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Cyclodextrin-Promoted Fluorescence Detection of Aromatic Toxicants and Toxicant Metabolites in Commercial Milk Products

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Abstract

The detection of polycyclic aromatic hydrocarbons (PAHs) and their metabolites in food and in agricultural sources is an important research objective due to the PAHs’ known persistence, carcinogenicity, and toxicity. PAHs have been found in the milk of lactating cows and in the leaves and stems of plants grown in PAH-contaminated areas, thereby making their way into both cow milk and plant milk alternatives. Reported herein is the rapid, sensitive, and selective detection of 10 PAHs and PAH metabolites in a variety of cow milks and plant milk alternatives using fluorescence energy transfer from the PAH to a high quantum yield fluorophore, combined with subsequent array-based statistical analyses of the fluorescence emission signals. This system operates with high sensitivity (low micromolar detection limits), selectivity (100% differentiation even between structurally similar analytes), and general applicability (for both unmodified lipophilic PAHs and highly polar oxidized PAH metabolites, as well as for different cow and plant milk samples). These promising results show significant potential to be translated into solid-state devices for the rapid, sensitive, and selective detection of PAHs and their metabolites in complex, commercial food products.

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References

  • Aiken AC, DeCarlo PF, Jimenez JL (2007) Elemental analysis of organic species with electron ionization high-resolution mass spectrometry. Anal Chem 79:8350–8358

    Article  CAS  PubMed  Google Scholar 

  • Allan SE, Smith BW, Anderson KA (2012) Impact of the Deepwater Horizon oil spill on bioavailable polycyclic aromatic hydrocarbons in Gulf of Mexico coastal waters. Environ Sci Technol 46:2033–2039

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Amini M, Esmaillzadeh A, Shafaeizadeh S, Behrooz J, Zare M (2010) Relationship between major dietary patterns and metabolic syndrome among individuals with impaired glucose tolerance. Nutrition 26:986–992

    Article  CAS  PubMed  Google Scholar 

  • Baduel C, Mueller JF, Tsai H, Ramos MJG (2015) Development of sample extraction and clean-up strategies for target and non-target analysis of environmental contaminants in biological matrices. J Chromatogr A 1426:33–47

    Article  CAS  PubMed  Google Scholar 

  • Bahri A, Martin M, Gergely C, Pugniere M, Chevalier-Lucia D, Marchesseau S (2017) Atomic force microscopy study of the topography and nanomechanics of casein micelles captured by an antibody. Langmuir 33:4720–4728

    Article  CAS  PubMed  Google Scholar 

  • Bajaj A, Miranda OR, Phillips R, Kim I, Jerry DJ, Bunz UHF, Rotello VM (2010) Array based sensing of normal, cancerous and metastatic cells using conjugated fluorescent polymers. J Am Chem Soc 132:1018–1022

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Brown AS, Brown RJC, Coleman PJ, Conolly C, Sweetman AJ, Jones KC, Butterfield DM, Sarantaridis D, Donovan BJ, Roberts I (2013) Twenty years of measurements of polycyclic aromatic hydrocarbons (PAHs) in UK ambient air by nationwide air quality networks. Environ Sci Process Impacts 15:1199–1215

    Article  CAS  PubMed  Google Scholar 

  • Ceccaroli C, Pulliero A, Geretto M, Izzotti A (2015) Molecular fingerprints of environmental carcinogens in human cancer. J Environ Sci Health C 33:188–228

    Article  CAS  Google Scholar 

  • Cheng D, Zhao W, Yang H, Huang Z, Liu X, Han A (2016) Detection of Hg2+ by a FRET ratiometric fluorescent probe based on a novel BODIPY-RhB system. Tetrahedron Lett 57:2655–2659

    Article  CAS  Google Scholar 

  • Chepelev NL, Moffat ID, Labib S, Bourdon-Lacombe J, Kuo B, Buick JK, Lemieux F, Malik AI, Halappanavar S, Williams A, Yauk CL (2015) Integrating toxicogenomics into human health risk assessment: lessons learned from the benzo[a]pyrene case study. Critical Rev Toxicol 45:44–52

    Article  CAS  Google Scholar 

  • Choudhury B, Das BP (1983) Larvicidal activity of some reduced carbazoles and compounds containing the methylenedioxyphenyl ring. Current Sci 52:1130–1132

