Photoadduct between tris(1,4,5,8-tetraazaphenanthrene)ruthenium(<scp>II</scp>) and guanosine monophosphate–a model for a new mode of covalent binding of metal complexes to DNA

Jacquet, L.; Kelly, John M.; Mesmaeker, Andrée Kirsch-De

doi:10.1039/c39950000913

Cited by 83 publications

(82 citation statements)

References 17 publications

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“…[4] Interestingly, the recombination of the two radical species generated by this PET process produces an irreversible covalent adduct between the guanine (G) moiety and the Ru II complex (Figure 1, a). [8] Owing to the interest in the study of Ru II complexes in the presence of biomolecules, these metallic compounds were also examined in the presence of living cells to investigate their cellular penetration, intracellular distributions, and interactions with the different cellular components. [9,10] Most Ru II polypyridyl complexes are unable to cross the membranes of living cells, as demonstrated with the standard complexes [Ru(bpy) 3 ] 2+ , [Ru(phen) 3 ] 2+ , [9] and some of their analogues.…”

Section: Introductionmentioning

confidence: 99%

Highly DNA‐Photoreactive Ruthenium 1,4,5,8‐Tetraazaphenanthrene Complex Conjugated to the TAT Peptide: Efficient Vectorization inside HeLa Cells without Phototoxicity – The Importance of Cellular Distribution

et al. 2016

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Section: Introductionmentioning

confidence: 99%

Highly DNA‐Photoreactive Ruthenium 1,4,5,8‐Tetraazaphenanthrene Complex Conjugated to the TAT Peptide: Efficient Vectorization inside HeLa Cells without Phototoxicity – The Importance of Cellular Distribution

et al. 2016

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“…Such processes are applied successfully in gene photo-silencing of human papillomavirus cancer cells. [Ru(TAP) 2 Structure of a Ru-TAP photo-adduct as determined by nuclear magnetic resonance spectroscopy [25]. …”

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confidence: 99%

Ru–TAP complexes and DNA: from photo-induced electron transfer to gene photo-silencing in living cells

Marcélis

Moucheron

Mesmaeker

2013

Phil. Trans. R. Soc. A.

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In this review, examples of applications of the photoinduced electron transfer (PET) process between photo-oxidizing Ru-TAP (TAP = 1,4,5,8-tetraazaphenanthrene) complexes and DNA or oligodeoxynucleotides (ODNs) are discussed. Applications using a free Ru-TAP complex (not chemically anchored to an ODN) are first considered. In this case, the PET gives rise to the production of an irreversible adduct of the Ru complex on a guanine (G) base, with formation of a covalent bond. After absorption of a second photon, this adduct can generate a bi-adduct, whereby the same complex binds to a second G moiety. These bi-adduct formations are responsible for photo-cross-linking between two strands of a duplex, each containing a G base, or between two G moieties of a single strand such as a telomeric sequence, as demonstrated by polyacrylamide gel electrophoresis analyses or mass spectrometry. Scanning force microscopy also allows the detection of such photobridgings with plasmid DNA. Other applications, for example with Ru-

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“…20 The substitution of the aqua ligand by DNA constituents is believed to follow a similar reaction course as found for other transition metal complex based anticancer drugs action 21 . We found that [Ru(tpy)(dppz)Cl](PF 6 ) is kinetically stable in acetone-H 2 O mixture (1:1, v/v) at room temperature, but as the temperature increases (from 37º -55ºC), the equilibrium is shifted giving more aqua species. Subsequently, 1 H-NMR spectroscopy analysis of [Ru(tpy)(dppz)Cl](PF 6 ) treated with aqueous NH 3 (25%) at 55ºC for 17 h indicated partial formation of two compounds assigned as products of Cl substitution by H 2 O and NH 3 .…”

Section: O)mentioning

confidence: 93%

“…22a (6) and the amino-functionalized linker tetherd to oligonucleotide at the desired position. Compound 1 24 has been used uniformly to incorporate the amino function with a long linker to either 3'-or 5'-terminal or between two nucleotides in the ODN.…”

Section: O)mentioning

confidence: 99%

Synthesis of the DNA−[Ru(tpy)(dppz)(CH₃CN)]²⁺ Conjugates and Their Photo Cross-Linking Studies with the Complementary DNA Strand

2002

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We here report our studies on the conjugation of photoreactive Ru 2+ complex to oligonucleotides (ODNs), which give stable duplex with the complementary target DNA strand. These functionalized DNA duplexes bearing photoreactive Ru 2+ complex can be specifically photolyzed to give the reactive aqua derivative, [Ru(tpy)(dppz)(H 2 O)] 2+ -ODN, in situ, which successfully cross-links to give photoproduct(s) with the target DNA strand in a sequence specific manner. Thus, the stable precursor of aqua-ruthenium complex, monofunctional polypyridyl ruthenium complex:[Ru(tpy)(dppz)(CH 3 CN)] 2+ (tpy = 2,2':6',2''-terpyridine, dppz = dipyrido[3,2-a:2',3'-c]phenazine), has been site-specifically tethered to ODN, for the first time, both by solid phase synthesis and post- Table 1). This shows that with the rigidly packed structure, as in the duplex with middle-Ru 2+ ODN, the metal center flexibility is considerably reduced, and consequently the accessibility of target G residue by the aquaruthunium moiety becomes severely restricted, which results in a poor yield in the cross-coupling reaction. The crosslinked product was characterized by PAGE, followed by MALDI-TOF MS.

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Photoadduct between tris(1,4,5,8-tetraazaphenanthrene)ruthenium(II) and guanosine monophosphate–a model for a new mode of covalent binding of metal complexes to DNA

Cited by 83 publications

References 17 publications

Highly DNA‐Photoreactive Ruthenium 1,4,5,8‐Tetraazaphenanthrene Complex Conjugated to the TAT Peptide: Efficient Vectorization inside HeLa Cells without Phototoxicity – The Importance of Cellular Distribution

Highly DNA‐Photoreactive Ruthenium 1,4,5,8‐Tetraazaphenanthrene Complex Conjugated to the TAT Peptide: Efficient Vectorization inside HeLa Cells without Phototoxicity – The Importance of Cellular Distribution

Ru–TAP complexes and DNA: from photo-induced electron transfer to gene photo-silencing in living cells

Synthesis of the DNA−[Ru(tpy)(dppz)(CH₃CN)]²⁺ Conjugates and Their Photo Cross-Linking Studies with the Complementary DNA Strand

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Photoadduct between tris(1,4,5,8-tetraazaphenanthrene)ruthenium(II) and guanosine monophosphate–a model for a new mode of covalent binding of metal complexes to DNA

Cited by 83 publications

References 17 publications

Highly DNA‐Photoreactive Ruthenium 1,4,5,8‐Tetraazaphenanthrene Complex Conjugated to the TAT Peptide: Efficient Vectorization inside HeLa Cells without Phototoxicity – The Importance of Cellular Distribution

Highly DNA‐Photoreactive Ruthenium 1,4,5,8‐Tetraazaphenanthrene Complex Conjugated to the TAT Peptide: Efficient Vectorization inside HeLa Cells without Phototoxicity – The Importance of Cellular Distribution

Ru–TAP complexes and DNA: from photo-induced electron transfer to gene photo-silencing in living cells

Synthesis of the DNA−[Ru(tpy)(dppz)(CH3CN)]2+ Conjugates and Their Photo Cross-Linking Studies with the Complementary DNA Strand

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Synthesis of the DNA−[Ru(tpy)(dppz)(CH₃CN)]²⁺ Conjugates and Their Photo Cross-Linking Studies with the Complementary DNA Strand