Modular synthesis of 4-aminocarbonyl substituted 1,8-naphthalimides and application in single molecule fluorescence detection

Hearn, Kyle N; Nalder, Tim D.; Cox, R. P.; Maynard, Heather D.; Bell, Toby D. M.; Pfeffer, Frederick M.; Ashton, Trent D.

doi:10.1039/c7cc07922b

Cited by 48 publications

(26 citation statements)

References 29 publications

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“…Reduction to the alcohol and Boc protection of the amine furnished 3 , which was further converted into the corresponding benzaldehyde 4 serving as important intermediate to access both 6 and 8 . For the subsequent Buchwald‐Hartwig type coupling with either tert ‐butyl carbamate or 4‐nitrobenzyl carbamate, XantPhos Pd G3 was employed as a palladacycle precatalyst . This reaction served as key step in the synthesis of both the carbostyril 6 and the caged antenna precursor 8 and allowed us to selectively introduce and discriminate between the two functionalized amines at C‐2 and C‐4 in compound 7 .…”

Section: Methodsmentioning

confidence: 99%

An Activatable Lanthanide Luminescent Probe for Time‐Gated Detection of Nitroreductase in Live Bacteria

et al. 2020

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Herein we report the development of a turn‐on lanthanide luminescent probe for time‐gated detection of nitroreductases (NTRs) in live bacteria. The probe is activated through NTR‐induced formation of the sensitizing carbostyril antenna and resulting energy transfer to the lanthanide center. This novel NTR‐responsive trigger is virtually non‐fluorescent in its inactivated form and features a large signal increase upon activation. We show that the probe is capable of selectively sensing NTR in lysates as well as in live bacteria of the ESKAPE family which are clinically highly relevant multiresistant pathogens responsible for the majority of hospital infections. The results suggest that our probe could be used to develop diagnostic tools for bacterial infections.

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Section: Methodsmentioning

confidence: 99%

An Activatable Lanthanide Luminescent Probe for Time‐Gated Detection of Nitroreductase in Live Bacteria

et al. 2020

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“…The following compounds and their respective precursors were prepared using literature methods and full reaction details can be found in the supplementary information; 3 ,[34] 5 ,[23] 8 ,[23] 14 ,[63] 17 ,[24] 22 ,[35] 35 [64, 65] and 36 . [66] Compound 11 was kindly donated by the Schmuck research group and its synthesis has been previously reported.…”

Section: Methodsmentioning

confidence: 99%

Norbornane-based cationic antimicrobial peptidomimetics targeting the bacterial membrane

Hickey

Ashton

Boer

et al. 2018

European Journal of Medicinal Chemistry

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The design, synthesis and evaluation of a small series of potent amphiphilic norbornane antibacterial agents has been performed (compound 10 MIC = 0.25 μg/mL against MRSA). Molecular modelling indicates rapid aggregation of this class of antibacterial agent prior to membrane association and insertion. Two fluorescent analogues (compound 29 with 4-amino-naphthalimide and 34 with 4-nitrobenz-2-oxa-1,3-diazole fluorophores) with good activity (MIC = 0.5 μg/mL against MRSA) were also constructed and confocal microscopy studies indicate that the primary site of interaction for this family of compounds is the bacterial membrane.

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“…For this purpose, we designed and synthesized NpCN1, a 4-amino-1,8-naphthalimide with a 3-benzonitrile substituted at the 3-position (Figure 1). We had also tested alkyne tagged naphthalimides [35,36] (Scheme S2, Figure S1), but the benzonitrile tagged naphthalimide had superior properties (Figure 2). NpCN1 was synthesised in a three-step reaction (Scheme S1).…”

Section: Design and Synthesis Of Npcn1mentioning

confidence: 99%

A Bimodal Fluorescence-Raman Probe for Cellular Imaging

Lin

Graziotto

Lay

et al. 2021

Cells

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Biochemical changes in specific organelles underpin cellular function, and studying these changes is crucial to understand health and disease. Fluorescent probes have become important biosensing and imaging tools as they can be targeted to specific organelles and can detect changes in their chemical environment. However, the sensing capacity of fluorescent probes is highly specific and is often limited to a single analyte of interest. A novel approach to imaging organelles is to combine fluorescent sensors with vibrational spectroscopic imaging techniques; the latter provides a comprehensive map of the relative biochemical distributions throughout the cell to gain a more complete picture of the biochemistry of organelles. We have developed NpCN1, a bimodal fluorescence-Raman probe targeted to the lipid droplets, incorporating a nitrile as a Raman tag. NpCN1 was successfully used to image lipid droplets in 3T3-L1 cells in both fluorescence and Raman modalities, reporting on the chemical composition and distribution of the lipid droplets in the cells.

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Modular synthesis of 4-aminocarbonyl substituted 1,8-naphthalimides and application in single molecule fluorescence detection

Cited by 48 publications

References 29 publications

An Activatable Lanthanide Luminescent Probe for Time‐Gated Detection of Nitroreductase in Live Bacteria

An Activatable Lanthanide Luminescent Probe for Time‐Gated Detection of Nitroreductase in Live Bacteria

Norbornane-based cationic antimicrobial peptidomimetics targeting the bacterial membrane

A Bimodal Fluorescence-Raman Probe for Cellular Imaging

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