Derivatives of 1,10-Phenanthroline-5,6-quinone

Dickeson, JE; Summers, L. A.

doi:10.1071/ch9701023

Cited by 347 publications

(253 citation statements)

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“…ESI MS spectra were recorded on a Finnigan AQA instrument equipped with an electrospray ionization (ESI) interface. The ligands phendione (1,10-phenanthroline-5,6-dione [20] ) and dppz (dipyrido[3,2-a:2',3'-c]phenazine [25] ) were synthesized according to published methods. Cisplatin was synthesized from K 2 -…”

Section: Methodsmentioning

confidence: 99%

Phenanthroline Derivatives with Improved Selectivity as DNA‐Targeting Anticancer or Antimicrobial Drugs

et al. 2008

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Phenanthroline derivatives are of interest due to their potential activity against cancer, and viral, bacterial, and fungal infections. In a search for highly specific antitumor and antibacterial compounds, we report the activities of 1,10‐phenanthroline‐5,6‐dione (phendione or L1), dipyrido[3,2‐a:2′,3′‐c]phenazine (dppz or L2), and their corresponding platinum complexes ([PtL1Cl2] and [PtL2Cl2]), and provide the solid‐state 3D structure for [PtL1Cl2]. It is generally known that a toxic metal ion coordinated to an active organic moiety leads to a synergistic effect; however, we report herein that the platinum complexes [PtL1Cl2] and [PtL2Cl2] have weaker activities relative to those of the free ligands, especially against bacteria. Testing these agents against a variety of human cancer cell lines revealed that L1 and [PtL1Cl2] were at least as active as cisplatin against several of the cell lines (including a cisplatin‐resistant cell line). The absence of antibacterial activity of [PtL1Cl2] removes the detrimental effect of phenanthrolines toward intestinal flora, suggesting a highly promising new strategy for the development of anticancer drugs with reduced side effects.

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Section: Methodsmentioning

confidence: 99%

Phenanthroline Derivatives with Improved Selectivity as DNA‐Targeting Anticancer or Antimicrobial Drugs

et al. 2008

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“…Bidistilled water was used for preparing buffer solutions. The dppz ligand was synthesized and characterized by closely following previously reported methods [22].…”

Section: Methodsmentioning

confidence: 99%

The interaction of native calf thymus DNA with FeIII-dipyrido[3,2-a:2′,3′-c]phenazine

Terenzi

Barone

Silvestri

et al. 2009

Journal of Inorganic Biochemistry

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a b s t r a c tThe mono and bis dipyrido[3,2-a:2 0 ,3 0 -c]phenazine (dppz) adducts of iron(III) chloride, i.e. [Fe(dppz)]Cl 3 and [Fe(dppz) 2 ]Cl 3 , have been synthesized and characterized. The interaction of the Fe III dppz hydrolyzed aquo complex with native calf thymus DNA has been monitored as a function of the metal complex-DNA molar ratio, by variable temperature UV absorption spectrophotometry, circular dichroism (CD) and fluorescence spectroscopy. The results obtained in solution at various ionic strength values give support for a tight intercalative binding of the Fe III dppz cation with DNA. In particular, the appearance of induced CD bands, caused by the addition of Fe III dppz, indicate the existence of a rigid metal complex-DNA-binding leading to dominating chiral organization of Fe III dppz species within the DNA double helix. The trend of selected CD bands with the molar concentration of Fe III dppz emphasizes that the presence of high amounts of metal complex induces also the formation of DNA-Fe III dppz supramolecular aggregates in solution. The analysis of fluorescence measurements allowed us to calculate a value of the intercalative binding constant comparable to that obtained by UV spectrophotometric titration. Finally, the temperature dependence of the absorbance at 258 nm shows that the metal complex strongly increases the DNA melting temperature already at metal complex-DNA molar ratio equal to 0.25 suggesting that metal complex intercalation effectively hinders DNA denaturation. Overall, the results of the present study point out that the Fe III dppz aquo complex has DNA-binding properties analogous to those previously reported for the tris-chelate Fe II (phen) 2 dppz complex (phen = 1,10-phenantroline).

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“…Toluene and pentane were dried over sodium and distilled while CH 2 Cl 2 was purified by passage through a column of activated alumina. Toluene-d 8 , pyridine-d 5 and C 6 D 6 were dried over sodium. All the solvents were degassed prior to use.…”

Section: Methodsmentioning

confidence: 99%

Thermal Dihydrogen Elimination from Cp*₂Yb(4,5-diazafluorene)

et al. 2012

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The reaction of 4,5-diazafluorene with Cp* 2 Yb(OEt 2 ), where Cp* is pentamethylcyclopentadienyl, affords the isolable adduct Cp* 2 Yb(4,5-diazafluorene) (1), which slowly eliminates H 2 to form Cp* 2 Yb(4,5-diazafluorenyl) (2); the net reaction is therefore 1 → 2 + H • . The ytterbium atom in 1 is shown to be intermediate valent by variable-temperature L III -edge X-ray absorption near-edge (XANES) spectroscopy, consistent with its low effective magnetic moment (μ eff ). The experimental studies are supported by complete active space self-consistent field (CASSCF) calculations, showing that two open-shell singlets lie below the triplet state. The two open-shell singlets are calculated to be multiconfigurational and closely spaced, in agreement with the observed temperature dependence of the XANES and χ data, which are fit to a Boltzmann distribution. A mechanism for dihydrogen formation is proposed on the basis of kinetic and labeling studies to involve the bimetallic complex (Cp* 2 Yb) 2 (4,5diazafluorenyl) 2 , in which the heterocyclic amine ligands are joined by a carbon−carbon bond at C(9)−C(9′).

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Derivatives of 1,10-Phenanthroline-5,6-quinone

Cited by 347 publications

References 0 publications

Phenanthroline Derivatives with Improved Selectivity as DNA‐Targeting Anticancer or Antimicrobial Drugs

Phenanthroline Derivatives with Improved Selectivity as DNA‐Targeting Anticancer or Antimicrobial Drugs

The interaction of native calf thymus DNA with FeIII-dipyrido[3,2-a:2′,3′-c]phenazine

Thermal Dihydrogen Elimination from Cp*₂Yb(4,5-diazafluorene)

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Derivatives of 1,10-Phenanthroline-5,6-quinone

Cited by 347 publications

References 0 publications

Phenanthroline Derivatives with Improved Selectivity as DNA‐Targeting Anticancer or Antimicrobial Drugs

Phenanthroline Derivatives with Improved Selectivity as DNA‐Targeting Anticancer or Antimicrobial Drugs

The interaction of native calf thymus DNA with FeIII-dipyrido[3,2-a:2′,3′-c]phenazine

Thermal Dihydrogen Elimination from Cp*2Yb(4,5-diazafluorene)

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Thermal Dihydrogen Elimination from Cp*₂Yb(4,5-diazafluorene)