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1.
Molecules ; 26(16)2021 Aug 13.
Artigo em Inglês | MEDLINE | ID: mdl-34443508

RESUMO

INTRODUCTION: Chemotherapy with anti-cancer drugs is considered the most common approach for killing cancer cells in the human body. However, some barriers such as toxicity and side effects would limit its usage. In this regard, nano-based drug delivery systems have emerged as cost-effective and efficient for sustained and targeted drug delivery. Nanotubes such as carbon nanotubes (CNT) and boron nitride nanotubes (BNNT) are promising nanocarriers that provide the cargo with a large inner volume for encapsulation. However, understanding the insertion process of the anti-cancer drugs into the nanotubes and demonstrating drug-nanotube interactions starts with theoretical analysis. METHODS: First, interactions parameters of the atoms of 5-FU were quantified from the DREIDING force field. Second, the storage capacity of BNNT (8,8) was simulated to count the number of drugs 5-FU encapsulated inside the cavity of the nanotubes. In terms of the encapsulation process of the one drug 5-FU into nanotubes, it was clarified that the drug 5-FU was more rapidly adsorbed into the cavity of the BNNT compared with the CNT due to the higher van der Waals (vdW) interaction energy between the drug and the BNNT. RESULTS: The obtained values of free energy confirmed that the encapsulation process of the drug inside the CNT and BNNT occurred spontaneously with the free energies of -14 and -25 kcal·mol-1, respectively. DISCUSSION: However, the lower value of the free energy in the system containing the BNNT unraveled more stability of the encapsulated drug inside the cavity of the BNNT comparing the system having CNT. The encapsulation of Fluorouracil (5-FU) anti-cancer chemotherapy drug (commercial name: Adrucil®) into CNT (8,8) and BNNT (8,8) with the length of 20 Å in an aqueous solution was discussed herein applying molecular dynamics (MD) simulation.


Assuntos
Antineoplásicos/farmacologia , Compostos de Boro/química , Composição de Medicamentos , Fluoruracila/farmacologia , Nanotubos de Carbono/química , Estabilidade de Medicamentos , Fluoruracila/química , Conformação Molecular , Simulação de Dinâmica Molecular , Termodinâmica
2.
Chem Commun (Camb) ; 57(65): 8039-8042, 2021 Aug 12.
Artigo em Inglês | MEDLINE | ID: mdl-34291259

RESUMO

Two-dimensional (2D) hexagonal boron nitride nanosheet (h-BNNS) is proposed as an effective nanoquencher for fluorescence detection of biocompatible microRNA. Compared with bulk hexagonal boron nitride (h-BN), the exfoliated ultrathin nanosheet has a narrow band gap and increased conductivity, thus enabling fast electron transfer with this electron acceptor for more effective fluorescence detection of microRNA. Remarkably, using the nanoprobe consisting of h-BNNS and FAM dye-labeled ssDNA, a low detection limit of 2.39 nM is achieved and a rapid fluorescence response is observed compared with previously reported fluorescence sensing materials. More importantly, this sensing system could also distinguish base-mismatched microRNA, suggesting that the proposed sensing platform held excellent selectivity and great promise for application in the detection of nucleotide polymorphism. This work will benefit microRNA-related fundamental research and disease diagnosis.


Assuntos
Compostos de Boro/química , Corantes Fluorescentes/química , MicroRNAs/análise , Nanoestruturas/química , Pareamento Incorreto de Bases , Biomarcadores Tumorais/análise , Biomarcadores Tumorais/genética , DNA de Cadeia Simples/química , DNA de Cadeia Simples/genética , Fluoresceínas/química , Fluorescência , Ácidos Nucleicos Imobilizados/química , Ácidos Nucleicos Imobilizados/genética , Limite de Detecção , MicroRNAs/genética , Hibridização de Ácido Nucleico , Espectrometria de Fluorescência
3.
Int J Nanomedicine ; 16: 4277-4288, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-34194228

