Browse
Submit Data
Databases
API
Help

Dataset Information

18 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Synthesis and spectroscopy of near infrared fluorescent dyes for investigating dichromic fluorescence.

ABSTRACT: We developed a series of near infrared (NIR) cyanine dyes to study dichromic fluorescence phenomenon, which provides new protocols for in vivo optical imaging. Preliminary spectroscopic studies show that dichromic fluorescence correlates with structural symmetry. This feature suggests the potential use of dichromic fluorescent molecules to study biological processes that can alter the structural symmetry of the molecular probes.

SUBMITTER: Bai M

PROVIDER: S-EPMC3010286 | biostudies-literature | 2011 Jan

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Synthesis and spectroscopy of near infrared fluorescent dyes for investigating dichromic fluorescence.

Bai Mingfeng M Achilefu Samuel S

Bioorganic & medicinal chemistry letters 20101106 1

We developed a series of near infrared (NIR) cyanine dyes to study dichromic fluorescence phenomenon, which provides new protocols for in vivo optical imaging. Preliminary spectroscopic studies show that dichromic fluorescence correlates with structural symmetry. This feature suggests the potential use of dichromic fluorescent molecules to study biological processes that can alter the structural symmetry of the molecular probes. ...[more]

PMID: 21106373

Similar Datasets

Investigating fluorescent dyes in fluorescence-assisted screenings.

Project description:Screening of bead-based peptide libraries against fluorescent dye-labeled target proteins was found to be significantly influenced by the dye characteristics. Commercially available red fluorescent dyes with net negative charges adversely showed strong interactions with library beads. The introduction of zwitterionic dyes significantly reduced the unwanted interactions, which sheds light upon using the right fluorescent probe for acquisition of reliable results in various fluorescence-assisted applications.

| S-EPMC4224607 | biostudies-literature

The Development of Novel Near-Infrared (NIR) Tetraarylazadipyrromethene Fluorescent Dyes.

Project description:Novel structures of an near-infrared (NIR) tetraarylazadipyrromethene (aza-BODIPY) series have been prepared. We designed the core structure containing two amido groups at the para-position of the aromatic rings. The amido group was incorporated to secure insensitivity to pH and to ensure a bathochromic shift to the NIR region. Forty members of aza-BODIPY compounds were synthesized by substitution of the acetyl group with commercial amines on the alpha bromide. The physicochemical properties and photostability were investigated and the fluorescence emission maxima (745~755 nm) were found to be in the near infrared (NIR) range of fluorescence.

| S-EPMC5452499 | biostudies-literature

Quantitative Tissue Spectroscopy of Near Infrared Fluorescent Nanosensor Implants.

Project description:Implantable, near infrared (nIR) fluorescent nanosensors are advantageous for in vivo monitoring of biological analytes since they can be rendered selective for a particular target molecule while utilizing their unique optical properties and the nIR tissue transparency window for information transfer without an internal power source or telemetry. However, basic questions remain regarding the optimal encapsulation platform, geometrical properties, and concentration ranges required for high signal to noise ratio and effective detection through biological tissue. In this work, we systematically explore these variables quantitatively to optimize the performance of such optical nanosensors for biomedical applications. We investigate both alginate and polyethylene glycol (PEG) as model hydrogel systems, encapsulating d(GT)15 ssDNA-wrapped single-walled carbon nanotubes (SWNT) as model fluorescent nanoparticle sensors, responsive to riboflavin. Hydrogel sensors implanted 0.5 mm into thick tissue samples exhibit 50% reduction of initial fluorescence intensity, allowing an optical detection limit of 5.4 mm and 5.1 mm depth in tissue for alginate and PEG gels, respectively, at a SWNT concentration of 10 mg L(-1), and 785 nm laser excitation of 80 mW and 30 s exposure. These findings are supported with in vivo nIR fluorescent imaging of SWNT hydrogels implanted subcutaneously in mice. For the case of SWNT, we find that the alginate system is preferable in terms of emission intensity, sensor response, rheological properties, and shelf life.

| S-EPMC5307332 | biostudies-literature

Synthesis of Silica Nanoparticles with Physical Encapsulation of Near-Infrared Fluorescent Dyes and Their Tannic Acid Coating.

Project description:This study reports a novel method for the synthesis of silica nanoparticles (NPs) encapsulating near-infrared (NIR) fluorescent dyes through physical adsorption. Although a NIR cationic fluorescent dye, oxazine 725 (OXA), has no chemical bonding moiety toward silica NPs such as the triethoxysilyl group, the dyes were successfully incorporated into silica NPs without denaturation under the mild reaction conditions. Next, tannic acid (TA) molecules were coated in the presence of Fe3+ on the particle surface for the functionalization of silica NPs encapsulating OXA (OXA@SiO2 NPs). The TA coating on the surface of OXA@SiO2 NPs was confirmed by transmission electron microscopy and X-ray photoelectron spectroscopy. The TA coating significantly contributed to the resistance improvement against photobleaching and leakage of the dyes in the NPs. Furthermore, the obtained TA-coated silica NPs encapsulating OXAs (OXA@SiO2@TA NPs) were used for the fluorescence imaging of African green monkey kidney (COS-7) cells, and it was shown that the fluorescence originated from OXA@SiO2@TA NPs was clearly observed in the COS-7 cells.

| S-EPMC8280675 | biostudies-literature

Optical imaging of gastric cancer with near-infrared heptamethine carbocyanine fluorescence dyes.

