Murugesan, Jayadeepa R., Shahout, Fatma, Dlim, Marwa, Langella, M. Michele, Cuadra-Foy, Ernesto, Forgione, Pat and LaPlante, Steven R. (2018) Revealing dye and dye-drug aggregation into nano-entities using NMR. Dyes and Pigments . ISSN 01437208 (In Press)
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Official URL: http://dx.doi.org/10.1016/j.dyepig.2018.02.026
Abstract
It is becoming increasingly apparent that small molecules can self-assemble into a wide-range of nano-entities in solution that have intriguing properties. The recently introduced NMR aggregation assay is playing an important role in revealing these nano-entities. Here, we employ the NMR aggregation assay to expose the self-aggregation tendencies of dyes in solution. This dilution-based assay demonstrates that some dyes can exist as single-molecule entities whereas others can adopt aggregates of distinct sizes. Interestingly, dyes with highly related chemical structures can adopt largely different sized aggregates - demonstrating the existence of structure-nanoentity relationships – which suggests that they can assume and/or be designed to have distinct properties. One property was evaluated where the drug Quetiapine (Seroquel) was added to the dye Congo red which resulted in the absorption of the drug into the dye nano-entity. This showed a direct drug-dye interaction, and it demonstrated that dye aggregates can have influences on drug solution behaviors. The NMR method described in this study provides a practical and valuable tool to monitor dye aggregates and to better understand their associated properties (e.g. toxicity, off-target activity) and potential utility (e.g. drug encapsulation, drug delivery systems).
| Divisions: | Concordia University > Faculty of Arts and Science > Chemistry and Biochemistry |
|---|---|
| Item Type: | Article |
| Refereed: | Yes |
| Authors: | Murugesan, Jayadeepa R. and Shahout, Fatma and Dlim, Marwa and Langella, M. Michele and Cuadra-Foy, Ernesto and Forgione, Pat and LaPlante, Steven R. |
| Journal or Publication: | Dyes and Pigments |
| Date: | 21 February 2018 |
| Digital Object Identifier (DOI): | 10.1016/j.dyepig.2018.02.026 |
| Keywords: | Dye; Drug; Aggregation; NMR; Nano-entities; Colloids |
| ID Code: | 983526 |
| Deposited By: | Monique Lane |
| Deposited On: | 26 Feb 2018 21:22 |
| Last Modified: | 21 Feb 2020 01:00 |
References:
S.R. LaPlante, N. Aubry, G. Bolger, P. Bonneau, R. Carson, R. Coulombe, et al. Monitoring drug self-aggregation and potential for promiscuity in off-target in vitro pharmacology screens by a practical nmr strategy J Med Chem, 56 (2013), pp. 7073–7083 https://doi.org/10.1021/jm4008714S.R. Laplante, R. Carson, J. Gillard, N. Aubry, R. Coulombe, S. Bordeleau, et al. Compound aggregation in drug discovery: implementing a practical NMR assay for medicinal chemists J Med Chem, 56 (2013), pp. 5142–5150 https://doi.org/10.1021/jm400535b
K.E.D. Coan, B.K. Shoichet Stoichiometry and physical chemistry of promiscuous aggregate-based inhibitors J Am Chem Soc, 130 (2008), pp. 9606–9612 https://doi.org/10.1021/ja802977h
https://chemaxon.com/.
S.L. McGovern, E. Caselli, N. Grigorieff, B.K. Shoichet A common mechanism underlying promiscuous inhibitors from virtual and high-throughput screening J Med Chem, 45 (2002), pp. 1712–1722 https://doi.org/10.1021/jm010533y
D. Heger, J. Jirkovský, P. Klán Aggregation of methylene blue in frozen aqueous solutions studied by absorption spectroscopy J Phys Chem A, 109 (2005), pp. 6702–6709 https://doi.org/10.1021/jp050439j
S.A. Al-Thabaiti, E.S. Aazam, Z. Khan, O. Bashir Aggregation of Congo red with surfactants and Ag-nanoparticles in an aqueous solution Spectrochim Acta Part A Mol Biomol Spectrosc, 156 (2016), pp. 28–35 https://doi.org/10.1016/j.saa.2015.11.015
Y. Zhang, J. Xiang, Y. Tang, G. Xu, W. Yan Aggregation behaviour of two thiacarbocyanine dyes in aqueous solution Dyes Pigments, 76 (2008), pp. 88–93
N.G. Zhegalova, S. He, H. Zhou, D.M. Kim, M.Y. Berezin Minimization of self-quenching fluorescence on dyes conjugated to biomolecules with multiple labeling sites via asymmetrically charged NIR fluorophores Contrast Media Mol Imaging, 9 (2014), pp. 355–362 https://doi.org/10.1002/cmmi.1585
V.R. Horowitz, L.A. Janowitz, A.L. Modic, P.A. Heiney, P.J. Collings Aggregation behavior and chromonic liquid crystal properties of an anionic monoazo dye Phys Rev E - Stat Nonlinear Soft Matter Phys, 72 (2005) https://doi.org/10.1103/PhysRevE.72.041710
D.J. Edwards, J.W. Jones, O. Lozman, A.P. Ormerod, M. Sintyureva, G.J.T. Tiddy Chromonic liquid crystal formation by edicol sunset yellow J Phys Chem B, 112 (2008), pp. 14628–14636 https://doi.org/10.1021/jp802758m
F. Chami, M.R. Wilson Molecular order in a chromonic liquid crystal: a molecular simulation study of the anionic azo dye sunset yellow J Am Chem Soc, 132 (2010), pp. 7794–7802 https://doi.org/10.1021/ja102468g
M. Ishiyama, M. Shiga, K. Sasamoto, M. Mizoguchi, P. He A new sulfonated tetrazolium salt that produces a highly water-soluble formazan dye Chem Pharm Bull (Tokyo), 41 (1993), pp. 1118–1122 https://doi.org/10.1248/cpb.41.1118
R.A. Swerlick, C.F. Campbell Medication dyes as a source of drug allergy J Drugs Dermatol, 12 (2013), pp. 99–102
https://www.epa.gov/assessing-and-managing-chemicals-under-tsca/pigment-violet-29-anthra219-def6510-defdiisoquinoline-0.
A.M. Boutajangout, E.K. Sigurdsson, P. Krishnamurthy Tau as a therapeutic target for Alzheimer's disease Curr Alzheimer Res, 8 (2011), pp. 666–677 https://doi.org/10.2174/156720511796717195
Y.V. Frenkel, A.D. Clark, K. Das, Y.H. Wang, P.J. Lewi, P.A.J. Janssen, et al. Concentration and pH dependent aggregation of hydrophobic drug molecules and relevance to oral bioavailability J Med Chem, 48 (2005), pp. 1974–1983 https://doi.org/10.1021/jm049439i
S.C. Owen, A.K. Doak, P. Wassam, M.S. Shoichet, B.K. Shoichet Colloidal aggregation affects the efficacy of anticancer drugs in cell culture ACS Chem Biol, 7 (2012), pp. 1429–1435 https://doi.org/10.1021/cb300189b
https://www.food.gov.uk/science/additives/foodcolours.
https://www.ncbi.nlm.nih.gov/books/NBK304402/.
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