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1.
ACS Sens ; 9(9): 4560-4567, 2024 Sep 27.
Artigo em Inglês | MEDLINE | ID: mdl-39231251

RESUMO

Among pathogenic bacteria, Escherichia coli, Enterococcus faecium, Staphylococcus aureus, Klebsiella pneumoniae, Acinetobacter baumannii, and Pseudomonas aeruginosa were the six leading causes for the deaths associated with antibiotic resistance in 2019. Although new treatment options are urgently needed, the precise identification of the bacterial species remains pivotal for an accurate diagnosis and effective treatment. Clinically, mass spectrometry is used to distinguish these bacteria based on their protein mass pattern at the genus and species level. Herein, we report an alternative approach to identify these bacteria using the nitroreductase-based "turn-on" fluorescent probes (ETH1-NO2 and ETH2-NO2), with potential visual indicators for the six individual bacteria species. The limits of detection (LODs) of the probes for NTRs are 0.562 (ETH1-NO2) and 0.153 µg/mL (ETH2-NO2), respectively. They respond effectively to both Gram-positive and Gram-negative bacteria, with the lowest LOD at 1.2 × 106 CFU/mL for E. coli. In particular, different bacteria show noticeable difference in the apparent color of ETH1-NO2 samples, allowing possible identification of these bacteria visually. In addition, ETH1-NO2 also has potential applications in bacterial fluorescence imaging. Thus, our study provides an alternative approach for bacteria identification and new reagents for bacteria imaging.


Assuntos
Corantes Fluorescentes , Nitrorredutases , Nitrorredutases/metabolismo , Corantes Fluorescentes/química , Bactérias/enzimologia , Limite de Detecção
2.
Spectrochim Acta A Mol Biomol Spectrosc ; 325: 125049, 2024 Aug 30.
Artigo em Inglês | MEDLINE | ID: mdl-39217958

RESUMO

As a severe threat to human health, cancer has always been one of the most significant challenges facing the medical field. However, there is currently no effective technology or method to diagnose and treat cancer simultaneously. Therefore, developing a new approach that integrates diagnosis and treatment holds promise as a means of achieving personalized and precise cancer therapy. In this study, we developed a novel dual-functional near-infrared mitochondrial-targeted photosensitizer, Hcy-I, which is capable of simultaneously monitoring cellular viscosity and specifically targeting mitochondria for photodynamic therapy. Compared with traditional hemicyanine dyes, the introduction of iodine atoms in Hcy-I enhanced spin-orbit coupling (SOC) and promoted the intersystem crossing (ISC) rate, thereby increasing the efficiency of singlet oxygen (1O2) generation. In vitro experiments demonstrated that Hcy-I exhibited high sensitivity to viscosity variations and efficiently generated 1O2 under 638 nm laser irradiation, with an 1O2 quantum yield of up to 48.9 %. Cell experiments further revealed that this photosensitizer could effectively target mitochondria for photodynamic therapy, disrupting mitochondrial membrane potential and inducing cell death. When treated with Hcy-I at a concentration of 0.8 µM, the survival rate of HepG-2 cells was only 13 %. These results suggested that Hcy-I had the potential to integrate cancer diagnosis and treatment. The research not only promotes the development of photodynamic thereby technology, but also opens up new avenues for the diagnosis and treatment of cancer.

3.
Appl Spectrosc ; 78(7): 744-752, 2024 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-39096170

RESUMO

Hemicyanine dyes are an ideal structure for building near-infrared fluorescent probes due to their excellent emission wavelength properties and biocompatibility in biological imaging field. Developing a near-infrared fluorescent probe capable of detecting cysteine (Cys) was the aim of this study. A novel developed fluorescent probe P showed high selectivity and sensitivity to Cys in the presence of various analytes. The detection limit of P was found to be 0.329 µM. The MTT assay showed that the probe was essentially non-cytotoxic. Furthermore, the probe was successfully used as cysteine imaging in living cells and mice.