    CAS  Google Scholar 

  • Creran B, Bunz UHF, Rotello VM (2015) Polymer-nanoparticle assemblies for array based sensing. Curr Org Chem 109:1054–1062

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Dai L, Liu K, Wang L, Liu J, He J, Liu X, Lei J (2017) Injectable and thermosensitive supramolecular hydrogels by inclusion complexation between binary-drug loaded micelles and α-cyclodextrin. Mater Sci Eng C 76:966–974

    Article  CAS  Google Scholar 

  • Das BP, Das K, Chowdhury DN, Das GK, Choudhury B (1998) Comparative pesticidal studies of 1,2,3,4-tetrahydrocarbazole and 2-methyl-1, 2, 3,4-tetrahydrocarbazole. Environment. Ecology 16:405–408

    CAS  Google Scholar 

  • Delgado B, Pino V, Ayala JH, González V, Afonso AM (2004) Nonionic surfactant mixtures: a new cloud-point extraction approach for the determination of PAHs in seawater using HPLC with fluorimetric detection. Anal Chim Acta 528:165–172

    Article  CAS  Google Scholar 

  • DiScenza DJ, Levine M (2016a) Selective detection of non-aromatic pesticides via cyclodextrin-promoted fluorescence modulation. New J Chem 40:789–793

    Article  CAS  Google Scholar 

  • DiScenza DJ, Levine M (2016b) Sensitive and selective detection of alcohols via fluorescence modulation. Supramol Chem 28:881–889

    Article  CAS  Google Scholar 

  • DiScenza DJ, Gareau L, Serio N, Roque J, Prignano L, Verderame M, Levine M (2016a) Cyclodextrin-promoted detection of toxicants and toxicant metabolites in urine. Anal Chem Lett 6:345–355

    Article  CAS  Google Scholar 

  • DiScenza DJ, Verderame M, Levine M (2016b) Detection of benzene and alkylated benzene derivatives in fuel contaminated environments. CLEAN: Soil Air Water 44:1621–1627

    CAS  Google Scholar 

  • DiScenza DJ, Lynch J, Verderame M, Serio N, Prignano L, Gareau L, Levine M (2017a) Efficient fluorescence detection of aromatic toxicants and toxicant metabolites in human breast milk. Supramol Chem https://doi.org/10.1080/1610278.2017.1343947

  • DiScenza DJ, Lynch J, Miller J, Verderame M, Levine M (2017b) Detection of organochlorine pesticides in contaminated marine environments via cyclodextrin-promoted fluorescence modulation. ACS Omega 2:8591–8599

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Balcioglu EB (2016) Potential effects of polycyclic aromatic hydrocarbons (PAHs) in marine foods on human health: a critical review. Toxin Rev 35:98–105

    Article  CAS  Google Scholar 

  • Fagbemi TN (2009) Effect of processing on chemical composition of cashew nut (Anacardium occidentale). J Food Sci Technol 46:36–40

    CAS  Google Scholar 

  • Forth HP, Mitchelmore CL, Morris JM, Lipton J (2017) Characterization of oil and water accommodated fractions used to conduct aquatic toxicity testing in support of the Deepwater Horizon oil spill natural resource damage assessment. Environ Sci Technol 36:1450–1459

    CAS  Google Scholar 

  • Frysinger GS, Gaines RB, Xu L, Reddy CM (2003) Resolving the unresolved complex mixture in petroleum-contaminated sediments. Environ Sci Technol 37:1653–1662

    Article  CAS  PubMed  Google Scholar 

  • Ghosh P, Mandal S, Das T, Maity A, Gupta P, Purkayastha P (2012) “Extra stabilization” of a pyrene based molecular couple by γ-cyclodextrin in the excited electronic state. Phys Chem Chem Phys 14:11500–11507

    Article  CAS  PubMed  Google Scholar 

  • Girello AM, Sperati D, Tarola AM (2014) Determination of polycyclic aromatic hydrocarbons in Italian milk by HPLC with fluorescence detection. Food Addit Contam 31:703–710

    Article  CAS  Google Scholar 

  • Haug A, Hostmark AT, Harstad OM (2007) Bovine milk in human nutrition—a review. Lipids Health Dis 6:25–41

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Hayakawa K (2016) Environmental behaviors and toxicities of polycyclic aromatic hydrocarbons and nitropolycyclic aromatic hydrocarbons. Chem Pharm Bull 64:83–94

