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1.
Chem Commun (Camb) ; 57(86): 11386-11389, 2021 Oct 28.
Artigo em Inglês | MEDLINE | ID: mdl-34647549

RESUMO

We report a chemiluminescent probe (CLPT1) that permits the paired detection of tyrosinase (Tyr) and biological thiols. Tyr only leads to a poor chemiluminescence response, a finding ascribed to the formation of a stable o-benzoquinone intermediate. The addition of glutathione (GSH), or ascorbate to the o-benzoquinone intermediate results in thiol conjugation or reduction to this intermediate, respectively. This produces a strong chemiluminescence response. Thiol co-dependence was demonstrated in live cells using the cell permeable analogue, CLPT3. The present chemiluminescence-based strategy allows the concurrent detection of tyrosinase activity and biological thiols.

2.
Chem Sci ; 12(33): 11089-11097, 2021 Aug 25.
Artigo em Inglês | MEDLINE | ID: mdl-34522306

RESUMO

Triple negative breast cancer (TNBC) is one of the most malignant subtypes of breast cancer. Here, we report the construction of graphene nanoribbon (GNR)-based supramolecular ensembles with dual-receptor (mannose and αvß3 integrin receptors) targeting function, denoted as GNR-Man/PRGD, for targeted photothermal treatment (PTT) of TNBC. The GNR-Man/PRGD ensembles were constructed through the solution-based self-assembly of mannose-grafted GNRs (GNR-Man) with a pyrene-tagged αvß3 integrin ligand (PRGD). Enhanced PTT efficacies were achieved both in vitro and in vivo compared to that of the non-targeting equivalents. Tumor-bearing live mice were administered (tail vein) with GNR-Man/PRGD and then each mice group was subjected to PTT. Remarkably, GNR-Man/PRGD induced complete ablation of the solid tumors, and no tumor regrowth was observed over a period of 15 days. This study demonstrates a new and promising platform for the development of photothermal nanomaterials for targeted tumor therapy.

3.
Chem Sci ; 12(29): 9916-9921, 2021 Jul 28.
Artigo em Inglês | MEDLINE | ID: mdl-34377389

RESUMO

Photoacoustic imaging (PAI) relies on the use of contrast agents with high molar absorptivity in the NIR-I/NIR-II region. Expanded porphyrins, synthetic analogues of natural tetrapyrrolic pigments (e.g. heme and chlorophyll), constitute as potentially attractive platforms due to their NIR-II absorptivity and their ability to respond to stimuli. Here, we evaluate two expanded porphyrins, naphthorosarin (1) and octaphyrin (4), as stimuli responsive PA contrast agents for functional PAI. Both undergo proton-coupled electron transfer to produce species that absorb well in the NIR-II region. Octaphyrin (4) was successfully encapsulated into 1,2-distearoyl-sn-glycero-3-phosphoethanolamine-poly(ethylene glycol) (DSPE-PEG2000) nanoparticles to afford OctaNPs. In combination with PAI, OctaNPs allowed changes in the acidic environment of the stomach to be visualized and cancerous versus healthy tissues to be discriminated.

4.
Chem Soc Rev ; 50(17): 9391-9429, 2021 Sep 07.
Artigo em Inglês | MEDLINE | ID: mdl-34232230

RESUMO

Chemical tools that allow the real-time monitoring of organ function and the visualisation of organ-related processes at the cellular level are of great importance in biological research. The upregulation/downregulation of specific biomarkers is often associated with the development of organ related diseases. Small-molecule fluorescent probes have the potential to create advances in our understanding of these disorders. Viable probes should be endowed with a number of key features that include high biomarker sensitivity, low limit of detection, fast response times and appropriate in vitro and in vivo biocompatibility. In this tutorial review, we discuss the development of probes that allow the targeting of organ related processes in vitro and in vivo. We highlight the design strategy that underlies the preparation of various promising probes, their optical response to key biomarkers, and proof-of-concept biological studies. The inherent drawbacks and limitations are discussed as are the current challenges and opportunities in the field. The hope is that this tutorial review will inspire the further development of small-molecule fluorescent probes that could aid the study of pathogenic conditions that contribute to organ-related diseases.


