Distearoyl phosphatidyl ethanolamine

Phosphate-buffered saline (PBS) and VCM were purchased from Sigma-Aldrich (St. Louis, MO, USA) and RFB from Pharmacy Biotech AB (Uppsala, Sweden). The pure phospholipids, dimyristoyl phosphatidyl choline (DMPC), dimyristoyl phosphatidyl glycerol (DMPG), dipalmitoyl phosphatidyl choline (DPPC), dipalmitoyl phosphatidyl glycerol (DPPG), and distearoyl phosphatidyl ethanolamine covalently linked to poly(ethylene glycol)2000 (DSPE-PEG) were purchased from Lipoid (Ludwigshafen, Germany). Rhodamine covalently linked to phosphatidylethanolamine (Rho-PE) were purchased from Avanti Polar Lipids (Alabaster, AL, USA). Thiazolyl blue tetrazolium bromide (MTT), crystal violet (CV), and glycerol were obtained from Panreac AppliChem, ITW Reagents (Darmstadt, Germany). Culture media Mueller–Hinton Agar (MHA) and Mueller–Hinton Broth (MHB) were obtained from Oxoid, Ltd. (Basingstoke, UK) and Tryptic Soy Broth (TSB) from Biokar (Pantin, France). The fluorescent stain SYTO 9 was obtained from Molecular Probes (Eugene, OR, USA). D(+)-glucose monohydrate was acquired from Merck KGaA (Darmstadt, Germany). Dimethyl sulfoxide (DMSO) and ethanol absolute anhydrous were obtained from Carlo Erba Reagents S.A.S. (Val de Reuil, France). All other reagents were of analytical grade.

Distearoylphosphatidylethanolamine–polyethylene glycol (DSPE–PEG, PEG Mw of 550 and 2000 Da) were purchased from Avanti polar lipids (Alabama, USA). Distearoylphosphatidylethanolamine (DSPE) and hydrogenated soy phosphatidylcholine (HSPC) were purchased from Lipoid (Ludwigshafen, Germany). Triethylamine (99%), 2-(methacryloyloxy)ethyl phosphorylcholine (MPC), copper(i) bromide (CuBr, 99.999%), 2-bromoisobutyryl bromide (BIBB, 98%), N,N,N′,N′′,N′′-pentamethyldiethylenetriamine (PMDETA, 99%), bovine serum albumin (BSA), anhydrous dichloromethane (DCM), and anhydrous chloroform were purchased from Sigma-Aldrich (Israel). DiR (1,1′-dioctadecyl-3,3,3′,3′-tetramethylindotricarbocyanine iodide), DiI (1,1′-Dioctadecyl-3,3,3′,3′-tetramethylindocarbocyanine perchlorate), fetal bovine serum (FBS), and RPMI-1640 medium were purchased from Thermo Fisher Scientific (UK). Hyaluronate-DyLight 755 (2.5 MDa) was purchased from Creative PEG Works (US).

The reagents and chemicals used in this study were of analytical grade and are commercially available. Specifically, Dioleoylphosphatidylethanolamine (DOPE, LIPOID PE 18:1/18:1), distearoylphosphatidylethanolamine (DSPE, LIPOID PE 18:0/18:0), and distearoylphosphatidylethanolamine polyethyleneglycol2000(DSPE-PEG2000, LIPOID PE 18:0/18:0–PEG2000) were supplied by Lipoid GmbH (Ludwigshafen, Germany). Cholesteryl hemisuccinate (CHEMS, Cat. # 850524P) was purchased from Sigma-Aldrich Chemical Company (St Louis, MO, USA). Doxorubicin hydrochloride (DOX, >98% purity) was purchased from ACIC Chemicals (Brantford, Ontario, Canada). D-(+)-Glucose (99,5% purity) was purchased from Vetec Química Fina Ltd.a (São Paulo, Brazil). The analytical reagents and solvents (high-performance liquid chromatography analytical grade) were purchased from Sigma-Aldrich (São Paulo, Brazil).