A critical overview on the chemistry, clean-up and recent advances in analysis of biogenic amines in foodstuffs

Mohammed, Gharam I.; Bashammakh, Abdulaziz S.; Al-Sibaai, A.A.; Alwael, H.; El-Shahawi, M.S.

doi:10.1016/j.trac.2016.02.007

Cited by 94 publications

(67 citation statements)

References 95 publications

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“…To associate amine recognition to af luorescent response, our strategy for receptord esign was the following: 1) Generate ac alix [6]-complex with as ingle exchangeable coordination site governed by the cavity.F or this purpose, we selected ar eadily available molecular scaffold, ac alix [6]arene core bearing three imidazole arms at the small rim and at ransition metal ion that displays as trong affinity for the tris-imidazole core. Ar edox-inactivem etal ion was chosen (Zn II )t oa void photo-induced electron transfer processes (PET); 2) Functionalize the calixarene large rim with three fluorophores that may act synergistically without disruptingt he smallrim coordination site; 3) The fluorophore, ideally,s hould display different responses, both in terms of wavelength and intensity,a safunctiono f the analyte.…”

Section: Receptor Design and Synthesismentioning

confidence: 99%

“…Calix [6]arene 1 bearingt hree aniline functions at its large rim was chosen as aprecursor to graft three quinoline moieties (see compound 2,F igure 1c). This choice wasd irected by several considerations.…”

Section: Receptor Design and Synthesismentioning

confidence: 99%

“…The design of macrocyclic hosts being inherently fluorescent responsive is much more rare and has been explored mainly with small scaffolds (such as calix[4]arenes [12] or cyclotriveratrilenes). [13] Over the last years, we have described and developed an originala pproachf or molecular recognition, based on the association of host-guest and coordination chemistry using macrocyclic receptorsdisplaying ametal ion in awell-defined coordination site at one edge of the cavity.T his biomimetic strategy led us to develop the concepts of funnel and bowl complexes, [14] based on the calix [6]arene andr esorcin[4]arene scaf-folds, respectively.W hereas the latter presentss trong affinities for organic anions, [15] the funnel complexes display remarkable guest recognition properties for neutral molecules having aL ewis base availablef or metal-ion coordination. The recognition pattern of the calix [6]-based funnel complexes is highly selectivet owards primary amines vs. secondary and tertiary due to the narrowness of the smallrim (Figure 1a).…”

Section: Introductionmentioning

confidence: 99%

“…[13] Over the last years, we have described and developed an originala pproachf or molecular recognition, based on the association of host-guest and coordination chemistry using macrocyclic receptorsdisplaying ametal ion in awell-defined coordination site at one edge of the cavity.T his biomimetic strategy led us to develop the concepts of funnel and bowl complexes, [14] based on the calix [6]arene andr esorcin[4]arene scaf-folds, respectively.W hereas the latter presentss trong affinities for organic anions, [15] the funnel complexes display remarkable guest recognition properties for neutral molecules having aL ewis base availablef or metal-ion coordination. The recognition pattern of the calix [6]-based funnel complexes is highly selectivet owards primary amines vs. secondary and tertiary due to the narrowness of the smallrim (Figure 1a). [16] The cone shape of the funnel adds selectivity in favor of guest ligands displaying i) ap rotic coordination group for H-bonding with the well-defineds econd coordination sphere( oxygen lone pairs of the calix core), and ii)alinear alkyl moiety that fits into the cavity,i np articular those bearing two or more methylene groups connected to the amino donor,w hich is ap attern commonf or many biogenic amines (e.g.,d opamine).…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Selective Fluorimetric Detection of Primary Alkylamines by a Calix[6]arene Funnel Complex

Rémy

Guyon

Rebilly

et al. 2017

Chemistry A European J

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The association of host-guest and coordination chemistry was used to develop a fluorescent molecular sensor. A calix[6]arene bearing three imidazole arms at the small rim and three quinoline fluorophores at the large rim was synthesized and characterized. A two-step coordination sequence was observed upon addition of Zn . The first Zn center binds the tris-imidazole small rim site, leading only to a small perturbation of the fluorescence. In contrast, a large bathochromic shift is observed upon binding of the second Zn center at the large rim as a result of the direct interaction of Zn with the quinoline fluorophores. The system acts as a selective receptor for primary amines. Host-guest adduct formation could be identified by a shift and enhancement of the fluorescence emission that is dependent on the length and shape of the primary amine. This system constitutes a fluorescent reporter with a selective response among primary amines.

