Fluorescence studies of the interaction of pyrenylmethyl tributylphosphonium bromide with double-strand polynucleotides

Oliveira, M. Elisabete; Baptista, A. L. F.; Coutinho, Paulo J. G.; Castanheira, Elisabete M. S.; Hungerford, Graham

doi:10.1039/b305225g

Cited by 8 publications

(5 citation statements)

References 36 publications

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“…In our case we need also a higher [nucleic acid]/[compound] ratio to achieve complete binding in spectral terms which can be due to the low lactam concentration used in our assays (4 × 10 −6 M). This compound concentration influence was also observed in binding studies of a pyrene derivative with polynucleotides [17].…”

Section: Spectroscopic Studies Of Interaction With Salmon Sperm Dna Asupporting

confidence: 57%

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Synthesis of fluorescent tetracyclic lactams by a “one pot” three steps palladium-catalyzed borylation, Suzuki coupling (BSC) and lactamization

Queiroz

Castanheira

Lopes

et al. 2007

Journal of Photochemistry and Photobiology A: Chemistry

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Tetracyclic lactams (benzothieno[2,3-c]quinolones) were prepared by "one pot" three steps palladium-catalyzed borylation, Suzuki coupling (BSC) and lactamization, starting from ortho-haloanilines and alkyl 3-bromobenzo[b]thiophene-2-carboxylates. The former were used as the components to be borylated with pinacolborane, and the latter as the brominated component in the Suzuki coupling. The amidation occurred with loss of the alkyl alcohol, presumably in the Suzuki coupling product, giving the corresponding tetracyclic lactam. This constitutes a novel application of the BSC reaction using sterically hindered substrates. In this work studies of absorption and fluorescence in several solvents and in presence of salmon sperm DNA or synthetic double-stranded (ds) heteropolynucleotides, poly(dA-dT)·(dA-dT) and poly(dG-dC)·(dG-dC), were performed. The binding constant values (K i = 2.6 × 10 5 to 4.5 × 10 5 M −1 ) point to a high affinity of the lactams to DNA. It was shown that the intercalation is the preferred mode of binding and that the substituted new lactams (with F or OMe) exhibit a higher affinity for A-T regions.Quenching experiments with iodide show that the methoxylated lactam is the more intercalative in DNA. The same type of experiments using this compound bound to heteropolynucleotides show a very low accessibility (f a = 0.07) of the lactam in poly(dG-dC)·(dG-dC) to the quencher showing a large majority of intercalative binding while the high affinity for A-T regions together with a higher accessibility (f a = 0.25) point to the possibility of both intercalative (75%) and groove modes of binding.

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Section: Spectroscopic Studies Of Interaction With Salmon Sperm Dna Asupporting

confidence: 57%

“…The results are summarized in Table 3. Anionic quenchers can be used to distinguish between DNA binding modes [17,21,22]. Intercalated chromophores are less accessible to quenching by iodide due to electrostatic repulsion between the negatively charged DNA and iodide ion [22].…”

Section: Spectroscopic Studies Of Interaction With Salmon Sperm Dna Amentioning

confidence: 99%

Synthesis of fluorescent tetracyclic lactams by a “one pot” three steps palladium-catalyzed borylation, Suzuki coupling (BSC) and lactamization

Queiroz

Castanheira

Lopes

et al. 2007

Journal of Photochemistry and Photobiology A: Chemistry

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“…Anthracenemethylamine 7 and pyrenemethylamine 9 have already been shown to intercalate with DNA, 15,25 and UV-visible titration spectra obtained with our guanidinium derivatives are similar to those generally reported for other pyrene-or anthracene-based compounds in the presence of DNA. [26][27][28] Figure 2 provides an example illustrating the characteristic changes in the absorption spectra during titration of 14 with increasing amounts of CT-DNA. The binding of the drug was characterized by a strong hypochromicity (75%), an 11 nm red shift (from 341 to 352 nm), and the formation of a well-defined isosbestic point at 347 nm.…”