Assuntos
Cisteína , Corantes Fluorescentes , Cisteína/análise , Cisteína/química , Corantes Fluorescentes/química , Animais , Camundongos , Humanos , Espectroscopia de Luz Próxima ao Infravermelho/métodos , Limite de Detecção , Carbocianinas/química , Espectrometria de Fluorescência/métodos , Células HeLa , Imagem Óptica/métodos
4.
Chembiochem ; : e202400467, 2024 Jul 22.
Artigo em Inglês | MEDLINE | ID: mdl-39039605

RESUMO

Cyanine-based near-infrared (NIR) fluorescent probes have played vital roles in biological application due to their low interference from background fluorescence, deep tissue penetration, high sensitivity, and minimal photodamage to biological samples. They are widely utilized in molecular recognition, medical diagnosis, biomolecular detection, and biological imaging. Herein, we provide a review of recent advancements in cyanine-based NIR fluorescent probes for the detection of pH, cells, tumor as well as their application in photothermal therapy (PTT) and photodynamic therapy (PDT).

5.
Chemistry ; : e202402019, 2024 Jun 26.
Artigo em Inglês | MEDLINE | ID: mdl-38923040

RESUMO

Photoacoustic (PA) tomography is an emerging biomedical imaging technology for precision cancer medicine. Conventional small-molecule PA probes usually exhibit a single PA signal and poor tumor targeting that lack the imaging reliability. Here, we introduce a series of cyanine/hemicyanine interconversion dyes (denoted Cy-HCy) for PA/fluorescent dual-mode probe development that features optimized ratiometric PA imaging and tunable tumor-targeting ability for precise diagnosis and resection of colorectal cancer (CRC). Importantly, Cy-HCy can be presented in cyanine (inherent tumor targeting and long NIR PA wavelength) and hemicyanine (poor tumor targeting and short NIR PA wavelength) by fine-tuning torsion angle and the ingenious transformation between cyanine and hemicyanine through regulation optically tunable group endows the NIR ratiometric PA and tunable tumor-targeting properties. To demonstrate the applicability of Cy-HCy dyes, we designed the first small-molecule tumor-targeting and NIR ratiometric PA probe Cy-HCy-H2S for precise CRC liver metastasis diagnosis, activated by H2S (a CRC biomarker). Using this probe, we not only visualized the subcutaneous tumor and liver metastatic cancers in CRC mouse models but also realized PA and fluorescence image-guided tumor excision. We expect that Cy-HCy will be generalized for creating a wide variety of inherently tumor-targeting NIR ratiometric PA probes in oncological research and practice.

6.
Chemistry ; : e202402146, 2024 Jun 24.
Artigo em Inglês | MEDLINE | ID: mdl-38923172

RESUMO

We have synthesized an acidic pH-activatable dual targeting ratiometric fluorescent probe-peptide conjugate using the SPPS protocol on Rink amide AM resin. Living carcinoma cell specific active targeting, successive cell penetration, and selective staining of lysosomes are accomplished. Real-time monitoring of lysosomes, 3D, and multicolor cancer cell imaging are also attained. The de novo design consists of the integration of multifunctionality into a single molecular scaffold, e. g., RGDS peptide residue to target cancer cell surface overexpressed receptor αVß3 integrin, live-cell penetrating organic unsymmetrical rhodamine-hemicyanine chromophore comprising a lysosome targeting morpholine group, and an acidic pH openable spiro-lactam ring for a visible-to-NIR switchable ratiometric response. Water-soluble fluorescent probe-peptide conjugate exhibits intramolecular spirolactamization at basic pH through Arg amide N. The visible spirolactam state predominantly exists at physiological and basic pH and can be switched to the highly conjugated NIR open amide state (λem=735 nm) through spiro-lactam ring opening triggered by acidic pH with a huge bathochromic shift (Δλabs=336 nm, ΔλFL=265 nm). Moreover, pH-sensitive ratiometric optical switching is achieved. This in situ acidic cancer cell lysosome activatable multifunctional fluorophore-peptide conjugate shows augmented molar absorptivity, enhanced quantum yield, and improved fluorescence lifetime at acidic lysosomal pH; negligible cytotoxicity; and dual targeted ratiometric imaging capability of living cancer cell selective lysosomes with a pKa value of 5.1.