Assuntos
Corantes Fluorescentes , Biomarcadores , Fluorescência
5.
Chem Sci ; 12(21): 7547-7553, 2021 Apr 26.
Artigo em Inglês | MEDLINE | ID: mdl-34163845

RESUMO

Recent decades have witnessed the emergence of Au(i) bis-N-heterocyclic carbenes (NHCs) as potential anticancer agents. However, these systems exhibit little interaction with serum proteins (e.g., human serum albumin), which presumably impacts their pharmacokinetic profile and tumor exposure. Anticancer drugs bound to human serum albumin (HSA) often benefit from significant advantages, including longer circulatory half-lives, tumor targeted delivery, and easier administration relative to the drug alone. In this work, we present Au(i) bis-NHCs complexes, 7 and 9, capable of binding to HSA. Complex 7 contains a reactive maleimide moiety for covalent protein conjugation, whereas its congener 9 contains a naphthalimide fluorophore for non-covalent binding. A similar drug motif was used in both cases. Complexes 7 and 9 were prepared from a carboxylic acid functionalized Au(i) bis-NHC (complex 2) using a newly developed post-synthetic amide functionalization protocol that allows coupling to both aliphatic and aromatic amines. Analytical, and in vitro techniques were used to confirm protein binding, as well as cellular uptake and antiproliferative activity in A549 human lung cancer cells. The present findings highlight a hitherto unexplored approach to modifying Au(i) bis-NHC drug candidates for protein ligation and serve to showcase the relative benefits of covalent and non-covalent HSA binding.

6.
Coord Chem Rev ; 4272021 Jan 15.
Artigo em Inglês | MEDLINE | ID: mdl-34108734

RESUMO

Since as early as 1867, molecular sensors have been recognized as being intelligent "devices" capable of addressing a variety of issues related to our environment and health (e.g., the detection of toxic pollutants or disease-related biomarkers). In this review, we focus on fluorescence-based sensors that incorporate supramolecular chemistry to achieve a desired sensing outcome. The goal is to provide an illustrative overview, rather than a comprehensive listing of all that has been done in the field. We will thus summarize early work devoted to the development of supramolecular fluorescent sensors and provide an update on recent advances in the area (mostly from 2018 onward). A particular emphasis will be placed on design strategies that may be exploited for analyte sensing and corresponding molecular platforms. Supramolecular approaches considered include, inter alia, binding-based sensing (BBS) and indicator displacement assays (IDAs). Because it has traditionally received less treatment, many of the illustrative examples chosen will involve anion sensing. Finally, this review will also include our perspectives on the future directions of the field.

7.
Biomater Sci ; 9(12): 4433-4439, 2021 Jun 15.
Artigo em Inglês | MEDLINE | ID: mdl-34075906

RESUMO

Alkaline phosphatase (ALP) is an important enzyme-based biomarker present in several bacterial species; however, it is currently undervalued as a strategy to detect pathogenic bacteria. Here, we explore our ALP-responsive colorimetric and fluorescent probe (TCF-ALP) for such applications. TCF-ALP displayed a colorimetric and fluorescence response towards Staphylococcus aureus (S. aureus), with a limit of detection of 3.7 × 106 CFU mL-1 after 24 h incubation. To our surprise, TCF-ALP proved selective towards Staphylococcus bacteria when compared with Enterococcus faecalis (E. faecalis), and Gram-negative P. aeruginosa and E. coli. Selectivity was also seen in clinically relevant S. aureus biofilms. Owing to the high prevalence and surface location of S. aureus in chronic wounds, TCF-ALP was subsequently encapsulated in polyvinyl alcohol (PVA)-based hydrogels as a proof-of-concept "smart" wound dressing. TCF-ALP hydrogels were capable of detecting S. aureus in planktonic and biofilm assays, and displayed a clear colour change from yellow to purple after 24 h incubation using ex vivo porcine skin models. Overall, TCF-ALP is a simple tool that requires no prior knowledge, training, or specialist equipment, and has the potential to overcome issues related to invasive swabbing and tissue biopsy methods. Thus, TCF-ALP could be used as a tool to monitor the early development of infection in a wound and allow for the rapid provision of appropriate treatment for Staphylococcal bacterial infections.


