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A highly selective fluorescent probe for the detection of nitroreductase based on a naphthalimide scaffold
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Abstract
The development of fluorescent probes for nitroreductase (NTR) has received intense attention because of its biological significance and wide aplications. In this work, a novel fluorescent probe (MNI-NTR) based on a nitrobenzene switch for the detection of NTR in aqueous solution has been designed and synthesized on a 1,8-naphthalimide scaffold. The probe exhibited a high selectivity for NTR over various analyes with a detection limit of 9.8 ng/ml, especially without the interference from hydrogen sulfide. With the presence of NTR and NADH, MNI-NTR is converted into a 4-hydroxy-1,8-naphthalimide derivative under physiological conditions, showing a strong fluorescence peak at 550 nm. Theoretical calculations reveal that the reason for the fluorescence quenching of MNI-NTR is the photoinduced electron transfer (PET) from the nitrobenzene and morpholine groups to the naphthalimide fluorophore.
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Title: A highly selective fluorescent probe for the detection of nitroreductase based on a naphthalimide scaffold
Description:
Abstract
The development of fluorescent probes for nitroreductase (NTR) has received intense attention because of its biological significance and wide aplications.
In this work, a novel fluorescent probe (MNI-NTR) based on a nitrobenzene switch for the detection of NTR in aqueous solution has been designed and synthesized on a 1,8-naphthalimide scaffold.
The probe exhibited a high selectivity for NTR over various analyes with a detection limit of 9.
8 ng/ml, especially without the interference from hydrogen sulfide.
With the presence of NTR and NADH, MNI-NTR is converted into a 4-hydroxy-1,8-naphthalimide derivative under physiological conditions, showing a strong fluorescence peak at 550 nm.
Theoretical calculations reveal that the reason for the fluorescence quenching of MNI-NTR is the photoinduced electron transfer (PET) from the nitrobenzene and morpholine groups to the naphthalimide fluorophore.
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