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1.
Chem Commun (Camb) ; 56(57): 7945-7948, 2020 Jul 21.
Artigo em Inglês | MEDLINE | ID: mdl-32531009

RESUMO

Two-photon active mitochondriotropic lanthanide nanorods for high resolution fluorescence imaging. The presence of Gd in the nanorods also enabled us to utilize this material as a T1-T2 dual-mode contrast reagent for recording magnetic resonance images of the mouse brain.

2.
Chem Sci ; 11(1): 70-79, 2020 Jan 07.
Artigo em Inglês | MEDLINE | ID: mdl-32110358

RESUMO

In previous studies we reported that specific dinuclear RuII complexes are particularly active against pathogenic Gram-negative bacteria and, unusually for this class of compounds, appeared to display lowered activity against Gram-positive bacteria. With the aim of identifying resistance mechanisms specific to Gram-positive bacteria, the uptake and antimicrobial activity of the lead complex against Staphylococcus aureus SH1000 and other isolates, including MRSA was investigated. This revealed differential, strain specific, sensitivity to the complex. Exploiting the inherent luminescent properties of the RuII complex, super-resolution STED nanoscopy was used to image its initial interaction with S. aureus and confirm its cellular internalization. Membrane damage assays and transmission electron microscopy confirm that the complex disrupts the bacterial membrane structure before internalization, which ultimately results in a small amount of DNA damage. A known resistance mechanism against cationic antimicrobials in Gram-positive bacteria involves increased expression of the mprF gene as this results in an accumulation of positively charged lysyl-phosphatidylglycerol on the outer leaflet of the cytoplasmic membrane that electrostatically repel cationic species. Consistent with this model, it was found that an mprF deficient strain was particularly susceptible to treatment with the lead complex. More detailed co-staining studies also revealed that the complex was more active in S. aureus strains missing, or with altered, wall teichoic acids.

3.
Chem Commun (Camb) ; 56(10): 1464-1480, 2020 Feb 04.
Artigo em Inglês | MEDLINE | ID: mdl-31967621

RESUMO

This review discusses the advantages of using luminescent d6-transition-metal complexes as cell probes for optical microscopy. In particular it focusses on the Thomas group's use of specific complexes as "building blocks" toward the construction of biomolecular binding substrates, with DNA being a particular target. Using this approach, a range of new imaging probes for conventional optical microscopy, nanoscopy and transmission electron microscopy have been identified. Through selection of specific metal centres and by substitution of coordinated ligands we illustrate how new chemotherapeutics, photo-therapeutics, and theranostics have been identified and developed from the original architectures.


Assuntos
Complexos de Coordenação/química , DNA/química , Anti-Infecciosos/química , Anti-Infecciosos/farmacologia , Apoptose/efeitos dos fármacos , Bactérias/efeitos dos fármacos , Meios de Contraste/química , Meios de Contraste/metabolismo , Complexos de Coordenação/metabolismo , Complexos de Coordenação/toxicidade , DNA/metabolismo , Humanos , Sondas Moleculares/química , Sondas Moleculares/metabolismo , Nanomedicina Teranóstica
4.
J Am Chem Soc ; 142(2): 1101-1111, 2020 01 15.
Artigo em Inglês | MEDLINE | ID: mdl-31846306

RESUMO

The synthesis of new dinuclear complexes containing linked RuII(dppz) and ReI(dppz) moieties is reported. The photophysical and biological properties of the new complex, which incorporates a N,N'-bis(4-pyridylmethyl)-1,6-hexanediamine tether ligand, are compared to a previously reported RuII/ReI complex linked by a simple dipyridyl alkane ligand. Although both complexes bind to DNA with similar affinities, steady-state and time-resolved photophysical studies reveal that the nature of the linker affects the excited state dynamics of the complexes and their DNA photocleavage properties. Quantum-based DFT calculations on these systems offer insights into these effects. While both complexes are live cells permeant, their intracellular localizations are significantly affected by the nature of the linker. Notably, one of the complexes displayed concentration-dependent localization and possesses photophysical properties that are compatible with SIM and STED nanoscopy. This allowed the dynamics of its intracellular localization to be tracked at super resolutions.

