Determination of Free Fatty Acids in o/w Injectable Emulsions by HPLC with Fluorescence Detection Using 4-(N,N-Dimethylaminosulfonyl)-7-N-piperazino-2,1,3-benzoxadiazole.

Ueno, Yumiko; Matsunaga, Hirokazu; Umemoto, Kazuichi; Nishijima, Koji

doi:10.1248/cpb.47.1375

Cited by 5 publications

(3 citation statements)

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“…The detection limits for DBD-PZ-carboxylic acids derivatives were 3.2-4.7 fmol (S/N = 3) using HPLC (Toyo'oka et al, 1991a). DBD-PZ was applied to the determination of prostaglandins (Toyo'oka et al, 1992b), a novel H 1 -receptor antagonist HSR-609 (Hasegawa et al, 1996), 2-arylpropionic acids on reversedphase and chiral stationary phase , D-and L-lactate on reversed-phase and chiral stationary phase Ichihara et al, 1999), free fatty acids (Ueno et al, 1999), and 2,7,8-trimethyl-2-(b-carboxyethyl)-6-hydroxy chroman (LLUa) on reversed-phase and chiral stationary phase (Hattori et al, 2000).…”

Section: For Carboxylic Acids Nbd-pzmentioning

confidence: 99%

Fluorogenic and fluorescent labeling reagents with a benzofurazan skeleton

Uchiyama

Santa

Okiyama

et al. 2001

Biomedical Chromatography

151

101

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Fluorogenic and fluorescent labeling reagents having a benzofurazan (2,1,3-benzoxadiazole) skeleton such as 4-fluoro-7-nitro-2,1,3-benzoxadiazole (NBD-F), 4-N,N-dimethylaminosulfonyl-7-fluoro-2,1,3-benzoxadiazole (DBD-F), 4-aminosulfonyl-7-fluoro-2,1,3-benzoxadiazole (ABD-F), ammonium 7-fluoro-2,1,3-benzoxadiazole-4-sulfonate (SBD-F), 4-hydrazino-7-nitro-2,1,3-benzoxadiazole (NBD-H), 4-N,N-dimethylaminosulfonyl-7-hydrazino-2,1,3-benzoxadiazole (DBD-H), 4-nitro-7-N-piperazino-2,1,3-benzoxadiazole (NBD-PZ), 4-N,N-dimethylaminosulfonyl-7-N-piperazino-2,1,3-benzoxadiazole (DBD-PZ), 4-(N-chloroformylmethyl-N-methyl)amino-7-N,N-dimethylaminosulfonyl-2,1,3-benzoxadiazole (DBD-COCl) and 7-N,N-dimethylaminosulfonyl-4-(2,1,3-benzoxadiazolyl) isothiocyanate (DBD-NCS) are reviewed in terms of synthetic method, reactivity, fluorescence characteristics, sensitivity and application to analytes.

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Section: For Carboxylic Acids Nbd-pzmentioning

confidence: 99%

Fluorogenic and fluorescent labeling reagents with a benzofurazan skeleton

Uchiyama

Santa

Okiyama

et al. 2001

Biomedical Chromatography

151

101

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“…An atmospheric pressure chemical ionization mass spectrometer (APCI-MS) is used as a detector. A sufficient number of works have been devoted to studies of fatty acid composition using HPLC [12][13][14][15][16][17][18][19][20][21].…”

Section: Introductionmentioning

confidence: 99%

Ultrasonic Cavitation Effect on the Fatty Acid Composition of Linseed Oil-Based Emulsions

Feofilaktova,

Feigelman,

Aboushanab

et al. 2023

JCPRM

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Ultrasonic homogenization is a promising method of emulsion formation. Linseed oil containing polyunsaturated fatty acids in the optimal ratio was used as a control sample and the fat base of the emulsions. The effect of ultrasonic treatment can lead to a change in the percentage of fatty acids due to the acceleration and initiation of several chemical reactions. To assess the feasibility of using ultrasound in food production, the fatty acid composition of natural linseed oil and emulsions obtained from it, treated by ultrasound with different durations were studied. The study monitored the formation of radicals since increasing temperature and pressure during the collapse of cavitation bubbles initiates the formation of free hydrogen H- and hydroxyl OH- radicals within and next to them. These may initiate the oxidation of bioorganic compounds in the food product. The research results show that emulsions exposure to the ultrasound at a frequency of 20 kHz for 10, 20 and 30 minutes are capable to maintain the ratio of fatty acids while obtaining a homogeneous, finely dispersed and stable food emulsion. Deviations in the values characterizing the fatty acids content in the emulsions treated by ultrasound for 10, 20 and 30 minutes as compared with the control sample – linseed oil are insignificant (0.02±0.015% to 0.83±0.015). Using the method of electron paramagnetic resonance, the absence of free radicals was established both in the control sample – flax oil, and in emulsions obtained on its basis, homogenized using ultrasonic exposure.