RESUMO

Introduction: Antimicrobial peptides are potential therapeutics as anti-bacteria, anti-viruses, anti-fungi, or anticancers. However, they suffer from a short half-life and drug resistance which limit their long-term clinical usage. Methods: Herein, we captured the encapsulation of antimicrobial peptide HA-FD-13 into boron nitride nanotube (BNNT) (20,20) and its release due to subsequent insertion of BNNT (14,14) with molecular dynamics simulation. Results: The peptide-BNNT (20,20) van der Waals (vdW) interaction energy decreased to -270 kcal·mol-1 at the end of the simulation (15 ns). However, during the period of 0.2-1.8 ns, when half of the peptide was inside the nanotube, the encapsulation was paused due to an energy barrier in the vicinity of BNNT and subsequently the external intervention, such that the self-adjustment of the peptide allowed full insertion. The free energy of the encapsulation process was -200.12 kcal·mol-1, suggesting that the insertion procedure occurred spontaneously. Discussion: Once the BNNT (14,14) entered into the BNNT (20,20), the peptide was completely released after 83.8 ps. This revealed that the vdW interaction between the BNNT (14,14) and BNNT (20,20) was stronger than between BNNT (20,20) and the peptide; therefore, the BNNT (14,14) could act as a piston pushing the peptide outside the BNNT (20,20). Moreover, the sudden drop in the vdW energy between nanotubes to the value of the -1300 Kcal·mol-1 confirmed the self-insertion of the BNNT (14,14) into the BNNT (20,20) and correspondingly the release of the peptide.


Assuntos
Compostos de Boro/química , Nanotubos/química , Proteínas Citotóxicas Formadoras de Poros/química , Proteínas Citotóxicas Formadoras de Poros/farmacocinética , Simulação de Dinâmica Molecular , Conformação Proteica em alfa-Hélice
4.
Int J Mol Sci ; 22(13)2021 Jun 23.
Artigo em Inglês | MEDLINE | ID: mdl-34201648

RESUMO

The present study is devoted to the combined experimental and theoretical description of the photophysical properties and photodegradation of the new boron-dipyrromethene (BODIPY) derivatives obtained recently for biomedical applications, such as bacteria photoinactivation (Piskorz et al., Dyes and Pigments 2020, 178, 108322). Absorption and emission spectra for a wide group of solvents of different properties for the analyzed BODIPY derivatives were investigated in order to verify their suitability for photopharmacological applications. Additionally, the photostability of the analyzed systems were thoroughly determined. The exposition to the UV light was found first to cause the decrease in the most intensive absorption band and the appearance of the hypsochromically shifted band of similar intensity. On the basis of the chromatographic and computational study, this effect was assigned to the detachment of the iodine atoms from the BODIPY core. After longer exposition to UV light, photodegradation occurred, leading to the disappearance of the intensive absorption bands and the emergence of small intensity signals in the strongly blue-shifted range of the spectrum. Since the most intensive bands in original dyes are ascribed to the molecular core bearing the BF2 moiety, this result can be attributed to the significant cleavage of the BF2 ring. In order to fully characterize the obtained molecules, the comprehensive computational chemistry study was performed. The influence of the intermolecular interactions for their absorption in solution was analyzed. The theoretical data entirely support the experimental outcomes.


Assuntos
Compostos de Boro/química , Corantes Fluorescentes/química , Teoria da Densidade Funcional , Iodo/química , Conformação Molecular , Fotólise , Solventes/química , Espectrometria de Fluorescência , Espectrofotometria Ultravioleta
5.
Nat Commun ; 12(1): 3483, 2021 06 09.
Artigo em Inglês | MEDLINE | ID: mdl-34108481

