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.
Highlights
Formaldehyde (FA) is both the simplest aldehyde and a highly reactive carbonyl species that is well known for its applications in food, textiles, and wood processing [1,2,3]
Biological FA is produced at levels of 0.2–0.4 mM that are maintained endogenously via enzymatic processes [7]
As shown in Scheme 1, the probe consisted of a hydrazine-containing naphthalimide fluorophore with an FA-binding site along with a phenylsulfonamide group for targeting the Golgi apparatus [15,18,20,21]
Summary
Formaldehyde (FA) is both the simplest aldehyde and a highly reactive carbonyl species that is well known for its applications in food, textiles, and wood processing [1,2,3]. FA exists at low levels in most living organisms and can be found in natural foods such as fruits, vegetables, meats, seafood, and dairy products [4]. FA has been recognized as the third largest indoor chemical pollutant, and exposure to FA may induce severe central nervous system damage, cancer, and even death [5,6,7]. Biological FA is produced at levels of 0.2–0.4 mM that are maintained endogenously via enzymatic processes [7]. Whereas cell proliferation can be promoted, and memory formation mediated, at healthy FA levels, cognitive impairments, neurodegeneration, and memory loss have been reported at elevated concentrations due to potent protein and DNA cross-linking mechanisms
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