20] and protein [9,21,22] but also as cellular probes with cellular uptake like cytotoxicity and bioimaging application [9,22].…”

Section: Introductionmentioning

confidence: 99%

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Re(I) tricarbonyl complex of 1,10-phenanthroline-5,6-dione: DNA binding, cytotoxicity, anti-inflammatory and anti-coagulant effects towards platelet activating factor

Kaplanis

Stamatakis

Papakonstantinou

et al. 2014

Journal of Inorganic Biochemistry

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The complex fac-[Re(CO) 3 (phendione)Cl] (1) (where phendione=1,10-phenanthroline-5,6-dione) has been synthesized and fully characterized by UV-visible, FTIR, and NMR techniques.The DNA binding properties of 1 are investigated by UV-spectrophotometric (melting curves), covalent binding assay, CV (cyclic voltammetry), circular dichroism (CD) and viscosity measurements. Experimental data indicate that 1 fits into the major groove without disrupting the helical structure of the B-DNA in contrast to the free phendione which intercalates within the base pairs of DNA. Upon irradiation, complex 1 promotes the cleavage of plasmid pBR322 DNA from supercoiled form I to nicked form II via a proton coupled electron transfer mechanism. This comes as a result of experimental data in anaerobic /aerobic conditions and in the presence of DMSO. The biological activities of 1 and its precursors [Re(CO) 5 Cl] and phendione are tested towards a series of cancerous cell lines as glioblastoma (T98G), prostate cancer (PC3) and breast cancer (MCF-7) as well as platelet activating factor (PAF)-aggregation. Moreover, all the aforementioned compounds are tested for their ability to modulate PAF-basic metabolic enzymes activities in preparations of rabbit leukolytes. The in vitro experiments indicate that phendione has a better antitumor effect than cisplatin whereas [Re(CO) 5 Cl] is a better PAF inhibitor than both the phendione ligand and 1.Moreover, for the first time it is indicated that [Re(CO) 5 Cl], with a IC 50 of 17 nM is comparable to the widely used PAF receptor antagonists, BN52021 and WEB2170 with IC 50 of 30 and 20 nM, respectively, whereas 1 affects PAF-catabolism.

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supporting

confidence: 79%

Section: Synthesis Of Fac-[re(co)3(phendione)cl] (1)mentioning

confidence: 99%

“…4 complexes with an intercalative ligand (such as dppz) [8,16,20], due to the non-intercalative mode of the phendione ligand.…”

Section: Absorption Titrationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Re(I) tricarbonyl complex of 1,10-phenanthroline-5,6-dione: DNA binding, cytotoxicity, anti-inflammatory and anti-coagulant effects towards platelet activating factor

Kaplanis

Stamatakis

Papakonstantinou

et al. 2014

Journal of Inorganic Biochemistry

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Electronic absorption, resonance Raman and excited-state resonance Raman spectroscopy of rhenium(I) and copper(I) complexes, with substituted dipyrido[3,2-a : 2′,3′-c]phenazine ligands, and their electron reduced products

Waterland

Gordon

2000

J. Raman Spectrosc.

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The electronic absorption and resonance Raman spectra of a series of rhenium(I) and copper(I) complexes with substituted dipyrido[3,2-a : 2 ,3 -c]phenazine (dppz) ligands were investigated. The ligands were benzo[i ]dipyrido[3,2-a : 2 ,3 -c]phenazine, 11,12-dimethyldipyrido[3,2-a : 2 ,3 -c]phenazine, 10-methyldipyrido[3,2-a : 2 ,3 -c]phenazine and 11-methyoxydipyrido[3,2-a : 2 ,3 -c]phenazine. The spectroelectrochemistry of the reduced complexes and the emission and resonance Raman spectra of the excited states are reported. Vibrational wavenumber calculations of the unsubstituted ligand suggest the presence of normal modes that are localized to various sections of the ligand structure; the resonance Raman spectra of the complexes are interpreted with reference to these calculations. The analysis of the spectra revealed that the Franck-Condon state initially formed by visible photoexcitation (450 nm) is metal-to-ligand charge-transfer in nature. Spectroelectrochemical resonance Raman and electronic absorption measurements revealed the spectral signatures for the radical anions of each of the ligands used in this study. These spectral features were used to assign the excited states formed by the complexes. Most of the complexes studied show spectral features in their excited-states that suggest that the predominant state formed within 5 ns of excitation is ligand-centred.a See Fig. 1 for numbering scheme. b The values in parentheses show the difference between the corresponding free ligand resonance, i.e. υ(complex) υ(ligand). c Insufficiently soluble in CDCl 3 to obtain a spectrum.

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Luminescence Behavior & Photochemistry of Organotransition Metal Compounds

Yam

2005

Encyclopedia of Inorganic Chemistry

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In this article, the luminescence and photochemical properties of a selection of organotransition metal compounds are reviewed and discussed. The examples are classified according to the identity of the carbon‐containing ligands, which include the carbonyl, isocyanide, cyanide, alkynyl, alkenyl, arene, aryl, alkylidene, alkylidyne, cyclometalating, and alkyl ligands. The luminescence and photochemistry of selected tungsten, molybdenum, and rhenium carbonyl compounds are described in this article, followed by some examples with the analogous isocyanide and cyanide ligands. The luminescence properties and potential applications of these systems are discussed. Transition metal complexes containing alkynyl ligands display a very wide structural diversity and catalytic properties, and many systems also show intriguing photoluminescence properties, especially those of rhenium(I), platinum(II), palladium(II), and the coinage metals. Studies focused on the photophysical studies and the excited‐state chemistry of selected alkynyl systems and related alkenyl, arene, and aryl complexes are outlined and discussed. Luminescent metal–carbon multiple bonded systems including the alkylidene and alkylidyne compounds have received relatively little attention, and examples have been confined to the complexes of molybdenum and tungsten. However, much effort has recently been devoted to exploring the interesting emission properties of alkylidene and alkylidyne systems with other metal centers such as rhenium, ruthenium, osmium, platinum, and coinage metals, which are outlined in this article. Some recent examples in the areas of cyclometalated complexes, especially those of rhodium(III), iridium(III), platinum(II), and gold(III) centers are highlighted in this article as many examples display impressive photophysical and photochemical behavior. Metal alkyl systems represent a special class of luminescent organometallic system due to their strong σ‐donating properties of the alkyl ligands, and the photophysical and excited‐state properties of some selected examples are described. Finally, luminescent organotransition metal compounds with application potentials in the development of new materials, photodevices, and sensory systems are summarized in various parts of this article.

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Unusual Photophysics of a Rhenium(I) Dipyridophenazine Complex in Homogeneous Solution and Bound to DNA

Cited by 215 publications

References 2 publications

Re(I) tricarbonyl complex of 1,10-phenanthroline-5,6-dione: DNA binding, cytotoxicity, anti-inflammatory and anti-coagulant effects towards platelet activating factor

Re(I) tricarbonyl complex of 1,10-phenanthroline-5,6-dione: DNA binding, cytotoxicity, anti-inflammatory and anti-coagulant effects towards platelet activating factor

Electronic absorption, resonance Raman and excited-state resonance Raman spectroscopy of rhenium(I) and copper(I) complexes, with substituted dipyrido[3,2-a : 2′,3′-c]phenazine ligands, and their electron reduced products

Luminescence Behavior & Photochemistry of Organotransition Metal Compounds

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