Browse
Submit Data
Databases
API
Help

Dataset Information

10 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

The Unexpected Selectivity Switching from Mitochondria to Lysosome in a D-π-A Cyanine Dye.

ABSTRACT: Two interesting benzothizolium-based D-π-A type hemicyanine dyes (3a-3b) with a diphenylamine (-NPh₂) donor group were evaluated for fluorescence confocal microscopy imaging ability in live cells (MO3.13, NHLF). In sharp contrast to previously reported D-π-A dyes with alkyl amine donor (-NR₂) groups (1), 3a and 3b exhibited significantly different photophysical properties and organelle selectivity. Probes 3a and 3b were nearly non-fluorescent in many polar and non-polar solvents but exhibited a bright red fluorescence (λ_em ≈ 630-640 nm) in stained MO3.13 and NHLF with very low probe concentrations (i.e., 200 nM). Fluorescence confocal microscopy-based co-localization studies revealed excellent lysosome selectivity from the probes 3a-3b, which is in sharp contrast to previously reported D-π-A type benzothiazolium dyes (1) with an alkyl amine donor group (-NR₂) (exhibiting selectivity towards cellular mitochondria). The photostability of probe 3 was found to be dependent on the substituent (R') attached to the quaternary nitrogen atom in the cyanine dye structure. The observed donor-dependent selectivity switching phenomenon can be highly useful in designing novel organelle-targeted fluorescent probes for live-cell imaging applications.

SUBMITTER: Abeywickrama CS

PROVIDER: S-EPMC9313378 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Targeting and Imaging of Mitochondria Using Near-Infrared Cyanine Dye and Its Application to Multicolor Imaging.

Project description:Herein, we report water-soluble mitochondria-selective molecules that consist of a target-specific moiety conjugated with a near-infrared (NIR) imaging agent through variable spacer length. The presented NIR fluorescent cyanine-5 (Cy-5) chromophore exhibits excellent photostability, narrow NIR absorption and emission bands, high molar extinction coefficient, high fluorescence quantum yield, and long fluorescence lifetime. The biological compatibility and negligible cytotoxicity further make the dye an attractive choice for biological applications. Confocal fluorescence microscopic studies in the fixed human lung carcinoma cell line (A549) stained with the targeting NIR Cy-5 dyes (Cy-5a and Cy-5b) at 700 nM concentration show their cellular uptake and localization, which is compared with the nontargeting Cy-5c. Mitochondrial target specificity is demonstrated by colocalization experiments using the mitochondrion-tracking probe, MitoTracker Red and lysosome-tracking probe, LysoTracker Green. Multicolor imaging of cellular organelles in A549 cells is achieved in combination with suitable target-specific dyes with distinct excitation and emission, such as green emitting FM 1-43FX to selectively image the plasma membrane, blue-fluorescent DAPI to stain the nucleus, and the synthesized NIR Cy-5 to image the mitochondria. Higher accumulation of the dye inside the cancer cell mitochondria compared to the noncancerous cell is also demonstrated.

| S-EPMC6740405 | biostudies-literature

Near IR heptamethine cyanine dye-mediated cancer imaging.

Project description:Near-IR fluorescence imaging has great potential for noninvasive in vivo imaging of tumors. In this study, we show the preferential uptake and retention of two hepatamethine cyanine dyes, IR-783 and MHI-148, in tumor cells and tissues.IR-783 and MHI-148 were investigated for their ability to accumulate in human cancer cells, tumor xenografts, and spontaneous mouse tumors in transgenic animals. Time- and concentration-dependent dye uptake and retention in normal and cancer cells and tissues were compared, and subcellular localization of the dyes and mechanisms of the dye uptake and retention in tumor cells were evaluated using organelle-specific tracking dyes and bromosulfophthalein, a competitive inhibitor of organic anion transporting peptides. These dyes were used to detect human cancer metastases in a mouse model and differentiate cancer cells from normal cells in blood.These near-IR hepatamethine cyanine dyes were retained in cancer cells but not normal cells, in tumor xenografts, and in spontaneous tumors in transgenic mice. They can be used to detect cancer metastasis and cancer cells in blood with a high degree of sensitivity. The dyes were found to concentrate in the mitochondria and lysosomes of cancer cells, probably through organic anion transporting peptides, because the dye uptake and retention in cancer cells can be blocked completely by bromosulfophthalein. These dyes, when injected to mice, did not cause systemic toxicity.These two heptamethine cyanine dyes are promising imaging agents for human cancers and can be further exploited to improve cancer detection, prognosis, and treatment.