7.
Spectrochim Acta A Mol Biomol Spectrosc ; 316: 124324, 2024 Aug 05.
Artigo em Inglês | MEDLINE | ID: mdl-38676983

RESUMO

Antibiotic-free therapies are highly needed due to the limited success of conventional approaches especially against biofilm related infections. In this direction, antimicrobial phototherapy, either in the form of antimicrobial photothermal therapy (aPTT) or antimicrobial photodynamic therapy (aPDT), have appeared to be highly promising candidates in recent years. These are local and promising approaches for antibiotic resistant bacterial infections and biofilms. Organic small photosensitizers (PSs) are extensively preferred in antimicrobial phototherapy applications as they offer a great opportunity to combine therapeutic action (aPTT, aPDT or both) with fluorescence imaging on a single molecule. In this study, the bactericidal effect of cationic chlorinated hemicyanine (Cl-Hem)-based type I PS, which can function as a dual aPDT/aPTT agent, was investigated on both planktonic cells and biofilms of different gram-positive (E. faecalis and S. epidermidis) and gram-negative bacteria (P. aeruginosa and K. pneumoniae) with and without 640 nm laser irradiation. Cl-Hem was shown to induce a selective phototheranostic activity against gram-positive bacteria (E. faecalis and S. epidermidis). Cl-Hem exhibited both dose and laser irradiation time dependent bactericidal effect on planktonic and biofilms of S. epidermidis. These results clearly showed that highly potent Cl-Hem can treat resistant microbial infections, while allowing fluorescence detection at the same time. High biofilm reduction observed with combined aPDT/aPTT action of Cl-Hem together with its non-cytotoxic nature points out that Cl-Hem is a promising PS for antibacterial and antibiofilm treatments.


Assuntos
Antibacterianos , Biofilmes , Bactérias Gram-Positivas , Halogenação , Testes de Sensibilidade Microbiana , Biofilmes/efeitos dos fármacos , Antibacterianos/farmacologia , Antibacterianos/química , Bactérias Gram-Positivas/efeitos dos fármacos , Bactérias Gram-Positivas/fisiologia , Fármacos Fotossensibilizantes/farmacologia , Fármacos Fotossensibilizantes/química , Carbocianinas/química , Carbocianinas/farmacologia , Humanos
8.
J Fluoresc ; 2024 Apr 12.
Artigo em Inglês | MEDLINE | ID: mdl-38607530

RESUMO

Hypochloric acid (HClO) is a reactive oxygen species (ROS) that functions as a bacteriostatic and disinfectant in food production. Excessive levels of ClO-, however, have been linked to various health issues, including cardiovascular diseases (Halliwell and Gutteridge in Oxford University press, USA, 2015), arthritis, and neurodegenerative diseases (Heinzelmann and Bauer in Biol Chem. 391(6):675-693, 2010). Therefore, synthesizing highly selective and sensitive probes for rapidly detecting endogenous ClO- in daily foods is currently a popular research topic (Kalyanaraman et al. in Redox Biol. 15:347-362, 2018; Winterbourn in Nat Chem Biol. 4(5):278-286, 2008; Turrens in J Physiol. 552(2):335-344, 2003). Thus, we have developed two highly selective ratiometric fluorescent probes (Probe1 and Probe2) based on indole-phenothiazine to detect ClO- in common vegetables, fruits and beverages qualitatively and quantitatively. Moreover, Both Probe1 and Probe2 have shown good specificity and stability, with high fluorescence intensity and long duration (Feng et al. in Adv Sci. 5:1800397, 2018; Wei et al. in Angew Chem. 131(14):4595-4599, 2019; Baruah et al. in J Mater Chem B, 2022).

9.
Small Methods ; : e2400122, 2024 Apr 02.
Artigo em Inglês | MEDLINE | ID: mdl-38564786

RESUMO

Near-infrared fluorescence (NIRF)/photoacoustic (PA) dual-modality imaging integrated high-sensitivity fluorescence imaging with deep-penetration PA imaging has been recognized as a reliable tool for disease detection and diagnosis. However, it remains an immense challenge for a molecule probe to achieve the optimal NIRF and PA imaging by adjusting the energy allocation between radiative transition and nonradiative transition. Herein, a simple but effective strategy is reported to engineer a NIRF/PA dual-modality probe (Cl-HDN3) based on the near-infrared hemicyanine scaffold to optimize the energy allocation between radiative and nonradiative transition. Upon activation by H2S, the Cl-HDN3 shows a 3.6-fold enhancement in the PA signal and a 4.3-fold enhancement in the fluorescence signal. To achieve the sensitive and selective detection of H2S in vivo, the Cl-HDN3 is encapsulated within an amphiphilic lipid (DSPE-PEG2000) to form the Cl-HDN3-LP, which can successfully map the changes of H2S in a tumor-bearing mouse model with the NIRF/PA dual-modality imaging. This work presents a promising strategy for optimizing fluorescence and PA effects in a molecule probe, which may be extended to the NIRF/PA dual-modality imaging of other disease-relevant biomarkers.

