Application of 4-chloro-7-nitrobenzo-2-oxa-1,3-diazole in analysis: Fluorescent dyes and unexpected reaction with tertiary amines

Annenkov, Vadim V.; Verkhozina, O. N.; Shishlyannikova, Tatyana A.; Danilovtseva, Elena N.

doi:10.1016/j.ab.2015.06.025

Cited by 15 publications

(8 citation statements)

References 44 publications

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“…In the NBD-Cl method, VP was found to react with NBD-Cl in borate buffer pH 8 yielding a highly fluorescent yellow product with maximum absorption at 436 nm and exhibiting strong fluorescence at 550 nm, after excitation at 480 nm (Fig. 5b) (Miyano et al, 1985;Walash et al, 2011;El-Yazbi et al, 2016;Darwish et al, 2009;Attia et al, 2017;Annenkov et al, 2015;Rageh et al, 2010;Omar et al, 2017;Mohamed et al, 2019). This reaction occurs as NBD-Cl reacts with the amine group in the VP under mild alkaline conditions yielding a highly fluorescent yellow colored derivative as shown in Scheme 1 (Miyano et al, 1985;Walash et al, 2011;El-Yazbi et al, 2016;Darwish et al, 2009;Attia et al, 2017;Annenkov et al, 2015;Rageh et al, 2010;Omar et al, 2017;Mohamed et al, 2019).…”

Section: Determination Of Vp In Presence Of Sf Using Nbd-clmentioning

confidence: 99%

Eco-friendly analytical methods for the determination of compounds with disparate spectral overlapping: application to antiviral formulation of sofosbuvir and velpatasvir

et al. 2021

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Green analytical chemistry is one of the newest trends in analytical chemistry nowadays targeting the concept of green laboratory practices on chemists and environment. In this text, green practices are proposed in this work for the determination of sofosbuvir (SF) and velpatasvir (VP) in their pharmaceutical formulation. The analysis of SF in a binary mixture with VP represents an analytical challenge due to the complete overlapping of the UV spectrum of SF by that of VP. Therefore, the direct absorbance and derivative measurements cannot resolve such interference and failed to determine SF. In this paper, three direct and simple methods were developed for the analysis of SF without any interference from VP without sample pre-treatment. The proposed methods include measuring the second derivative amplitude of the ratio spectrum of the mixture using VP as a divisor, measuring the absorbance difference of the mixture in NaOH solution against its HCl solution, and using the derivative compensation technique. On the other hand, VP was determined specifically in presence of SF by two methods. Firstly, by its reaction with 4-chloro-7-nitrobenzofurazan (NBD-Cl) where the reaction product was measured spectrophotometrically and spectrofluorometrically and secondly through the reaction of VP with 3-methyl-2-benzothiazolinone hydrazone hydrochloride (MBTH). The calibration curves showed good correlation coefficient (r2 > 0.999). The developed methods were highly precise with RSD% values less than 2%. The method greenness profile was compared with other published methods by applying the eco-scale protocol. Assessment results proved that our analytical procedure is greener than other reported methods. Moreover, upon comparison with other methods, the proposed methods showed better or comparable sensitivity in addition to being inexpensive and ecofriendly. Accordingly, these methods could be readily applied for quality control purposes as an eco-friendly, simple and efficient analytical tool.

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Section: Determination Of Vp In Presence Of Sf Using Nbd-clmentioning

confidence: 99%

Eco-friendly analytical methods for the determination of compounds with disparate spectral overlapping: application to antiviral formulation of sofosbuvir and velpatasvir

et al. 2021

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“…6). Generally, the flash chromatography did not enable individual NBD-tagged polyamines to be obtained but allowed the dye to be purified from short-chain molecules that are formed due to cleavage of the polyamine chain in the reaction with NBD-Cl (Annenkov et al, 2015). Preparative isolation of the NBD-tagged polyamines was done with preparative HPLC in 0.1% TFA and resulted in several mg of pure samples 2NBD-N6, 2NBD-N9, 2NBD-N12, NBD-N9NH, NBD-N12NH, and a mixture of long polyamines 2NBD-N15 and 2NBD-N18.…”

