A Golgi Apparatus-Targeting, Naphthalimide-Based Fluorescent Molecular Probe for the Selective Sensing of Formaldehyde

Abstract

Formaldehyde (FA) is a colorless, flammable, foul-smelling chemical used in building materials and in the production of numerous household chemical goods. Herein, a fluorescent chemosensor for FA is designed and prepared using a selective organ-targeting probe containing naphthalimide as a fluorophore and hydrazine as a FA-binding site. The amine group of the hydrazine reacts with FA to form a double bond and this condensation reaction is accompanied by a shift in the absorption band of the probe from 438 nm to 443 nm upon the addition of FA. Further, the addition of FA is shown to enhance the emission band at 532 nm relative to the very weak fluorescent emission of the probe itself. Moreover, a high specificity is demonstrated towards FA over other competing analytes such as the calcium ion (Ca2+), magnesium ion (Mg2+), acetaldehyde, benzaldehyde, salicylaldehyde, glucose, glutathione, sodium sulfide (Na2S), sodium hydrosulfide (NaHS), hydrogen peroxide (H2O2), and the tert-butylhydroperoxide radical. A typical two-photon dye incorporated into the probe provides intense fluorescence upon excitation at 800 nm, thus demonstrating potential application as a two-photon fluorescent probe for FA sensing. Furthermore, the probe is shown to exhibit a fast response time for the sensing of FA at room temperature and to facilitate intense fluorescence imaging of breast cancer cells upon exposure to FA, thus demonstrating its potential application for the monitoring of FA in living cells. Moreover, the presence of the phenylsulfonamide group allows the probe to visualize dynamic changes in the targeted Golgi apparatus. Hence, the as-designed probe is expected to open up new possibilities for unique interactions with organ-specific biological molecules with potential application in early cancer cell diagnosis.

Design of a New Hydrazine Moiety-Based Near-Infrared Fluorescence Probe for Detection and Imaging of Endogenous Formaldehyde In Vivo

“…Moreover, the overexpression of FA can induce many diseases such as heart disease, Alzheimer’s disease, and cancer. − Ahead of extending the practical field of Probe - NHNH 2 , its cytotoxicity in HepG2 cells was evaluated in accordance with standard MTT assays Figure S7).…”

Subcellular Delivery of Hydrogen Sulfide Using Small Molecule Donors Impacts Organelle Stress

“…GolgiNH was prepared according to the reported procedures. , 4-Bromo-1,8-napthalic anhydride (478 mg, 2.00 mmol, 1.0 equiv) and sulfanilamide (344 mg, 2.00 mmol, 1.0 equiv) were dissolved in acetic acid (5 mL) and refluxed for 8 h. The reaction mixture was cooled to room temperature for 1 h, and the precipitate was filtered and dried to yield a gray solid (0.326 g, 38%). The crude product (GolgiBr) was carried over to the next step without further purification.…”

Computational chemistry‐assisted design of hydrazine‐based fluorescent molecular rotor for viscosity sensors

“…Na‐FA was developed by connecting the hydrazine group to the naphthalimide unit. Following the pioneer report, many hydrazine‐based formaldehyde fluorescent probes were reported based on the naphthalimide skeleton [15–19] . Though convincing evidence is lacking, the PET effect has been regarded as the default fluorescence quenching mechanism in these hydrazine‐based fluorescent probes.…”

“…Following the pioneer report, many hydrazine-based formaldehyde fluorescent probes were reported based on the naphthalimide skeleton. [15][16][17][18][19] Though convincing evidence is lacking, the PET effect has been regarded as the default fluorescence quenching mechanism in these hydrazine-based fluorescent probes. Besides, abundant hydrazine-based fluorescent probes based on different fluorophores have also been reported.…”