10.
Photochem Photobiol ; 2024 Apr 16.
Artigo em Inglês | MEDLINE | ID: mdl-38623769

RESUMO

The field of biofabrication imposes stringent requirements on the polymerization activity and biosafety of photopolymeric hydrogel systems. In this investigation, we designed and synthesized four hemicyanine dyes with a D-π-A structure specifically tailored for biofabrication purposes. These novel dyes, incorporating carbazole (CZ), triphenylamine (TPA), anthracene (AN), and benzodithiophene (BDT) as electron donors, along with heterocyclic salt (IN) as electron acceptors, were prepared using a straightforward synthesis method. The absorption maxima of ANIN, CZIN, and TPAIN exceeded 500 nm, rendering them suitable co-initiators for the free radical photopolymerization of acrylates under green-red light exposure facilitated by light-emitting diodes (LEDs) and the co-initiator iodonium salt (ION). Notably, CZIN and TPAIN, due to their robust dye absorption and efficient electron transfer to ION, functioned as high-performance photosensitizers. Meanwhile, BDTIN, with its strong and broad absorption range (400-600 nm), enhanced the accuracy of visible light photopolymerization. These dyes exhibit characteristics such as facile synthesis, heightened photo stability, and non-toxicity and also demonstrate the ability to discern the alkalinity of a solution to some extent. Furthermore, we explored the application of these hemicyanine dyes in 3D printing, showing potential to enhance printing resolution in DLP 3D printing (digital light process 3D printing).

11.
ACS Nano ; 18(11): 8437-8451, 2024 Mar 19.
Artigo em Inglês | MEDLINE | ID: mdl-38501308

RESUMO

Molecular imaging in the second near-infrared window (NIR-II) provides high-fidelity visualization of biopathological events in deep tissue. However, most NIR-II probes produce "always-on" output and demonstrate poor signal specificity toward biomarkers. Herein, we report a series of hemicyanine reporters (HBCs) with tunable emission to NIR-II window (715-1188 nm) and structurally amenable to constructing activatable probes. Such manipulation of emission wavelengths relies on rational molecular engineering by integrating benz[c,d]indolium, benzo[b]xanthonium, and thiophene moieties to a conventional hemicyanine skeleton. In particular, HBC4 and HBC5 possess bright and record long emission over 1050 nm, enabling improved tissue penetration depth and superior signal to background ratio for intestinal tract mapping than NIR-I fluorophore HC1. An activatable inflammatory reporter (AIR-PE) is further constructed for pH-triggered site-specific release in colon. Due to minimized background interference, oral gavage of AIR-PE allows clear delineation of irritated intestines and assessment of therapeutic responses in a mouse model of inflammatory bowel disease (IBD) through real-time NIRF-II imaging. Benefiting from its high fecal clearance efficiency (>90%), AIR-PE can also detect IBD and evaluate the effectiveness of colitis treatments via in vitro optical fecalysis, which outperforms typical clinical assays including fecal occult blood testing and histological examination. This study thus presents NIR-II molecular scaffolds that are not only applicable to developing versatile activatable probes for early diagnosis and prognostic monitoring of deeply seated diseases but also hold promise for future clinical translations.


Assuntos
Carbocianinas , Doenças Inflamatórias Intestinais , Imagem Óptica , Animais , Camundongos , Prognóstico , Imagem Óptica/métodos , Corantes Fluorescentes , Doenças Inflamatórias Intestinais/diagnóstico por imagem , Diagnóstico Precoce
12.
Molecules ; 29(3)2024 Jan 27.
Artigo em Inglês | MEDLINE | ID: mdl-38338363

