2513-33-9

Usage

Chemical Properties

Brownish Yellow Solid

Uses

A by-product of Fluorescein.

InChI:InChI=1/C14H10O5/c15-8-5-6-11(12(16)7-8)13(17)9-3-1-2-4-10(9)14(18)19/h1-7,15-16H,(H,18,19)

Upstream product

• 85-44-9 phthalic anhydride 
• 108-46-3 recorcinol 
• 94109-78-1 spiro[isobenzofuran-3',6'-dihydroxy-1(3H),9'-[9H]thioxanthen]-3-one 
• 2321-07-5 fluorescein 
• 630-88-6 3',6'-dichloro-spiro[phthalan-1,9'-xanthen]-3-one 
• 13460-50-9 metaboric acid 
• 7664-93-9 sulfuric acid 
• 1384988-00-4 C₁₈H₁₈O₇ 
• 295788-93-1 1-bromo-2,4-bis(methoxymethoxy)benzene 
• 518-44-5 dihydrofluorescein 
• 518-45-6 fluorescein free acid 

Downstream Products

• 21147-36-4 2-(2,4-dihydroxy-benzoyl)-benzoic acid methyl ester 
• 83469-76-5 6-Hydroxy-2-methylxanthen-9-spiro-1'-isobenzofuran-3'-one 
• 91000-72-5 2-(2,4-dihydroxy-benzyl)-benzoic acid 
• 3341-06-8 3,5-dibromo-2'-carboxy-2,4-dihydroxybenzophenone 
• 2321-07-5 fluorescein 
• 855470-11-0 2-(2,4-dimethoxy-benzoyl)-benzoic acid methyl ester 
• 4756-45-0 NSC 79888 
• 856806-61-6 3-(2,4-dihydroxy-phenyl)-3-(4-hydroxy-phenyl)-phthalide 
• 2513-30-6 2-(3,5-dichloro-2,4-dihydroxy-benzoyl)-benzoic acid 
• 518-44-5 dihydrofluorescein 
• 87569-96-8 2-(6'-ethoxy-3'-oxo-3'H-xanthene-9'-yl)benzoic acid ethyl ester 
• 630-88-6 3',6'-dichloro-spiro[phthalan-1,9'-xanthen]-3-one 
• 596-03-2 4',5'-dibromofluorescein 

Relevant academic research and scientific papers

Ratiometric Visualization of NO/H2S Cross-Talk in Living Cells and Tissues Using a Nitroxyl-Responsive Two-Photon Fluorescence Probe

It is of scientific significance to explore the intricate relationship between two crucial gasotransmitters nitric oxide (NO) and hydrogen sulfide (H2S) because they exert similar and interdependent biological actions within the living organisms. Nevertheless, visualization of the NO/H2S crosstalk using effective molecular imaging tools remains challenging. To address this issue, and given that nitroxyl (HNO) has been implicated as the interdependent production of NO and H2S via a network of cascading chemical reactions, we herein design a ratiometric two-photon fluorescent probe for HNO, termed TP-Rho-HNO, which consists of benzo[h]chromene-rhodol scaffold as two-photon energy transfer cassette with phosphine moiety as specific HNO recognition unit. The newly proposed probe has been successfully applied in ratiometric two-photon bioimaging of endogenous HNO derived from NO and H2S interaction in the human umbilical vein cells (HUVECs) and as well as in rat brain tissues. Intriguingly, the imaging results consistently demonstrate that the mutually dependent upgeneration of H2S and NO are present in living biosystems, indicating that this molecular probe would provide a powerful approach to elucidate the chemical foundation for the anfractuous cross-talk between the NO and H2S signaling pathways in biology.

A novel FRET-based ratiometric fluorescent probe for highly sensitive detection of hydrogen sulfide

A novel FRET-based ratiometric fluorescent probe H2S-CR for the quantitative detection of H2S was designed and synthesized. It exhibits a response time of 20 min, a considerable fluorescence signal enhancement (15 fold), and an extremely low detection limit (19 nM). It can be successfully applied to imaging H2S in living cells. This journal is

Ratiometric and colorimetric detection of hydrogen sulfide with high selectivity and sensitivity using a novel FRET-based fluorescence probe

Abstract With recognition of the biological significance of H2S, we have designed and synthesized a novel ratiometric and colorimetric fluorescence probe, CR-DNP based on a H2S induced thiolysis reaction as well as the fluorescence resonance energy transfer process. It displayed some desirable properties, such as good photostability, high selectivity and excellent sensitivity. Also, a considerably fluorescence enhancement (15-fold) and distinct visible color change (colorless to bright orange) was observed. A good linear relationship between the emission intensity ratios and NaHS concentrations suggested that it can detect H2S quantitatively with a detection limit as low as 0.4 μM. Furthermore, due to its biocompatibility, the sensor could easily permeate through the cell membrane and trace the intracellular H2S levels change.

