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13 protocols using sodium myristate

1

Removal of Styrene Inhibitor

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All solvents used were pro analysi (p.a.) grade. Prior to polymerization the inhibitor of the styrene (Sigma, St. Louis, MO, USA, ≥99%) was removed by an aluminum oxide column. 2-cyano-propyl dodecyl trithiocarbonate (CPDTTC) (Sigma, St. Louis, MO, USA, 97%), 1-butylamine (Alfa Aesar, Ward Hill, MA, USA, 99%), silver nitrate (Alfa Aesar, Ward Hill, MA, USA, 99.9995%), triethylamine (Alfa Aesar, Ward Hill, MA, USA, 99%), and sodium myristate (Sigma, St. Louis, MO, USA, ≥99%) were all used as received.
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2

Producing Unlabeled Myristoylated Arf1-HIS

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For the production of unlabeled myr-Arf1-HIS, co-transformed BL21 (star) cells were cultured in M9 media [reference] at 37°C until OD600 = 0.8. Sodium myristate (Sigma-Aldrich Cat. No. M8005) was added to a final concentration of 100 μM per liter. Coenzyme-A was added as one-half of a CoA supplement capsule (Coenzyme-A Technologies™) per liter of culture. Following an additional 30 min of growth, 1 mM IPTG was added to induce protein expression, and the cells were incubated for another 4 h at 37°C. The cells were pelleted by centrifugation at 7000 RCF for 30 min. The cell pellet was collected and frozen at −80°C. Production of isotope labelled myr-Arf1-HIS for NMR experiments is as described in the Supplemental section S1.
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3

Synthesis of Multicomponent Nanostructures

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Sodium myristate (≥99%), cadmium nitrate tetrahydrate (99.997%), selenium powder (99.99%), cadmium acetate hydrate (≥99.99%) and 1-octadecene (technical grade, 90%) were purchased from Sigma Aldrich. Chloroform (≥99.9%) was purchased from P.P.H. “STANLAB” (Poland). 1-butanol (≥99.999%) was purchased from Avantor Chemicals (Poland). Poly(ethylene oxide) (PEO) and poly(propylene oxide) (PPO) block co-polymer (PEO–PPO–PEO) - Pluronic P-123 was purchased from Sigma Aldrich.
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4

Synthesis of Colloidal Quantum Dots

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Cadmium nitrate tetrahydrate (Cd(NO3)2·4H2O, >98%), sodium myristate (Na(myr), >99%), 1-octadecene (ODE, 90%), cadmium acetate dihydrate (Cd(OAc)2·2H2O, >98%), oleic acid (OLA, >90%), n-hexane (≥99%), 11-mercaptoundecanoic acid (MUA, 95%), acetone (99.5%), potassium hydroxide (KOH, >85%), ammonium hydroxide (NH4OH, 28–30%), hydrogen peroxide (H2O2, 30%), toluene (99.7%), (3-mercaptopropyl)trimethoxysilane (MPTMS, 95%), sulfuric acid (H2SO4) (95–97%), potassium ferricyanide(iii) trihydrate (≥98.5%), sodium dihydrogen phosphate dihydrate (99%), and disodium hydrogen phosphate dodecahydrate (99%) were purchased from Sigma-Aldrich. Methanol (MeOH, ≥99.8%), 2-propanol (99.5%), and ethanol (EtOH, ≥99.8%) were purchased from Roth. Selenium (200 mesh, 99.999%) was purchased from Alfa Aesar. Sodium sulfite (Na2SO3) (>97%) was purchased from Fisher Scientific. All chemicals were used as received without further purification.
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5

Synthesis of Cadmium-based Nanoplatelets

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Cadmium
acetate dihydrate [Cd(OAc)2·2(H2O), Sigma-Aldrich,
98%], oleic acid (OA, Sigma-Aldrich,
90%), ODE (Sigma-Aldrich, 90%), hexadecane (Sigma-Aldrich, 98%), trioctylphosphine
(TOP, Cytec, 90%), selenium powder (Sigma-Aldrich, 99.5%), sodium
octanoate (Sigma-Aldrich, 99%), sodium myristate (Sigma-Aldrich, 99%),
cadmium nitrate tetrahydrate (Sigma-Aldrich, 98%), cadmium oxide (Sigma-Aldrich,
99.99%), decanoic acid (Sigma-Aldrich, 98%), acetic acid (Sigma-Aldrich,
99.85%), propionic acid (Sigma-Aldrich, 99.5%), butyric acid (Sigma-Aldrich,
99%), n-hexane (VWR, 95%), and ethanol (Carlo Erba,
99.8%) are purchased for the synthesis of NPLs and used without any
further purification.
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6

Colloidal Semiconductor Nanocrystal Synthesis

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Cadmium
nitrate tetrahydrate (99.997%), sodium myristate (99%), cadmium(II)
acetate (Cd(OAc)2; 99.995%), cadmium acetate dihydrate
(Cd(OAc)2·2H2O), octadecene (ODE; 90%),
oleic acid (90%), trioctylphosphine (TOP; 90%), propionic acid (99.5%)
methanol (99.9%), and hexane (95%) were purchased from Sigma-Aldrich.
Cadmium oxide (99.999%) sulfur (S; 99.9%), selenium powder (Se; 99.99%),
and tellurium (Te; 99.99%) were purchased from Strem Chemicals.
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7