5.
ACS Nano ; 13(5): 5133-5146, 2019 05 28.
Artigo em Inglês | MEDLINE | ID: mdl-30964642

RESUMO

Medicinal leads that are also compatible with imaging technologies are attractive, as they facilitate the development of therapeutics through direct mechanistic observations at the molecular level. In this context, the uptake and antimicrobial activities of several luminescent dinuclear RuII complexes against E. coli were assessed and compared to results obtained for another ESKAPE pathogen, the Gram-positive major opportunistic pathogen Enterococcus faecalis, V583. The most promising lead displays potent activity, particularly against the Gram-negative bacteria, and potency is retained in the uropathogenic multidrug resistant EC958 ST131 strain. Exploiting the inherent luminescent properties of this complex, super-resolution STED nanoscopy was used to image its initial localization at/in cellular membranes and its subsequent transfer to the cell poles. Membrane damage assays confirm that the complex disrupts the bacterial membrane structure before internalization. Mammalian cell culture and animal model studies indicate that the complex is not toxic to eukaryotes, even at concentrations that are several orders of magnitude higher than its minimum inhibitory concentration (MIC). Taken together, these results have identified a lead molecular architecture for hard-to-treat, multiresistant, Gram-negative bacteria, which displays activities that are already comparable to optimized natural product-based leads.

6.
J Am Chem Soc ; 141(11): 4644-4652, 2019 03 20.
Artigo em Inglês | MEDLINE | ID: mdl-30799603

RESUMO

Herein we report the separation of the three stereoisomers of the DNA light-switch compound [{Ru(bpy)2}2(tpphz)]4+ (tpphz = tetrapyrido[3,2-a:2',3'-c:3″,2″-h:2‴,3‴-j]phenazine) by column chromatography and the characterization of each stereoisomer by X-ray crystallography. The interaction of these compounds with a DNA octanucleotide d(GCATATCG).d(CGATATGC) has been studied using NMR techniques. Selective deuteration of the bipyridyl rings was needed to provide sufficient spectral resolution to characterize structures. NMR-derived structures for these complexes show a threading intercalation binding mode with slow and chirality-dependent rates. This represents the first solution structure of an intercalated bis-ruthenium ligand. Intriguingly, we find that the binding site selectivity is dependent on the nature of the stereoisomer employed, with Λ RuII centers showing a better intercalation fit.

7.
J Am Chem Soc ; 141(7): 2925-2937, 2019 02 20.
Artigo em Inglês | MEDLINE | ID: mdl-30595016

RESUMO

Drug resistance to platinum chemotherapeutics targeting DNA often involves abrogation of apoptosis and has emerged as a significant challenge in modern, non-targeted chemotherapy. Consequently, there is great interest in the anti-cancer properties of metal complexes-particularly those that interact with DNA-and mechanisms of consequent cell death. Herein we compare a parent cytotoxic complex, [Ru(phen)2(tpphz)]2+ [phen = 1,10-phenanthroline, tpphz = tetrapyridyl[3,2- a:2',3'- c:3″,2″- h:2‴,3‴- j]phenazine], with a mononuclear analogue with a modified intercalating ligand, [Ru(phen)2(taptp)]2+ [taptp = 4,5,9,18-tetraazaphenanthreno[9,10- b] triphenylene], and two structurally related dinuclear, tpphz-bridged, heterometallic complexes, RuRe and RuPt. All three of these structural changes result in a switch from intercalation to groove-binding DNA interaction and concomitant reduction in cytotoxic potency, but no significant change in relative cytotoxicity toward platinum-resistant A2780CIS cancer cells, indicating that the DNA interaction mode is not critical for the mechanism of platinum resistance. All variants exhibited a light-switch effect, which for the first time was exploited to investigate timing of cell death by live-cell microscopy. Surprisingly, cell death occurred rapidly as a consequence of oncosis, characterized by loss of cytoplasmic volume control, absence of significant mitochondrial membrane potential loss, and lack of activation of apoptotic cell death markers. Importantly, a novel, quantitative proteomic analysis of the A2780 cell genome following exposure of the cells to either mononuclear complex reveals changes in protein expression associated with global cell responses to oxidative stress and DNA replication/repair cellular pathways. This combination of multiple targeting modalities and induction of a non-apoptotic death mechanism makes these complexes highly promising chemotherapeutic cytotoxicity leads.