RESUMO

In this study, we synthesized a coumarin-hemicyanine-based deep red fluorescent dye that exhibits an intramolecular charge transfer (ICT). The probe had a large Stokes shift of 287 nm and a large molar absorption coefficient (ε = 7.5 × 105 L·mol-1·cm-1) and is best described as a deep red luminescent fluorescent probe with λem = 667 nm. The color of probe W changed significantly when it encountered cyanide ions (CN-). The absorption peak (585 nm) decreased gradually, and the absorption peak (428 nm) increased gradually, so that cyanide (CN-) could be identified by the naked eye. Moreover, an obvious fluorescence change was evident before and after the reaction under irradiation using 365 nm UV light. The maximum emission peak (667 nm) decreased gradually, whilst the emission peak (495 nm) increased gradually, which allowed for the proportional fluorescence detection of cyanide (CN-). Using fluorescence spectrometry, the fluorescent probe W could linearly detect CN- over the concentration range of 1-9 µM (R2 = 9913, RSD = 0.534) with a detection limit of 0.24 µM. Using UV-Vis spectrophotometry, the linear detection range for CN- was found to be 1-27 µM (R2 = 0.99583, RSD = 0.675) with a detection limit of 0.13 µM. The sensing mechanism was confirmed by 1H NMR spectroscopic titrations, 13C NMR spectroscopy, X-ray crystallographic analysis and HRMS. The recognition and detection of CN- by probe W was characterized by a rapid response, high selectivity, and high sensitivity. Therefore, this probe provides a convenient, effective and economical method for synthesizing and detecting cyanide efficiently and sensitively.


Assuntos
Cianetos , Corantes Fluorescentes , Cianetos/química , Corantes Fluorescentes/química , Carbocianinas , Cumarínicos/química , Espectrometria de Fluorescência/métodos
13.
Int J Biol Macromol ; 261(Pt 1): 129209, 2024 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-38266835

RESUMO

Hydrogel systems based on natural polymer materials have provided alternative opportunities for preparing antimicrobial dressings. A composite antibacterial hydrogel system containing gelatin (Gel), alginate (Alg) and hemicyanine derivatives with different chain lengths (C3, C6 and C10) was constructed. The composite hydrogels have excellent swelling ability and low degradability due to the classical three-dimensional network structure. Because of the photosensitization ability of C3, C6 and C10, hydrogels containing these molecules can also effectively produce reactive oxygen species (ROS) under light. Importantly, the hydrogel containing C3 molecules that have higher spatial extension structure and shorter alkyl chain than C6 and C10 shows better photo-responsive antibacterial effect against drug-resistant Escherichia coli. The bacterial killing activity of the composite hydrogel system could be regulated by changing the alkyl chain length of the photosensitizers. This effective and photo-responsive composite hydrogel system is expected to be used for bacteria-infected wound repair and promoting wound healing.


Assuntos
Antibacterianos , Carbocianinas , Gelatina , Antibacterianos/farmacologia , Alginatos , Escherichia coli , Hidrogéis/farmacologia
14.
Angew Chem Int Ed Engl ; 62(52): e202315457, 2023 Dec 21.
Artigo em Inglês | MEDLINE | ID: mdl-37949837

RESUMO

Drug-induced renal failure (DIRF) poses a serious medical complication with high mortality risk. However, early diagnosis or prognosis of DIRF remain challenging, as current methods rely on detecting late-stage biomarkers. Herein we present a library of zwitterionic unimolecular hemicyanines (ZCs) available for constructing activatable reporters to detect DIRF since its initial stage. Zwitterionic properties of these probes are achieved through interspersedly integrating alkyl sulfonates and quaternary ammonium cations onto hemicyanine skeleton, which result in record low plasma protein binding (<5 %) and remarkable renal clearance efficiencies (≈96 %). An activatable reporter ZCRR is further developed by masking the optimal candidate ZC6 with a tetrapeptide specifically cleavable by caspase-8, an initiating indicator of apoptosis. In living mice with cisplatin-induced DIRF, systematically administered ZCRR efficiently accumulates in kidneys and responds to elevated caspase-8 for near-infrared fluorescence signals 'turn-on', enabling sensitive detection of intrarenal apoptosis 60 h earlier than clinical methods, and precise evaluation of apoptosis remediation effects by different medications on DIRF mice. As it's urinary excretable, ZCRR also allows for remote detection of DIRF and predicting renoprotective efficacy through in vitro optical urinalysis. This study thus presents unimolecular renal clearable scaffolds that are applicable to developing versatile activatable reporters for renal diseases management.