A highly sensitive endoplasmic reticulum-targeting fluorescent probe for the imaging of endogenous H2S in live cells

Hydrogen sulfide (H2S) as an important signaling biomolecule participates in a series of complex physiological and pathological processes. In situ and rapid detection of H2S levels in endoplasmic reticulum (ER) is of great importance for the in-depth study of its virtual functional roles. However, the ER-targeting fluorescent probe for the detection of H2S in live cells is still quite rare. Herein, a new ER-targeting fluorescent probe (FER-H2S) for detecting H2S in live cells was characterized in the present study. This probe FER-H2S was built from the hybridization of three parts, including fluorescein-based skeleton, p-toluenesulfonamide as ER-specific group, and 2,4-nitrobenzene sulfonate as a response site for H2S. The response mechanism of the probe FER-H2S to H2S is on the basis of the ring-opening and ring-closing processes in fluorescein moiety. Moreover, the probe FER-H2S was successfully used for the imaging of exogenous and endogenous H2S in ER of live cells.

A FRET-based ratiometric fluorescent probe for highly selective detection of cysteine based on a coumarin-rhodol derivative

Cysteine, as an important amino acid in the human body, plays a vital role in people's normal life activities. In this paper, a ratiometric fluorescent probe for detecting cysteine was designed and synthesized based on the fluorescence resonance energy transfer (FRET) process. In this FRET system, a coumarin derivative was used as the energy donor, a rhodol fluorophore was chosen as the energy receptor, and an acrylate group was utilized as a cysteine recognition unit. In the absence of cysteine, the rhodol receptor was in the non-fluorescent lactone state and the FRET process was inhibited. Upon addition of cysteine, the closed spirolactone form was converted to a conjugated fluorescent xanthene form to induce the occurrence of FRET which resulted in a fluorescent signal decrease at 470 nm and enhancement at 543 nm. The ratiometric fluorescent probe exhibited excellent selectivity to Cys over Hcy and GSH. In addition, I543nm/I470nm of the probe for cysteine displayed a good linear relationship in the range of 5.0 × 10-7-1.0 × 10-4 mol L-1, and the detection limit was 2.0 × 10-7 mol L-1. Furthermore, the probe showed low cell toxicity and was successfully applied to the confocal imaging of cysteine in HepG2 cells using dual emission channels.

A novel FRET-based fluorescent probe for the selective detection of hydrogen sulfide (H2S) and its application for bioimaging

Hydrogen sulfide (H2S) is an endogenously produced gaseous signaling molecule with multiple functions in many physiological and pathological processes. Herein, our group developed a novel fluorescent probe (Flu-N3) for H2S

Gasotransmitter Regulation of Phosphatase Activity in Live Cells Studied by Three-Channel Imaging Correlation

Enzyme activity in live cells is dynamically regulated by small-molecule transmitters for maintaining normal physiological functions. A few probes have been devised to measure intracellular enzyme activities by fluorescent imaging, but the study of the re

MOLECULAR PROBES FOR DETECTION AND IMAGING OF PANCREATIC CANCER

Molecular probes for detecting and imaging pancreatic cancer are disclosed. The probes are modified benzoxanthene fluorophores, which are selectively taken up by pancreatic cancer cells, such as pancreatic ductal adenocarcinoma cells. Embodiments of the disclosed probes are useful for pancreatic cancer detection, therapeutic monitoring, and/or image-guided surgery.

A reactive cysteine probe and its preparation method (by machine translation)

The invention discloses a reactive cysteine probe and its preparation method, in order to rhodamine derivative is a fluorophore, acrylic ester structure is a cysteine specific reactive group; probe itself fluorescence is extremely weak, strong fluorescent after reaction with cysteine, can be used for detection of the cysteine. The probe in PBS 7.4 (30% ethanol) system in half-cystine reaction is more rapid, has good selectivity and higher sensitivity; can be used to determine in biological and environmental system of the cysteine content of the fluorescence detection, visual qualitative detection, cell imaging detection. (by machine translation)

Rhodamine fluorescence dye and preparation method thereof

The invention discloses a rhodamine fluorescence dye and a preparation method thereof. A classic rhodamine synthesis method is used as a basis, chemical groups having different functions are introduced to a rhodamine parent through reasonable structural modification, a conjugative effect is added, and hyperchromic groups, such as hydroxy, diethylin and azabicyalo, are changed. The prepared novel rhodamine fluorescence dye has a larger emission wavelength and higher light quantum yield and also has more reaction loci, so that follow-up reaction is more convenient. In addition, the rhodamine fluorescence dye has appropriate Stokes shift, and wavelength interference excitation can be avoided in follow-up fluorescence detection, so that analysis results are more accurate.