8.
Chem Commun (Camb) ; 55(4): 521-524, 2019 Jan 03.
Artigo em Inglês | MEDLINE | ID: mdl-30556083

RESUMO

Biocompatible graphene quantum dots (GQDs), obtained from extracts of neem root, are found to be suitable for structured illumination microscopy and two-photon microscopy (TPM). Results of TPM and confocal luminescence microscopy ensure lysosome specificity in live cells and tissue-dependent localization in zebrafish, respectively, of GQDs.


Assuntos
Materiais Biocompatíveis/química , Grafite/química , Imagem Óptica , Fótons , Pontos Quânticos/química , Animais , Azadirachta/química , Materiais Biocompatíveis/isolamento & purificação , Grafite/isolamento & purificação , Humanos , Lisossomos/química , Células MCF-7 , Camundongos , Microscopia Confocal , Microscopia de Fluorescência , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Raízes de Plantas/química , Células RAW 264.7 , Peixe-Zebra
9.
Dalton Trans ; 47(35): 12300-12307, 2018 Sep 11.
Artigo em Inglês | MEDLINE | ID: mdl-30113065

RESUMO

The synthesis of two new tetracationic mononuclear RuII complexes containing the tetrapyridyl [3,2-a:2',3'-c:3'',2''-h:2''',3'''-j] phenazine ligand in which the uncoordinated site has been converted into a dicationic ethylene-bipyridyldiylium unit is reported. The structure of the complexes is fully assigned through detailed NMR studies and, in one case, through an X-ray crystallography study. Voltammetry, optical spectroscopy and computational studies confirm that the bipyridyldiylium moiety has a low-lying reduction that quenches the 3MLCT-based emission usually observed in such systems. The new complexes interact with DNA in a quite different manner to their dicationic analogues: they both bind to duplex DNA with micromolar affinity through groove binding. These observations are rationalized through a consideration of their structural and electronic properties.


Assuntos
Complexos de Coordenação/química , DNA/química , Fenazinas/química , Rutênio/química , Sítios de Ligação , Cátions/química , Complexos de Coordenação/síntese química , Cristalografia por Raios X , Técnicas Eletroquímicas , Modelos Moleculares , Conformação Molecular , Processos Fotoquímicos , Teoria Quântica
10.
Bioconjug Chem ; 29(11): 3532-3543, 2018 11 21.
Artigo em Inglês | MEDLINE | ID: mdl-30036048

RESUMO

Surface engineering of nanocarriers allows fine-tuning of their interactions with biological organisms, potentially forming the basis of devices for the monitoring of intracellular events or for intracellular drug delivery. In this context, biodegradable nanocarriers or nanocapsules capable of carrying bioactive molecules or drugs into the mitochondrial matrix could offer new capabilities in treating mitochondrial diseases. Nanocapsules with a polymeric backbone that undergoes programmed rupture in response to a specific chemical or enzymatic stimulus with subsequent release of the bioactive molecule or drug at mitochondria would be particularly attractive for this function. With this goal in mind, we have developed biologically benign nanocapsules using polyurethane-based, polymeric backbone that incorporates repetitive ester functionalities. The resulting nanocapsules are found to be highly stable and monodispersed in size. Importantly, a new non-isocyanate route is adapted for the synthesis of these non-isocyanate polyurethane nanocapsules (NIPU). The embedded ester linkages of these capsules' shells have facilitated complete degradation of the polymeric backbone in response to a stimulus provided by an esterase enzyme. Hydrophilic payloads like rhodamine or doxorubicin can be loaded inside these nanocarriers during their synthesis by an interfacial polymerization reaction. The postgrafting of the nanocapsules with phosphonium ion, a mitochondria-targeting receptor functionality, has helped us achieve the site-specific release of the drug. Co-localization experiments with commercial mitotracker green as well as mitotracker deep red confirmed localization of the cargo in mitochondria. Our in vitro studies confirm that specific release of doxorubicin within mitochondria causes higher cytotoxicity and cell death compared to free doxorubicin. Endogenous enzyme triggered nanocapsule rupture and release of the encapsulated dye is also demonstrated in a zebrafish model. The results of this proof-of-concept study illustrate that NIPU nanocarriers can provide a site-specific delivery vehicle and improve the therapeutic efficacy of a drug or be used to produce organelle-specific imaging studies.


