Aminomethylanthracene Dyes as High‐Ionic‐Strength DNA‐Photocleaving Agents: Two Rings are Better than One

Safiarian, Mohammad S.; Sawoo, Sudeshna; Mapp, Carla T.; Williams, Dominique E.; Gude, Lourdes; Fernández, M. J.; Lorente, Antonio; Grant, Kathryn B.

doi:10.1002/slct.201703019

Cited by 2 publications

(22 citation statements)

References 96 publications

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“…Therefore, the limited changes in the spectral profile of the gold complex suggest a different type of interaction with double-stranded DNA such as external/groove binding [ 42 ] (see also viscometric tests below). Literature data also confirm that, while hypochromic and bathochromic shifts in anthracene vibronic bands indicate the occurrence ofDNA intercalation, hypochromicity in the absence of red shifting is a characteristic of anthracene minor groove interactions [ 43 , 44 ].…”

Section: Resultsmentioning

confidence: 91%

On the Different Mode of Action of Au(I)/Ag(I)-NHC Bis-Anthracenyl Complexes Towards Selected Target Biomolecules

et al. 2020

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Gold and silver N-heterocyclic carbenes (NHCs) are emerging for therapeutic applications. Multiple techniques are here used to unveil the mechanistic details of the binding to different biosubstrates of bis(1-(anthracen-9-ylmethyl)-3-ethylimidazol-2-ylidene) silver chloride [Ag(EIA)2]Cl and bis(1-(anthracen-9-ylmethyl)-3-ethylimidazol-2-ylidene) gold chloride [Au(EIA)2]Cl. As the biosubstrates, we tested natural double-stranded DNA, synthetic RNA polynucleotides (single-poly(A), double-poly(A)poly(U) and triple-stranded poly(A)2poly(U)), DNA G-quadruplex structures (G4s), and bovine serum albumin (BSA) protein. Absorbance and fluorescence titrations, mass spectrometry together with melting and viscometry tests show significant differences in the binding features between silver and gold compounds. [Au(EIA)2]Cl covalently binds BSA. It is here evidenced that the selectivity is high: low affinity and external binding for all polynucleotides and G4s are found. Conversely, in the case of [Ag(EIA)2]Cl, the binding to BSA is weak and relies on electrostatic interactions. [Ag(EIA)2]Cl strongly/selectively interacts only with double strands by a mechanism where intercalation plays the major role, but groove binding is also operative. The absence of an interaction with triplexes indicates the major role played by the geometrical constraints to drive the binding mode.

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Section: Resultsmentioning

confidence: 91%

On the Different Mode of Action of Au(I)/Ag(I)-NHC Bis-Anthracenyl Complexes Towards Selected Target Biomolecules

et al. 2020

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“…In previously published work, we described the synthesis of N 1 - (anthracen-9-ylmethyl)ethane-1,2-diaminium dichloride ( 2 ) (Scheme ). Using the fluorometric, hydroxyl radical probe hydroxyphenyl fluorescein (HPF) and ROS scavengers such as sodium benzoate, we then demonstrated that this chromophore photosensitized the production of high levels of DNA-damaging hydroxyl radicals in the presence of 150 mM NaCl in combination with 260 mM KCl, salts which we used to approximate Na + and K + concentrations typical of those found in the cell nucleus. − …”

Section: Resultsmentioning

confidence: 99%

“…The known compound N 1 -(anthracen-9-ylmethyl)ethane-1,2-diaminium dichloride 2 was synthesized and characterized as reported in our previous publication (Scheme 1). 30 For long-term storage, 10−15 mM stock solutions of 2 were prepared in dimethyl sulfoxide (DMSO) and kept at −20 °C.…”