RESUMO

The hexameric AAA-ATPase Drg1 is a key factor in eukaryotic ribosome biogenesis and initiates cytoplasmic maturation of the large ribosomal subunit by releasing the shuttling maturation factor Rlp24. Drg1 monomers contain two AAA-domains (D1 and D2) that act in a concerted manner. Rlp24 release is inhibited by the drug diazaborine which blocks ATP hydrolysis in D2. The mode of inhibition was unknown. Here we show the first cryo-EM structure of Drg1 revealing the inhibitory mechanism. Diazaborine forms a covalent bond to the 2'-OH of the nucleotide in D2, explaining its specificity for this site. As a consequence, the D2 domain is locked in a rigid, inactive state, stalling the whole Drg1 hexamer. Resistance mechanisms identified include abolished drug binding and altered positioning of the nucleotide. Our results suggest nucleotide-modifying compounds as potential novel inhibitors for AAA-ATPases.


Assuntos
ATPases Associadas a Diversas Atividades Celulares/química , Adenosina Trifosfatases/química , Compostos de Boro/química , Proteínas de Saccharomyces cerevisiae/química , Domínio AAA , ATPases Associadas a Diversas Atividades Celulares/antagonistas & inibidores , ATPases Associadas a Diversas Atividades Celulares/genética , ATPases Associadas a Diversas Atividades Celulares/metabolismo , Adenosina Trifosfatases/antagonistas & inibidores , Adenosina Trifosfatases/genética , Adenosina Trifosfatases/metabolismo , Sítios de Ligação , Compostos de Boro/farmacologia , Resistência a Medicamentos/genética , Ativação Enzimática/efeitos dos fármacos , Ativação Enzimática/genética , Mutação , Nucleotídeos/química , Proteínas de Saccharomyces cerevisiae/antagonistas & inibidores , Proteínas de Saccharomyces cerevisiae/genética , Proteínas de Saccharomyces cerevisiae/metabolismo
6.
ACS Appl Mater Interfaces ; 13(26): 30295-30305, 2021 Jul 07.
Artigo em Inglês | MEDLINE | ID: mdl-34165969

RESUMO

As viruses have been threatening global public health, fast diagnosis has been critical to effective disease management and control. Reverse-transcription quantitative polymerase chain reaction (RT-qPCR) is now widely used as the gold standard for detecting viruses. Although a multiplex assay is essential for identifying virus types and subtypes, the poor multiplicity of RT-qPCR makes it laborious and time-consuming. In this paper, we describe the development of a multiplex RT-qPCR platform with hydrogel microparticles acting as independent reactors in a single reaction. To build target-specific particles, target-specific primers and probes are integrated into the particles in the form of noncovalent composites with boron nitride nanotubes (BNNTs) and carbon nanotubes (CNTs). The thermal release characteristics of DNA, primer, and probe from the composites of primer-BNNT and probe-CNT allow primer and probe to be stored in particles during particle production and to be delivered into the reaction. In addition, BNNT did not absorb but preserved the fluorescent signal, while CNT protected the fluorophore of the probe from the free radicals present during particle production. Bicompartmental primer-incorporated network (bcPIN) particles were designed to harness the distinctive properties of two nanomaterials. The bcPIN particles showed a high RT-qPCR efficiency of over 90% and effective suppression of non-specific reactions. 16-plex RT-qPCR has been achieved simply by recruiting differently coded bcPIN particles for each target. As a proof of concept, multiplex one-step RT-qPCR was successfully demonstrated with a simple reaction protocol.


Assuntos
Hidrogéis/química , Reação em Cadeia da Polimerase Multiplex/métodos , Nanotubos de Carbono/química , RNA Viral/análise , Reação em Cadeia da Polimerase Via Transcriptase Reversa/métodos , Compostos de Boro/química , Coronavirus/química , Primers do DNA/química , DNA de Cadeia Simples/química , Corantes Fluorescentes/química , Grafite/química , Vírus da Influenza A/química , Vírus da Doença de Newcastle/química , Estudo de Prova de Conceito , RNA Viral/química , Viroses/diagnóstico
7.
J Med Chem ; 64(13): 9330-9353, 2021 07 08.
Artigo em Inglês | MEDLINE | ID: mdl-34181409