Assuntos
Esterases/metabolismo , Mitocôndrias/efeitos dos fármacos , Nanocápsulas/química , Poliuretanos/farmacologia , Animais , Espectroscopia de Ressonância Magnética Nuclear de Carbono-13 , Doxorrubicina/farmacologia , Portadores de Fármacos , Liberação Controlada de Fármacos , Interações Hidrofóbicas e Hidrofílicas , Isocianatos/química , Microscopia Eletrônica de Varredura , Microscopia Eletrônica de Transmissão , Microscopia de Fluorescência , Polimerização , Poliuretanos/química , Espectroscopia de Infravermelho com Transformada de Fourier , Peixe-Zebra
11.
Nanoscale ; 10(22): 10596-10608, 2018 Jun 07.
Artigo em Inglês | MEDLINE | ID: mdl-29808844

RESUMO

Radiolabelled, drug-loaded nanoparticles may combine the theranostic properties of radionuclides, the controlled release of chemotherapy and cancer cell targeting. Here, we report the preparation of poly(lactic-co-glycolic acid) (PLGA) nanoparticles surface conjugated to DTPA-hEGF (DTPA = diethylenetriaminepentaacetic acid, hEGF = human epidermal growth factor) and encapsulating the ruthenium-based DNA replication inhibitor and radiosensitizer Ru(phen)2(tpphz)2+ (phen = 1,10-phenanthroline, tpphz = tetrapyridophenazine) Ru1. The functionalized PLGA surface incorporates the metal ion chelator DTPA for radiolabelling and the targeting ligand for EGF receptor (EGFR). Nanoparticles radiolabelled with 111In are taken up preferentially by EGFR-overexpressing oesophageal cancer cells, where they exhibit radiotoxicity through the generation of cellular DNA damage. Moreover, nanoparticle co-delivery of Ru1 alongside 111In results in decreased cell survival compared to single-agent formulations; an effect that occurs through DNA damage enhancement and an additive relationship between 111In and Ru1. Substantially decreased uptake and radiotoxicity of nanoparticles towards normal human fibroblasts and oesophageal cancer cells with normal EGFR levels is observed. This work demonstrates nanoparticle co-delivery of a therapeutic radionuclide plus a ruthenium-based radiosensitizer can achieve combinational and targeted therapeutic effects in cancer cells that overexpress EGFR.


Assuntos
Neoplasias Esofágicas/terapia , Radioisótopos de Índio , Nanopartículas/química , Radiossensibilizantes/farmacologia , Rutênio/farmacologia , Adenocarcinoma , Animais , Carcinoma de Células Escamosas , Linhagem Celular Tumoral , Receptores ErbB/metabolismo , Feminino , Humanos , Camundongos , Camundongos Endogâmicos BALB C , Ácido Poliglicólico , Copolímero de Ácido Poliláctico e Ácido Poliglicólico
12.
Chem Sci ; 9(4): 841-849, 2018 Jan 28.
Artigo em Inglês | MEDLINE | ID: mdl-29629151

RESUMO

Substitutionally inert ruthenium(ii) polypyridyl complexes have been developed as DNA intercalating agents yet cellular DNA damage responses to this binding modality are largely unexplored. Here, we show the nuclear-targeting complex [Ru(phen)2(tpphz)]2+ (phen = 1,10-phenanthroline, tpphz = tetrapyridophenazine) generates rapid and pronounced stalling of replication fork progression in p53-deficient human oesophageal cancer cells. In response, replication stress and double-strand break (DSB) DNA damage response (DDR) pathways are activated and cell proliferation is inhibited by growth arrest. Moreover, mitotic progression is compromised by [Ru(phen)2(tpphz)]2+, where the generation of metaphase chromosome spindle attachment failure results in spindle assembly checkpoint (SAC) activation. This dual mechanism of action results in preferential growth inhibition of rapidly-proliferating oesophageal cancer cells with elevated mitotic indices. In addition to these single-agent effects, [Ru(phen)2(tpphz)]2+ functions as a radiosensitizer with efficiency comparable to cisplatin, which occurs through a synergistic enhancement of DNA damage. These results establish that DNA replication is the target for [Ru(phen)2(tpphz)]2+ and provide the first experimental evidence that ruthenium-based intercalation targets multiple genome integrity pathways in cancer cells, thereby achieving enhanced selectivity compared to existing DNA-damaging agents such as cisplatin.