Assuntos
Fosfatase Alcalina , Staphylococcus aureus , Animais , Bactérias , Bandagens , Biofilmes , Escherichia coli , Corantes Fluorescentes , Pseudomonas aeruginosa , Suínos
8.
Chem Commun (Camb) ; 57(46): 5678-5681, 2021 Jun 08.
Artigo em Inglês | MEDLINE | ID: mdl-33977921

RESUMO

We report here strategic functionalization of the FDA approved chelator deferasirox (1) in an effort to produce organelle-targeting iron chelators with enhanced activity against A549 lung cancer cells. Derivative 8 was found to have improved antiproliferative activity relative to 1. Fluorescent cell imaging revealed that compound 8 preferentially localises within the lysosome.


Assuntos
Antineoplásicos/farmacologia , Deferasirox/farmacologia , Quelantes de Ferro/farmacologia , Neoplasias Pulmonares/tratamento farmacológico , Organelas/química , Células A549 , Antineoplásicos/química , Proliferação de Células/efeitos dos fármacos , Deferasirox/química , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Quelantes de Ferro/química , Neoplasias Pulmonares/diagnóstico por imagem , Lisossomos/química , Microscopia Confocal , Estrutura Molecular , Imagem Óptica
9.
J Mater Chem B ; 9(17): 3640-3661, 2021 05 05.
Artigo em Inglês | MEDLINE | ID: mdl-33870985

RESUMO

The excessive use of antibiotics has led to a rise in drug-resistant bacteria. These "superbugs" are continuously emerging and becoming increasingly harder to treat. As a result, new and effective treatment protocols that have minimal risks of generating drug-resistant bacteria are urgently required. Advanced nanomaterials are particularly promising due to their drug loading/releasing capabilities combined with their potential photodynamic/photothermal therapeutic properties. In this review, 0-dimensional, 1-dimensional, 2-dimensional, and 3-dimensional nanomaterial-based systems are comprehensively discussed for bacterial-based diagnostic and treatment applications. Since the use of these platforms as antibacterials is relatively new, this review will provide appropriate insight into their construction and applications. As such, we hope this review will inspire researchers to explore antibacterial-based nanomaterials with the aim of developing systems for clinical applications.


Assuntos
Antibacterianos/química , Portadores de Fármacos/química , Nanoestruturas/química , Fármacos Fotossensibilizantes/química , Animais , Antibacterianos/farmacologia , Carbono/química , Corantes/química , Terapia Combinada , Liberação Controlada de Fármacos , Resistência Microbiana a Medicamentos , Humanos , Metais/química , Conformação Molecular , Fotoquimioterapia , Fármacos Fotossensibilizantes/farmacologia , Polímeros/química , Propriedades de Superfície
10.
J Am Chem Soc ; 143(18): 7196-7202, 2021 05 12.
Artigo em Inglês | MEDLINE | ID: mdl-33905646

RESUMO

Photoacoustic (PA) imaging has emerged as a reliable in vivo technique for diverse biomedical applications ranging from disease screening to analyte sensing. Most contemporary PA imaging agents employ NIR-I light (650-900 nm) to generate an ultrasound signal; however, there is significant interference from endogenous biomolecules such as hemoglobin that are PA active in this window. Transitioning to longer excitation wavelengths (i.e., NIR-II) reduces the background and facilitates the detection of low abundance targets (e.g., nitric oxide, NO). In this study, we employed a two-phase tuning approach to develop APNO-1080, a NIR-II NO-responsive probe for deep-tissue PA imaging. First, we performed Hammett and Brønsted analyses to identify a highly reactive and selective aniline-based trigger that reacts with NO via N-nitrosation chemistry. Next, we screened a panel of NIR-II platforms to identify chemical structures that have a low propensity to aggregate since this can diminish the PA signal. In a head-to-head comparison with a NIR-I analogue, APNO-1080 was 17.7-fold more sensitive in an in vitro tissue phantom assay. To evaluate the deep-tissue imaging capabilities of APNO-1080 in vivo, we performed PA imaging in an orthotopic breast cancer model and a heterotopic lung cancer model. Relative to control mice not bearing tumors, the normalized turn-on response was 1.3 ± 0.12 and 1.65 ± 0.07, respectively.

