A new insight into the interaction of cisplatin with DNA: ROA spectroscopic studies on the therapeutic effect of the drug

Gasior-Glogowska, Marlena; Malek, Kamilla; Zając, Grzegorz; Barańska, Małgorzata

doi:10.1039/c5an02140e

Cited by 23 publications

(18 citation statements)

References 38 publications

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“…These studies provide valuable information about the intermolecular interactions 8 , base pairing 9 , and tautomerization 10 of nucleobases. IR and Raman spectroscopy have been used extensively in the investigations of the structure, interactions and properties of nucleobases and related compounds 11–13 . In contrast, investigations of near-infrared (near-IR; NIR) spectra of nucleobases are very rare 14,15 .…”

Section: Introductionmentioning

confidence: 99%

Simulated NIR spectra as sensitive markers of the structure and interactions in nucleobases

Beć

Grabska

Ozaki

et al. 2019

Sci Rep

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Near-infrared (near-IR; NIR) spectroscopy is continuously advancing in biophysical and biochemical fields of investigation. For instance, recent progresses in NIR hyperspectral imaging of biological systems may be noted. However, interpretation of NIR bands for biological samples is difficult and creates a considerable barrier in exploring the full potential of NIR spectroscopy in bioscience. For this reason, we carried out a systematic study of NIR spectra of adenine, cytosine, guanine, and thymine in polycrystalline state. Interpretation of NIR spectra of these nucleobases was supported by anharmonic vibrational analysis using Deperturbed Vibrational Second-Order Perturbation Theory (DVPT2). A number of molecular models of nucleobases was applied to study the effect of the inter-molecular interactions on the NIR spectra. The accuracy of simulated NIR spectra appears to depend on the intra-layer interactions; in contrast, the inter-layer interactions are less influential. The best results were achieved by combining the simulated spectra of monomers and dimers. It is of particular note that in-plane deformation bands are far more populated than out-of-plane ones and the importance of ring modes is relatively small. This trend is in contrast to that observed in mid-IR region. As shown, the local, short-range chemical neighborhood of nucleobase molecules influence their NIR spectra more considerably. This suggests that NIR spectra are more sensitive probe of the nucleobase pairing than mid-IR ones. The obtained results allow, for the first time, to construct a frequency correlation table for NIR spectra of purines and pyrimidines.

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Section: Introductionmentioning

confidence: 99%

Simulated NIR spectra as sensitive markers of the structure and interactions in nucleobases

Beć

Grabska

Ozaki

et al. 2019

Sci Rep

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“…Cisplatin (cis-diaminedichloro-platinum, CDDP) is one of the most active chemotherapeutic agents used for the treatment of a large variety of malignancies, especially testicular and ovarian carcinomas, even if its clinical utility is restricted by both toxicological and tumor resistance drawbacks [ 1 , 2 ]. CDDP activity and toxicity is mainly due to DNA binding [ 3 , 4 ], occurring via both inter- and intrastrand crosslinks, that suppresses DNA replication and also RNA transcription. Specifically, CDDP interacts with the DNA nucleobases forming stable platinum–nitrogen covalent bonds, which lead to irreversible adducts responsible for cisplatin antitumor activity [ 1 , 4 ].…”

Section: Introductionmentioning

confidence: 99%

“…CDDP activity and toxicity is mainly due to DNA binding [ 3 , 4 ], occurring via both inter- and intrastrand crosslinks, that suppresses DNA replication and also RNA transcription. Specifically, CDDP interacts with the DNA nucleobases forming stable platinum–nitrogen covalent bonds, which lead to irreversible adducts responsible for cisplatin antitumor activity [ 1 , 4 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antiproliferative Activity, and DNA Binding Studies of Nucleoamino Acid-Containing Pt(II) Complexes

et al. 2020

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We here report our studies on the reaction with the platinum(II) ion of a nucleoamino acid constituted by the l-2,3-diaminopropanoic acid linked to the thymine nucleobase through a methylenecarbonyl linker. The obtained new platinum complexes, characterized by spectroscopic and mass spectrometric techniques, were envisaged to exploit synergistic effects due to the presence of both the platinum center and the nucleoamino acid moiety. The latter can be potentially useful to protect the complexes from early deactivation, as well as to facilitate their cell internalization. The biological activity of the complexes in terms of antiproliferative effects was evaluated in vitro on different cancer cell lines and healthy cells, showing the best results on human cervical adenocarcinoma (HeLa) cells along with good selectivity for cancer over normal cells. In contrast, the metal-free nucleoamino acid did not show any cytotoxicity on both normal and cancer cell lines. Finally, the ability of the novel Pt(II) complexes to bind various DNA model systems was investigated by circular dichroism (CD) spectroscopy and polyacrylamide gel electrophoresis analyses proving that the newly obtained compounds can potentially target DNA, similarly to other well-known anticancer Pt complexes, with a peculiar G-quadruplex vs. duplex selectivity.