13.
Chem Commun (Camb) ; 54(30): 3735-3738, 2018 Apr 10.
Artigo em Inglês | MEDLINE | ID: mdl-29589001

RESUMO

A new physiologically benign and cell membrane permeable BODIPY based molecular probe, MB-Sn, specifically senses intracellular hydrogen polysulfides (H2Sn, n > 1) localized in the endoplasmic reticulum. This reagent is suitable for mapping the intracellular distribution of H2Sn by wide-field as well as super-resolution Structured Illumination Microscopy (SIM).

14.
Chem Commun (Camb) ; 54(15): 1849-1852, 2018 Feb 15.
Artigo em Inglês | MEDLINE | ID: mdl-29384535

RESUMO

BODIPY derivative, SF-1, exclusively shows a fluorescence ON response to HOCl and images endogenously generated HOCl in RAW 264.7 macrophages. Widefield and super resolution structured illumination microscopy images confirm localization in the Golgi complex and lysosomes, and hence specifically detects HOCl generated in these organelles. SF-1 is compatible with 3D-SIM imaging of individual cells.


Assuntos
Compostos de Boro/química , Corantes Fluorescentes/química , Ácido Hipocloroso/análise , Macrófagos/química , Microscopia/métodos , Organelas/química , Animais , Imageamento Tridimensional , Camundongos , Células RAW 264.7 , Fatores de Tempo
16.
J Am Chem Soc ; 139(44): 15907-15913, 2017 11 08.
Artigo em Inglês | MEDLINE | ID: mdl-28976195

RESUMO

Detailed studies on the live cell uptake properties of a dinuclear membrane-permeable RuII cell probe show that, at low concentrations, the complex localizes and images mitochondria. At concentrations above ∼20 µM, the complex images nuclear DNA. Because the complex is extremely photostable, has a large Stokes shift, and displays intrinsic subcellular targeting, its compatibility with super-resolution techniques was investigated. It was found to be very well suited to image mitochondria and nuclear chromatin in two color, 2C-SIM, and STED and 3D-STED, both in fixed and live cells. In particular, due to its vastly improved photostability compared to that of conventional SR probes, it can provide images of nuclear DNA at unprecedented resolution.


Assuntos
Cromatina , Metais/análise , Microscopia Eletrônica de Transmissão , Microscopia de Fluorescência/métodos , Mitocôndrias , Imagem Multimodal/métodos , Sobrevivência Celular , Cromatina/ultraestrutura , Cor , DNA , Fixadores , Humanos , Células MCF-7 , Metais/química , Mitocôndrias/ultraestrutura
17.
Anal Chem ; 89(22): 12087-12093, 2017 11 21.
Artigo em Inglês | MEDLINE | ID: mdl-29069900

RESUMO

Selective detection of nitroxyl (HNO), which has recently been identified as a reactive nitrogen species, is a challenging task. We report a BODIPY-based luminescence ON reagent for detection of HNO in aqueous solution and in live RAW 264.7 cells, based on the soft nucleophilicity of the phosphine oxide functionality toward HNO. The probe shows high selectivity to HNO over other reactive oxygen/nitrogen and sulfur species. Luminescence properties of the BODIPY-based chemodosimetric reagent make it an ideal candidate for use as a reagent for super-resolution structured illumination microscopy. The viability of the reagent for biological in vivo imaging application was also confirmed using Artemia as a model.


Assuntos
Retículo Endoplasmático/química , Corantes Fluorescentes/química , Óxidos de Nitrogênio/análise , Animais , Artemia , Camundongos , Imagem Óptica , Células RAW 264.7
18.
Angew Chem Int Ed Engl ; 56(41): 12628-12633, 2017 10 02.
Artigo em Inglês | MEDLINE | ID: mdl-28834038

RESUMO

Using a new mononuclear "building block," for the first time, a dinuclear RuII (dppn) complex and a heteroleptic system containing both RuII (dppz) and RuII (dppn) moieties are reported. The complexes, including the mixed dppz/dppn system, are 1 O2 sensitizers. However, unlike the homoleptic dppn systems, the mixed dppz/dppn complex also displays a luminescence "switch on" DNA light-switch effect. In both cisplatin sensitive and resistant human ovarian carcinoma lines the dinuclear complexes show enhanced uptake compared to their mononuclear analogue. Thanks to a favorable combination of singlet oxygen generation and cellular uptake properties all three of the new complexes are phototoxic and display potent activity against chemotherapeutically resistant cells.