11.
J Am Chem Soc ; 143(3): 1278-1283, 2021 01 27.
Artigo em Inglês | MEDLINE | ID: mdl-33428381

RESUMO

Deferasirox, ExJade, is an FDA-approved iron chelator used for the treatment of iron overload. In this work, we report several fluorescent deferasirox derivatives that display unique photophysical properties, i.e., aggregation-induced emission (AIE), excited state intramolecular proton transfer, charge transfer, and through-bond and through-space conjugation characteristics in aqueous media. Functionalization of the phenol units on the deferasirox scaffold afforded the fluorescent responsive pro-chelator ExPhos, which enabled the detection of the disease-based biomarker alkaline phosphatase (ALP). The diagnostic potential of these deferasirox derivatives was supported by bacterial biofilm studies.


Assuntos
Deferasirox/análogos & derivados , Corantes Fluorescentes/química , Fosfatase Alcalina/análise , Antibacterianos/farmacologia , Proteínas de Bactérias/análise , Biofilmes/efeitos dos fármacos , Biomarcadores/análise , Cefoperazona/farmacologia , Deferasirox/farmacologia , Deferasirox/efeitos da radiação , Corantes Fluorescentes/farmacologia , Corantes Fluorescentes/efeitos da radiação , Luz , Staphylococcus aureus Resistente à Meticilina/efeitos dos fármacos , Staphylococcus aureus Resistente à Meticilina/enzimologia , Staphylococcus aureus Resistente à Meticilina/fisiologia , Testes de Sensibilidade Microbiana , Microscopia Confocal , Microscopia de Fluorescência , Pseudomonas aeruginosa/efeitos dos fármacos , Pseudomonas aeruginosa/enzimologia , Pseudomonas aeruginosa/fisiologia , Sulbactam/farmacologia
12.
Chem Soc Rev ; 50(1): 9-38, 2021 Jan 07.
Artigo em Inglês | MEDLINE | ID: mdl-33169731

RESUMO

Indicator displacement assays (IDAs) offer a unique and innovative approach to molecular sensing. IDAs can facilitate the detection of a range of biologically/environmentally important species, provide a method for the detection of complex analytes or for the determination and discrimination of unknown sample mixtures. These attributes often cannot be achieved by traditional molecular sensors i.e. reaction-based sensors/chemosensors. The IDA pioneers Inouye, Shinkai, and Anslyn inspired researchers worldwide to develop various extensions of this idea. Since their early work, the field of indicator displacement assays has expanded to include: enantioselective indicator displacement assays (eIDAs), fluorescent indicator displacement assays (FIDAs), reaction-based indicator displacement assays (RIAs), DimerDye disassembly assays (DDAs), intramolecular indicator displacement assays (IIDAs), allosteric indicator displacement assay (AIDAs), mechanically controlled indicator displacement assays (MC-IDAs), and quencher displacement assays (QDAs). The simplicity of these IDAs, coupled with low cost, high sensitivity, and ability to carry out high-throughput automation analysis (i.e., sensing arrays) has led to their ubiquitous use in molecular sensing, alongside the other common approaches such as reaction-based sensors and chemosensors. In this review, we highlight the various design strategies that have been used to develop an IDA, including the design strategies for the newly reported extensions to these systems. To achieve this, we have divided this review into sections based on the target analyte, the importance of each analyte and then the reported IDA system is discussed. In addition, each section includes details on the benefit of the IDAs and perceived limitations for each system. We conclude this Tutorial Review by highlighting the current challenges associated with the development of new IDAs and suggest potential future avenues of research.

13.
Future Med Chem ; 12(22): 2035-2065, 2020 11.
Artigo em Inglês | MEDLINE | ID: mdl-33169622

RESUMO

As bacteria continue to develop resistance to our existing treatment options, antibiotic innovation remains overlooked. If current trends continue, then we could face the stark reality of a postantibiotic era, whereby routine bacterial infections could once again become deadly. In light of a warning signaled by the WHO, a number of new initiatives have been established in the hope of reinvigorating the antibiotic drug development pipeline. In this perspective, we aim to summarize some of these initiatives and funding options, as well as providing an insight into the predicament that we face. Using clinical trials data, company website information and the most recent press releases, a current update of the antibiotic drug development pipeline is also included.