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“…In order to meet these criteria, we have developed fluorescent tagging reagents with the benzofuran (2,1,3-benzoxadiazole) skeleton with the advantages of high fluorescence quantum yield, high reactivity to the analytes, long excitation/emission wavelengths and large Stokes shifts. 4,5 These reagents, such as (4-nitro-7-N-piperazino-2,1,3-benzoxadiazole (NBD-PZ), 4-N,N-dimethylaminosulfonyl-7-N-piperazino-2,1,3-benzoxadiazole (DBD-PZ), 6 4-(2-aminoethylamino)-7-nitro-2,1,3-ben-zoxadiazole (NBD-ED), 4-N,N-dimethylaminosulfonyl-7-N-(2-aminoethyl)amino-2,1,3-benzoxadiazole (DBD-ED), 7 4-(N-hydrazinoformylmethy-N-methylamino-7-N,N-dimethylaminosulfonyl-2,1,3-benzoxadiazole (DBD-CO-Hz), 8 N-(4-nitro-2,1,3-benzoxadiazoyl-7-yl)-N-methyl-2-aminoacetohydrazide (NBD-CO-Hz), 9 4-N,N-dimethylaminosulfonyl-7-(3-aminopyrrolidin-1-yl)-2,1,3-benzoxadiazole (DBD-APy) 10 and 7-acetylamino-4-mercapto-2,1,3-benzoadiazole (AABD-SH), 11 have been developed for the sensitive quantification of prostaglandins, 12 H1-receptor antagonist HSR-609, 13 2-arylpropionic acids, 9 free fatty acids 14 and naproxen 15 in samples such as plasma, 9,15 urine, 13 drinks, 16 and bile. 17 Of these benzofuran reagents for the separation and quantification of saturated carboxylic acids, DBD-PZ is the best in terms of the sensitivity and reactivity, 5 but it is also hydrophobic.…”

Section: Introductionmentioning

confidence: 99%

Development of 7-(N,N-dimethylaminosulfonyl)-5-N-(4-N- aminoethyl)piperazino-2,1,3-benzoxadiazole as a water-soluble fluorogenic reagent for the sensitive liquid chromatographic determination of saturated carboxylic acids

Huang

Santa

Imai

2002

Analyst

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A reversed-phase high-performance liquid chromatographic (HPLC) method for the femtomole determination of nine saturated carboxylic acids, n-butyric (C4), n-hexanoic (C6), n-caprylic (C8), n-decanoic (C10), lauric (C12), n-tetradecanoic (C14), palmitic (C16), stearic (C18) and arachidic (C20), based on the condensation reaction of these acids with a newly synthesized water-soluble benzofurazan fluorescent reagent, 7-(N,N-dimethylaminosulfonyl)-4-N-(4-N-aminoethyl)piperazino-2,1,3-benzoxadiazole (DBD-PZ-NH2), was developed. The derivatization reaction proceeds with 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide (EDC) in the presence of the catalyst 4-(dimethylamino)pyridine (DMAP). A model derivative of the reagent with n-caprylic acid (C8) was synthesized for fluorescence excitation/emission characterization. Depending on the solvents, including water, methanol, acetonitrile, 1,4-dioxane or N.N-dimethyformamide (DMF), the C8 derivative has a fluorescence emission with a fluorescence quantum yield (phi) ranging from 0.01 to 0.20 in the region from 545 to 580 nm. An exponential increase in phi was observed with increasing acetonitrile content. The calculated detection limits (signal-to-noise ratio = 3:1) of the proposed method for the above nine carboxylic acids were 9.1, 4.0, 2.5, 2.2, 2.0, 1.8, 1.2, 1.0 and 1.3 fmol, respectively. Biological samples including Intralipos 20% and rat plasma were analysed satisfactorily.

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Determination of Free Fatty Acids in o/w Injectable Emulsions by HPLC with Fluorescence Detection Using 4-(N,N-Dimethylaminosulfonyl)-7-N-piperazino-2,1,3-benzoxadiazole.

Cited by 5 publications

References 0 publications

Fluorogenic and fluorescent labeling reagents with a benzofurazan skeleton

Fluorogenic and fluorescent labeling reagents with a benzofurazan skeleton

Ultrasonic Cavitation Effect on the Fatty Acid Composition of Linseed Oil-Based Emulsions

Development of 7-(N,N-dimethylaminosulfonyl)-5-N-(4-N- aminoethyl)piperazino-2,1,3-benzoxadiazole as a water-soluble fluorogenic reagent for the sensitive liquid chromatographic determination of saturated carboxylic acids

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