    Article  CAS  PubMed  Google Scholar 

  • Hizir MS, Robertson NM, Balcioglu M, Alp E, Rana M, Yigit MV (2017) Universal sensor array for highly selective system identification using two-dimensional nanoparticles. Chem Sci 8:5735–5745

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Howsam M, Jones KC, Ineson P (2001) PAHs associated with the leaves of three deciduous tree species. II: uptake during a growing season. Chemosphere 44:155–164

    Article  CAS  PubMed  Google Scholar 

  • Jaiswal P, Jha SN, Borah A, Jindal G (2015) Detection and quantification of soymilk in cow-buffalo milk using attenuated total reflectance Fourier transform infra-red spectroscopy (ATR-FTIR). Food Chem 168:41–47

    Article  CAS  PubMed  Google Scholar 

  • Jarvis IW, Dreij K, Mattsson A, Jernstrom B, Stenius U (2014) Interactions between polycyclic aromatic hydrocarbons in complex mixtures and implications for cancer risk assessment. Toxicology 321:27–39

    Article  CAS  PubMed  Google Scholar 

  • Ji H, Xi K, Zhang Q, Jia X (2017) Photodegradable hydrogels for external manipulation of cellular microenvironments with real-time monitoring. RSC Adv 7:24331–24337. https://doi.org/10.1039/c7ra02629c

    Article  CAS  Google Scholar 

  • Jiang N, Fan J, Liu T, Cao J, Qiao B, Wang J, Gao P, Peng X (2013) A near-infrared dye based on BODIPY for tracking morphology changes in mitochondria. Chem Commun 4:10620–10622

    Article  CAS  Google Scholar 

  • Jongeneelen FJ, Anzion RBM, Henderson PT (1987) Determination of hydroxylated metabolites of polycyclic aromatic hydrocarbons in urine. J Chromatogr Biomed Appl 413:227–232

    Article  CAS  Google Scholar 

  • Kamath S, Webb RE, Deeth HC (2011) The composition of interfacial material from skim milk foams. J Dairy Sci 94:2707–2718

    Article  CAS  PubMed  Google Scholar 

  • Khalili NR, Scheff PA, Holsen TM (1995) PAH source fingerprints for coke ovens, diesel and gasoline engines, highway tunnels, and wood combustion emissions. Atmos Environ 29:533–542

    Article  CAS  Google Scholar 

  • Lee SY, Lee JY, Shin HS (2015) Evaluation of chemical analysis method and determination of polycyclic aromatic hydrocarbons content from seafood and dairy products. Toxicol Res 31:265–271

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Leroux C, Bernard L, Faulconnier Y, Rouel J, de la Foye A, Domagalski J, Chilliard Y (2016) Bovine mammary nutrigenomics and changes in the milk composition due to rapeseed or sunflower oil supplementation of high-forage or high-concentrate diets. J Nutrigenet Nutrigenomics 9:65–82

    Article  CAS  PubMed  Google Scholar 

  • Ma Y, Liu A, Egodawatta P, McGree J, Goonetilleke A (2017) Assessment and management of human health risk from toxic metals and polycyclic aromatic hydrocarbons in urban stormwater arising from anthropogenic activities and traffic congestion. Sci Total Environ 579:202–211

    Article  CAS  PubMed  Google Scholar 

  • Madhavan ND, Naidu KA (1995) Polycyclic aromatic hydrocarbons in placenta, maternal blood, umbilical cord blood and milk of Indian women. Human Experiment Toxicol 14:503–506

    Article  CAS  Google Scholar 

  • Mako T, Marks P, Cook N, Levine M (2012) Fluorescent detection of polycyclic aromatic hydrocarbons in ternary cyclodextrin complexes. Supramol Chem 24:743–747

    Article  CAS  Google Scholar 

  • Manzetti S (2013) Polycyclic aromatic hydrocarbons in the environment: environmental fate and transformation. Polycyclic Aromatic Comp 33:311–330

    Article  CAS  Google Scholar 

  • Marfin YS, Merkushev DA, Levshanov GA, Rumyantsev EV (2014) Fluorescent properties of 8-phenyl-BODIPY in ethanol-ethylene glycol mixed solutions. J Fluoresc 24:1613–1619