Project description:Near-infrared fluorescence (NIRF) imaging agents are promising tools for noninvasive cancer imaging. Here, we explored the tumor-specific targeting ability of NIRF heptamethine carbocyanine MHI-148 dye in cultured gastric cancer cells, gastric cancer cell-derived and patient-derived tumor xenograft (PDX) models. We show that the NIRF dye specifically accumulated in tumor regions of both xenograft models, suggesting the potential utility of the dye for tumor-specific imaging and targeting in gastric cancer. We also demonstrated significant correlations between NIRF signal intensity and tumor volume in PDX models. Mechanistically, the higher cellular uptake of MHI-148 in gastric cancer cells than in normal cells was stimulated by hypoxia and activation of a group of organic anion-transporting polypeptide (OATP) genes. Importantly, this NIRF dye was not retained in inflammatory stomach tissues induced by gastric ulcer in mice. In addition, fresh clinical gastric tumor specimens, when perfused with NIR dye, exhibited increased uptake of NIR dye in situ. Together, these results show the possibility of using NIRF dyes as novel candidate agents for clinical imaging and detection of gastric cancer.

| S-EPMC5302988 | biostudies-literature

Microwave-assisted synthesis of near-infrared fluorescent sphingosine derivatives.

Project description:Microwave-assisted synthesis of near-infrared fluorescent sphingosine derivatives is described, and the utility of the probes demonstrated by co-localization studies with visible wavelength fluorescent sphingosine derivatives.

| S-EPMC2696400 | biostudies-literature

Near-infrared fluorescent reporter stem cell model

Project description:Near-infrared fluorescent reporter stem cell model

| PRJEB51223 | ENA

1,7-Bis-(<i>N</i>,<i>N</i>-dialkylamino)perylene Bisimides: Facile Synthesis and Characterization as Near-Infrared Fluorescent Dyes.

Project description:Three symmetric alkylamino-substituted perylene bisimides with different n-alkyl chain lengths (n = 6, 12, or 18), 1,7-bis-(N,N-dialkylamino)perylene bisimides (1a-1c), were synthesized under mild condition and were characterized by ¹H NMR, ¹³C NMR and high resolution mass spectroscopy. Their optical and electrochemical properties were measured using UV-Vis and emission spectroscopic techniques as well as cyclic voltammetry (CV). These compounds show deep green color in both solution and solid state, and are highly soluble in dichloromethane and even in nonpolar solvents such as hexane. The shapes of the absorption spectra of 1a-1c in the solution and solid state were found to be almost the same, indicating that the long alkyl chains could efficiently prevent intermolecular contact and aggregation. They show a unique charge transfer emission in the near-infrared region, of which the peak wavelengths exhibit strong solvatochromism. The dipole moments of the molecules have been estimated using the Lippert-Mataga equation, and upon excitation, they show larger dipole moment changes than that of 1,7-diaminoperylene bisimide (2). Moreover, all the dyes exhibit two irreversible one-electron oxidations and two quasi-reversible one-electron reductions in dichloromethane at modest potentials. Complementary density functional theory calculations performed on these chromophores are reported in order to rationalize their electronic structure and optical properties.

| S-EPMC5512673 | biostudies-literature

Near-infrared-emitting squaraine dyes with high 2PA cross-sections for multiphoton fluorescence imaging.

Project description:Designed to achieve high two-photon absorptivity, new near-infrared (NIR) emitting squaraine dyes, (E)-2-(1-(2-(2-methoxyethoxy)ethyl)-5-(3,4,5-trimethoxystyryl)-1H-pyrrol-2-yl)-4-(1-(2-(2-methoxyethoxy)ethyl)-5-(3,4,5-trimethoxystyryl)-2H-pyrrolium-2-ylidene)-3-oxocyclobut-1-enolate (1) and (Z)-2-(4-(dibutylamino)-2-hydroxyphenyl)-4-(4-(dibutyliminio)-2-hydroxycyclohexa-2,5-dienylidene)-3-oxocyclobut-1-enolate (2), were synthesized and characterized. Their linear photophysical properties were investigated via UV-visible absorption spectroscopy and fluorescence spectroscopy in various solvents, while their nonlinear photophysical properties were investigated using a combination of two-photon induced fluorescence and open aperture z-scan methods. Squaraine 1 exhibited a high two-photon absorption (2PA) cross-section (?2PA), ?20?000 GM at 800 nm, and high photostability with the photochemical decomposition quantum yield one order of magnitude lower than Cy 5, a commercially available pentamethine cyanine NIR dye. The cytotoxicity of the squaraine dyes were evaluated in HCT 116 and COS 7 cell lines to assess the potential of these probes for biomedical imaging. The viability of both cell lines was maintained above 80% at dye concentrations up to 30 ?M, indicating good biocompatibility of the probes. Finally, one-photon fluorescence microscopy (1PFM) and two-photon fluorescence microscopy (2PFM) imaging was accomplished after incubation of micelle-encapsulated squaraine probes with HCT 116 and COS 7 cells, demonstrating their potential in 2PFM bioimaging.

| S-EPMC3439554 | biostudies-literature

Sterically Shielded Heptamethine Cyanine Dyes for Bioconjugation and High Performance Near-Infrared Fluorescence Imaging.

Project description:The near-infrared window of fluorescent heptamethine cyanine dyes greatly facilitates biological imaging because there is deep penetration of the light and negligible background fluorescence. However, dye instability, aggregation, and poor pharmacokinetics are current drawbacks that limit performance and the scope of possible applications. All these limitations are simultaneously overcome with a new molecular design strategy that produces a charge balanced and sterically shielded fluorochrome. The key design feature is a meso-aryl group that simultaneously projects two shielding arms directly over each face of a linear heptamethine polyene. Cell and mouse imaging experiments compared a shielded heptamethine cyanine dye (and several peptide and antibody bioconjugates) to benchmark heptamethine dyes and found that the shielded systems possess an unsurpassed combination of photophysical, physiochemical, and biodistribution properties that greatly enhance bioimaging performance.

| S-EPMC7473488 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data