5-Ethynylarylnaphthalimides as antitumor agents: Synthesis and biological evaluation

Quintana-Espinoza, Patricia; Martín-Acosta, Pedro; Amesty, Ángel; Martín-Rodríguez, Patricia; Lorenzo-Castrillejo, Isabel; Fernández-Pérez, Leandro; Machín, Félix; Estévez‐Braun, Ana

doi:10.1016/j.bmc.2017.02.024

Cited by 6 publications

(3 citation statements)

References 26 publications

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“…We have synthesized the probes based on the literature-reported procedure with slight modifications . The synthetic routes of the 1,8-naphthalimide-based fluorescent probes NIT-NO 2 and NIT-OH are depicted in Schemes 1 and 2 (Supporting Information).…”

Section: Resultsmentioning

confidence: 99%

“…We have synthesized the probes based on the literature-reported procedure with slight modifications. 49 The synthetic routes of the 1,8-naphthalimide-based fluorescent probes NIT-NO 2 and NIT-OH are depicted in Schemes 1 and 2 (Supporting Information). Both probes are well characterized by NMR spectroscopy and mass spectrometry (Figures S1−S16, Supporting Information).…”

Section: ■ Introductionmentioning

confidence: 99%

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Multi-action of a Fluorophore in the Sight of Light: Release of NO, Emergence of FONs, and Organelle Switching

Chakraborty

Biswas

Pramanik

et al. 2022

ACS Appl. Mater. Interfaces

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Light, as an external stimulus, has begun to engage a phenomenal role in the diverse field of science. Encouraged by recent progress from biology to materials chemistry, various light-responsive fluorescent probes have been developed. Herein, we present a 1,8-naphthalimide-based probe NIT-NO 2 capable of releasing nitric oxide (NO) along with the formation of fluorescent organic nanoparticles (FONs) upon exposure to near-visible UV light. By synthesizing the photoproduct NIT-OH, we unveiled that initially NIT-NO 2 released NO and converted to NIT-OH, while prolonged irradiation led to the formation of FONs that is corroborated by the red-edge excitation shift as well as microscopic investigation. Finally, we have successfully applied NIT-NO 2 and NIT-OH for specific labeling of lipid droplets and plasma membranes, respectively, and demonstrated the switching from lipid droplets to plasma membranes by using light as a stimulus. These two probes show unique imaging applications inside the cells depending on the polarity and hydrophobicity of the environment. This work paves a fascinating way for the generation of excitation-dependent FONs from a small organic fluorophore and highlights its potency as an exclusive imaging tool.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Multi-action of a Fluorophore in the Sight of Light: Release of NO, Emergence of FONs, and Organelle Switching

Chakraborty

Biswas

Pramanik

et al. 2022

ACS Appl. Mater. Interfaces

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show abstract

“…To test cytotoxicity against tumor cell lines, we performed the MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide] assay as previously described. 23 ■ ASSOCIATED CONTENT * S Supporting Information…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

Lawsone, Juglone, and β-Lapachone Derivatives with Enhanced Mitochondrial-Based Toxicity

et al. 2018

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Naphthoquinones are among the most active natural products obtained from plants and microorganisms. Naphthoquinones exert their biological activities through pleiotropic mechanisms that include reactivity against cell nucleophiles, generation of reactive oxygen species (ROS), and inhibition of proteins. Here, we report a mechanistic antiproliferative study performed in the yeast Saccharomyces cerevisiae for several derivatives of three important natural naphthoquinones: lawsone, juglone, and β-lapachone. We have found that (i) the free hydroxyl group of lawsone and juglone modulates toxicity; (ii) lawsone and juglone derivatives differ in their mechanisms of action, with ROS generation being more important for the former; and (iii) a subset of derivatives possess the capability to disrupt mitochondrial function, with β-lapachones being the most potent compounds in this respect. In addition, we have cross-compared yeast results with antibacterial and antitumor activities. We discuss the relationship between the mechanistic findings, the antiproliferative activities, and the physicochemical properties of the naphthoquinones.

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1,2,3-Triazole-totarol conjugates as potent PIP5K1α lipid kinase inhibitors

Haidar,

Amesty,

Oramas-Royo

et al. 2024

Bioorganic & Medicinal Chemistry

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5-Ethynylarylnaphthalimides as antitumor agents: Synthesis and biological evaluation

Cited by 6 publications

References 26 publications

Multi-action of a Fluorophore in the Sight of Light: Release of NO, Emergence of FONs, and Organelle Switching

Multi-action of a Fluorophore in the Sight of Light: Release of NO, Emergence of FONs, and Organelle Switching

Lawsone, Juglone, and β-Lapachone Derivatives with Enhanced Mitochondrial-Based Toxicity

1,2,3-Triazole-totarol conjugates as potent PIP5K1α lipid kinase inhibitors

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