Section: Synthesis Of Nbd-tagged Polyaminesmentioning

confidence: 99%

“…The previously obtained dye NBD-N5NH (Annenkov et al, 2015) was used to determine an optimal concentration for the staining of diatom frustules (Fig. 7) and a 2 μM concentration was chosen for further work.…”

Section: Staining Of Siliceous Diatom Frustules With Nbd-tagged Polyamentioning

confidence: 99%

“…Fluorescent derivatives of short-chain polyamines were obtained by reaction with 4-chloro-7-nitro-2,1,3benzoxadiazole (NBD-Cl) (Annenkov et al, 2010;Danilovtseva et al, 2013) and these substances were used in the study of the biosilicification mechanism (Annenkov et al, 2014). NBD-tagged polyamines containing 4 or 5 nitrogen atoms were used for the staining of diatom frustules in addition to the spicules of siliceous sponges (Annenkov et al, 2015). Diatom frustules and sponge spicules consist of transparent material which complicates study of these objects by light microscopy.…”

Section: Introductionmentioning

confidence: 99%

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Fluorescently-tagged polyamines for the staining of siliceous materials

Annenkov

Danilovtseva

Pal’shin

et al. 2018

Plant Physiology and Biochemistry

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Siliceous frustules of diatom algae contain unique long-chain polyamines, including those having more than six nitrogen atoms. These polyamines participate in the formation of the siliceous frustules of the diatoms but their precise physiological role is not clear. The main hypotheses include formation of a polyamine and polyphosphate supramolecular matrix. We have synthesized novel fluorescent dyes from a synthetic oligomeric mixture of polyamines and the fluorophore 7-nitro-2,1,3-benzoxadiazole. The long polyamine chain ensures the high affinity of these dyes to silica, which allows their application in the staining of siliceous materials, such as valves of diatom algae and fossilized samples from sediments. The fluorescently stained diatom valves were found to be promising liquid flow tracers in hydrodynamic tests. Furthermore, complexation of the polyamine component of the dyes with carbonic polymeric acids results in changes to the visible spectrum of the fluorophore, which allows study of the stability of the complex vs the length of the polyamine chain. Using poly (vinyl phosphonic acid) as a model for phosphate functionality in silaffins (a potential matrix in the formation of biogenic silica) little complexation with the polyamine fluorophores was observed, bringing into question the role of a polyamine - polymeric phosphate matrix in biosilicification.

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“…Study of NBD-Cl interaction with LCPAs (more than 4 nitrogen atoms) resulted in unexpected reaction of NBD-Cl with tertiary nitrogen atoms giving rise to NBD derivatives and unsaturated compounds (Annenkov et al, 2015). A set of new dyes containing relatively long polyamine substituents (≥3 nitrogen atoms) was prepared in this work (Fig.…”

Section: Fluorescent Derivatives Of Long Chain Polyaminesmentioning

confidence: 99%

Vital ﬂuorescent dyes for study of silicifying organisms

Annenkov

Zelinskiy

Pal’shin

et al. 2018

LFWB

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The mini-review describes application of vital fluorescent dyes to study silica biosynthesis in diatom algae and siliceous sponges. Mechanisms of these processes are not clear and study of growing siliceous constructions in living organisms is complicated with silica transparency and presence of mature elements (siliceous valves of diatoms and spicules of sponges). Specific fluorescence dyes stain growing siliceous elements of skeletons and also primary siliceous particles which are formed during silicon capture from the environment. Vital fluorescent dyes based on 7-nitro-2,1,3-benzoxadiazole, pyridyl oxazole and coumarin fluorophores are described as well as examples of application of these dyes to study diatom algae and siliceous sponges.

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Application of 4-chloro-7-nitrobenzo-2-oxa-1,3-diazole in analysis: Fluorescent dyes and unexpected reaction with tertiary amines

Cited by 15 publications

References 44 publications

Eco-friendly analytical methods for the determination of compounds with disparate spectral overlapping: application to antiviral formulation of sofosbuvir and velpatasvir

Eco-friendly analytical methods for the determination of compounds with disparate spectral overlapping: application to antiviral formulation of sofosbuvir and velpatasvir

Fluorescently-tagged polyamines for the staining of siliceous materials

Vital ﬂuorescent dyes for study of silicifying organisms

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