| S-EPMC2871283 | biostudies-literature

Cancer-mitochondria-targeted photodynamic therapy with supramolecular assembly of HA and a water soluble NIR cyanine dye.

Project description:Mitochondria-targeted cancer therapies have proven to be more effective than other similar non-targeting techniques, especially in photodynamic therapy (PDT). Indocyanine dye derivatives, particularly IR-780, are widely known for their PDT utility. However, poor water solubility, dark toxicity, and photobleaching are limiting factors for these dyes, which otherwise show promise based on their good absorption in the near-infrared (NIR) region and mitochondria targeting ability. Herein, we introduce an indocyanine derivative (IR-Pyr) that is highly water soluble, exhibiting higher mitochondrial targetability and better photostability than IR-780. Furthermore, electrostatic interactions between the positively charged IR-Pyr and negatively charged hyaluronic acid (HA) were utilized to construct a micellar aggregate that is selective towards cancer cells. The cancer mitochondria-targeted strategy confirms high PDT efficacy as proved by in vitro and in vivo experiments.

| S-EPMC5858757 | biostudies-other

Transparent organic photodetector using a near-infrared absorbing cyanine dye.

Project description:Organic photodetectors are interesting for low cost, large area optical sensing applications. Combining organic semiconductors with discrete absorption bands outside the visible wavelength range with transparent and conductive electrodes allows for the fabrication of visibly transparent photodetectors. Visibly transparent photodetectors can have far reaching impact in a number of areas including smart displays, window-integrated electronic circuits and sensors. Here, we demonstrate a near-infrared sensitive, visibly transparent organic photodetector with a very high average visible transmittance of 68.9%. The transmitted light of the photodetector under solar irradiation exhibits excellent transparency colour perception and rendering capabilities. At a wavelength of 850?nm and at -1?V bias, the photoconversion efficiency is 17% and the specific detectivity is 10(12) Jones. Large area photodetectors with an area of 1.6?cm(2) are demonstrated.

| S-EPMC4371738 | biostudies-literature

Sensing of transcription factor binding via cyanine dye pair fluorescence lifetime changes.

Project description:We designed and synthesized sensors for imaging transcription factor-DNA interactions using a complementary pair of 21-base pair long oligonucleotides (ODNs) carrying two internucleoside phosphate-linked cyanine fluorophores that can either engage in Förster's resonance energy transfer (FRET) with fluorescence emission or assemble into a ground state quenched dimer with short fluorescence lifetimes (FL). Cyanine fluorophores were linked to ODNs within the NF-?B binding site. These sensors were tested in the presence of recombinant p50 and p65 NF-?B proteins or constitutively NF-?B activating HeLa cell lysates. By using a coherent light excitation source we followed changes in fluorescence lifetime of the donor (Cy5.5) at the donor's excitation and emission light wavelengths, as well as the acceptor (800CW or Cy7 cyanine fluorophores) in FRET mode. We observed increases in the donor lifetime in both emitting (0.08-0.15 ns) and non-emitting quenched (0.21 ns) sensors in response to protein binding. The measurements of lifetimes in FRET mode in quenched pair-carrying ODN duplex sensors showed significant differences in FL of the acceptor cyanine fluorophore between NF-?B-containing and NF-?B-free samples but not in control sensors with ODN sequences that have decreased binding affinity to NF-?B. We anticipate that the observed effects will be instrumental for developing sensors enabling non-invasive imaging in cells that undergo activation of NF-?B.

| S-EPMC3544408 | biostudies-literature

A dioxaborine cyanine dye as a photoluminescence probe for sensing carbon nanotubes.