    Article  CAS  PubMed  Google Scholar 

  • Marini M, Frapiccini E (2013) Persistence of polycyclic aromatic hydrocarbons in ocean sediments. Chemosphere 90:1839–1846

    Article  CAS  PubMed  Google Scholar 

  • Massey LK (2003) Dietary animal and plant protein and human bone health: a whole foods approach. J Nutrition 133:862S–865S

    Article  CAS  Google Scholar 

  • Mearns AJ, Reish DJ, Oshida PS, Ginn T, Rempel-Hester MA, Arthur C, Rutherford N, Pryor R (2015) Effects of pollution on marine organisms. Water Environ Res 87:1718–1816

    Article  CAS  PubMed  Google Scholar 

  • Milles S, Meyer T, Scheidt HA, Schwarzer R, Thomas L, Marek M, Szente L, Bittman R, Herrmann A, Guenther Pomorski T, Huster D, Mueller P (2013) Organization of fluorescent cholesterol analogs in lipid bilayers—lessons from cyclodextrin extraction. Biochim Biophys Acta 1828:1822–1828

    Article  CAS  PubMed  Google Scholar 

  • Miranda OR, Creran B, Rotello VM (2010) Array-based sensing with nanoparticles: ‘chemical noses’ for sensing biomolecules and cell surfaces. Curr Opin Chem Biol 14:728–736

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Mousset E, Oturan MA, Van Hullebusch ED, Guibaud G, Esposito G (2014) Soil washing/flushing treatments of organic pollutants enhanced by cyclodextrins and integrated treatments: state of the art. Critical Rev Environ Sci Technol 44:705–795

    Article  CAS  Google Scholar 

  • Munoz de la Pena A, Ndou T, Zung ZB, Warner IM (1991) Stoichiometry and formation constants of pyrene inclusion complexes with .beta.- and .gamma.-cyclodextrin. J Phys Chem 95:3330–3334

    Article  CAS  Google Scholar 

  • Nieva-Cano MJ, Rubio-Barroso S, Santos-Delgado MJ (2001) Determination of PAH in food samples by HPLC with fluorimetric detection following sonication extraction without sample clean-up. Analyst 126:1326–1331

    Article  CAS  PubMed  Google Scholar 

  • Nik AM, Tosh S, Poysa V, Woodrow L, Corredig M (2008) Physicochemical characterization of soymilk after step-wise centrifugation. Food Res Int 41:286–294

    Article  CAS  Google Scholar 

  • Occupational Safety & Health Administration (OSHA) (2012). Chemical sampling information: coal tar pitch volatiles (benzene soluble fractions). Occupational Safety & Health Administration. https://www.osha.gov/dts/chemicalsampling/data/CH_229000.html. Accessed Jul 5, 2017

  • Pfannkoch EA, Stuff JR, Whitecavage JA (2010) High throughput method for the determination of PAHs in seafood by QuEChERS-SBSE-GC-MS. AppNote Global Analytical Solutions AN/2010/6b-1/AN/2010/6b-11

  • Phatangare KR, Lanke SK, Sekar N (2014) Fluorescent coumarin derivatives with viscosity sensitive emission—synthesis, photophysical properties and computational studies. J Fluoresc 24:1263–1274

    Article  CAS  PubMed  Google Scholar 

  • Qin YY, Leung CKM, Lin CK, Leung AOW, Wang HS, Giesy JP, Wong MH (2011) Halogenated POPs and PAHs in blood plasma of Hong Kong residents. Environ Sci Technol 45:1630–1637

    Article  CAS  PubMed  Google Scholar 

  • Ren L, Kim YJ, Park SY, Lee S, Lee J, Park CP, Lim YT (2016) Rapid fluorescence detection of hypoxic microenvironments by nitro-benzyl conjugated chitosan nanoparticles encapsulating hydrophobic fluorophores. J Mater Chem B 4:4832–4838

    Article  CAS  Google Scholar 

  • Rodionova OA, Puzyk MV, Balashev KP (2008) Effect of cyclopalladation on the spectroscopic properties of a Coumarin dye. Opt Spectosc 105:62–66

