Napthalimide-based fluorescent probe for selective and sensitive sensing of formaldehyde and biological applications

Nasirian, Azam; Tikum, Anjong Florence; Fortibui, Maxine Mambo; Lee, SoHyun; Kim, Jinheung

doi:10.1016/j.dyepig.2021.109156

Cited by 20 publications

(6 citation statements)

References 42 publications

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“…The intensity enhancement of Nap –Pd was also obtained at low pH and the most significant differences between Nap –Pd and Nap –Pd/CO were observed at pH values less than 5. Such fluorescent probes containing a pyridyl group were also reported to exhibit analyte-specific emission enhancements over a wide pH range. , The enhanced emission at low pH would derive from the protonation of the pyridyl moiety. However, the emission intensity of Nap –Pd also shows meaningful differences in the absence and presence of CO near biological pH.…”

Section: Resultsmentioning

confidence: 99%

“…Such fluorescent probes containing a pyridyl group were also reported to exhibit analyte-specific emission enhancements over a wide pH range. 33,36 The enhanced emission at low pH would derive from the protonation of the pyridyl moiety. However, the emission intensity of Nap−Pd also shows meaningful differences in the absence and presence of CO near biological pH.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…On the other hand, emission sensing using fluorescent probes has been used as one of the powerful tools to detect and monitor various important molecules in living systems. − However, developing a convenient, sensitive, and noninvasive probe is still needed for the fluorescent detection of CO. Recently, fluorescent CO probes for the imaging of CO in living cells were reported from He’s and Chang’s research groups. , Besides these reports, some other probes have been prepared and applied to cell imaging of CO. − However, new probes are still required to improve the difficulties of synthesis, resolution in color or emission, selectivity, excitation wavelength, and use of organic solvent. ,,, Recently, we reported a study of a formaldehyde sensing probe based on 1,8-naphthalimide . It is well known that naphthalimide-based sensors are capable of one- and two-photon imaging and show interesting changes in the photoinduced electron transfer by analyte-induced modifications of the dye. ,− …”

Section: Introductionmentioning

confidence: 99%

“…19,20,22,23 Recently, we reported a study of a formaldehyde sensing probe based on 1,8-naphthalimide. 33 It is well known that naphthalimide-based sensors are capable of one-and two-photon imaging and show interesting changes in the photoinduced electron transfer by analyte-induced modifications of the dye. 29,33−35 Herein quenches the fluorescence of naphthalimide through the electronic effect by a heavy metal atom.…”

Section: ■ Introductionmentioning

confidence: 99%

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Palladium Probe Consisting of Naphthalimide and Ethylenediamine for Selective Turn-On Sensing of CO and Cell Imaging

et al. 2021

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An assay to detect carbon monoxide (CO), one of the gaseous signaling molecules, has been prepared using a new palladium complex probe. The ethylenediamine group linked to the naphthalimide fluorophore coordinates to Pd(II) which intramolecularly quenches the emission. Upon treatment with CO, the absorbance of the turn-on fluorescent sensor changes due to the formation of a complex between Pd(II) and CO at room temperature in a phosphate buffer. As the concentration of CO increases, the probe peak emission intensity at 527 nm gradually increases. Other analyte controls, such as K+, Mg2+, Al3+, Zn2+, Cr3+, Hg2+, Fe3+, alanine, glycine, leucine, lysine, serine, threonine, tyrosine, F–, Cl–, Br–, NO, NO2 –, NO3 –, HCO3 –, CH3COO–, H2O2, •OH, and t BuOO•, exhibit no significant effect on emission intensity. The response time of the probe to CO was quite fast because of the relatively weak coordination of Pd(II) to the pendent ethylenediamine group. The Pd probe is capable of detecting CO in aqueous buffer as well as in living cells with high selectivity and stability, providing a potential real-time indicator for studying CO-involved reactions in biological systems.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

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Palladium Probe Consisting of Naphthalimide and Ethylenediamine for Selective Turn-On Sensing of CO and Cell Imaging

et al. 2021

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“…At the same time, hydrazine derivatives based on different fluorophores have been reported as well, such as anthracene (68), BODIPY (69), NBD (70), as well as 1,8-naphthalimide (71-74) and perylenebisimide (75). [92][93][94][95][96][97][98][99] For example, in 2018, Hou et al developed fluorescent probe 68 for FA sensing based on anthracene by introducing the hydrazine group as the reaction group (Fig. 15).…”

Section: Methylenehydrazine-based Mechanismmentioning

confidence: 99%

Reaction-based fluorescent and chemiluminescent probes for formaldehyde detection and imaging

Huang

Liu

et al. 2022

Chem. Commun.

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Synthesis of an Amine Moiety‐Based Fluorescent Probe and the Relationship Between the Amino Substitution Position and Formaldehyde Detection Performance

Tan,

Hua,

Wang

et al. 2024

ChemistrySelect

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A novel amine moiety‐based fluorescent probe (BA) was prepared using diphenylacetylene as fluorophore and amino group as acceptor. The probe achieves detection of formaldehyde through fluorescence enhancement by inhibition the photoinduced electron transfer (PET) between diphenylacetylene and amino group. And the different formaldehyde detection performance of 2‐(phenylethynyl)aniline (BA‐1), 3‐(phenylethynyl)aniline (BA‐2) and 4‐(phenylethynyl)aniline (BA‐3) indicates that the position of amino recognition group on the benzene ring of diphenylacetylene has a significant impact on the detection ability of this type fluorescent probe. When the amino group is in the ortho‐position of the benzene ring, probe BA‐1 can rapidly enhance the fluorescence intensity within 20 min with limit of detection as low as 0.75 μM; When the amino group is located in meta‐position of benzene ring, the solution of BA‐2 also exhibited a certain degree of fluorescence enhancement, but it is weaker than BA‐1; When the amino group is at the para‐position of benzene ring, BA‐3 has almost no response to formaldehyde.

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Napthalimide-based fluorescent probe for selective and sensitive sensing of formaldehyde and biological applications

Cited by 20 publications

References 42 publications

Palladium Probe Consisting of Naphthalimide and Ethylenediamine for Selective Turn-On Sensing of CO and Cell Imaging

Palladium Probe Consisting of Naphthalimide and Ethylenediamine for Selective Turn-On Sensing of CO and Cell Imaging

Reaction-based fluorescent and chemiluminescent probes for formaldehyde detection and imaging

Synthesis of an Amine Moiety‐Based Fluorescent Probe and the Relationship Between the Amino Substitution Position and Formaldehyde Detection Performance

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