A DNA-intercalating compound derived from 7H-pyridocarbazole: the structure of 10-methoxy-2-methyl-7H-pyrido[4,3-c]carbazolium iodide

Courseille, C.; Pélaprat, Didier; Tsai, Chun Che

doi:10.1107/s0108270188008558

Cited by 2 publications

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“…[27][28][29][30][31][32] It is suggested that the particular geometry and size of the 7H-PyC nucleus and the presence of some small substitutions (methyl or methoxy) at certain positions are the structural elements that determine the strong capacity to intercalate into the DNA double helix to a similar extent as ellipticine. [30] We examined 3-methyl-6-methoxy-7H-pyridoA C H T U N G T R E N N U N G [2,3-c]carbazole as a basic nucleus and, with the aim of improving the cytotoxicity of the heterocycle system, we synthesized some new branched 7H-tetrahydro-PyCs (7H-THPyC) and 7H-PyCs ( Figure 1) with one or two diethylaminoethyl side chains grafted onto PyC.…”

Section: Introductionmentioning

confidence: 99%

DNA Binding Ellipticine Analogues: Synthesis, Biological Evaluation, and Structure–Activity Relationships

et al. 2009

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In connection with our interest in the synthesis and study of the biological properties of ellipticine analogues as anticancer agents, some 7H-pyrido[2,3-c]carbazoles (7H-PyC) and their corresponding tetrahydro derivatives (7H-THPyC) were synthesized. A common multistep pathway characterized by conventional reactions involving carbazole Fischer and Conrad-Limpach quinoline syntheses yielded the tetracyclic compounds. With the aim to improve the cytotoxic activity of the new 7H-PyC derivatives, we provided them with one or two diethylaminoethyl side chains. The new THPyCs, PyCs, and smaller pyrroloquinoline (PQ) derivatives were tested for their in vitro cytotoxic properties against several human tumor cell lines. Most of the compounds tested showed considerable cytotoxic activity, particularly compound 24, which, with two basic alkylamino chains, has IC(50) values in the sub-micromolar range, about one order of magnitude lower than those of the reference compound, ellipticine. Chemosensitivity tests on cisplatin-, mitoxantrone-, and multidrug-resistant (MDR) phenotypes indicated that compound 24 shows no cross-resistance; this suggests that, besides not being a potential MDR substrate, it might act as a mixed inhibitor of topoisomerases I and II. Flow cytometric and caspase-3 activation analyses revealed that 24 induces a caspase-3-dependent apoptotic cell-death mechanism. Linear dichroism and unwinding experiments suggested that the most active compounds act as DNA intercalators. For compound 24, an inhibitory concentration-dependent effect on topoisomerases II and I was demonstrated. Herein we discuss interesting structure-activity relationships with respect to molecular size and planarity, as well as the substitution and position of one side chain on the PyC nucleus, in comparison with corresponding smaller PQs.

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Section: Introductionmentioning

confidence: 99%

DNA Binding Ellipticine Analogues: Synthesis, Biological Evaluation, and Structure–Activity Relationships

et al. 2009

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“…Tertiary iminium π-systems analogous to the parent N -methyl- N -methylenemethanaminium trifluoroacetate and N -methyl- N -methylenemethanaminium iodide salts were stabilized thanks to superacids, and reported to be useful building blocks for organic synthesis. π-Extended structures comprising a conjugated iminium function are well-known chemicals with interesting electro- and photochemical properties like cyanine, hemicyanine, squaraine, or methine dyes with various applications in material science, − biophotonics, − and nonlinear optics. , The N-heteroaromatic cationic N ↔ N bridge ( E )-((amino)phenyl)allylidene-aminium has already been isolated and reported as perchlorate, − chloride, hexafluorophosphate, or triflate salts with various alkyl and aryl substituents.…”

Section: Introductionmentioning

confidence: 99%

Deep Blue Asymmetrical Streptocyanine Dyes: Synthesis, Spectroscopic Characterizations, and Ion-Specific Cooperative Adsorption at the Surface of TiO₂ Anatase Nanoparticles

et al. 2017

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Various triflate (TfO–), tetrafluoroborate (BF4 –), and perchlorate (ClO4 –) salts of (E)-9-(3-(4-(diphenylamino)phenyl)allylidene)-9H-carbazol-9-ium chromophores, asymmetrical streptocyanine blue dyes, were synthesized, and their structures and photochemical and electrochemical properties were characterized. Displaying a high absorption band in the wavelength range 620–640 nm in acidified benzonitrile, the dyes provide an intense absorption at longer wavelength thanks to their oxidized π-conjugated systems. The π-electronic structure underwent twisting and bending, counteracting the electron-donating/withdrawing induction of its different substituents with a propensity to cancel its dipole moment and HOMO–LUMO charge-transfer coefficient. Zeta potential measurements of colloidal suspensions of sensitized TiO2 anatase nanoparticles outlined the difference in electric behavior of the organic ionic pairs at the surface of the nanoparticles: The noncoordinating or coordinating characters of the counterions were found governing the molecular density at the surface and the adsorption/desorption kinetics of the ionic pairs. Dye-sensitized solar cell (DSSC) measurements performed with I–/I3 – as redox shuttle outlined the availability of the dyes for solar cell sensitization and the conditions for best stability/efficiency of such π-conjugated structures according to the nature of the counterion.

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A DNA-intercalating compound derived from 7H-pyridocarbazole: the structure of 10-methoxy-2-methyl-7H-pyrido[4,3-c]carbazolium iodide

Cited by 2 publications

References 4 publications

DNA Binding Ellipticine Analogues: Synthesis, Biological Evaluation, and Structure–Activity Relationships

DNA Binding Ellipticine Analogues: Synthesis, Biological Evaluation, and Structure–Activity Relationships

Deep Blue Asymmetrical Streptocyanine Dyes: Synthesis, Spectroscopic Characterizations, and Ion-Specific Cooperative Adsorption at the Surface of TiO₂ Anatase Nanoparticles

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A DNA-intercalating compound derived from 7H-pyridocarbazole: the structure of 10-methoxy-2-methyl-7H-pyrido[4,3-c]carbazolium iodide

Cited by 2 publications

References 4 publications

DNA Binding Ellipticine Analogues: Synthesis, Biological Evaluation, and Structure–Activity Relationships

DNA Binding Ellipticine Analogues: Synthesis, Biological Evaluation, and Structure–Activity Relationships

Deep Blue Asymmetrical Streptocyanine Dyes: Synthesis, Spectroscopic Characterizations, and Ion-Specific Cooperative Adsorption at the Surface of TiO2 Anatase Nanoparticles

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Product

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Deep Blue Asymmetrical Streptocyanine Dyes: Synthesis, Spectroscopic Characterizations, and Ion-Specific Cooperative Adsorption at the Surface of TiO₂ Anatase Nanoparticles