    Article  CAS  Google Scholar 

  • Rozenberg S, Body JJ, Bruyere O, Bergmann P, Brandi ML, Cooper C, Devogelaer JP, Gielen E, Goemaere S, Kaufman JM, Rizzoli R, Reginster JY (2016) Effects of dairy products consumption on health: benefits and beliefs- a commentary from the Belgian Bone Club and the European Society for clinical and economic aspects of osteoporosis, osteoarthritis, and musculoskeletal diseases. Calcif Tissue Int 98:1–17

    Article  CAS  PubMed  Google Scholar 

  • Ruby MV, Lowney YW (2012) Selective soil particle adherence to hands: implications for understanding oral exposure to soil contaminants. Environ Sci Technol 46:12759–12771

    Article  CAS  PubMed  Google Scholar 

  • Santonicola S, Albrizio S, Murru N, Ferrante MC, Mercogliano R (2017) Study on the occurrence of polycyclic aromatic hydrocarbons in milk and meat/fish based baby food available in Italy. Chemosphere 184:467–472

    Article  CAS  PubMed  Google Scholar 

  • Sarkar I, Prakash RHS, Desai A, Mishra AK (2015) Utilizing an aggregate forming microenvironment sensitive coumarin-cholesterol conjugate as a sensor of pluronic organization and micro-polarity. RSC Adv 5:97279–97288

    Article  CAS  Google Scholar 

  • Scilewski da Costa Zanatta T, Manica-Berto R, Ferreira CD, Cardozo MMC, Rombaldi CV, Zambiazi RC, Dias ARG (2017) Phosphate fertilizer and growing environment change the phytochemicals, oil quality, and nutritional composition of roundup ready genetically modified and conventional soybean. J Agric Food Chem 65:2661–2669

    Article  CAS  PubMed  Google Scholar 

  • Serio N, Levine M (2015) Efficient extraction and detection of aromatic toxicants from crude oil and tar balls using multiple cyclodextrin derivatives. Marine Poll Bull 95:242–247

    Article  CAS  Google Scholar 

  • Serio N, Levine M (2016) Solvent effects in the extraction and detection of polycyclic aromatic hydrocarbons from complex oils in complex environments. J Incl Phenom Macrocycl Chem 84:61–70

    Article  CAS  Google Scholar 

  • Serio N, Chanthalyma C, Prignano L, Levine M (2013a) Cyclodextrin-enhanced extraction and energy transfer of carcinogens in complex oil environments. ACS Appl Mater Interfaces 5:11951–11957

    Article  CAS  PubMed  Google Scholar 

  • Serio N, Miller K, Levine M (2013b) Efficient detection of polycyclic aromatic hydrocarbons and polychlorinated biphenyls via three-component energy transfer. Chem Commun 49:4821–4823

    Article  CAS  Google Scholar 

  • Serio N, Chanthalyma C, Prignano L, Levine M (2014a) Cyclodextrin-promoted energy transfer for broadly applicable small-molecule detection. Supramol Chem 26:714–721

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Serio N, Prignano L, Peters S, Levine M (2014b) Detection of medium-sized polycyclic aromatic hydrocarbons via fluorescence energy transfer. Polycyclic Aromatic Comp 34:561–572

    Article  CAS  Google Scholar 

  • Serio N, Chanthalyma C, Peters S, Levine D, Levine M (2015a) 2-Hydroxypropyl beta-cyclodextrin for the enhanced performance of dual function extraction and detection systems in complex oil environments. J Incl Phenom Macrocycl Chem 81:341–346

    Article  CAS  Google Scholar 

  • Serio N, Moyano DF, Rotello VM, Levine M (2015b) Array-based detection of persistent organic pollutants via cyclodextrin-promoted energy transfer. Chem Commun 51:11615–11618

    Article  CAS  Google Scholar 

  • Serio N, Roque J, Badwal A, Levine M (2015c) Rapid and efficient pesticide detection via cyclodextrin-promoted energy transfer. Analyst 140:7503–7507

    Article  CAS  PubMed  Google Scholar 

  • Shepherd JL, Kell A, Chung E, Sinclar CW, Workentin MS, Bizzotto D (2004) Selective reductive desorption of a SAM-coated gold electrode revealed using fluorescence microscopy. J Am Chem Soc 126:8329–8335

    Article  CAS  PubMed  Google Scholar 

  • Srogi K (2007) Monitoring of environmental exposure to polycyclic aromatic hydrocarbons: a review. Environ Chem Lett 5:169–195

