Bio-metal-organic frameworks for molecular recognition and sorbent extraction of hydrophilic vitamins followed by their determination using HPLC-UV

Microchimica Acta - Tập 187 - Trang 1-8 - 2020
Héctor Martínez Pérez-Cejuela1, Marta Mon2, Jesús Ferrando-Soria2, Emilio Pardo2, Donatella Armentano3, Ernesto F. Simó-Alfonso1, José Manuel Herrero-Martínez1
1Department of Analytical Chemistry, University of Valencia, Valencia, Spain
2Department of Inorganic Chemistry, Institute of Molecular Science (ICMOL), University of Valencia, Valencia, Spain
3Dipartimento di Chimica e Tecnologie Chimiche (CTC), Università della Calabria, Rende, Italy

Tóm tắt

A bio-metal-organic framework (bio-MOF) derived from the amino acid L-serine has been prepared in bulk form and evaluated as sorbent for the molecular recognition and extraction of B-vitamins. The functional pores of bio-MOF exhibit high amounts of hydroxyl groups jointly directing other supramolecular host-guest interactions thus providing the recognition of B-vitamins in fruit juices and energy drinks. Single-crystal X-ray diffraction studies reveal the specific B-vitamin binding sites and the existence of multiple hydrogen bonds between these target molecules and the framework. It offered unique snapshots to accomplish an efficient capture of these solutes in complex aqueous matrices. Four B-vitamins (thiamin, nicotinic acid, nicotinamide, and pyridoxine) were investigated. They were eluted from the sorbent with phosphate buffer at pH 7 and analyzed by HPLC with UV detection. The sorbent was compared with commercial C18 cartridges. Following the procedure, acceptable reproducibility (RSD values < 14%) was achieved, and the detection limits were in the range 0.4 to 1.4 ng mL−1. The method was applied to the analysis of energy drink and juice samples and the recoveries were between 75 and 123% in spiked beverage samples.

