1 1 dioctadecyl 3 3 3 3 tetramethylindodicarbocyanine

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1,1'-dioctadecyl-3,3,3',3'-tetramethylindodicarbocyanine is a fluorescent dye used for labeling lipophilic structures in biological samples. It has an absorption maximum at 644 nm and an emission maximum at 663 nm.

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11 protocols using 1 1 dioctadecyl 3 3 3 3 tetramethylindodicarbocyanine

PLGA Nanoparticle Formulation and Characterization

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Ester-terminated poly(lactic-co-glycolic)acid (PLGA 85:15) was obtained from Lactel (Birmingham, AL, USA). Dichloromethane (DCM), acetonitrile (MeCN), dimethyl sulfoxide (DMSO), poly(vinyl alcohol) (PVA, 31,000–50,000 Da, 87–89% hydrolyzed), chitosan (low molecular weight (50,000–190,000 Da), 75–85% deacetylated) were purchased from Sigma-Aldrich (St. Louis, MO, USA). Simvastatin was obtained from Cayman Chemical (Ann Arbor, MI, USA). Fetal bovine serum (FBS), penicillin-streptomycin, amphotericin B were from Life Technologies (Grand Island, NY, USA), 1,1’-dioctadecyl-3,3,3’,3’-tetramethylindodicarbocyanine, 4-chlorobenzenesulfonate salt (DiD) was from Thermofisher Scientific (Waltham, MA, USA) and cOmpleteTM protease inhibitor cocktail was obtained from Roche (Basel, Switzerland).

Yang F., Cabe M., Nowak H.A, & Langert K.A. (2022). Chitosan/poly(lactic-co-glycolic)acid Nanoparticle Formulations with Finely-Tuned Size Distributions for Enhanced Mucoadhesion. Pharmaceutics, 14(1), 95.

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Lipid Probes for Membrane Characterization

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The lipids DOPC, 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE), DOPS, 1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine-N-[4-(p-maleimidomethyl)cyclohexane-carboxamide] (16:0 MCC-PE), and 1,2-distearoyl-sn-glycero-3-phosphoethanolamine-N-[biotinyl(polyethylene glycol)-2000] (DSPE-PEG-Biotin) were obtained from Avanti Polar Lipids (Alabaster, AL). Alexa Fluor 488 SDP ester, Alexa Fluor 594 C5 maleimide, and the lipid fluorophore 1,1'-dioctadecyl-3,3,3',3'-tetramethylindodicarbocyanine, 4-chlorobenzenesulfonate salt (DiD), and BODIPY-FL-DHPE (N-(4,4-Difluoro-5,7-Dimethyl-4-Bora-3a,4a-Diaza-s-Indacene-3-Propionyl)-1,2-Dihexadecanoyl-sn-Glycero-3-Phosphoethanolamine, Triethylammonium Salt) were from ThermoFisher Scientific (USA). Streptavidin-conjugated microsphere beads (6 μm diameter) were from Polysciences (Warrington, PA). All common reagents used for the buffer preparation, such as HEPES, Tris, NaCl, Na₂HPO₄, NaH₂PO₄, ethylenediaminetetraacetic acid (EDTA), and dithiothreitol (DTT), were from Fisher Scientific (USA). β-casein from bovine milk was obtained from Sigma-Aldrich (USA). Unless otherwise specified, all chemicals from commercial sources were used without further purification.

Mondal S., Narayan K.B., Powers I., Botterbusch S, & Baumgart T. (2020). Endophilin recruitment drives membrane curvature generation through coincidence detection of GPCR loop interactions and negative lipid charge. The Journal of Biological Chemistry, 296, 100140.