RESUMO

Selective agonism of the estrogen receptor (ER) subtypes, ERα and ERß, has historically been difficult to achieve due to the high degree of ligand-binding domain structural similarity. Multiple efforts have focused on the use of classical organic scaffolds to model 17ß-estradiol geometry in the design of ERß selective agonists, with several proceeding to various stages of clinical development. Carborane scaffolds offer many unique advantages including the potential for novel ligand/receptor interactions but remain relatively unexplored. We synthesized a series of para-carborane estrogen receptor agonists revealing an ERß selective structure-activity relationship. We report ERß agonists with low nanomolar potency, greater than 200-fold selectivity for ERß over ERα, limited off-target activity against other nuclear receptors, and only sparse CYP450 inhibition at very high micromolar concentrations. The pharmacological properties of our para-carborane ERß selective agonists measure favorably against clinically developed ERß agonists and support further evaluation of carborane-based selective estrogen receptor modulators.


Assuntos
Compostos de Boro/farmacologia , Receptor beta de Estrogênio/agonistas , Estrogênios/farmacologia , Compostos de Boro/síntese química , Compostos de Boro/química , Relação Dose-Resposta a Droga , Estrogênios/síntese química , Estrogênios/química , Células HEK293 , Humanos , Estrutura Molecular , Relação Estrutura-Atividade
8.
Chem Commun (Camb) ; 57(54): 6612-6615, 2021 Jul 06.
Artigo em Inglês | MEDLINE | ID: mdl-34116566

RESUMO

Negative ion mode paper spray mass spectrometry (PS-MS) suffers from intense background noise and unstable MS signal. For the first time, we reported fluorinated boron nitride nanosheet (h-FBN) assisted negative ion PS-MS for the detection of a series of molecules. We demonstrated that the introduction of h-FBN can greatly improve the detection sensitivity and signal stability in the negative ion mode.


Assuntos
Compostos de Boro/química , Halogenação , Limite de Detecção , Espectrometria de Massas/métodos , Papel , Nanoestruturas/química , Razão Sinal-Ruído
9.
Molecules ; 26(9)2021 May 03.
Artigo em Inglês | MEDLINE | ID: mdl-34063643

RESUMO

BODIPY dyes are photostable neutral derivatives of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene. These are widely used as chemosensors, laser materials, and molecular probes. At the same time, BODIPY dyes have small or moderate Stokes shifts like most other fluorophores. Large Stokes shifts are preferred for fluorophores because of higher sensitivity of such probes and sensors. The new boron containing BODIPY dye was designed and synthesized. We succeeded to perform an annulation of pyrrole ring with coumarin heterocyclic system and achieved a remarkable difference in absorption and emission maximum of obtained fluorophore up to 100 nm. This BODIPY dye was equipped with linker arm and was functionalized with a maleimide residue specifically reactive towards thiol groups of proteins. BODIPY residue equipped with a suitable targeting protein core can be used as a suitable imaging probe and agent for Boron Neutron Capture Therapy (BNCT). As the most abundant protein with a variety of physiological functions, human serum albumin (HSA) has been used extensively for the delivery and improvement of therapeutic molecules. Thiolactone chemistry provides a powerful tool to prepare albumin-based multimodal constructions. The released sulfhydryl groups of the homocysteine functional handle in thiolactone modified HSA were labeled with BODIPY dye to prepare a labeled albumin-BODIPY dye conjugate confirmed by MALDI-TOF-MS, UV-vis, and fluorescent emission spectra. Cytotoxicity of the resulting conjugate was investigated. This study is the basis for a novel BODIPY dye-albumin theranostic for BNCT. The results provide further impetus to develop derivatives of HSA for delivery of boron to cancer cells.