Assuntos
Complexos de Coordenação/farmacologia , Substâncias Intercalantes/farmacologia , Neoplasias Ovarianas/tratamento farmacológico , Fármacos Fotossensibilizantes/farmacologia , Rutênio/farmacologia , Linhagem Celular Tumoral , Complexos de Coordenação/química , Complexos de Coordenação/farmacocinética , DNA/metabolismo , Feminino , Humanos , Substâncias Intercalantes/química , Substâncias Intercalantes/farmacocinética , Neoplasias Ovarianas/metabolismo , Fármacos Fotossensibilizantes/química , Fármacos Fotossensibilizantes/farmacocinética , Rutênio/química , Rutênio/farmacocinética , Oxigênio Singlete/metabolismo
19.
Dalton Trans ; 46(20): 6634-6644, 2017 May 23.
Artigo em Inglês | MEDLINE | ID: mdl-28474026

RESUMO

The synergistic effect of oxygen, light, and photosensitizer (PS) has found applications in medicine for the treatment of cancer through photodynamic therapy (PDT). Induction of apoptosis to cancerous cells will prevent tumor metastasis that spreads cancer cells to the neighboring organs/tissues. Herein, we report the two apoptotic Ru(ii)-polypyridyl complexes that are functionalized with pendant amino acid moieties tyrosine (1) and tryptophan (2), respectively. These two water soluble complexes were found to interact strongly (K = (1.18 ± 0.28) × 105 M-1 and K = (1.57 ± 0.77) × 105 M-1) with CT-DNA. Isothermal titration calorimetry (ITC) studies revealed that these complexes bind to CT-DNA through an entropically driven process. Both the complexes showed photo-induced cytotoxicity and exhibit apoptotic activity under photo-irradiation conditions. The comet assay indicated that these complexes can damage cellular DNA, which is attributed to the significant build-up of 1O2 level even on irradiation with low intensity light (10 J cm-2, λRange 450-480 nm). This photoinduced DNA damage and apoptosis in A549 cells was induced by reactive oxygen species (ROS) and occurred through up-regulation of apoptotic marker caspase-3. Control experiments under dark conditions revealed an insignificant cytotoxicity towards these cells for two photosensitive molecules.


Assuntos
Antineoplásicos/farmacologia , Complexos de Coordenação/farmacologia , Metaloporfirinas/química , Fármacos Fotossensibilizantes/farmacologia , Triptofano/química , Tirosina/química , Células A549 , Antineoplásicos/síntese química , Antineoplásicos/química , Apoptose/efeitos dos fármacos , Biomarcadores Tumorais/metabolismo , Caspase 3/metabolismo , Sobrevivência Celular/efeitos dos fármacos , DNA Tumoral Circulante/química , Complexos de Coordenação/síntese química , Complexos de Coordenação/química , Dano ao DNA/efeitos dos fármacos , Humanos , Metástase Neoplásica , Fotoquimioterapia , Fármacos Fotossensibilizantes/síntese química , Fármacos Fotossensibilizantes/química , Espécies Reativas de Oxigênio/metabolismo
20.
Dalton Trans ; 46(18): 6079-6086, 2017 May 09.
Artigo em Inglês | MEDLINE | ID: mdl-28430282

RESUMO

Herein we describe the DNA binding properties of two new water-soluble ruthenium complexes; experimental and computational data reveal that both complexes display dual emission from MLCT and LLCT excited states. The interaction of the new complexes with DNA was also investigated. Although one of the complexes only binds DNA though groove binding, the second complex has separate ligands capable of groove binding and intercalation. Nevertheless, it was found that both complexes interact with duplex DNA with high affinity. DNA induced distinctive changes in the emission of the complexes; although the groove binding complex only displays a modest increase in emission on binding, the complex that contains the intercalating RuII(dppz) moiety displays a large increase in MLCT-based emission on DNA binding while emission from the LLCT excited state is unaffected. This means that the complex functions as the first ratiometric sensor for DNA.


Assuntos
Complexos de Coordenação/química , DNA/química , Fenazinas/química , Rutênio/química , Animais , Bovinos , Complexos de Coordenação/síntese química , Complexos de Coordenação/metabolismo , DNA/metabolismo , Substâncias Intercalantes/química , Substâncias Intercalantes/metabolismo , Ligantes , Espectrometria de Fluorescência , Eletricidade Estática , Viscosidade
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