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2 protocols using n 7 nitrobenz 2 oxa 1 3 diazol 4 yl 1 2 dihexadecanoyl sn glycero 3 phosphoethanolamine triethylammonium salt

1

Characterization of Coumarins' Physicochemical Properties

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The solvents acetonitrile and formic acid were obtained from Tedia (HPLC grade, Radnor, PA, USA), and ultrapure water was obtained from the Milli-Q® Plus apparatus by Millipore (Billerica, MA, USA). Methanol, ethanol, isopropanol, polysorbate 80 (Tween® 80), dimethyl sulfoxide (DMSO), and sodium hydroxide were obtained from Vetec (Duque de Caxias, Brazil), and medium chain triglycerides (MCT) and egg lecithin (Lipoid® E80) were purchased from Lipoid GmbH (Ludwigshafen am Rhein, Germany). Monobasic potassium phosphate was obtained from Dinâmica (São Paulo, Brazil), and NBD-PE [N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)-1,2-dihexadecanoyl-sn-glycero-3-phosphoethanolamine, triethylammonium salt] fluorescent-labelled phospholipid was purchased from Thermo Fisher Scientific (Waltham, MA, USA). Roswell Park Memorial Institute 1640 broth medium (RPMI-1640), 3(N-morpholino) propane sulfonic acid (MOPS), 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT), and itraconazole were obtained from Sigma-Aldrich (St. Louis, MA, USA), and potato dextrose agar (PDA) was purchased from Acumedia (San Bernardino, CA, USA). Tissue-Tek® O.C.T.™ was purchased from Sakura Finetechnical Co. (Tokyo, Japan). Log P (calculated log P) values of the coumarins were assigned using SwissADME http://www.swissadme.ch/ (accessed on 10 March 2023).
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2

Lipid Membrane Characterization Protocol

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Poly (ethylene oxide)-b-poly (caprolactone) (PEO-PCL) 5k-4k, poly (ethylene oxide)-b-poly (styrene) (PEO-PS) 2,3k-3,1k were purchased from Polymer Source (Polymer Source, Inc., Dorval, Canada). 1,2-Dioleoyl-sn-glycero-3-phosphocholine (DOPC) and 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine-N- (lissamine rhodamine B sulphonyl) (ammonium salt) (Lys- Rhod-PE) come from Avanti Polar Lipids (Avanti Polar Lipids, Inc., USA). (N-(7-Nitrobenz-2-Oxa-1,3-Diazol-4-yl)-1,2-Dihexadecanoyl-sn-Glycero-3-Phosphoethanolamine, Triethylammonium Salt) was bought from Thermo Fisher (NBD-PE, N360, Waltham, MA, US). Pheophorbide-a was purchased from Wako (Japan). Chloroform, methanol, acetone, phosphate buffer (PBS, P4417) and carboxyfluorescein (CBF, 21877) were purchased from Sigma Aldrich (Merck, Darmstadt, Germany). The water used to prepare all PBS solutions was ultrapure water at 18 MΩ resistivity obtained with an ELGA Purelab Flex system (ELGA LabWater, High Wycombe, UK). Anthracene-9,10-dipropionic acid disodium salt (ADPA) was purchased from Santa Cruz Biotechnology (Dallas, TX, US).
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