Assuntos
Compostos de Boro/química , Terapia por Captura de Nêutron de Boro/métodos , Neoplasias/tratamento farmacológico , Albumina Sérica Humana/química , Corantes/química , Sistemas de Liberação de Medicamentos , Corantes Fluorescentes/química , Homocisteína/química , Humanos , Lactonas/química , Maleimidas/química , Sondas Moleculares , Medicina de Precisão , Espectrometria de Fluorescência , Espectrometria de Massas por Ionização por Electrospray , Espectrofotometria Ultravioleta
10.
Chem Pharm Bull (Tokyo) ; 69(6): 526-528, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-34078798

RESUMO

The optical property of fluorescent unit-conjugated aliphatic oxaboroles has been investigated. The oxaboroles provide good fluorescence quantum yields and selective recognition toward D-ribose and D-ribose containing molecules. The molecular recognition induced significant fluorescence quenching. The property of the boroles showed the possibility of the boron-based nicotinamide adenine dinucleotide (NAD) sensor probe.


Assuntos
Compostos de Boro/química , Corantes Fluorescentes/química , NAD/química , Açúcares/análise , Compostos de Boro/síntese química , Corantes Fluorescentes/síntese química , Estrutura Molecular , Fenômenos Ópticos
11.
Nat Commun ; 12(1): 3919, 2021 06 24.
Artigo em Inglês | MEDLINE | ID: mdl-34168128

RESUMO

The class Frizzled of G protein-coupled receptors (GPCRs), consisting of ten Frizzled (FZD1-10) subtypes and Smoothened (SMO), remains one of the most enigmatic GPCR families. While SMO relies on cholesterol binding to the 7TM core of the receptor to activate downstream signaling, underlying details of receptor activation remain obscure for FZDs. Here, we aimed to investigate the activation mechanisms of class F receptors utilizing a computational biology approach and mutational analysis of receptor function in combination with ligand binding and downstream signaling assays in living cells. Our results indicate that FZDs differ substantially from SMO in receptor activation-associated conformational changes. SMO manifests a preference for a straight TM6 in both ligand binding and functional readouts. Similar to the majority of GPCRs, FZDs present with a kinked TM6 upon activation owing to the presence of residue P6.43. Functional comparison of FZD and FZD P6.43F mutants in different assay formats monitoring ligand binding, G protein activation, DVL2 recruitment and TOPflash activity, however, underlines further the functional diversity among FZDs and not only between FZDs and SMO.


Assuntos
Receptores Frizzled/química , Receptores Frizzled/metabolismo , Receptor Smoothened/química , Sítios de Ligação , Técnicas de Transferência de Energia por Ressonância de Bioluminescência , Compostos de Boro/química , Microscopia Crioeletrônica , Proteínas Quinases Dependentes de AMP Cíclico/metabolismo , Receptores Frizzled/genética , Humanos , Simulação de Dinâmica Molecular , Mutação , Fosfoproteínas/metabolismo , Conformação Proteica , Receptor Smoothened/genética , Receptor Smoothened/metabolismo , Alcaloides de Veratrum/química , Alcaloides de Veratrum/metabolismo
12.
Inorg Chem ; 60(13): 10047-10055, 2021 Jul 05.
Artigo em Inglês | MEDLINE | ID: mdl-34142816

