To intercalate or semiintercalate, or both?

Turró, Claudia

doi:10.1073/pnas.1114519108

Cited by 16 publications

(7 citation statements)

References 17 publications

(24 reference statements)

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“…Intercalation occurs when planar aromatic compounds are inserted between adjacent base pairs in the DNA double helix. 107 Many Ru(II) polypyridyl complexes can intercalate DNA with high affinity in vitro , and serve as DNA molecular probes. For example, the well known complex [Ru(bpy) 2 (dppz)] 2+ was reported as a DNA light switch in vitro , 108 but this complex did not readily cross the cell membrane.…”

Section: The Cellular Uptake and Potential Targets Of Ru(ii) Complmentioning

confidence: 99%

The development of anticancer ruthenium(ii) complexes: from single molecule compounds to nanomaterials

et al. 2017

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Cancer is rapidly becoming the top killer in the world. Most of the FDA approved anticancer drugs are organic molecules, while metallodrugs are very scarce. The advent of first metal based therapeutic agent, cisplatin, launched a new era in the application of transition metal complexes for therapeutic design. Due to their unique and versatile biochemical properties, ruthenium-based compounds have emerged as promising anti-cancer agents that serve as alternatives to cisplatin and its derivertives. The ruthenium(III) complexes have successfully been used in clinical research and their mechanisms of anticancer action have been reported in large volumes over the past few decades. Ruthenium(II) complexes have also attracted significant attention as anticancer candidates; however, only few of them have been reported comprehensively. In this review, we discuss the development of ruthenium(II) complexes as anticancer candidates and biocatalysts, including arene ruthenium complexes, polypyridyl ruthenium complexes, and ruthenium nanomaterial complexes. This review focuses on the likely mechanisms of action of ruthenium(II)-based anticancer drugs and the relationship between their chemical structures and biological properties. This review also highlights the catalytic activity and the photoinduced activation of ruthenium(II) complexes, their targeted delivery, and their activity in nanomaterial systems.

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Section: The Cellular Uptake and Potential Targets Of Ru(ii) Complmentioning

confidence: 99%

The development of anticancer ruthenium(ii) complexes: from single molecule compounds to nanomaterials

et al. 2017

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“…3), has a longer excited state lifetime (0.962 μs in H 2 O and 1.1 μs in D 2 O) [52] and subsequently is a more efficient 1 O 2 producer in D 2 O ( Φ = 0.24) [49]. While [Ru(phen) 3 ] 2+ was initially believed to interact with DNA via inter-calation of the phen ligand, the currently accepted binding mode is its semi-intercalation [53,54]. The incorporation of the tridentate 2,2′ :2′ ,6′ -terpyridine (tpy) ligand to provide the [Ru(tpy) 2 ] 2+ analog results in a drastically shortened excited state lifetime of 0.12 ns due to the distorted octahedral geometry promoting population of the nonemissive 3 MC state (Fig.…”

Section: Oxygen-dependent Dna Modificationmentioning

confidence: 99%

Control and utilization of ruthenium and rhodium metal complex excited states for photoactivated cancer therapy

Knoll

Turró

2015

Coordination Chemistry Reviews

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376

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The use of visible light to produce highly selective and potent drugs through photodynamic therapy (PDT) holds much potential in the treatment of cancer. PDT agents can be designed to follow an O2-dependent mechanism by producing highly reactive species such as 1O2 and/or an O2 independent mechanism through processes such as excited state electron transfer, covalent binding to DNA or photoinduced drug delivery. Ru(II)-polypyridyl and Rh2(II,II) complexes represent an important class of compounds that can be tailored to exhibit desired photophysical properties and photochemical reactivity by judicious selection of the ligand set. Complexes with relatively long-lived excited states and planar, intercalating ligands localize on the DNA strand and photocleave DNA through 1O2 production or guanine oxidation by the excited state of the chromophore. Photoinduced ligand substitution occurs through the population of triplet metal centered (3MC) excited states and facilitates covalent binding of the metal complex to DNA in a mode similar to cisplatin. Ligand photodissociation also provides a route to selective drug delivery. The ability to construct metal complexes with desired light absorbing and excited state properties by ligand variation enables the design of PDT agents that can potentially provide combination therapy from a single metal complex.

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“…Conversely, compounds that only covalently bind to DNA, such as cisplatin and cis -H,H-[Rh 2 (OCCH 3 NH) 2 (bpy)(CH 3 CN eq ) 2 ] 2+ upon irradiation, destabilize the duplex and decrease the value of T m [22,44,45]. The modest ΔT m values measured for 1 and 2 are not consistent with full intercalation and are indicative of partial intercalation, as is the case for [Ru(phen) 3 ] 2+ when studied with CT-DNA [46–48]. …”

Section: Resultsmentioning

confidence: 99%

Dual photoreactivity of a new Rh2(II,II) complex for biological applications

Akhimie

White

Turró

2017

Inorganica Chimica Acta

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A new Rh2(II,II) complex containing one dppn (benzo[i]dipyrido[3,2-a:2,3-c]phenazine) ligand with an extended π-system, cis-H,H-[Rh2(OCCH3NH)2(dppn)(CH3CN)2]2+ (2), was synthesized and characterized. The dppn ligand, which serves as a DNA base pair intercalator, chelates to a single Rh center and is positioned trans to the amidato N atoms of the bridging acetamide ligand. This ligand also possesses a low-lying dppn-centered 3ππ* state that is advantageous for the sensitization of singlet oxygen (1O2), which complex 2 produced with a quantum yield, Φ1O2 460, of 0.22(7) with 460 nm excitation. In addition, one equivalent of CH3CN is released from 2 upon irradiation with visible light, generating cis-H,H-[Rh2(OCCH3NH)2(dppn)(H2O)(CH3CN)]2+ in aqueous media with photoinduced ligand exchange quantum yield, ΦLE 450, of 0.0033(1). Thermal denaturation and relative viscosity studies are consistent with a π-stacking interaction of 2 with double-stranded DNA together with covalent binding to the duplex upon irradiation with visible light. Therefore, 2 exhibits dual photoreactivity towards DNA, making it potentially useful for photochemotherapy with enhanced activity relative to compounds able to achieve only one mode of cell death upon irradiation.

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To intercalate or semiintercalate, or both?

Cited by 16 publications

References 17 publications

The development of anticancer ruthenium(ii) complexes: from single molecule compounds to nanomaterials

The development of anticancer ruthenium(ii) complexes: from single molecule compounds to nanomaterials

Control and utilization of ruthenium and rhodium metal complex excited states for photoactivated cancer therapy

Dual photoreactivity of a new Rh2(II,II) complex for biological applications

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