Assuntos
Injúria Renal Aguda , Corantes Fluorescentes , Camundongos , Animais , Corantes Fluorescentes/química , Caspase 8/metabolismo , Prognóstico , Injúria Renal Aguda/induzido quimicamente , Injúria Renal Aguda/diagnóstico , Diagnóstico Precoce
15.
ACS Sens ; 8(12): 4473-4477, 2023 Dec 22.
Artigo em Inglês | MEDLINE | ID: mdl-37982675

RESUMO

Legumain has been identified as a target for diagnosis and treatment of associated cancers. Therefore, real-time imaging of legumain activity in vivo is helpful in diagnosing and evaluating therapeutic efficacy of associated cancers. Fluorescent/photoacoustic (FL/PA) dual-modal imaging developed rapidly because of its good sensitivity and spatial resolution. As far as we know, a tumor-targeted probe for FL/PA imaging of legumain activity in vivo has not been reported. Hence, we intended to develop a tumor-targeted hemicyanine (HCy) probe (HCy-AAN-Bio) for FL/PA imaging of legumain in vivo. The control probe HCy-AAN does not have tumor-targeting ability. Legumain can specifically cleave HCy-AAN-Bio or HCy-AAN with the generation of FL/PA signal while more HCy-AAN-Bio could be recognized by legumain than HCy-AAN with higher sensitivity in vitro. Due to the tumor-targeting ability, HCy-AAN-Bio could image 4T1 cells with an additional 1.3-fold FL enhancement and 1.9-fold PA enhancement than HCy-AAN. In addition, HCy-AAN-Bio could image legumain activity in vivo with an additional 1.5-fold FL enhancement and 1.9-fold PA enhancement than HCy-AAN. We expected that HCy-AAN-Bio will be a powerful tool for early diagnosis of associated cancer.


Assuntos
Neoplasias , Técnicas Fotoacústicas , Humanos , Técnicas Fotoacústicas/métodos , Neoplasias/diagnóstico por imagem , Corantes Fluorescentes , Imagem Molecular/métodos
16.
Biotech Histochem ; 98(8): 545-553, 2023 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-37877362

RESUMO

The scientific literature contains many accounts of application of polymethine dyes, including cyanine dyes, as imaging agents, i.e., "biological stains," for microscopic investigation of biological materials. Currently, many such dyes are used as probes for living cells, i.e., "fluorescent probes." Polymethine dyes are defined here by two criteria. First, they possess a conjugated chain of (2n + 1) sp2-hybridized carbon atoms that connect a terminal π-electron-accepting (π-electron withdrawing) group with a terminal π-electron-donating group. Second, they have an odd number (2n + 3) of π-centers and an even number (2n + 4) of π-electrons in this chain, where n equals the number of -CR2=CR3- groups, usually vinylene groups -CH=CH-. Commercialization of diverse chemical types of many polymethine dyes has been attempted. The dyes that have achieved wide application, however, are limited in number and it is these dyes that are emphasized here. Because these polymethine dyes sometimes have been described by confusing, and sometimes confused, names, we clarify here the chemical categories and names of such dyes for the nonchemist, biomedical end user of such imaging agents. Nevertheless, the nomenclature presented here is not intended to replace the traditional "chromophore" categories of dyestuff chemistry, because the latter are held in place both by wide usage and by venerable authorities, such as the Colour Index.


Assuntos
Corantes Fluorescentes , Microscopia , Carbocianinas , Coloração e Rotulagem
17.
Adv Healthc Mater ; 12(29): e2301584, 2023 11.
Artigo em Inglês | MEDLINE | ID: mdl-37660278

RESUMO

The serious threat that cancer poses to human health highlights the significance of early detection and effective treatment. The integration of fluorescence diagnosis and photothermal therapy in NIR-II has gained attention due to its high sensitivity, fast response, and noninvasiveness. Fluorescence, produced by the radiative relaxation process of electrons in a molecule, and photothermal, generated by the nonradiative relaxation process of electrons in a molecule, are competing photophysical processes. Hence, it is a challenge for the molecule to balance between the properties of fluorescence and photothermal. In this study, a NIR-II hemicyanine with TICT character is designed to obtain molecules with both better fluorescence and photothermal properties, utilizing positively charged pyridine salt and triphenylamine as electron acceptor and donor, respectively, and oxole as the conjugated π-bridge. HCY-995, one of the synthesized compounds, has a quantum yield of 0.09%, photothermal conversion efficiency of 54.90%, and a significant Stoke shift of 232 nm, which makes it appropriate for the integration of photothermal therapy and high-resolution imaging. This study provides new insights into the development of NIR-II molecules with fluorescent and photothermal integrated properties.