Assuntos
Antibacterianos/farmacologia , Bactérias/efeitos dos fármacos , Desenvolvimento de Medicamentos , Antibacterianos/síntese química , Antibacterianos/química , Farmacorresistência Bacteriana/efeitos dos fármacos , Testes de Sensibilidade Microbiana
15.
Nanoscale ; 12(45): 23234-23240, 2020 Nov 26.
Artigo em Inglês | MEDLINE | ID: mdl-33206087

RESUMO

In this study, "core-shell" gold nanoparticles (AuNPs) have been functionalised using a simple one-pot approach to form fucose-based glycoconjugate AuNPs (Fuc-AuNPs) and galactose-based glycoconjugate AuNPs (Gal-AuNPs), respectively. Owing to the selective carbohydrate-based recognition of the key virulence factors of P. aeruginosa, LecB (fucose-specific lectin)/LecA (galactose-specific lectin), Fuc-AuNPs and Gal-AuNPs-based imaging and therapeutic strategies were evaluated towards P. aeruginosa. Both Fuc-AuNPs and Gal-AuNPs were non-covalently loaded with the fluorophore dicyanomethylene 4H-pyran (DCM) to afford two highly selective fluorescence imaging agents for the visualisation of P. aeruginosa. The loading of Fuc-AuNPs and Gal-AuNPs with the known antibiotic Ceftazidime (CAZ) exhibited an enhanced therapeutic effect, illustrating the significance of this targeted drug delivery strategy. Exploiting the phototherapeutic properties of AuNPs, photoirradiation (600 nm) of Fuc-AuNP@CAZ/Gal-AuNP@CAZ provided both photothermal and photodynamic therapeutic (PTT/PDT) effects, which facilitated the release of CAZ. Fuc-AuNP@CAZ and Gal-AuNP@CAZ were shown to be effective photo/chemotherapeutics resulting in almost complete eradication of P. aeruginosa biofilms formed on clinically relevant surfaces (glass slides and steel surface).


Assuntos
Nanopartículas Metálicas , Pseudomonas aeruginosa , Biofilmes , Glicoconjugados , Ouro
16.
Chem Sci ; 11(28): 7329-7334, 2020 Jul 28.
Artigo em Inglês | MEDLINE | ID: mdl-33033609

RESUMO

In this work, we have developed an ESIPT-based benzimidazole platform (MO-E1 and MO-E2) for the two-photon cell imaging of ONOO- and a potential ONOO--activated theranostic scaffold (MO-E3). Each benzimidazole platform, MO-E1-3, were shown to rapidly detect ONOO- at micromolar concentrations (LoD = 0.28 µM, 6.53 µM and 0.81 µM respectively). The potential theranostic MO-E3 was shown to release the parent fluorophore and drug indomethacin in the presence of ONOO- but unfortunately did not perform well in vitro due to low solubility. Despite this, the parent scaffold MO-E2 demonstrated its effectiveness as a two-photon imaging tool for the ratiometric detection of endogenous ONOO- in RAW264.7 macrophages and rat hippocampus tissue. These results demonstrate the utility of this ESIPT benzimidazole-based platform for theranostic development and bioimaging applications.

17.
J Am Chem Soc ; 142(42): 18005-18013, 2020 10 21.
Artigo em Inglês | MEDLINE | ID: mdl-32955867

RESUMO

Here, we report a ß-galactosidase (ß-Gal)-responsive photochromic fluorescent probe, NpG, that was designed to prebind to human serum albumin (HSA) to form the probe/protein hybrid, NpG@HSA. The formation of NpG@HSA led to an increase in fluorescence emission (520 nm) corresponding to the binding of the fluorescent naphthalimide unit with HSA. In addition, this enabled visualization of the spiropyran fluorescence emission in aqueous media. Our probe/protein hybrid approach afforded a unique imaging platform with enhanced cell permeability and solubility that was capable of visualizing the cellular uptake of NpG@HSA before its activation by ß-Gal. The ß-Gal-mediated cleavage of the galactose unit within the NpG@HSA hybrid resulted in the formation of NpM@HSA and an increase in red fluorescence emission (620 nm). The resultant merocyanine unit was then able to undergo photoisomerization (merocyanine ↔ spiropyran) to facilitate STORM (i.e., stochastic optical reconstruction microscopy) imaging with minimal phototoxicity and excellent photostability/reversibility. Using STORM, NpG@HSA was able to determine the subcellular distribution of ß-Gal activity between cell lines with nanoscale precision. We believe that this system represents a versatile imaging platform for the design of photochromic fluorescent probes suitable for illuminating the precise location of disease-specific biomarkers in various cellular processes.