Tài liệu tham khảo

Nouar F, Eubank JF, Bousquet T, Wojtas L, Zaworotko MJ, Eddaoudi M (2008) Supermolecular building blocks (SBBs) for the design and synthesis of highly porous metal-organic frameworks. J Am Chem Soc 130(6):1833–1835. https://doi.org/10.1021/ja710123s Férey G (2008) Hybrid porous solids: past, present, future. Chem Soc Rev 37(1):191–214. https://doi.org/10.1039/B618320B Safaei M, Foroughi MM, Ebrahimpoor N, Jahani S, Omidi A, Khatami M (2019) A review on metal-organic frameworks: synthesis and applications. TrAC Trends Anal Chem 118:401–425. https://doi.org/10.1016/j.trac.2019.06.007 Li H, Wang K, Sun Y, Lollar CT, Li J, Zhou HC (2018) Recent advances in gas storage and separation using metal-organic frameworks. Mater Today 21(2):108–121. https://doi.org/10.1016/j.mattod.2017.07.006 Liu C, Yu LQ, Zhao YT, Lv YK (2018) Recent advances in metal-organic frameworks for adsorption of common aromatic pollutants. Microchim Acta 185:342. https://doi.org/10.1007/s00604-018-2879-2 Zhang Q, Yu J, Cai J, Song R, Cui Y, Yang Y, Chen B, Qian G (2014) A porous metal-organic framework with –COOH groups for highly efficient pollutant removal. Chem Comm 50(92):14455–14458. https://doi.org/10.1039/c4cc06648k Zhao Y (2016) Emerging applications of metal–organic frameworks and covalent organic frameworks. Chem Mater 28(22):8079–8081. https://doi.org/10.1021/acs.chemmater.6b04677 Lin RB, Xiang S, Xing H, Zhou W, Chen B (2019) Exploration of porous metal–organic frameworks for gas separation and purification. Coord Chem Rev 378:87–103. https://doi.org/10.1016/j.ccr.2017.09.027 Zhao X, Wang Y, Li DS, Bu X, Feng P (2018) Metal-Organic Frameworks for Separation. Adv Mater 30(37):1705189. https://doi.org/10.1002/adma.201705189 Maya F, Cabello CP, Figuerola A, Palomino GT, Cerdà V (2019) Immobilization of metal–organic frameworks on supports for sample preparation and chromatographic separation. Chromatographia 82(1):361–375. https://doi.org/10.1007/s10337-018-3616-z Gu ZY, Yang CX, Chang NA, Yan XP (2012) Metal–organic frameworks for analytical chemistry: from sample collection to chromatographic separation. Acc Chem Res 45(5):734–745. https://doi.org/10.1021/ar2002599 Bautista PR, Fernandez IP, Pasan J, Pino V (2016) Are metal-organic frameworks able to provide a new generation of solid-phase microextraction coatings?–a review. Anal Chim Acta 939:26–41. https://doi.org/10.1016/j.aca.2016.07.047 McKinlay AC, Morris RE, Horcajada P, Férey G, Gref R, Couvreur P, Serre C (2010) BioMOFs: metal–organic frameworks for biological and medical applications. Angew Chem Int Ed 49(36):6260–6266. https://doi.org/10.1002/anie.201000048 Cai H, Huang YL, Li D (2019) Biological metal–organic frameworks: structures, host–guest chemistry and bio-applications. Coord Chem Rev 378:207–221. https://doi.org/10.1016/j.ccr.2017.12.003 Mon M, Qu X, Soria JF, Carreño IP, Escribano AS, Fernandez EVR, Jansen CJ, Armentano D, Pardo E (2017) Fine-tuning of the confined space in microporous metal–organic frameworks for efficient mercury removal. J Mater Chem A 5(38):20120–20125. https://doi.org/10.1039/C7TA06199D Ikezoe Y, Washino G, Uemura T, Kitagawa S, Matsui H (2012) Autonomous motors of a metal–organic framework powered by reorganization of self-assembled peptides at interfaces. Nat Mater 11(12):1081–1085. https://doi.org/10.1038/nmat3461 Sun RWY, Zhang M, Li D, Zhang ZF, Cai H, Li M, Xian YJ, Ng SW, Wong AST (2015) Dinuclear gold (I) pyrrolidinedithiocarbamato complex: cytotoxic and antimigratory activities on cancer cells and the use of metal–organic framework. Chem Eur J 21(51):18534–18538. https://doi.org/10.1002/chem.201503656 Ma Y, Su H, Kuang X, Li X, Zhang T, Tang B (2014) Heterogeneous nano metal–organic framework fluorescence probe for highly selective and sensitive detection of hydrogen sulfide in living cells. Anal Chem 86(22):11459–11463. https://doi.org/10.1021/ac503622n Zhao M, Wu CD (2017) Biomimetic activation of molecular oxygen with a combined metalloporphyrinic framework and co-catalyst platform. ChemCatChem 9(7):1192–1196. https://doi.org/10.1002/cctc.201601606 Yang J, Trickett CA, Alahmadi SB, Alshammari AS, Yaghi OM (2017) Calcium l-lactate frameworks as naturally degradable carriers for pesticides. J Am Chem Soc 139(24):8118–8121. https://doi.org/10.1021/jacs.7b04542 Zhang JH, Nong RY, Xie SM, Wang BJ, Ai P, Yuan LM (2017) Homochiral metal-organic frameworks based on amino acid ligands for HPLC separation of enantiomers. Electrophoresis. 