New preparation method for 9-anthryldiazomethane (ADAM) as a fluorescent labeling reagent for fatty acids and derivatives

Yoshida, Tsuguchika; Uetake, Atsuhiro; Yamaguchi, Hiroshi; Nimura, Noriyuki; Kinoshita, Toshio

doi:10.1016/0003-2697(88)90161-3

Cited by 59 publications

(30 citation statements)

References 30 publications

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“…One method that is widely used is liquid chromatography (LC) with fluorometric detection of 9-anthryldiazomethane (ADAM) derivatives, initially proposed by Lee et al (1987). Several laboratories have reported improvements to the method, such as the in situ method for preparation of the reagent (Yoshida et al, 1988;Quilliam et al, 1998) and better cleanup procedures (Quilliam, 1995;Stabell et al, 1991). LC combined with mass spectrometry (LC/ MS) is another method that is gaining acceptance as a good quantitative and confirmatory method for toxins (Quilliam, 1995;Quilliam et al, 1989).…”

Section: Introductionmentioning

confidence: 99%

Further Studies on the Analysis of DSP Toxin Profiles in Galician Mussels

Leão

Gago-Martı́nez

Vázquez

et al. 1999

J. Agric. Food Chem.

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Section: Introductionmentioning

confidence: 99%

Further Studies on the Analysis of DSP Toxin Profiles in Galician Mussels

Leão

Gago-Martı́nez

Vázquez

et al. 1999

J. Agric. Food Chem.

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“…The conditions previously optimized for application of "in situ" ADAM as derivatization reagent for DSP toxins [11] were applied in this work and the mobile phase was modified slightly with the aim of improving chromatographic resolution. Figure 3 (a and b) shows the chromatograms obtained after "in situ" ADAM derivatisation of a phytoplankton extract contaminated with DSP toxins.…”

Section: Resultsmentioning

confidence: 99%

“…Decomposition of the reagent can result in incomplete derivatization, and decomposition products can interfere in the analysis. Yoshida and co-workers [11] reported a method for "in situ" synthesis of ADAM. Improvements to the reaction conditions have been made in order to achieve the same reaction efficiency as with the commercial reagent [12].…”

Section: Introductionmentioning

confidence: 99%

Comparison of different fluorimetric HPLC methods for analysis of acidic polyether toxins in marine phytoplankton

Nogueiras

Gago-Martı́nez

Paniello

et al. 2003

Analytical and Bioanalytical Chemistry

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The human toxic syndrome, diarrhetic shellfish poisoning (DSP), is caused by polyether toxins that are present in bivalve molluscs but originate from some species of marine phytoplankton. During the last few years different HPLC methods with fluorescence detection (FLD) have been proposed for analysis of marine toxins, including polyether toxins, in shellfish and phytoplankton. Several derivatization reagents have been proposed in the literature, with the aim of converting the acidic DSP toxins into their corresponding fluorescent derivatives. In this work we report results obtained from HPLC-FLD analysis of extracts from phytoplankton, including Dinophysis spp.,harvested off the south-west coast of Ireland. Three different reagents were used for fluorescent derivatization: 3-bromomethyl-6,7-dimethoxy-1-methyl-2(1H)-quinoxalinone (BrDMEQ), 9-chloromethylanthracene (CA), and "in situ" 9-anthracenyldiazomethane (ADAM). Derivatization was performed under conditions previously optimised. The DSP derivatives were cleaned using different SPE procedures then analysed by HPLC-FLD. In this study, the use of BrDMEQ, CA, and "in situ" ADAM was compared in terms of sensitivity and selectivity. Evaluation of HPLC methods for analysis of DSP toxin derivatives was also conducted; the presence of okadaic acid (OA), dinophysistoxin-2 (DTX-2), and pectenotoxin-2 seco acids (PTX1SAs) was detected in the sample extracts studied.

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“…Therefore, derivatization of these analytes with labeling reagents has been widely adopted by HPLC with UV, especially fluorescence detection. The common reagents are as the following: (1) bromomethanes, such as 4-bromomethyl-7-methoxycoumarin(Br-Mmc) [23] and 4-bromomethyl-7-acetoxycoumarin (Br-Mac) [24]; (2) diazomethanes, such as 9-anthryldiazomethane (ADAM) [25,26] and 1-pyrenyldiazomethane (PDAM) [27]; (3) amines, such as 9-aminophenanthrene (9-AP) [28] and 5-(dimethylamino)-l-naphthalenesulponyl-semipiperazide (dansyl-semipiperazide) [29]; (4) hydrazides, such as 4-(1-methylphenanthro [9,10-d]imidazol-2-y1)benzohydrazide (MPIB-hydrazide) [30] and 4-(5,6-dimethoxy-2-benzimidazoyl)-benzohydrazide) (DMBI-hydrazide) [31]; (5) sulfonate ester reagents, such as 2-(2,3-naphthalimino)ethyl trifluoromethanesulphonate (NE-OTF) [32], 2-(2-naphthoxy)-ethyl-2-(piperidino)-ethanesulfonate (NOEPES) [33] and 2-(2,3-anthracene-dicarboximido) ethyl trifluoromethanesulfonate (AE-OTF) [34]. Nevertheless, Toyo'oka [35] has reported that many of these reagents have limitations in their applications such as low detection sensitivity, short detection wavelengths, poor stability, tedious analytical procedure and serious interferences in the biological sample analyses.…”

Section: Introductionmentioning

confidence: 99%

A Novel Labeling Reagent of 2-(12-Benzo[b]acridin-5-(12H)-yl)-acetohydrazide for Determination of Saturated and Unsaturated Fatty Acids in Traditional Chinese Herbs by HPLC-APCI-MS

Xie

You

et al. 2012

Chromatographia

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A new fluorescence labeling reagent 2-(12-benzo[b]acridin-5(12H)-yl)-acetohydrazide (BAAH) has been designed for fatty acids labeling. Eleven fatty acids containing seven saturated and four unsaturated fatty acids were used to evaluate the analytical potential of this reagent. The labeling reaction of BAAH with fatty acids was completed at 85°C for 60 min using 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (EDCÁHCl) as the condensing agent. Separation of the derivatized fatty acids was carried out on a reversed-phase Thermo Hypersil Gold C18 column (4.6 mm 9 250 mm, 5 lm) in combination with a gradient elution with a good baseline resolution. The fluorescence excitation and emission wavelengths were set at k ex 280 and k em 510 nm, respectively. The identification was carried out by the online APCI-MS in positive-ion detection mode. Linear correlation coefficients for all fatty acid derivatives were of [0.9994. Detection limits, at a signal-to-noise ratio of 3:1, were 3.89-12.5 nmol L -1 for the labeled fatty acids. The developed method was successfully applied to the accurate determination of fatty acids in five traditional Chinese herbs with satisfactory results.

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New preparation method for 9-anthryldiazomethane (ADAM) as a fluorescent labeling reagent for fatty acids and derivatives

Cited by 59 publications

References 30 publications

Further Studies on the Analysis of DSP Toxin Profiles in Galician Mussels

Further Studies on the Analysis of DSP Toxin Profiles in Galician Mussels

Comparison of different fluorimetric HPLC methods for analysis of acidic polyether toxins in marine phytoplankton

A Novel Labeling Reagent of 2-(12-Benzo[b]acridin-5-(12H)-yl)-acetohydrazide for Determination of Saturated and Unsaturated Fatty Acids in Traditional Chinese Herbs by HPLC-APCI-MS

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