RESUMO

Two novel fluorophore (BODIPY)-bearing complexes, pyriplatin (mCBP) and pyrimidine-chelated cisplatin (dCBP), were synthesized and characterized. The additional BODIPY-pyridine/pyridimine motifs of the two Pt(II) complexes resulted in stronger interactions with DNA in comparison with those of cisplatin. mCBP and cisplatin caused relative decreases in life span and body length in a cisplatin resistant in vivo model, N2 (wild-type) Caenorhabditis elegans. In contrast, dCBP resulted in a dramatic reduction in the two physiological parameters in N2 C. elegans, indicating high toxicity and sensitivity. The resistance factors (RF) of cisplatin, mCBP, and dCBP were determined to be 2.46, 1.04, and 0.91, respectively. The increasing RF folds for mCBP and dCBP against cisplatin were 2.36 and 2.70, respectively. This suggested they were featured with improved anti-chemoresistance capabilities. It is noteworthy that dCBP showed lowest lethal concentration (LC50) values of 0.56 and 0.61 mM in cisplatin resistant and sensitive in vivo models, respectively. Upregulation of several evolutionary conservation genes that regulate cisplatin chemoresistance through cisplatin effluxing, the DNA damage response, the unfolded protein response, and detoxification (asna-1, parp-1, enpl-1, and skn-1) was observed upon exposure to cisplatin but not to mCBP and dCBP. This could explain the improved anti-chemoresistance performances of synthesized Pt(II) complexes.


Assuntos
Antineoplásicos/farmacologia , Compostos de Boro/farmacologia , Caenorhabditis elegans/efeitos dos fármacos , Compostos Organoplatínicos/farmacologia , Animais , Antineoplásicos/síntese química , Antineoplásicos/química , Compostos de Boro/química , Sobrevivência Celular/efeitos dos fármacos , Cisplatino/química , Cisplatino/farmacologia , Relação Dose-Resposta a Droga , Camundongos , Estrutura Molecular , Compostos Organoplatínicos/síntese química , Compostos Organoplatínicos/química
13.
Nat Commun ; 12(1): 3389, 2021 06 07.
Artigo em Inglês | MEDLINE | ID: mdl-34099672

RESUMO

Bioorthogonal late-stage diversification of amino acids and peptides bears enormous potential for drug discovery and molecular imaging. Despite major accomplishments, these strategies largely rely on traditional, lengthy prefunctionalization methods, heavily involving precious transition-metal catalysis. Herein, we report on a resource-economical manganese(I)-catalyzed C-H fluorescent labeling of structurally complex peptides ensured by direct alkynylation and alkenylation manifolds. This modular strategy sets the stage for unraveling structure-activity relationships between structurally discrete fluorophores towards the rational design of BODIPY fluorogenic probes for real-time analysis of immune cell function.


Assuntos
Técnicas de Química Sintética/métodos , Corantes Fluorescentes/síntese química , Manganês/química , Peptídeos/síntese química , Compostos de Boro/química , Linfócitos T CD8-Positivos/citologia , Linfócitos T CD8-Positivos/metabolismo , Carbono/química , Catálise , Membrana Celular/metabolismo , Humanos , Hidrogênio/química , Células Jurkat , Microscopia Confocal , Microscopia de Fluorescência , Imagem Molecular/métodos
14.
Molecules ; 26(10)2021 May 14.
Artigo em Inglês | MEDLINE | ID: mdl-34068920

RESUMO

A convergent synthetic route to a tetrasaccharide related to PI-88, which allows the incorporation of a fluorescent BODIPY-label at the reducing-end, has been developed. The strategy, which features the use of 1,2-methyl orthoesters (MeOEs) as glycosyl donors, illustrates the usefulness of suitably-designed BODIPY dyes as glycosyl labels in synthetic strategies towards fluorescently-tagged oligosaccharides.


Assuntos
Antineoplásicos/farmacologia , Compostos de Boro/química , Oligossacarídeos/síntese química , Coloração e Rotulagem , Antineoplásicos/química , Glicosilação , Oligossacarídeos/química , Oligossacarídeos/farmacologia , Espectrometria de Fluorescência , Estereoisomerismo
15.
ACS Appl Mater Interfaces ; 13(20): 23452-23468, 2021 May 26.
Artigo em Inglês | MEDLINE | ID: mdl-34000197