Project description:The unique properties of carbon nanotubes have made them the material of choice for many current and future industrial applications. As a consequence of the increasing development of nanotechnology, carbon nanotubes show potential threat to health and environment. Therefore, development of efficient method for detection of carbon nanotubes is required. In this work, we have studied the interaction of indopentamethinedioxaborine dye (DOB-719) and single-walled carbon nanotubes (SWNTs) using absorption and photoluminescence (PL) spectroscopy. In the mixture of the dye and the SWNTs we have revealed new optical features in the spectral range of the intrinsic excitation of the dye due to resonance energy transfer from DOB-719 to SWNTs. Specifically, we have observed an emergence of new PL peaks at the excitation wavelength of 735 nm and a redshift of the intrinsic PL peaks of SWNT emission (up to 40 nm) in the near-infrared range. The possible mechanism of the interaction between DOB-719 and SWNTs has been proposed. Thus, it can be concluded that DOB-719 dye has promising applications for designing efficient and tailorable optical probes for the detection of SWNTs.

| S-EPMC5238636 | biostudies-literature

Albumin-chaperoned cyanine dye yields superbright NIR-II fluorophore with enhanced pharmacokinetics.

Project description:NIR-II fluorescence imaging greatly reduces scattering coefficients for nearly all tissue types at long wavelengths, benefiting deep tissue imaging. However, most of the NIR-II fluorophores suffer from low quantum yields and/or short circulation time that limit the quality of NIR-II imaging. Here, we engineered a supramolecular assembly of protein complex with lodged cyanine dyes to produce a brilliant NIR-II fluorophore, providing a NIR-II quantum yield of 21.2% with prolonged circulation time. Computational modeling revealed the mechanism for fluorescence enhancement and identified key parameters governing albumin complex for NIR-II fluorophores. Our complex afforded high-resolution microvessel imaging, with a 3-hour imaging window compared to 2 min for free dye alone. Furthermore, the complexation strategy was applied to an antibody-derived assembly, offering high-contrast tumor imaging without affecting the targeting ability of the antibody. This study provides a facile strategy for producing high-performance NIR-II fluorophores by chaperoning cyanine dyes with functional proteins.

| S-EPMC6744268 | biostudies-literature

Unexpected Charge Effects Strengthen π–Stacking Pancake Bonding

Project description:Phenalenyls (PLYs)

| S-EPMC8549058 | biostudies-literature

Effects of the cyanine dye 3,3'-dipropylthiocarbocyanine on mitochondrial energy conservation.

Project description:Mitochondrial respiration and oxidative phosphorylation were inhibited by the membrane potential probe 3,3'-dipropylthiocarbocyanine [diS-C3-(5)]. Evidence is presented that suggests that the dye acts as both an inhibitor of electron transport and an uncoupler of oxidative phosphorylation.

| S-EPMC1161108 | biostudies-other

Optimization of Cyanine Dye Stability and Analysis of FRET Interaction on DNA Microarrays.

Project description:The application of DNA microarrays for high throughput analysis of genetic regulation is often limited by the fluorophores used as markers. The implementation of multi-scan techniques is limited by the fluorophores' susceptibility to photobleaching when exposed to the scanner laser light. This paper presents combined mechanical and chemical strategies which enhance the photostability of cyanine 3 and cyanine 5 as part of solid state DNA microarrays. These strategies are based on scanning the microarrays while the hybridized DNA is still in an aqueous solution with the presence of a reductive/oxidative system (ROXS). Furthermore, the experimental setup allows for the analysis and eventual normalization of Förster-resonance-energy-transfer (FRET) interaction of cyanine-3/cyanine-5 dye combinations on the microarray. These findings constitute a step towards standardization of microarray experiments and analysis and may help to increase the comparability of microarray experiment results between labs.

| S-EPMC5192427 | 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