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Tao Y, Li M, Auguste DT (2017) Pattern-based sensing of triple negative breast cancer cells with dual-ligand cofunctionalized gold nanoclusters. Biomaterials 116:21–33

    Article  CAS  PubMed  Google Scholar 

  • Valdes A, Vidal L, Beltran A, Canals A, Garrigos MC (2015) Microwave-assisted extraction of phenolic compounds from almond skin byproducts (Prunus amygdalus): a multivariate analysis approach. J Agric Food Chem 63:5395–5402

    Article  CAS  PubMed  Google Scholar 

  • Vu AT, Taylor KM, Holman MR, Ding YS, Hearn B, Watson CH (2015) Polycyclic aromatic hydrocarbons in the mainstream smoke of popular U. S. cigarettes. Chem Res Toxicol 28:1616–1626

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Wang L, Xiang Z, Stevanovic S, Ristovski Z, Salimi F, Gao J, Wang H, Li L (2017b) Role of Chinese cooking emissions on ambient air quality and human health. Sci Total Environ 589:173–181

    Article  CAS  PubMed  Google Scholar 

  • Wang X, Thai PK, Mallet M, Desservettaz M, Hawker DW, Keywood M, Mijevic B, Paton-Walsh C, Gallen M, Mueller JF (2017a) Emissions of selected semivolatile organic chemicals from forest and savannah fires. Environ Sci Technol 51:1293–1302

    Article  CAS  PubMed  Google Scholar 

  • Wang YB, Liu CW, Kao YH, Jang CS (2015) Characterization and risk assessment of PAH-contaminated river sediment by using advanced multivariate methods. Sci Total Environ 524-525:63–73

    Article  CAS  PubMed  Google Scholar 

  • Wells PG, Kim PM, Laposa RR, Nicol CJ, Parman T, Winn LM (1997) Oxidative damage in chemical teratogenesis. Mutation Res 396:65–78

    Article  CAS  PubMed  Google Scholar 

  • Zgheib S, Moilleron R, Chebbo G (2008) Screening of priority pollutants in urban stormwater: innovative methodology. WIT Trans Ecol Environ 111:235–244

    Article  CAS  Google Scholar 

  • Zhang L, Chen Y, Jiang J (2016) Solid state fluorescent functionalized-triphenylamine Bodipy detector for HCl vapor with high stability and absolute fluorescent quantum yield. Dyes Pigments 124:110–119

    Article  CAS  Google Scholar 

  • Zhang X, Wang Z, Yue X, Ma Y, Kiesewetter DO, Chen X (2013) pH-sensitive fluorescent dyes: are they really pH-sensitive in cells? Mol Pharm 10:1910–1917

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Zhao L, Geng H, Liang ZF, Zhang ZQ, Zhang T, Yu DX, Zhong CY (2015) Benzidine induces epithelial-mesenchymal transition in human uroepithelial cells through ERK1/2 pathway. Biochem Biophys Res Commun 459:643–649

    Article  CAS  PubMed  Google Scholar 

  • Zhao N, Xuan S, Fronczek FR, Smith KM, Vicente MGH (2017) Enhanced hypsochromic shifts, quantum yield, and π-π interactions in a meso,β-heteroaryl-fused BODIPY. J Org Chem 82:3880–3885

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Zhao Y, Yang Y, Cun S, Hao Z, Hong Y, Huang R, Chi CM, Zhao Y (2010) Synthesis of novel bis(β-cyclodextrin)s linked with glycol and their inclusion complexation with organic dyes. Helv Chim Acta 93:1136–1148

    Article  CAS  Google Scholar 

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Funding

Funding is acknowledged from the National Cancer Institute (grant number: CA185435) and from the University of Rhode Island Project Completion Grant Program.

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Correspondence to Mindy Levine.

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Dana J. DiScenza declares that she has no conflict of interest. Julie Lynch declares that she has no conflict of interest. Molly Verderame declares that she has no conflict of interest. Melissa A. Smith declares that she has no conflict of interest. Mindy Levine declares that she has no conflict of interest.

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DiScenza, D.J., Lynch, J., Verderame, M. et al. Cyclodextrin-Promoted Fluorescence Detection of Aromatic Toxicants and Toxicant Metabolites in Commercial Milk Products. Food Anal. Methods 11, 2419–2430 (2018). https://doi.org/10.1007/s12161-018-1228-8

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