RESUMO

Utilization of antibacterial components-conjugated nanoparticles (NPs) is emerging as an attractive strategy for combating various pathogens. Herein, we demonstrate that Ag/BN NPs and antibiotic-loaded BN and Ag/BN nanoconjugates are promising carriers to fight bacterial and fungal infections. Extensive biological tests included two types of Gram-positive methicillin-resistant Staphylococcus aureus strains (B8469 and MW2), two types of Gram-negative Pseudomonas aeruginosa strains (ATCC27853 and B1307/17), and 47 types of Escherichia coli strains (including 41 multidrug-resistant ones), as well as five types of fungal cultures: Candida albicans (candidiasis-thrush) ATCC90028 and ATCC24433, Candida parapsilosis ATCC90018, Candida auris CBS109113, and Neurospora crassa wt. We have demonstrated that, even within a single genus Escherichia, there are many hospital E. coli strains with multi-drug resistance to different antibiotics. Gentamicin-loaded BN NPs have high bactericidal activity against S. aureus, P. aeruginosa, and 38 types of the E. coli strains. For the rest of the tested E. coli strains, the Ag nanoparticle-containing nanohybrids have shown superior bactericidal efficiency. The Ag/BN nanohybrids and amphotericin B-loaded BN and Ag/BN NPs also reveal high fungicidal activity against C. albicans, C. auris, C. parapsilosis, and N. crassa cells. In addition, based on the density functional theory calculations, the nature of antibiotic-nanoparticle interaction, the sorption capacity of the BN and Ag/BN nanohybrids for gentamicin and amphotericin B, and the most energetically favorable positions of the drug molecules relative to the carrier surface, which lead to lowest binding energies, have been determined. The obtained results clearly show high therapeutic potential of the antibiotic-loaded Ag/BN nanocarriers providing a broad bactericidal and fungicidal protection against all of the studied pathogens.


Assuntos
Antibacterianos , Compostos de Boro/química , Portadores de Fármacos/química , Nanopartículas/química , Prata/química , Antibacterianos/química , Antibacterianos/farmacologia , Antifúngicos/química , Antifúngicos/farmacologia , Bactérias/efeitos dos fármacos , Candida/efeitos dos fármacos , Gentamicinas/química , Gentamicinas/farmacologia
16.
Chem Commun (Camb) ; 57(47): 5750-5753, 2021 Jun 10.
Artigo em Inglês | MEDLINE | ID: mdl-34013923

RESUMO

The accessible at-boron-BINOLated 3,5-bis(4-aminostyryl)ated BODIPY scaffold is highlighted as a workable platform for developing enantiopure small organic molecules exhibiting CPL in the NIR region, even in water solution, the latter being key for CPL-based bioapplications. Synthetic simplicity, noticeable chiroptical efficiency in the NIR and the possibility to access water-soluble emitters pave the way for advancing CPL tools based on organic emitters and NIR radiation.


Assuntos
Compostos de Boro/química , Luminescência , Compostos de Boro/síntese química , Raios Infravermelhos , Medições Luminescentes , Estrutura Molecular , Solubilidade , Água/química
18.
Chem Commun (Camb) ; 57(39): 4807-4810, 2021 May 13.
Artigo em Inglês | MEDLINE | ID: mdl-33982709

RESUMO

Probing receptors at the cell surface to monitor their expression level can be performed with fluorogenic dyes. Biotin receptors (BRs) are particularly interesting as they are overexpressed in cancer cells. Herein, to image BRs, we adapted and systematically compared two fluorogenic systems based on BODIPYs: a molecular rotor and a self-quenched dimer that light up in response to high viscosity and low polarity of the membrane, respectively. The fluorogenic dimer proved to be more efficient than the rotor and allowed BRs to be imaged in cancer cells, which can effectively be discriminated from non-cancer cells.


