Ratiometric Detection of Mitochondrial Thiols with a Two-Photon Fluorescent Probe

Abstract

We report a ratiometric two-photon probe (SSH-Mito) for mitochondrial thiols. This probe shows a marked blue-to-yellow emission color change in response to RSH, a significant two-photon cross section, good mitochondrial thiol selectivity, low cytotoxicity, and insensitivity to pH over the biologically relevant pH range, allowing the direct visualization of RSH levels in live cells as well as in living tissues at 90-190 μm depth without interference from other biologically relevant species through the use of two-photon microscopy.

Reaction-based fluorescent sensor for investigating mobile Zn 2+ in mitochondria of healthy versus cancerous prostate cells

“…In targeting mitochondria, we relied on an aminoethyl derivative of triphenylphosphine to generate the lipophilic TPP cation (31). TPP delivers payloads, including fluorescent sensors (21)(22)(23)(24)(25)(26)(27), to the mitochondrial matrix by exploiting the negative potential maintained by actively respiring mitochondria (32). The free amino group on the aminoethyl TPP derivative provided a convenient synthetic handle for attachment of 6-CO 2 H ZP1 (33).…”

A New Two-Photon Ratiometric Fluorescent Probe for Detecting Alkaline Phosphatase in Living Cells

“…Then, compound 3 was deprotected by bromotrimethylsilane to furnish probe 1 [38]. The structures of compound 3 and probe 1 were well characterized using 1 H-NMR, 13 C-NMR, 31 P-NMR and MS (Figures S3-S9). …”

“…An ideal tool to overcoming such limitations is two-photon microscopy (TPM), which involves fluorophore excitation by two low-energy (longer wavelength) photons [25][26][27][28][29]. There are many excellent properties, such as large two-photon active absorption cross-section, high fluorescence quantum yield and good photo-chemostability about naphthalene derivatives with a donor-π-acceptor (D-π-A) structure, which has thus been employed extensively as an efficient two-photon platform for designing two-photon probes for various targets [30][31][32][33]. In this work, we have developed a naphthalene-based compound with ICT character as a fluorescent probe (probe 1, Scheme 1) for the detection of ALP.…”

FITC functionalized magnetic core–shell Fe3O4/Ag hybrid nanoparticle for selective determination of molecular biothiols

“…In recent years, a great amount of interesting studies have focused on the determination and sensing of biothiols. Various analytical methods including high-performance liquid chromatography [10,11], capillary electrophoresis [12,13], mass spectrometry [14], chemiluminescence [15,16], electrochemistry assay [17,18], fluorimetry [19][20][21], and nanoparticles-based colorimetric sensing strategy [22][23][24][25][26][27] for biothiols have been developed. Among these methods, fluorescent probes and gold-nanoparticle-based colorimetric sensing gradually stand out in the rapid, sensitive, and selective determination of biothiols.…”

“…Our team has developed a series of fluorescent probes that can be used for rapid detection of thiols under physiological conditions, with emission in the near infrared (NIR) region [28,29]. Yet, in most of the reported fluorescent methods, organic solvents are required to be introduced into the system to increase the solubility of fluorescent dyes [19][20][21]. As a type of recently developed biothiol sensor, gold-nanoparticlebased colorimetric sensing in general involves the aggregation, coupling, or assembly of gold nanospheres [22,23] and nanorods [24,25].…”