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Liposome-Based Delivery System Development

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Hydrogenated soya phosphatidylcholine (HSPC) and Methoxypolyethyleneglycol (Mw 2000)-distearylphosphatidylethanolamine (mPEG2000-DSPE) were purchased from Lipoid (Ludwigshafen, Germany). Maleimide-PEG2000 distearoylphosphatidylethanolamine (Mal-PEG2000-DSPE) and 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine-N-(lissamine rhodamine B sulfonyl) (Liss Rhod, PE) were purchased from Avanti Polar Lipids (Alabaster, AL, USA). Then, 3,3′-Dioctadecyloxacarbocyanine perchlorate (DiO); 1,1′-Dioctadecyl-3,3,3′,3′-Tetramethylindodicarbocyanine; 4-Chlorobenzenesulfonate Salt (DiD); and LysoTracker Red were purchased from Thermo Fisher Scientific (Waltham, MA, USA). Ammonium sulfate, Cholesterol, and doxorubicin hydrochloride (Dox) were purchased from Sigma-Aldrich (St Louis, MO, USA). RGDf[N-met]C was synthesized by Ansynth Service B.V. (Roosendaal, The Netherlands). A TAT peptide analog equipped with 3G as a spacer and a C for conjugation (CGGG-RKKRRQRRRGYG) was synthesized by Peptron Inc. (Daejeon, South Korea). All other solvents and reagents were used as chemical grade.

Amin M., Mansourian M., Burgers P.C., Amin B., Jaafari M.R, & ten Hagen T.L. (2022). Increased Targeting Area in Tumors by Dual-Ligand Modification of Liposomes with RGD and TAT Peptides. Pharmaceutics, 14(2), 458.

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Lipid Nanoparticle Formulation and Characterization

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Hydrogenated soya phosphatidylcholine (HSPC) and methoxypolyethyleneglycol (MW 2000)-distearylphosphati-dylethanolamine (mPEG2000-DSPE) were purchased from Lipoid (Ludwigshafen, Germany), maleimide-PEG2000 distearoylphosphatidylethanolamine (Mal-PEG2000-DSPE) was purchased from Avanti Polar Lipids (Alabaster, AL, USA). 3,3′-Dioctadecyloxacarbocyanine perchlorate (DiO), 1,1′-dioctadecyl-3,3,3′,3′-tetramethylindodicarbocyanine, and 4-chlorobenzenesulfonate salt (DiD) were purchased from Thermo Fisher Scientific (Waltham, MA, USA). Ammonium sulfate, cholesterol, α-tocopherol, XTT, PMS and DXR hydrochloride were purchased from Sigma-Aldrich Co. (St Louis, MO, USA). TAT peptide analog equipped with 3G as spacer and a C for conjugation (CGGG-RK-KRRQRRRGYG) was synthesized by Peptron Inc. (Daejeon, South Korea) with purity of 98%. Commercially available Caelyx was purchased from pharmacy. All other solvents and reagents were used as chemical grade.

Amin M., Bagheri M., Mansourian M., Jaafari M.R, & ten Hagen T.L. (2018). Regulation of in vivo behavior of TAT-modified liposome by associated protein corona and avidity to tumor cells. International Journal of Nanomedicine, 13, 7441-7455.

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Preparation of Lipid Vesicles with Fluorescent Dyes

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1-Palmitoyl-2-oleoyl-glycero-3-phosphocholine (POPC) and 1-palmitoyl-2-oleoyl-sn-glycero-3-phospho-L-serine (POPS) lipids in chloroform were purchased from Avanti Polar Lipids and used without any additional purification. 1,1′-Dioctadecyl-3,3,3′,3′ tetramethylindocarbocyanine perchlorate (DiI) and 1,1-dioctadecyl-3,3,3,3-tetramethylindodicarbocyanine (DiD) were obtained from Thermo Fisher Scientific. Synthetic vesicles were prepared via the extrusion method as previously described (Dalgarno et al., 2019 (link); Juan-Colas et al., 2020 (link)). Briefly, mixtures of lipids and membrane stains were mixed in chloroform at final lipid concentrations of 10 mg lipid/ml. The solvent was then evaporated by nitrogen flow to create a dry lipid film, subsequently hydrated in 50 mM Tris buffer (pH 8.0), and mixed by a vortex. The resuspended solution was then extruded through a polycarbonate membrane filter to produce vesicles of appropriate diameter.

Quinn S.D., Dresser L., Graham S., Conteduca D., Shepherd J, & Leake M.C. (2022). Crowding-induced morphological changes in synthetic lipid vesicles determined using smFRET. Frontiers in Bioengineering and Biotechnology, 10, 958026.