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Section: Receptor Design and Synthesismentioning

confidence: 99%

Section: Receptor Design and Synthesismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Selective Fluorimetric Detection of Primary Alkylamines by a Calix[6]arene Funnel Complex

Rémy

Guyon

Rebilly

et al. 2017

Chemistry A European J

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show abstract

“…Artigos de revisão para análise de aminas biogênicas 14,15,16,17,18 e aminas aromáticas heterocíclicas 19 , em matrizes alimentícias são bastante comuns. Apesar de não estarem estritamente relacionadas com o tema dessa dissertação, tais compilações ajudam a melhorar o nosso entendimento sobre as possibilidades e estratégias de análise para aminas, num sentido mais amplo, e foram considerados na presente revisão.…”

Section: Determinação De Aminasunclassified

Determinação de dimetilaminopropilamina (DMAPA) por eletroforese capilar, após destilação por arraste de vapor, em formulações do tensoativo cocoamidopropil betaína (CAPB)

Santos¹

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DedicatóriasAo Prof. Dr. Joao P.S. Farah, pelas conversas sempre muito incentivadoras e principalmente pela colaboração crucial no desfecho positivo desta dissertação.Ao meu gerente Lívio Caribe da Rocha, que possibilitou a minha participação neste programa de mestrado, disponibilizando todos os recursos necessários para conclusão do mesmo.Ao meu gestor Marcelo Minghetti, que sempre me apoiou neste trabalho, permitindo sempre a minha saída da empresa, mesmo com tantas tarefas a serem executadas.A Gilberto Santos e Cláudio Leão, que me selecionaram entre muitos para participar deste programa, me possibilitando a realização deste sonho.A todos do grupo de pesquisa da Profa. Dra. Marina Franco Maggi Tavares que do menor ao maior envolvimento com este projeto, ajudaram a elabora-lo. Atualmente, o método adotado pela empresa Clariant S/A utiliza para a determinação desta substância, cromatografia líquida de alta eficiência (HPLC), entretanto, esta metodologia apresenta elevado tempo de análise e consumo de solventes, comprometendo a produtividade na indústria, por manter os reatores inoperantes na espera do resultado da análise. Meus sinceros agradecimentos a CarolinaExiste uma demanda crescente na indústria de cosméticos para utilização de metodologias que abordem critérios de tempo e custo na determinação de impurezas, para assegurar a qualidade dos produtos finais. Assim, com o intuito de aumentar a eficiência no processo de produção, este trabalho tem como objetivo propor um método rápido e confiável por eletroforese capilar para determinar o teor de DMAPA durante a produção (controles de processo) e no produto final do tensoativo CAPB.Neste trabalho foram abordadas diversas técnicas de preparo de amostra e condições instrumentais, para se alcançar um limite de quantificação (LOQ)≤ 10 mg kg -1 (especificação exigida pelo cliente no produto final).O DMAPA foi analisado como cátion, utilizando um eletrólito de corrida com imidazol e HIBA (ácido alpha hidroxibutírico), ambos com concentração de 0,01 mol L -1 e pH acertado para 4,0 utilizando uma solução de HCl 1,0 mol L -1 . The amphoteric surfactant cocoamidopropyl betaine (CAPB) is widely used in pharmaceuticals and cosmetics industries, and is considered an essential input for the formulation of liquid soaps, shampoos and facial cleansing gels. Its synthesis is based on the reaction between fatty acid and coconut dimethylaminopropylamine (DMAPA) and subsequent reaction with monocloroacetic acid (MCA). The excess of DMAPA, regarded as an impurity, needs to be monitored because of its skin, eyes and mucous membranes irritability and in some cases, it causes dermatitis.Currently, the method adopted by Clariant S/A Industry for the determination of this substance is based on high performance liquid chromatography (HPLC).However, this method has a high analysis time and solvent consumption, compromising the productivity because of the inactive reactors which cannot be operated without the results of DMAPA analysis.There is a growing demand in the cosmetics industry to...

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Impact of time and temperature of storage on the spoilage of swordfish and the evolution of biogenic amines through a multiway model

Ortiz

Sanllorente

Herrero

et al. 2017

Journal of Chemometrics

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A new multiway/multivariate approach is proposed to study and model the spoilage of swordfish with time and temperature of storage through the profiles of putrescine, spermidine, histamine, tyramine, tryptamine, cadaverine, spermine, and 2-phenylethylamine. The evolution of these biogenic amines in food is a complex process that cannot be characterized by a single parameter but by a modification of the amine profiles. An experimental strategy is designed to determine these profiles in such a way that data are structurally 3-way. Modeling the joint evolution of the biogenic amines with a PARAFAC model which explains 97.8% of variability (CORCONDIA index equals 100%) leads to estimate the storage time, storage temperature, and biogenic amines profiles. A multiple regression (determination coefficient of 0.98) based on the loadings of the 2 factors of the time profile of the PARAFAC model enables the estimation of the storage time with an error of 0.5 days.KEYWORDS biogenic amines, false discovery rate, HPLC-FLD, parallel factor analysis, spoilage of fish, 3-way data

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A critical overview on the chemistry, clean-up and recent advances in analysis of biogenic amines in foodstuffs

Cited by 94 publications

References 95 publications

Selective Fluorimetric Detection of Primary Alkylamines by a Calix[6]arene Funnel Complex

Selective Fluorimetric Detection of Primary Alkylamines by a Calix[6]arene Funnel Complex

Determinação de dimetilaminopropilamina (DMAPA) por eletroforese capilar, após destilação por arraste de vapor, em formulações do tensoativo cocoamidopropil betaína (CAPB)

Impact of time and temperature of storage on the spoilage of swordfish and the evolution of biogenic amines through a multiway model

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