DNA Intercalated Psoralen Undergoes Efficient Photoinduced Electron Transfer

Fröbel, Sascha; Reiffers, Anna; Ziegenbein, Christian Torres; Gilch, Peter

doi:10.1021/acs.jpclett.5b00307

Cited by 18 publications

(49 citation statements)

References 34 publications

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“…Values of 1.8

\times

10 −4 m and 4.4

\times

10 −4 m were obtained from UV/Vis titration experiments (Figures S1 and S2). These values are given with respect to the base pair concentration of DNA, while in our previous study we specified a value related to the concentration of DNA duplexes. The values seem to indicate a slight preference of AMT to intercalate between GC base pairs.…”

Section: Resultsmentioning

confidence: 99%

“…The DNA samples showed no significant transient absorption signal under the chosen excitation conditions. As described in our recent study, a scaling factor is required to remove the contribution of free psoralen molecules from the psoralen/DNA data after subtracting the solvent signatures from both data sets. Due to the hypochromic effect upon intercalation, the absorption of the mixture

A_{mix}

at the excitation wavelength is lower than the one of the free psoralens

A_{free}

.…”

Section: Methodsmentioning

confidence: 99%

“…The dissociation constant K

_{D}

was determined in UV/Vis titration experiments (Supporting Information, Figures S1–S4) . Analysis of these experiments was performed using a self‐written Mathcad routine.…”

Section: Methodsmentioning

confidence: 99%

“…Bottom: Sequences of the DNA molecules employed. The PET was discovered in our previous study using the mixed sample . Here, GC‐only and AT‐only DNA are used.…”

Section: Introductionmentioning

confidence: 99%

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Photoinduced Electron Transfer between Psoralens and DNA: Influence of DNA Sequence and Substitution

et al. 2015

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Psoralens are heterocyclic compounds which are, among other uses, used to treat skin deseases in the framework of PUVA therapy. In the dark, they intercalate into DNA and can form photoadducts with thymines upon UV-A excitation, which harms the affected cells. We have recently discovered that after excitation of intercalated psoralens, an efficient photoinduced electron transfer (PET) from DNA occurs. Here, the PET is studied in detail by means of femtosecond transient absorption spectroscopy. Using DNA samples that contain either only GC or AT base pairs, we show that only guanine donates the electrons. Additionally, the substituent effects on PET are studied relying on three different psoralen derivatives. The substitution alters spectroscopic and electrochemical properties of the psoralens, which are determined by cyclic voltammetry and steady state spectroscopy. These experiments allow us to estimate the PET energetics, which are in line with the measured kinetics. Implications for the applications of psoralens are discussed.

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“…Values of 1.8

\times

10 −4 m and 4.4

\times

Section: Resultsmentioning

confidence: 99%

A_{mix}

at the excitation wavelength is lower than the one of the free psoralens

A_{free}

.…”

Section: Methodsmentioning

confidence: 99%

“…The dissociation constant K

_{D}

was determined in UV/Vis titration experiments (Supporting Information, Figures S1–S4) . Analysis of these experiments was performed using a self‐written Mathcad routine.…”

Section: Methodsmentioning

confidence: 99%

“…Bottom: Sequences of the DNA molecules employed. The PET was discovered in our previous study using the mixed sample . Here, GC‐only and AT‐only DNA are used.…”

Section: Introductionmentioning

confidence: 99%

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Photoinduced Electron Transfer between Psoralens and DNA: Influence of DNA Sequence and Substitution

et al. 2015

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“…JM intermediates may be lost through spontaneous branch migration, which is exacerbated by DNA purification treatments that employ heat and EDTA to inhibit nucleases (Panyutin & Hsieh, 1994). To preserve JMs, cells sampled from meiotic time courses are treated with psoralen and UV light to induce interstrand DNA cross-links (Frobel, Reiffers, Torres Ziegenbein, & Gilch, 2015). One- and two-dimensional (1D and 2D) electrophoresis is applied to resolve DNA species of interest.…”

Section: Introductionmentioning

confidence: 99%

Monitoring Recombination During Meiosis in Budding Yeast

Owens

Tang

Hunter

2018

Methods in Enzymology

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Homologous recombination is fundamental to sexual reproduction, facilitating accurate segregation of homologous chromosomes at the first division of meiosis, and creating novel allele combinations that fuel evolution. Following initiation of meiotic recombination by programmed DNA double-strand breaks (DSBs), homologous pairing and DNA strand exchange form joint molecule (JM) intermediates that are ultimately resolved into crossover and noncrossover repair products. Physical monitoring of the DNA steps of meiotic recombination in Saccharomyces cerevisiae (budding yeast) cultures undergoing synchronous meiosis has provided seminal insights into the molecular basis of meiotic recombination and affords a powerful tool for dissecting the molecular roles of recombination factors. This chapter describes a suit of electrophoretic and Southern hybridization techniques used to detect and quantify the DNA intermediates of meiotic recombination at recombination hotspots in budding yeast. DSBs and recombination products (crossovers and noncrossovers) are resolved using one-dimensional electrophoresis and distinguished by restriction site polymorphisms between the parental chromosomes. Psoralen cross-linking is used to stabilize branched JMs, which are resolved from linear species by native/native two-dimensional electrophoresis. Native/denaturing two-dimensional electrophoresis is employed to determine the component DNA strands of JMs and to measure the processing of DSBs. These techniques are generally applicable to any locus where the frequency of recombination is high enough to detect intermediates by Southern hybridization.

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Spectroscopic view on the interaction between the psoralen derivative amotosalen and DNA

Rademacher,

Rohn,

Haselbach

et al. 2024

Photochem Photobiol Sci

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Psoralens are eponymous for PUVA (psoralen plus UV-A radiation) therapy, which inter alia can be used to treat various skin diseases. Based on the same underlying mechanism of action, the synthetic psoralen amotosalen (AMO) is utilized in the pathogen reduction technology of the INTERCEPT® Blood System to inactivate pathogens in plasma and platelet components. The photophysical behavior of AMO in the absence of DNA is remarkably similar to that of the recently studied psoralen 4′-aminomethyl-4,5′,8-trimethylpsoralen (AMT). By means of steady-state and time-resolved spectroscopy, intercalation and photochemistry of AMO and synthetic DNA were studied. AMO intercalates with a higher affinity into A,T-only DNA (KD = 8.9 × 10−5 M) than into G,C-only DNA (KD = 6.9 × 10−4 M). AMO covalently photobinds to A,T-only DNA with a reaction quantum yield of ΦR = 0.11. Like AMT, it does not photoreact following intercalation into G,C-only DNA. Femto- and nanosecond transient absorption spectroscopy reveals the characteristic pattern of photobinding to A,T-only DNA. For AMO and G,C-only DNA, signatures of a photoinduced electron transfer are recorded. Graphical abstract

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DNA Intercalated Psoralen Undergoes Efficient Photoinduced Electron Transfer

Cited by 18 publications

References 34 publications

Photoinduced Electron Transfer between Psoralens and DNA: Influence of DNA Sequence and Substitution

Photoinduced Electron Transfer between Psoralens and DNA: Influence of DNA Sequence and Substitution

Monitoring Recombination During Meiosis in Budding Yeast

Spectroscopic view on the interaction between the psoralen derivative amotosalen and DNA

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