Assuntos
Compostos de Boro/química , Corantes Fluorescentes/química , Neoplasias/diagnóstico por imagem , Receptores de Fatores de Crescimento/análise , Animais , Compostos de Boro/síntese química , Linhagem Celular , Corantes Fluorescentes/síntese química , Humanos , Camundongos , Estrutura Molecular , Neoplasias/química
19.
Food Chem ; 359: 129984, 2021 Oct 15.
Artigo em Inglês | MEDLINE | ID: mdl-33964660

RESUMO

A boron nitride modified multiwalled carbon nanotube material (BN@MWCNTs) was synthesized, and the synthesis conditions were optimized. The BN@MWCNTs was then used as the SPME fiber coating adsorbent for the extraction of eleven organochlorine pesticides (OCPs) from fruit and vegetable samples. Under the optimal conditions, the SPME coupled with the detection by GC-ECD had a linear response for the determination of the target analytes in the range of 0.03 to 200 ng g-1 with the coefficients of determination (r2) ≥ 0.9977. Based on the signal-to-noise ratios of 3 and 10, the limits of detection and the limits of quantification were measured to be 0.01-0.20 ng g-1 and 0.03-0.67 ng g-1, respectively. The relative recoveries of the analytes for spiked samples under three concentration levels (1.0, 10.0 and 100 ng g-1) were between 83.7% and 124% with the relative standard deviations ≤ 10.9%. The established method was successfully applied to the determination of OCPs in real fruit and vegetable samples.


Assuntos
Compostos de Boro/química , Frutas/química , Nanotubos de Carbono/química , Praguicidas/análise , Microextração em Fase Sólida/métodos , Verduras/química , Cromatografia Gasosa/métodos , Hidrocarbonetos Clorados/análise , Limite de Detecção
20.
Eur J Med Chem ; 220: 113438, 2021 Aug 05.
Artigo em Inglês | MEDLINE | ID: mdl-33915370

RESUMO

Boron-dipyrromethene (BODIPY) based photosensitizers as porphyrinoids and curcumin as natural product possess exciting photophysical features suitable for theranostic applications, namely, imaging and photodynamic therapy (PDT). Limited aqueous solubility and insufficient physiological stability, however, reduce their efficacy significantly. We have designed a novel strategy to deliver these two unusable cytotoxins simultaneously in cancer cells and herein, report the synthesis, characterization and imaging-assisted photocytotoxicity of three zinc(II) complexes containing N3-donor dipicolylamine (dpa) ligands (L1-3) and O,O-donor curcumin (Hcur) viz. [Zn(L1)(cur)]Cl (1), [Zn(L2)(cur)]Cl (2) and [Zn(L3)(cur)]Cl (3), where L2 and L3 have pendant fluorescent BODIPY and non-emissive di-iodo-BODIPY moieties. Metal chelation imparted remarkable biological stability (pH ∼7.4) to the respective ligands and induces significant aqueous solubility. These ternary complexes could act as replacements of the existing metalloporphyrin-based PDT photosensitizers as their visible-light photosensitizing ability is reinforced by the dual presence of blue light absorbing curcumin and green light harvesting BODIPY units. Complex 2 having emissive BODIPY unit L2 and curcumin, showed mitochondria selective localization in HeLa, MCF-7 cancer cells and complex 3, the di-iodinated analogue of complex 2, exhibited type-I/II PDT activity via inducing apoptosis through mitochondrial membrane disruption in cancer cells while being significantly nontoxic in dark and to the healthy cells.


Assuntos
Antineoplásicos/farmacologia , Complexos de Coordenação/farmacologia , Luz , Imagem Óptica , Fotoquimioterapia , Fármacos Fotossensibilizantes/farmacologia , Antineoplásicos/síntese química , Antineoplásicos/química , Compostos de Boro/química , Compostos de Boro/farmacologia , Linhagem Celular , Proliferação de Células/efeitos dos fármacos , Complexos de Coordenação/síntese química , Complexos de Coordenação/química , Curcumina/química , Curcumina/farmacologia , Relação Dose-Resposta a Droga , Humanos , Estrutura Molecular , Fármacos Fotossensibilizantes/síntese química , Fármacos Fotossensibilizantes/química , Relação Estrutura-Atividade , Zinco/química , Zinco/farmacologia
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