Assuntos
Corantes Fluorescentes/química , beta-Galactosidase/análise , Biomarcadores/análise , Biomarcadores/metabolismo , Linhagem Celular , Corantes Fluorescentes/síntese química , Humanos , Microscopia Confocal , Estrutura Molecular , Imagem Óptica , Processos Fotoquímicos , Albumina Sérica Humana/química , beta-Galactosidase/metabolismo
18.
J Am Chem Soc ; 142(38): 16156-16160, 2020 09 23.
Artigo em Inglês | MEDLINE | ID: mdl-32914968

RESUMO

The NIR absorptivity of the metallotexaphyrin derivatives MMn, MGd, and MLu for photoacoustic (PA)-based imaging is explored in this study. All three complexes demonstrated excellent photostabilities; however, MMn provided the greatest PA signal intensities in both doubly distilled water and RAW 264.7 cells. In vivo experiments using a prostate tumor mouse model were performed. MMn displayed no adverse toxicity to major organs as inferred from hematoxylin and eosin (H&E) staining and cell blood count testing. MMn also allowed for PA-based imaging of tumors with excellent in vivo stability to provide 3D tumor diagnostic information. Based on the present findings and previous magnetic resonance imaging (MRI) studies, we believe MMn may have a role to play either as a stand-alone PA contrast agent or as a single molecule dual modal (PA and MR) imaging agent for tumor diagnosis.


Assuntos
Meios de Contraste/química , Manganês/química , Técnicas Fotoacústicas , Porfirinas/química , Neoplasias da Próstata/diagnóstico por imagem , Animais , Linhagem Celular Tumoral , Humanos , Raios Infravermelhos , Imageamento por Ressonância Magnética , Masculino , Camundongos , Camundongos Nus , Estrutura Molecular , Neoplasias Experimentais/diagnóstico por imagem , Células RAW 264.7
19.
Chem Soc Rev ; 49(15): 5110-5139, 2020 Aug 07.
Artigo em Inglês | MEDLINE | ID: mdl-32697225

RESUMO

In this tutorial review, we will explore recent advances in the construction and application of Förster resonance energy transfer (FRET)-based small-molecule fluorescent probes. The advantages of FRET-based fluorescent probes include: a large Stokes shift, ratiometric sensing and dual/multi-analyte responsive systems. We discuss the underlying energy donor-acceptor dye combinations and emphasise their applications for the detection or imaging of cations, anions, small neutral molecules, biomacromolecules, cellular microenvionments and dual/multi-analyte responsive systems.


Assuntos
Transferência Ressonante de Energia de Fluorescência/métodos , Compostos Inorgânicos/análise , Animais , Transporte Biológico , Melhoramento Biomédico , Técnicas Biossensoriais , Linhagem Celular , Microambiente Celular , Humanos , Íons/análise , Potencial da Membrana Mitocondrial , Microscopia de Fluorescência , Neoplasias/diagnóstico por imagem , Imagem Óptica , Espectrometria de Fluorescência , Propriedades de Superfície
20.
Chem Commun (Camb) ; 56(57): 7877-7880, 2020 Jul 21.
Artigo em Inglês | MEDLINE | ID: mdl-32520019

RESUMO

A post-synthetic strategy is reported that allows for functionalisation of Au(i)-bis NHCs via carbonate formation. The scope of this methodology was explored using both aromatic and aliphatic alcohols. As a demonstration of potential utility, the fluorescent Au(i)-bis NHC conjugate 5 was prepared; it was found to have enhanced stability when formulated with bovine serum albumin, localise within the mitochondria of A549 cells and do so without compromising the high cytotoxicity seen for the parent Au(i)-bis NHC system.


Assuntos
Antineoplásicos/farmacologia , Complexos de Coordenação/farmacologia , Ouro/farmacologia , Compostos Heterocíclicos/farmacologia , Metano/análogos & derivados , Células A549 , Antineoplásicos/síntese química , Antineoplásicos/química , Proliferação de Células/efeitos dos fármacos , Complexos de Coordenação/síntese química , Complexos de Coordenação/química , Ensaios de Seleção de Medicamentos Antitumorais , Ouro/química , Compostos Heterocíclicos/química , Humanos , Metano/química , Metano/farmacologia , Estrutura Molecular , Imagem Óptica
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