Colloidal Semiconductor Nanocrystal Synthesis

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1-Butanol
(BuOH, anhydrous, 99.8%), cadmium
acetate (Cd(OAc)2, 99.995%), cadmium acetate dihydrate
(Cd(OAc)2·2H2O, ≥98.0%), cadmium
nitrate tetrahydrate (Cd(NO3)2·4H2O, 98%), methanol (MeOH, anhydrous, 99.8%), 1-octadecene (ODE, technical
grade 90%), oleic acid (OA, technical grade 90%), oleylamine (OLAM,
technical grade 70%), and sodium myristate (≥99%) were bought
from Sigma-Aldrich. n-Hexane (anhydrous), selenium
(200 mesh, 99.99%), and tri-n-butyl-phosphine (TBP,
95%) were bought from Alfa Aesar, STREM Chemicals, and Acros Organics,
respectively.
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8

Synthesis and Characterization of Novel Surfactants

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Deuterated methanol was purchased from Eurotop (Cambridge, UK). Mueller-Hinton Broth was purchased from Difco Laboratories (Detroit, MI, USA). Water from a Milli-Q Millipore system (Millipore, Burlington, MA, USA) was used to prepare aqueous solutions. Sodium myristate was from Sigma (San Luis, MO, USA). The N(π),N(τ)-bis(methyl)-L-Histidine tetradecyl amide (DMHNHC14) was synthesized in our laboratory following a three-step procedure [15 (link)]: (a) Synthesis of N(α)-Cbz-N(π),N(τ)-bis(methyl)-L-Histidine using (CH3)2SO4 (Sigma, San Luis, MO, USA) as a methylating agent, (b) preparation of the N(α)-Cbz-N(τ),N(π)-bis(methyl)-histidine tetradecyl amide simply heating the first intermediated with the tetradecyl amine (Sigma, San Luis, MO, USA) and (c) catalytic hydrogenation of intermediate 2 using Pd over charcoal (Sigma, San Luis, MO, USA). The detailed synthetic procedure as well as the characterization of DMHNHC14 High-Performance Liquid Chromatography (HPLC), Mass spectrometry (MS) and (NMR) are provide elsewhere [15 (link)]. The Nα-lauroyl-Nεacetyl lysine (C12C3L) was obtained with a purity of 99% by the condensation of the dodecyl chloride (Sigma, San Luis, MO, USA) to the ε-amino group of the commercial acetyl-lysine. Its characterization is shown in the Supporting Information (Figures S9–S13).
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9

Formulation Development of Drug Delivery Systems

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Affinisol HPMC-AS 126
G (>94% purity), Affinisol
HPMC-AS 716 G (>94%), Affinisol HPMC-AS 912 G (>94% purity),
and Methocel
E3 Premium LV Hydroxypropyl Methylcellulose (HPMC E3) were purchased
from Dow Chemicals. Poly(styrene)1.6kDa-block-poly(ethylene glycol)5kDa (PS-PEG) and polycaprolactone3.9 kDa-block-poly(ethylene glycol)5kDa (PCL-PEG) were purchased from Polymer Source Inc. Vitamin E (±-α-tocopherol),
Vitamin E succinate (d-α-tocopherol succinate), pamoic
acid disodium salt (>97% purity), sodium deoxycholate (>97%
purity),
sodium dodecyl sulfate (>99% purity), sodium myristate (>98%
purity),
and sucrose BioXtra (>99.95% purity) were purchased from Sigma-Aldrich.
Tetrahydrofuran (HPLC grade, 99.9%), methanol (HPLC grade, 99.9% purity),
and acetone (HPLC grade, 99.9% purity) were purchased from Fisher
Chemicals. Sodium oleate (>97% purity) was purchased from TCI America.
Phosphate buffered saline 10X (PBS) without calcium or magnesium was
purchased from Lonza.28 Fasted-state simulated
intestinal fluid (FaSSIF), fed-state simulated intestinal fluid (FeSSIF),
and fasted-state simulated gastric fluid (FaSSGF) were purchased from
biorelevant.com.27 Mannitol (>96.0%
purity)
from BDH was purchased from VWR. OZ439 mesylate was supplied by Medicines
for Malaria Venture (MMV).
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10

Synthesis of Cadmium Oxide Nanocrystals

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Cadmium oxide (≥99.99%), sodium myristate (Na(myr), ≥99%), octanoic acid (≥98.0%), 1,2,3,4-tetrahydronaphthalene (tetralin, synthesis grade) and chloroform-d (CDCl3, d, 99.8%) were purchased from Merck/Sigma-Aldrich. n-Hexadecane (HD, 95%) was purchased from Fiers. 1-Octadecene (ODE, 90%), oleic acid (OA, 90%) were purchased by Alfa Aesar. Cadmium nitrate tetrahydrate (99+%), propionic acid (99.5+%), toluene (>99%), methanol (99.8+%) and 2-propanol (IPA, 99+%) were purchased from Chem Lab. Acetonitrile (ACN, 99.9%) was purchased from Carl-Roth. Selenium powder (≥99.99%) and cadmium acetate dihydrate 98% were purchased by Acros Organics. All chemicals were used without further purification. A vacuum/dry nitrogen gas Schlenk line was used for nanocrystal syntheses. The purifications were conducted in air unless specified otherwise.
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