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“…The interaction of cisplatin with deoxyribonucleic acid (DNA) inside the nucleus causes cell death and apoptosis. Previous studies have found that the interaction occurs between cisplatin and the DNA bases, especially guanine-N(7) but also adenine-N(3) [8]. The interaction of cisplatin with DNA has been studied extensively using X-ray crystallography and NMR spectroscopy in addition to Liquid Chromatography Mass Spectrometry (LCMS) [5,9,10].…”

Section: Introductionmentioning

confidence: 99%

“…Because the main target of the platinum complexes is DNA, understanding the effect of these drugs on DNA conformation is essential [8,15]. After hydrolysis of the chloride leaving group the complex is in a form in which it can interact with DNA [11,16,17].…”

Section: Introductionmentioning

confidence: 99%

The Application of ATR-FTIR Spectroscopy and the Reversible DNA Conformation as a Sensor to Test the Effectiveness of Platinum(II) Anticancer Drugs

Al-Jorani

Rüther

Martin

et al. 2018

Sensors

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Platinum(II) complexes have been found to be effective against cancer cells. Cisplatin curbs cell replication by interacting with the deoxyribonucleic acid (DNA), reducing cell proliferation and eventually leading to cell death. In order to investigate the ability of platinum complexes to affect cancer cells, two examples from the class of polyfluorophenylorganoamidoplatinum(II) complexes were synthesised and tested on isolated DNA. The two compounds trans-[N,N′-bis(2,3,5,6-tetrafluorophenyl)ethane-1,2-diaminato(1-)](2,3,4,5,6-pentafluorobenzoato)(pyridine)platinum(II) (PFB) and trans-[N,N′-bis(2,3,5,6-tetrafluorophenyl)ethane-1,2-diaminato(1-)](2,4,6-trimethylbenzoato)(pyridine)platinum(II) (TMB) were compared with cisplatin through their reaction with DNA. Attenuated Total Reflection Fourier Transform Infrared (ATR-FTIR) spectroscopy was applied to analyse the interaction of the Pt(II) complexes with DNA in the hydrated, dehydrated and rehydrated states. These were compared with control DNA in acetone/water (PFB, TMB) and isotonic saline (cisplatin) under the same conditions. Principle Component Analysis (PCA) was applied to compare the ATR-FTIR spectra of the untreated control DNA with spectra of PFB and TMB treated DNA samples. Disruptions in the conformation of DNA treated with the Pt(II) complexes upon rehydration were mainly observed by monitoring the position of the IR-band around 1711 cm−1 assigned to the DNA base-stacking vibration. Furthermore, other intensity changes in the phosphodiester bands of DNA at ~1234 cm−1 and 1225 cm−1 and shifts in the dianionic phosphodiester vibration at 966 cm−1 were observed. The isolated double stranded DNA (dsDNA) or single stranded DNA (ssDNA) showed different structural changes when incubated with the studied compounds. PCA confirmed PFB had the most dramatic effect by denaturing both dsDNA and ssDNA. Both compounds, along with cisplatin, induced changes in DNA bands at 1711, 1088, 1051 and 966 cm−1 indicative of DNA conformation changes. The ability to monitor conformational change with infrared spectroscopy paves the way for a sensor to screen for new anticancer therapeutic agents.

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A new insight into the interaction of cisplatin with DNA: ROA spectroscopic studies on the therapeutic effect of the drug

Cited by 23 publications

References 38 publications

Simulated NIR spectra as sensitive markers of the structure and interactions in nucleobases

Simulated NIR spectra as sensitive markers of the structure and interactions in nucleobases

Synthesis, Antiproliferative Activity, and DNA Binding Studies of Nucleoamino Acid-Containing Pt(II) Complexes

The Application of ATR-FTIR Spectroscopy and the Reversible DNA Conformation as a Sensor to Test the Effectiveness of Platinum(II) Anticancer Drugs

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