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Chitosan-Based Thermosensitive Hydrogel

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High molecular weight chitosan, β-glycerophosphate disodium salt hydrate, glacial acetic acid, and pluronic F-127 were purchased from Sigma Aldrich. Acetone, nitric acid (trace metal grade), hydrochloric acid (trace metal grade) were purchased from Fisher Scientific. AF was purchased from Enzo Life Sciences. 1,1′-dioctadecyl-3,3,3′,3′-tetramethylindodicarbocyanine, 4-chlorobenzenesulfonate salt (DiD; excitation/emission, 644/665 nm) were purchased from ThermoFisher Scientific. PLGA (50:50, 0.67 dL/g) was purchased from LACTEL Absorbable Polymers.

Zhang Y., Miyamoto Y., Ihara S., Yang J.Z., Zuill D.E., Angsantikul P., Zhang Q., Gao W., Zhang L, & Eckmann L. (2019). Composite thermoresponsive hydrogel with auranofin-loaded nanoparticles for topical treatment of vaginal trichomonad infection. Advanced therapeutics, 2(12), 1900157.

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Multifunctional Adipose-Targeting Nanoparticles

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The following materials were purchased: metformin and propranolol from Cayman Chemical Co. (Ann Arbor, MI, USA); PLGA, lactide:glycolide (50:50) and lactide:glycolide (75:25), and anti-UCP1, anti-AMPK, anti-pAMPK antibodies and primers from Sigma-Aldrich, Inc. (St. Louis, MO, USA); polydimethylsiloxane (PDMS) micro-molds from Micro point Technologies, Singapore; 1,1′-dioctadecyl-3,3,3′,3′-tetramethylindodicarbocyanine, 4-chlorobenzenesulfonate salt (DID), and 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine-N-(lissamine rhodamine B sulfonyl) (ammonium salt) (Rohd-PE) dyes from Thermo Fisher Scientific Co. (San Jose, CA, USA); TRIzol reagent, Maxima First Strand cDNA Synthesis Kit, and PowerUp SYBR Green Master Mix from Thermo Fisher Scientific (Pittsburgh, PA, USA); and the Vectastain ABC kit and Vector Hematoxylin QS from Vector Laboratories (Burlingame, CA, USA). The TENS and IOMED electrodes were from Isokinetics, Inc. (De Queen, AR, USA). A Keithley 2400 current source was used as the power supply from INT Instruments Co. (Cleveland, OH, USA).

Abbasi M., Fan Z., Dawson J.A, & Wang S. (2022). Transdermal Delivery of Metformin Using Dissolving Microneedles and Iontophoresis Patches for Browning Subcutaneous Adipose Tissue. Pharmaceutics, 14(4), 879.

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Polylactic Acid Nanoparticle Synthesis and Characterization

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Polylactic acid (Mw = 20.2 kDa, Mn = 12.4kDa) was obtained from Lactel. H₂N-PEG(5000)-OCH₃ was obtained from Laysan. Anhydrous dimethylformamide, dichloromethane, diisopropylcarboimide, dimethylaminopyridine, potassium methoxide, camptothecin, polyvinyl alcohol, paraformaldehyde, Tween 80, and 1,1,1-trihydroxymethyl propane were obtained from the Sigma-Aldrich. Anhydrous dry ether, methanol, acetonitrile and dimethylsulfoxide were obtained from J.T. Baker. The 1,1′-Dioctadecyl-3,3,3′,3′-Tetramethylindodicarbocyanine,4 Chlorobenzenesulfonate Salt (DiD) and DAPI stain were ordered from Invitrogen. Super frost microscope slides were obtained from Thermo Scientific. Donkey normal serum and Rabbit-anti-CD31 antibody was ordered from Abcam and the Donkey-anti-rabbit secondary antibody tagged with Alexa488 fluorophore was from Invitrogen. Cell titer blue was obtained from Promega. Microdialysis tubing was from Thermo Scientific. Phorbol 12-myristate 13-acetate (PMA) was from Abcam.