38(19):2513–2520. https://doi.org/10.1002/elps.201700122 Sánchez JN, García AIA, Martínez YM, Sanjuán DR, Antypov D, Falco PC, Rosseinsky MJ, Gastaldo CM (2017) Peptide metal–organic frameworks for enantioselective separation of chiral drugs. J Am Chem Soc 139(12):4294–4297. https://doi.org/10.1021/jacs.7b00280 Mon M, Soria JF, Grancha T, Pérez FRF, Gascon J, Pérez AL, Armentano D, Pardo E (2016) Selective gold recovery and catalysis in a highly flexible methionine-decorated metal–organic framework. J Am Chem Soc 138(25):7864–7867. https://doi.org/10.1021/jacs.6b04635 Stough C, Scholey A, Lloyd J, Spong J, Myers S, Downey LA (2011) The effect of 90 day administration of a high dose vitamin B-complex on work stress. Hum Psychopharm Clin 26(7):470–476. https://doi.org/10.1002/hup.1229 Heckman MA, Sherry K, De Mejia EG (2010) Energy drinks: an assessment of their market size, consumer demographics, ingredient profile, functionality, and regulations in the United States. Compr Rev Food Sci F 9(3):303–317. https://doi.org/10.1111/j.1541-4337.2010.00111.x Eiroa AA, Canle M, Cancellieri VL, Cerdà V (2016) Solid-phase extraction of organic compounds: a critical review (part I). TrAC-Trends Anal Chem 80:641–654. https://doi.org/10.1016/j.trac.2015.08.015 Fatima Z, Jin X, Zou Y, Kaw HY, Quinto M, Li D (2019) Recent trends in analytical methods for water-soluble vitamins. J Chromatogr A 1606:360245. https://doi.org/10.1016/j.chroma.2019.05.025 Heal KR, Carlson LT, Devol AH, Armbrust EV, Moffett JW, Stahl DA, Ingalls AE (2014) Determination of four forms of vitamin B12 and other B vitamins in seawater by liquid chromatography/tandem mass spectrometry. Rapid Commun Mass Spectrom 28(22):2398–2404. https://doi.org/10.1002/rcm.7040 Mon M, Bruno R, Soria JF, Bartella L, Donna LD, Talia M, Lappano R, Maggiolini M, Armentano D, Pardo E (2018) Crystallographic snapshots of host–guest interactions in drugs@ metal–organic frameworks: towards mimicking molecular recognition processes. Mat Horiz 5(4):683–690. https://doi.org/10.1039/C8MH00302E Ostovan A, Ghaedi M, Arabi M, Yang Q, Li J, Chen L (2018) Hydrophilic multitemplate molecularly imprinted biopolymers based on a green synthesis strategy for determination of B-family vitamins. ACS Appl Mater Inter 10(4):4140–4150. https://doi.org/10.1021/acsami.7b17500 Chatzimichalakis PF, Samanidou VF, Verpoorte R, Papadoyannis IN (2004) Development of a validated HPLC method for the determination of B-complex vitamins in pharmaceuticals and biological fluids after solid phase extraction. J Sep Sci 27(14):1181–1188. https://doi.org/10.1002/jssc.200401858 Ekinci R, Kadakal Ç (2005) Determination of seven water-soluble vitamins in tarhana, a traditional Turkish cereal food, by high-performance liquid chromatography. Acta Chromatogr 15:289 Chamkouri N, Khodadoust S, Ghalavandi F (2015) Solid-phase extraction coupled with HPLC-DAD for determination of B vitamin concentrations in halophytes. J Chromatogr Sci 53(10):1720–1724. https://doi.org/10.1093/chromsci/bmv080 Cubarsí MG, Sárraga C, Clariana M, Regueiro JAG, Castellari M (2011) Analysis of vitamin B1 in dry-cured sausages by hydrophilic interaction liquid chromatography (HILIC) and diode array detection. Meat Sci 87(3):234–238. https://doi.org/10.1016/j.meatsci.2010.10.017 Fan B, You J, Suo Y, Qian C (2018) A novel and sensitive method for determining vitamin B3 and B7 by pre-column derivatization and high-performance liquid chromatography method with fluorescence detection. PLoS One 13(6). https://doi.org/10.1371/journal.pone.0198102