High Stability of a Donor–Acceptor Type Oxazepine-Containing Fluorophore and Its Applications in Cellular Imaging and Two-Photon Deep Tissue Imaging

Abstract

A new donor (D)–acceptor (A) type naphthalene-based oxazepine-containing fluorophore, OXN-1, is reported, which shows unusually high stability in various environments. Its photophysical properties and structural stabilities under harsh conditions are thoroughly examined. The high stability of OXN-1 is explained by quantum chemical calculations. Its exceptional bioimaging capabilities for cells with low cytotoxicity are verified. In addition, its deep tissue imaging ability with two-photon microscopy (TPM) is evaluated.

Hydrazine-Selective Fluorescent Turn-On Probe Based on Ortho-Methoxy-Methyl-Ether (o-MOM) Assisted Retro-aza-Henry Type Reaction

“…Recently, our research team has focused on the development of a naphthalene-based donor (D)-acceptor (A) type of dipolar fluorescent dyes and its applications for the detection of metal ions, enzyme activity, amino acid, cell sub-organelles, disease biomarkers, and carcinogens [20,21,22,23,24,25]. During the research process, we found a fast hydrazone-formation between D-A type naphthaldehyde and hydrazine by o -MOM assistant, and we utilized this property in developing a fluorescent probe, HyP-1 [18] .…”

“…of product: 0.47, Figure S3). The generation of hydrazone compound was confirmed by spectrum analysis by comparing it with the known compound ( HyP-1 + N 2 H 4 ) [23], 1 H NMR analysis (Figure S4), and HR-mass spectrometry analysis (Supplementary Information, m / z = 273.1476, calc. = 273.1477).…”

Penta-fluorophenol: a Smiles rearrangement-inspired cysteine-selective fluorescent probe for imaging of human glioblastoma

“…We recently focused on the development of a donor-acceptor (D-A) dipolar type uorescent platform to monitor biologically essential species, such as enzyme activity, cell organelles, metal ions, and disease biomarkers. [32][33][34][35] We designed a new molecular sensing platform based on the nitrobenzoxadiazole (NBD) uorophore, using various aromatic substitutions at the electrondonating site (R): simple phenol (NPO-A), electron-decient penta-uorophenol (NPO-B), and electron-rich p-methoxyphenol (NPO-C). As a control probe we used chloro-substituted NBD (NBD-Cl) ( Fig.…”

Liposomal‐Encapsulated Near‐Infrared Fluorophore Based on π‐Extended Dipolar Naphthalene Platform and Its Imaging Applications in Human Cancer Cells

“…Recently, our research group has focused on the development of new fluorophores and molecular sensing probes based on a functionalized dipolar naphthalene platform (FDNP) (Figure 1). 10 The naphthalene‐based push‐pull type (electron donor‐acceptor; D‐A) FDNP has shown unique photophysical properties with advantages in the molecular sensing and bio‐imaging 11–14 . In our recent work, a hydrazine sensing probe based on FDNP was developed, which has an ortho‐methoxy‐methyl ether moiety ( o ‐MOM) that enhances the hydrazine sensing ability 12 .…”