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16 protocols using sodium trifluoroacetate

1

Synthesis of Rare-Earth Compound Precursors

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Yttrium (III) chloride hexahydrate (99.99%), erbium (III) chloride hexahydrate (99.9%), gadolinium (III) chloride hexahydrate (99.9%), yttrium (III) oxide (99.999%), gadolinium (III) oxide (99.9%), sodium trifluoroacetate (98%), lithium trifluoroacetate (95%), trifluoroacetic acid (98%), 1-octadecene (90%), and oleic acid (90%) were purchased from Sigma-Aldrich. Sodium hydroxide (98%), lithium hydroxide (98%), and ammonium fluoride (98%) were purchased from Aladdin Co. All chemicals were used as received.
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2

Solid-Phase Peptide Synthesis Protocol

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All Fmoc amino acids, Rink amide AM 200–400, 1-hydroxybenzotriazole (HOBt·H2O) and O-Benzotriazole-N,N,N’,N’-tetramethyluronium hexafluorophosphate (HBTU) were purchased and used as received from Iris Biotech GmbH (Marktredwitz, Germany). Triisopropylsilane (TIS), ethane-1,2-dithiol (EDT), trifluoroacetic acid (TFA), sodium trifluoroacetate (NaTFA), acryloyl chloride (99 %), diisopropylethylamine (DIEA, 98 %), dicyclohexylcarbodiimide (DCC, 99 %) cesium hydroxide monohydrate (99.95 %), ethyl vinyl ether (98 %), palladium on activated charcoal (10 % Pd), phosphate buffered saline sachets and α-cyanohydroxycinnamic acid were purchased from Sigma-Aldrich (Buchs, Switzerland). N,N-dimethylformamide was obtained from VWR, (Nyon, Switzerland) and N-methylpyrrolidone was obtained from Schweizerhall (Basel, Switzerland). Glycidol (96 %), ethanolamine (99 %), serinol (98 %), p-methoxybenzylalcohol (98 %), phosphorus tribromide (1.0 M solution in dichloromethane, AcroSeal®), potassium carbonate (99+ %), maleic anhydride (99 %), β-alanine (99 %), pentafluorophenol (99 %) and benzene (99 %) were obtained from Acros (Germany).
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3

Synthesis of Rare-Earth Oxide and Acetate Nanoparticles

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yttrium(III) oxide (Y2O3, 99.99%), ytterbium (III) oxide (Yb2O3, 99.9%), erbium (III) oxide (Er2O3, 99.99%), neodymium (III) oxide (Nd2O3, 99.99%), yttrium (III) acetate hydrate (Y(CH3COO)3, 99.99%), ytterbium (III) acetate tetrahydrate (Yb(CH3COO)3•4H2O, 99.99%), neodymium (III) acetate hydrate (Nd(CH3COO)3, 99.99%), trifluoroacetic acid (CF3COOH, 99%), sodium trifluoroacetate (CF3COONa, 98%), oleic acid (90%, tech grade) and octadecene (90%, tech grade), Indocyanine green, ammonia fluoride (NH4F, ≥99.99% trace metals basis), sodium hydroxide (NaOH, anhydrous, ≥97%) were obtained from Sigma Aldrich. Methanol (ACS reagent grade, ≥99.8%) and hexane (ACS reagent grade, ≥98.5%) were purchased from Fisher Scientific. All chemical reagents were used as received without any further purification.
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4

Synthesis of Lanthanide-Doped Nanoparticles

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Lanthanide oxides (gadolinium
oxide, ytterbium oxide, and erbium oxide), europium(III) chloride
hexahydrate, trifluoroacetic acid, sodium trifluoroacetate, oleic
acid, 1-octadecene, IGEPAL CO-520, ammonium hydroxide (28–30%),
tetraethyl orthosilicate (TEOS), and 2-thenoyltrifluoroacetone (tta)
were all purchased from Sigma (Sigma-Aldrich Co., St. Louis, MO, USA).
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5

Synthesis and Characterization of Lipid Membranes

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Ethylene oxide, propylene oxide, 1,2-epoxybutane, potassium tert-butoxide, tetrahydrofuran, 18-crown-6 ether, methanol, naphthalene, potassium metal, α-cyano-4-hydroxycinnamic acid (CHCA), sodium trifluoroacetate (NaTFA), and diphenylhexatriene (DPH), bioreagent grade buffer salts (sodium chloride, potassium chloride, calcium chloride, magnesium chloride, and HEPES) and Triton X-100 were purchased from Sigma Aldrich and used without further purification. 1-palmitoyl-2-oleoyl-glycero-3-phosphocholine (POPC) was purchased from Avanti Polar Lipids as a 10 mg/mL solution in chloroform.
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6