Deng Y., Saucier-Sawyer J., Hoimes C., Zhang J., Seo Y.E., Andrejecsk J.W, & Saltzman W.M. (2014). The Effect of Hyperbranched Polyglycerol Coatings on Drug Delivery Using Degradable Polymer Nanoparticles. Biomaterials, 35(24), 6595-6602.

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Lipid Reagents for Membrane Biophysical Studies

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2-Hydroxypropyl-β-cyclodextrin (H-107) and amiloride (A7410) were from Sigma. EndoH (P0702) and PNGaseF (P0704) were from New England Biolabs. Dynasore (14061) was from Cayman Chemical; Human HDL (J64903) and acetylated LDL (J65029) were from Alfa Aesar. 5A peptide (DWLKAFYDKVAEKLKEAF-P-DWAKAAYDKAAEKAKEAA, 4078379) was from Bachem Americas (Torrance, CA). 22A peptide (PVLDLFRELLNELLEALKQKLK) was synthesized by Genscript (Piscataway, NJ). Lipids including egg-sphingomyelin (SM, Coastome NM-10), 1,2-dimyristoyl-sn-glycero-3-phosphocholine (DMPC, Coastome MC-4040), and 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC, Coastome MC-6081) were from NOF America Corporation. 1,1′-Dioctadecyl-3,3,3′,3′-tetramethylindodicarbocyanine, 4-chlorobenzenesulfonate salt (DiD, D7757) and 4-(4-(dihexadecylamino)styryl)-N-methylpyridinium iodide (DiA, D3883) were from Invitrogen. Cholesteryl [1,2,6,7-3H(N)] linoleate (ART 1203) and sphingomyelin [choline methyl-3H] were from American Radiolabeled Chemicals (Saint Louis, MO). N-[6-[(7-Nitro-2-1,3-benxoxadiazol-4-yl)amino]-sphingosine-1-phosphocholine (NBD-Sphingomyelin, 810218P) was from Avanti Polar Lipids (Alabaster, AL).

Schultz M.L., Fawaz M.V., Azaria R.D., Hollon T.C., Liu E.A., Kunkel T.J., Halseth T.A., Krus K.L., Ming R., Morin E.E., McLoughlin H.S., Bushart D.D., Paulson H.L., Shakkottai V.G., Orringer D.A., Schwendeman A.S, & Lieberman A.P. (2019). Synthetic high-density lipoprotein nanoparticles for the treatment of Niemann–Pick diseases. BMC Medicine, 17, 200.

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Functionalized Magnetic Nanoparticles for Cell Labeling

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Gold-coated magnetic nanoparticles were purchased from Creative Diagnostics. All other chemicals were purchased from Sigma-Aldrich and used as received. Cell-culture plates, FBS, penicillin, streptomycin, sodium bicarbonate, cell-culture medium and PBS were purchased from GIBCO BRL (Frederick, MD). Lipofectamine 2000 transfection reagent and the Vibrant Multicolor Cell-Labeling Kit containing DiOC18 (3) (3,3′-dioctadecyloxacarbo-cyanine perchlorate) (DiO), 1,1′-dioctadecyl-3,3,3′,3′-tetramethylin-dodicarbocyanine, and 4-chlorobenzenesulfonate salt (DiD) solutions, protein gels, and buffers for gel electrophoresis and immunoblot analysis were purchased from Invitrogen (Carlsbad, CA). 4′,6-Diamidino-2-phenylindole (DAPI) was purchased from Sigma-Aldrich (Saint Louis, MO). Cy5-labeled anti-miR-21 RNA-oligo was synthesized from the Protein and Nucleic Acid facility at Stanford (PAN).

Bose R.J., Kumar S.U., Zeng Y., Afjei R., Robinson E., Lau K., Bermudez A., Habte F., Pitteri S.J., Sinclair R., Willmann J.K., Massoud T.F., Gambhir S.S, & Paulmurugan R. (2018). Tumor Cell-Derived Extracellular Vesicle-Coated Nanocarriers: An Efficient Theranostic Platform for the Cancer-Specific Delivery of Anti-miR-21 and Imaging Agents. ACS nano, 12(11), 10817-10832.

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