Photophysics of Aminoxanthone Derivatives and Their Application as Binding Probes for DNA†

Pace, Tamara C. S.; Monahan, S. L.; MacRae, Andrew I.; Kaila, Monica; Bohne, Cornelia

doi:10.1562/2005-05-16-ra-529

Cited by 10 publications

(7 citation statements)

References 64 publications

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“…It will also be important to develop methodologies that do not employ triplet excited states because, in some cases, these excited states can only be rendered nonreactive with the host by decreasing their triplet energy to such an extent that the quenching methodology cannot be applied. This situation was recently described for the binding dynamics of xanthone derivatives with DNA …”

Section: Discussionmentioning

confidence: 86%

Supramolecular Dynamics Studied Using Photophysics

Bohne

2006

Langmuir

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Dynamics is an essential feature of supramolecular systems, and it's understanding will be central in achieving new chemical function. The methodology to obtain association and dissociation rate constants for fast binding of guests to host systems in real time is described. Examples are provided for binding of guests to cyclodextrins or bile salt aggregates with an emphasis on the type of information and mechanistic insight that can only be uncovered from kinetic studies and is not apparent in thermodynamic investigations.

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Section: Discussionmentioning

confidence: 86%

Supramolecular Dynamics Studied Using Photophysics

Bohne

2006

Langmuir

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“…Antibacterial, antifungal and antiviral characteristics as well as cytotoxic activities towards cancer cells could be demonstrated. Initial reactions of xanthone 1 a, prepared in four steps from xanthone (see Supporting Information), [25][26][27] and hexafluorobenzene (2) (50-300 equiv.) [21][22][23][24] We therefore decided to choose the 2-isocyanoxanthone (1 a) bearing an isonitrile functionality.…”

Section: Resultsmentioning

confidence: 99%

“…[21][22][23][24] We therefore decided to choose the 2-isocyanoxanthone (1 a) bearing an isonitrile functionality. Initial reactions of xanthone 1 a, prepared in four steps from xanthone (see Supporting Information), [25][26][27] and hexafluorobenzene (2) (50-300 equiv.) were conducted under argon atmosphere and irradiation (λ exc = 350 nm) for up to 40 hours to give imidoyl fluoride 3 a (see Supporting Information).…”

Section: Resultsmentioning

confidence: 99%

Mild C−F Activation in Perfluorinated Arenes through Photosensitized Insertion of Isonitriles at 350 nm

et al. 2019

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Fluorinated compounds have become important in the fields of agrochemical industry, pharmaceutical chemistry and materials sciences. Accordingly, various methods for their preparation have been developed in the past. Fluorinated compounds can be accessed via conjugation with fluorinated building blocks, via CÀ H fluorination or via selective activation of perfluorinated compounds to give the partially fluorinated congeners. Especially the direct activation of CÀ F bonds, one of the strongest σ-bonds, still remains challenging and new strategies for CÀ F activation are desirable. Herein a method for the photochemical activation of aromatic CÀ F bonds is presented. It is shown that isonitriles selectively insert into aromatic CÀ F bonds while aliphatic CÀ F bonds remain unaffected. Mechanistic studies reveal the reaction to proceed via the indirect excitation of the isonitrile to its triplet state by photoexcited acetophenone at 350 nm. Due to the relatively mild light used, the process shows high functional group tolerance and various compounds of the class of benzimidoyl fluorides are accessible from aryl isonitriles and commercially available perfluorinated arenes.

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“…The important features for intercalation have been suggested to be a fused tricyclic aromatic backbone and the presence of substituent side chains. 11,12) However, there are only a few systematic studies on the relationship of the structure and the DNA-binding ability. 13) So many researchers made major efforts aimed at clarifying the structure-activity correlation that could be used to guide the discovery of potent antitumor drugs for medical use.…”

mentioning

confidence: 99%

Cytotoxic Activity and DNA-Binding Properties of Isoeuxanthone Derivatives

Wang

Yan

Gao

et al. 2014

CHEMICAL & PHARMACEUTICAL BULLETIN

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In this study, the interactions of different groups substituted isoeuxanthone derivatives with calf thymus DNA (ct DNA) were investigated by spectrophotometric methods and viscosity measurements. Results indicated that the xanthone derivatives could intercalate into the DNA base pairs by the plane of xanthone ring and the various substituents may influence the binding affinity with DNA according to the calculated quenching constant values. Furthermore, two tumor cell lines including the human cervical cancer cell line (HeLa) and human hepatocellular liver carcinoma cell line (HepG2) were used to evaluate the cytotoxic activities of xanthone derivatives by acid phosphatase assay. Analyses showed that the oxiranylmethoxy substituted xanthone exhibited more effective cytotoxic activity against the cancer cells than the other substituted xanthones. The effects on the inhibition of tumor cells in vitro agreed with the studies of DNA-binding.

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Photophysics of Aminoxanthone Derivatives and Their Application as Binding Probes for DNA†

Cited by 10 publications

References 64 publications

Supramolecular Dynamics Studied Using Photophysics

Supramolecular Dynamics Studied Using Photophysics

Mild C−F Activation in Perfluorinated Arenes through Photosensitized Insertion of Isonitriles at 350 nm

Cytotoxic Activity and DNA-Binding Properties of Isoeuxanthone Derivatives

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