Synthesis and Characterization of 12-ADA

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Synthesis of 12-ADA was performed as previously described by Heal et al.[11 (link)] Briefly, 2 g of 12-bromododecanoic acid (Sigma-Aldrich) was esterified in methanol (Sigma-Aldrich) at reflux for 3 h in the presence of concentrated sulfuric acid (EMD). The product (an oil) was then dissolved in 60 mL of dimethyl sulfoxide (DMSO,VWR) and 519 mg of sodium azide (Sigma-Aldrich) was added. This reaction was stirred at RT for 16 h, and then quenched with 1M hydrochloric acid (EMD). The product (an oil) was then purified via flash chromatography (9:1 cyclohexane:diethyl ether solvent system, both from Sigma-Aldrich). Finally, the eluate (an oil) was dissolved in 2M sodium hydroxide (VWR) and methanol. This was stirred at RT for 24 h, and then acidified using 2M hydrochloric acid. After concentrating, the final product (an off-white solid) was analyzed by electrospray ionization ion-trap mass spectrometry (ESI-IT-MS) and proton nuclear magnetic resonance (H1NMR). The results from these characterizations matched those previously published:[11 (link)] H1NMR (300 MHz, CDCl3) δ: 3.26, 2.35, 1.61-1.64, 1.28. ESI-IT-MS (in methanol with sodium trifluoroacetate, both Sigma-Aldrich): Calculated m/z = 240.1712, found = 240.8
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7

Synthesis and Purification of P3HT

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Regioregular Poly(3-hexylthiophene-2,5-diyl) (P3HT), was purchased from Rieke Metals Inc. (Nebraska, USA). Sodium trifluoroacetate (98%), yttrium (III) oxide (99.99%), ytterbium (III) oxide (99.9%), erbium (III) oxide (99.9%), trifluoroacetic acid (99%), toluene (99.8%), 1-octadecene (90%), oleic acid (90%) and oleylamine (70%) were purchased from Sigma-Aldrich (Sigma-Aldrich, St. Louis, MO). Chloroform (99.99%) was purchased from Aik Moh Chemicals Inc. All chemicals were used as received without any further purification
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8

Synthesis and Characterization of Rare-Earth Nanoparticles

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Gadolinium(III) oxide
(99.9%), yttrium(III)
oxide (99.9%), ytterbium(III) oxide (99.9%), and thulium(III) oxide
(99.9%) were purchased from Alfa-Aesar (Haverhill, MA, USA). OA (90%),
ODE (90%), oleylamine (97%), hydrochloric acid (37%), trifluoroacetic
acid (TFA, 99%), sodium trifluoroacetate (98%), sodium hydroxide (≥97%),
ammonium fluoride (≥98%), anhydrous methanol (99.8%), toluene
(99.7%), n-hexane (97%), ethanol (99.8%), PBS, and
AlamarBlue cell viability reagent were purchased from Sigma-Aldrich
(St. Louis, MO, USA). Sodium neridronate and PEG-Ner were prepared
according to earlier reports.40 (link),61 (link) The cellulose dialysis
membrane (Mw cutoff 14 kDa) was purchased
from Spectrum Europe (Breda, Netherlands). In the experiments, Q-water
ultrafiltered on a Milli-Q Gradient A10 purification system (Millipore,
Molsheim, France) and all chemicals were used as received without
further purification.
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9

Preparation of Mass Spectrometry Samples

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Methanol, diethyl ether and ultrapure water were purchased from Wako Pure Chemical Industries (Osaka, Japan). Sodium trifluoroacetate, used as the calibration standard, was purchased from Sigma-Aldrich Japan (Meguro, Japan)51 (link). A MALDI matrix, DHB, was purchased from Bruker Daltonics (Fremont, CA, USA)53 (link), whereas 100 Ω indium tin oxide (ITO)-coated glass slides were purchased from Matsunami Glass Ind., Ltd. (Osaka, Japan)55 (link).
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10

Lanthanide-Doped Upconversion Nanoparticles

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All the reagents including 1-octadecene (ODE, 90%), oleic acid (OA, 90%), ethanol (EtOH) and methanol (MeOH), dimethylformamide (DMF), chloroform, milli-Q water, tetrahydrofuran (THF), yttrium(III) chloride anhydrous (YCl3, 99.9%), ytterbium(III) chloride anhydrous (YbCl3, 99.9%), erbium(III) chloride anhydrous (ErCl3, 99.9%), ammonium fluoride (NH4F, 96%), Sodium hydroxide (NaOH, 96%), Sodium trifluoroacetate (Na-TFA, 98%), neodymium(III) chloride (NdCl3 99.9%), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC), N-hydroxysuccinimide (s-NHS), Rose Bengal (RB), 6-bromohexanoic acid (Br-HA), poly(isobutylene-alt-maleic anhydride), dodecylamine (DDA), dibenzocyclooctine-amine (DBCO-NH2), 1,3-Diphenylisobenzofuran (DPBF, 97%) were purchased from Sigma-Aldrich. Chlorin e6 (Ce6) was purchased from Santa Cruz Biotechnology. 3-azido-propylamine (NH2-N3) was purchased from Fluorochem Ltd.
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