Section: Methodsmentioning

confidence: 99%

“…To our surprise, levels of ROS production and concomitant DNA photocleavage were instead enhanced by the high-ionic-strength conditions (350 nm, pH 7.0). 30,31 Moreover, the phototoxicity of 9-aminomethylanthracene chromophores against Escherichia coli was increased by the 150 mM NaCl and 260 mM KCl salt combination. 30 To gain a better understanding of the mechanisms underlying the unanticipated phenomenon of redox-inactive chloride salts contributing to photooxidative DNA damage, in the current study, we have examined ROS generated by N 1 -(anthracen-9-ylmethyl)ethane-1,2-diaminium dichloride 2 when NaCl and KCl are present individually rather than in combination.…”

Section: Introductionmentioning

confidence: 99%

“…30,31 Moreover, the phototoxicity of 9-aminomethylanthracene chromophores against Escherichia coli was increased by the 150 mM NaCl and 260 mM KCl salt combination. 30 To gain a better understanding of the mechanisms underlying the unanticipated phenomenon of redox-inactive chloride salts contributing to photooxidative DNA damage, in the current study, we have examined ROS generated by N 1 -(anthracen-9-ylmethyl)ethane-1,2-diaminium dichloride 2 when NaCl and KCl are present individually rather than in combination. We have also compared the effects of NaCl and KCl to those of individual sodium(I) and potassium(I) fluoride, bromide, and iodide salts.…”

Section: Introductionmentioning

confidence: 99%

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New Insights into the Phototoxicity of Anthracene-Based Chromophores: The Chloride Salt Effect

Safiarian,

Ugboya,

Khan

et al. 2023

Chem. Res. Toxicol.

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Unraveling the causes underlying polycyclic aromatic hydrocarbon phototoxicity is an essential step in understanding the harmful effects of these compounds in nature. Toward this end, we have studied the DNA interactions and photochemistry of N 1-(anthracen-9-ylmethyl)ethane-1,2-diaminium dichloride in the presence and absence of NaF, KF, NaCl, KCl, NaBr, KBr, NaI, and KI (350 nm hν, pH 7.0). Exposing pUC19 plasmid to UV light in solutions containing 400 mM KCl formed significantly more direct strand breaks in DNA compared to no-salt control reactions. In contrast, NaCl increased DNA damage moderately, while the sodium(I) and potassium(I) fluoride, bromide, and iodide salts generally inhibited cleavage (I– > Br– > F–). A halide anion-induced heavy-atom effect was indicated by monitoring anthracene photodegradation and by employing the hydroxyl radical (•OH) probe hydroxyphenyl fluorescein (HPF). These studies revealed that among no-salt controls and the eight halide salts, only NaCl and KCl enabled the anthracene to photosensitize the production of high levels of DNA-damaging reactive oxygen species (ROS). Pre-irradiation of N 1-(anthracen-9-ylmethyl)ethane-1,2-diaminium dichloride at 350 nm increased the amounts of chloride salt-induced •OH detected by HPF in subsequent anthracene photoactivation experiments. Taking into consideration that •OH and other highly reactive ROS are extremely short-lived, this result suggests that the pre-irradiation step might lead to the formation of oxidized anthracene photoproducts that are exceedingly redox-active. The fluorometric probes HPF and Singlet Oxygen Sensor Green revealed that KCl concentrations ranging from 150 to 400 mM and from 100 to 400 mM, respectively, enhanced N 1-(anthracen-9-ylmethyl)ethane-1,2-diaminium dichloride photosensitized •OH and singlet oxygen (1O2) production over no-salt controls. Considering the relatively high levels of Na+, K+, and Cl– ions that exist in the environment and in living organisms, our findings may be relevant to the phototoxic effects exhibited by anthracenes and other polycyclic hydrocarbons in vivo.

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Aminomethylanthracene Dyes as High‐Ionic‐Strength DNA‐Photocleaving Agents: Two Rings are Better than One

Cited by 2 publications

References 96 publications

On the Different Mode of Action of Au(I)/Ag(I)-NHC Bis-Anthracenyl Complexes Towards Selected Target Biomolecules

On the Different Mode of Action of Au(I)/Ag(I)-NHC Bis-Anthracenyl Complexes Towards Selected Target Biomolecules

New Insights into the Phototoxicity of Anthracene-Based Chromophores: The Chloride Salt Effect

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