Section: Introductionmentioning

confidence: 99%

Amine−Guanidine Switch: A Promising Approach to Improve DNA Binding and Antiproliferative Activities

et al. 2007

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A series of polyaromatic guanidino derivatives was synthesized and evaluated for growth inhibitory properties in several human carcinoma cell lines. The properties of these guanidino compounds were compared to those of their corresponding synthetic amino precursors. The size of the polyaromatic ring system as well as the length of the tether attached to the ring had a direct impact on the observed antiproliferative profiles, compound 14 having the broadest spectrum of activity. As both series intercalate DNA, guanidine derivatives showed a remarkable affinity for DNA and the guanidinium group appeared to be essential, yet not sufficient for caspase-3/7 activation. Compound 14 also showed significant in vivo activity against breast cancer cell xenografts in NOG/SCID mice. These results suggest that the electronic nature of chain tethering an intercalator not only influences the DNA-binding process but also controls the antitumoral activity of the whole compound.

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“…A likely mechanism is intercalation by -stacking. In the present case, differently from the case of other planar aromatics interacting within nucleic acids [32,33], photoinduced electron transfer involving DNA bases is not expected to occur because the process is thermodynamically unfavourable.…”

Section: Interaction With Salmon Sperm Dna and With Synthetic Double-mentioning

confidence: 68%

Benzothienoquinolines: New one-pot synthesis and fluorescence studies of their interaction with DNA and polynucleotides

Rodrigues

Carvalho

Cardoso

et al. 2014

Journal of Photochemistry and Photobiology A: Chemistry

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a b s t r a c tIn this work, we were able to obtain the benzothieno[3,2-b]quinoline 1 and benzothieno[2,3-c]quinoline 2 using a new one-pot procedure from the reaction of the commercially available 3-bromobenzo[b]thiophene-2-carbaldehyde with 2-aminophenylpinacolborane under Suzuki coupling conditions using a stereochemically hindered ligand, 2-(cyclohexylphosphane)biphenyl and Ba(OH) 2 ·8H 2 O as the base.Fluorescence properties of the benzothieno[3,2-b]quinoline 1 and the benzothieno[2,3-c]quinoline 2 were studied in solvents of different polarity. Both compounds exhibit a solvent sensitive emission, compound 1 being less fluorescent (˚F < 0.05) than compound 2 (0.04 ≤ ˚F ≤ 0.10).The interaction of these compounds with salmon sperm DNA and synthetic double-stranded heteropolynucleotides, poly(dA-dT)·(dA-dT) and poly(dG-dC)·(dG-dC), was studied using spectroscopic methods, allowing the determination of the intrinsic binding constants and binding site sizes. The interaction of both compounds is stronger with adenine-thymine (A-T) base pairs. Compound 1 is the most intercalative in salmon sperm DNA (47%) and polynucleotides (46-49% of intercalated molecules), while for compound 2, 41% is intercalated in salmon sperm DNA and only 8% in poly(dG-dC)·(dG-dC). Docking studies indicate that compound 1 interacts more strongly with DNA than compound 2, with a significant value of binding free energy in the case of intercalation. Minor groove binding is also very favourable and, probably, both mechanisms occur with a preponderance of intercalation in the case of compound 1.Overall, these results indicate that both benzothienoquinolines interact with nucleic acids by both intercalation and groove binding.

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Fluorescence studies of the interaction of pyrenylmethyl tributylphosphonium bromide with double-strand polynucleotides

Cited by 8 publications

References 36 publications

Synthesis of fluorescent tetracyclic lactams by a “one pot” three steps palladium-catalyzed borylation, Suzuki coupling (BSC) and lactamization

Synthesis of fluorescent tetracyclic lactams by a “one pot” three steps palladium-catalyzed borylation, Suzuki coupling (BSC) and lactamization

Amine−Guanidine Switch: A Promising Approach to Improve DNA Binding and Antiproliferative Activities

Benzothienoquinolines: New one-pot synthesis and fluorescence studies of their interaction with DNA and polynucleotides

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