Assuntos
Nanopartículas , Neoplasias , Humanos , Terapia Fototérmica , Carbocianinas , Neoplasias/diagnóstico por imagem , Neoplasias/terapia , Imagem Óptica , Fototerapia
18.
Spectrochim Acta A Mol Biomol Spectrosc ; 303: 123249, 2023 Dec 15.
Artigo em Inglês | MEDLINE | ID: mdl-37579665

RESUMO

Adenosine 5'-triphosphate (ATP) and guanosine 5'-triphosphate (GTP) are the most essential energy source in enormous biological processes. Various probes for ATP or GTP sensing, have been widely established, but the probe that could simultaneously monitor ATP and GTP is still rarely reported. Herein, we report a bipolar hemicyanine cationic probe for simultaneous sensing of ATP and GTP via a one-step monitoring process. This probe exhibited strong affinity to ATP and GTP through intramolecular electrostatic and π-π stacking interactions, which the binding constant on each step were determined as 6.15 × 107 M-1 and 1.57 × 106 M-1 for ATP, 3.19 × 107 M-1 and 3.81 × 106 M-1 for GTP. The sensitivity and specificity of this probe toward ATP or GTP over other twelve biological analogues (adenosine 5'-diphosphate (ADP), adenosine 5'-monophosphate (AMP), guanosine 5'-diphosphate (GDP), guanosine 5'-monophosphate (GMP), Etc.) have also been successfully demonstrated. Furthermore, due to the rapid response rate (within 10 s), we also proved that this probe could be employed as a monitor tool during the ATP or GTP-related enzymatic reaction process.


Assuntos
Trifosfato de Adenosina , Adenosina , Guanosina Trifosfato/metabolismo , Trifosfato de Adenosina/metabolismo , Guanosina Difosfato/metabolismo
19.
Int J Biol Macromol ; 247: 125621, 2023 Aug 30.
Artigo em Inglês | MEDLINE | ID: mdl-37392920

RESUMO

The development of an accurate and sensitive sensor for detecting amyloid plaques, which are responsible for many protein disorders like Alzheimer's disease, is crucial for early diagnosis. Recently, there has been a notable increase in the development of fluorescence probes that exhibit emission in the red region (>600 nm), aiming to effectively tackle the challenges encountered when working with complex biological matrices. In the current investigation, a hemicyanine-based probe, called LDS730, has been used for the sensing of amyloid fibrils, which belong to the Near-Infrared Fluorescence (NIRF) family of dyes. NIRF probes provide higher precision in detection, prevent photo-damage, and minimize the autofluorescence of biological specimens. The LDS730 sensor emits in the near-infrared region and shows a 110-fold increase in fluorescence turn-on emission when bound to insulin fibrils, making it a highly sensitive sensor. The sensor has an emission maximum of ~710 nm in a fibril-bound state, which shows a significant red shift along with a Stokes' shift of ~50 nm. The LDS730 sensor also displays excellent performance in the complicated human serum matrix, with a limit of detection (LOD) of 103 nM. Molecular docking calculations suggest that the most likely binding location of LDS730 in the fibrillar structure is the inner channels of amyloid fibrils along its long axis, and the sensor engages in several types of hydrophobic interactions with neighboring amino acid residues of the fibrillar structure. Overall, this new amyloid sensor has great potential for the early detection of amyloid plaques and for improving diagnostic accuracy.


Assuntos
Amiloide , Placa Amiloide , Humanos , Simulação de Acoplamento Molecular , Corantes Fluorescentes/química , Proteínas Amiloidogênicas , Peptídeos beta-Amiloides
20.
Spectrochim Acta A Mol Biomol Spectrosc ; 295: 122587, 2023 Jul 05.
Artigo em Inglês | MEDLINE | ID: mdl-36931062

RESUMO

Hydrogen sulfide (H2S) plays an important role in regulating varieties of important physiological and pathological processes. Thus the development of fluorescent probe for the detection of H2S is of great significance and has attracted much attention recently. Herein, we reported a novel near-infrared (NIR) emitting fluorescent probe WFP-PC, which contained a positive charged hemicyanine-based WFP-OH as fluorophore and thiobenzoate unit as a specific reaction site. After treated with H2S, the probe exhibited significant fluorescence enhancement and response time within 4 min and detection limit as low as 0.47 µM, accompanied by color changes from purple to blue. The probe was successfully applied to imaging the exogenous/endogenous H2S in cells and mice, suggesting it could be a promising molecular tool for H2S detection in living systems.


Assuntos
Corantes Fluorescentes , Sulfeto de Hidrogênio , Humanos , Camundongos , Animais , Células HeLa , Imagem Óptica , Espectrometria de Fluorescência
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