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. 2024 Jun 11;29(12):2774.
doi: 10.3390/molecules29122774.

Synthesis and Characterization of Sulfonamide-Containing Naphthalimides as Fluorescent Probes

Zhi-Wei Liu  1   2 , Fan Liu  2 , Chun-Tao Shao  2 , Guo-Ping Yan  1 , Jiang-Yu Wu  2
Affiliations

Synthesis and Characterization of Sulfonamide-Containing Naphthalimides as Fluorescent Probes

Zhi-Wei Liu et al. Molecules. .

Abstract

A tumor-targeting fluorescent probe has attracted increasing interest in fluorescent imaging for the noninvasive detection of cancers in recent years. Sulfonamide-containing naphthalimide derivatives (SN-2NI, SD-NI) were synthesized by the incorporation of N-butyl-4-ethyldiamino-1,8-naphthalene imide (NI) into sulfonamide (SN) and sulfadiazine (SD) as the tumor-targeting groups, respectively. These derivatives were further characterized by mass spectrometry (MS), nuclear magnetic resonance spectroscopy (1H NMR), Fourier transform infrared spectroscopy (FT-IR), ultraviolet-visible spectroscopy (UV), and a fluorescence assay. In vitro properties, including cell cytotoxicity and the cell uptake of tumor cells, were also evaluated. Sulfonamide-containing naphthalimide derivatives possessed low cell cytotoxicity to B16F10 melanoma cells. Moreover, SN-2NI and SD-NI can be taken up highly by B16F10 cells and then achieve good green fluorescent images in B16F10 cells. Therefore, sulfonamide-containing naphthalimide derivatives can be considered to be the potential probes used to target fluorescent imaging in tumors.

Keywords: fluorescent imaging; fluorescent probe; naphthalimide; sulfadiazine; sulfonamide.

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Conflict of interest statement

The authors declare no conflicts of interest.

Figures

Scheme 1
Scheme 1
Synthetic route to sulfonamide-containing naphthalimides.
Figure 1
Figure 1
MS spectra of SN-2NI (a) and SD-NI (b).
Figure 2
Figure 2
1H NMR spectra of SN-2NI (a) and SD-NI (b).
Figure 3
Figure 3
IR spectra of SN-2NI (a) and SD-NI (b).
Figure 4
Figure 4
UV spectra of SN-2NI and SD-NI.
Figure 5
Figure 5
Fluorescent spectra of SN-2NI (a) and SD-NI (b).
Figure 6
Figure 6
In vitro cytotoxicity assay of SN-2NI and SD-NI to B16F10 cells.
Figure 7
Figure 7
In vitro fluorescent imaging of SN-2NI and SD-NI to B16F10 melanoma cells.
Figure 8
Figure 8
In vitro fluorescent imaging of SN-2NI to B16F10 cells. (A1 and B1: control B16F10 cells excited by white light and blue light, respectively; A2 and B2: B16F10 cells incubated with SN-2NI excited by white light and blue light, respectively; A3 and B3: B16F10 cells were previously incubated by SN (25 μmol/L) for 1 h and subsequently incubated with SN-2NI (0.25 μmol/L) and later excited by white light and blue light, respectively).
Figure 9
Figure 9
In vitro fluorescent imaging of SD-NI to B16F10 cells.(A4 and B4: control B16F10 cells excited by white light and blue light, respectively; A5 and B5: B16F10 cells incubated with SD-NI excited by white light and blue light, respectively; A6 and B6: B16F10 cells were previously incubated by SD (25 μmol/L) for 1 h and subsequently incubated with SD-NI (0.25 μmol/L) and later excited by white light and blue light, respectively.).
See this image and copyright information in PMC

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