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L lactide

Manufactured by Merck Group
Sourced in United States, Germany

L-lactide is a cyclic diester formed from two lactic acid molecules. It is a white crystalline solid used as a monomer in the production of polylactic acid (PLA), a biodegradable polymer with applications in various industries.

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42 protocols using l lactide

1

Biodegradable Polymer-Drug Conjugates for Cancer Therapy

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PEG (MW 2 kDa, abbreviated as 2 K), methoxy poly(ethylene glycol) (mPEG; MW 2 K), L-lactide ((3S)-cis-3,6-dimethyl-1,4-dioxane-2,5-dione), N,N-dicyclohexylcarbodiimide (DCC), stannous octoate (tin(II)-2-ethylhexanoate, Sn(Oct)2), 4-dimethylaminopyridine (DMAP), dimethylsulfoxide (DMSO), succinic anhydride, pyridine, and triethylamine (TEA) were purchased from Sigma-Aldrich (St. Louis, MO, USA). Tetrahydrofuran (THF), toluene, acetone, and dichloromethane (DCM) were purchased from Honeywell Burdick & Jackson® (Muskegon, MI, USA). Doxorubicin (DOX)•HCl was purchased from Boryung Co. (Jongro-gu, Seoul, Korea). Paclitaxel was obtained from Samyang Co. (Seongnam-si, Gyeonggi-do, Korea). Diethyl ether and hexane were purchased from Samchun Chemical (Gangnam-gu, Seoul, Korea). Fluorescein-5-isothiocyanate (FITC-5-isothiocyanate) was purchased from Thermo Fisher Scientific (Waltham, MA, USA). KB cells were obtained from the Korean Cell Line Bank (Jongno-gu, Seoul, Korea). RPMI 1640 medium, Dulbecco’s Phosphate-Buffered Saline (DPBS), penicillin–streptomycin solution, trypsin–EDTA solution, and FBS were purchased from Welgene (Gyeongsan-si, Gyeongsangbuk-do, Korea). The Cell Counting Kit-8 (CCK-8) was purchased from Dojindo Molecular Technologies, Inc. (Rockville, MD, USA). The PierceTM BCA Protein Assay Kit was obtained from Thermo Fisher Scientific.
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2

Synthesis and Evaluation of Polymer Nanoparticles

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Dulbecco’s Modified Eagle’s Medium (DMEM) was purchased from Invitrogen (Carlsbad, CA). All primary antibodies were purchased from Cell Signaling (Beverly, MA) and Santa Cruz Biotechnology (Dallas, TX). B16F10 mouse melanoma cell line and A375 human melanoma cell line were acquired from the American Type Culture Collection (ATCC). Cells were cultured in DMEM supplemented with 10% fetal bovine serum (FBS) (Atlanta Biologicals), and 1.0% antibiotic/antimycotic mixture (Invitrogen) PC3 and PC3-TXR cells were kindly provided by Dr. Evan T. Keller from the University of Michigan. These cells were cultured in RPMI-1640 medium supplemented with 10% FBS and 1% penicillin/streptomycin in a humidified incubator containing 5% CO2 at 37 °C and their resistance to taxane was maintained by adding 200 nM paclitaxel to growth media biweekly. 2,2-Bis(hydroxymethyl)propionic acid, methoxy poly(ethylene glycol) (mPEG, 5,000 Da), 8-diazabicycloundec-7-ene (DBU), benzyl bromide, L-lactide, and all other reagents were purchased from Sigma-Aldrich (St. Louis, MO) and used as received.
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3

Synthesis of Functional Azide-Containing Monomers

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Propargyloxylactic acid (5) was synthesized according to our previous report.31 (link) The tosylate of triethylene glycol monomethyl ether was prepared following a previous report.32 1-(2-azidoethoxy)-2-(methoxyethoxy) ethane (m3PEGN3)33 and 1-azidodecane (C10H21N3)34 were synthesized using literature procedures. Sodium azide, tosyl chloride (TsCl), p-toluenesulfonic acid monohydrate (TsOH), 4-tert-butylbenyl alcohol (TBBA), triethylene glycol monomethyl ether (m3PEG) and 1-bromo-decane were purchased from Sigma-Aldrich. l-Lactide (LA) was purchased from Sigma-Aldrich and recrystallized from ethyl acetate before use. Stannous octanoate (Sn(Oct)2) was freshly distilled under vacuum and kept in dry box before use. THF and toluene were dried over sodium/benzophenone and distilled before use. The silica gel (60 Å porosity) for column chromatography was purchased from SiliCycle Inc. All other reagents and solvents were ACS grade and used as received unless specified.
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4

Synthesis of Conjugated Polymer Precursor

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3-hexylthiophene ≥
98.0% (3HT) and hydroxymethyl EDOT ≥ 97.0% were supplied by
TCI; iron(III) chloride, sodium hydroxide, and methanol ≥ 99.9%
were purchased from Fluka; methanesulfonic acid ≥ 99.0% ≥
99.0% (MSA) and 4-(dimethylamino)pyridine ≥ 98.0% (DMAP) were
provided by Sigma-Aldrich and used as received. l-Lactide
≥ 85.0% (LA) was purchased from Sigma-Aldrich and purified
by solving the lactic acid in toluene at 60 °C, followed by the
precipitation and crystallization at room temperature twice. Then,
the toluene was removed by rotary evaporation, and the final product
was dried under vacuum.
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5

Enzymatic Polymerization of Lactide

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Adipic acid (AdA) (purity: >99.5%), poly(phosphoric acid) (PPA) and 1,3-propanediol (1,3-PD) (purity: >99.6%) were purchased from Fluka (Steinheim, Germany). Titanium butoxide (purity: >97.0%), Ti(OBu)4) and tin(II) 2-ethylhexanoate (Sn(Oct)2) were used as catalysts, l-Lactide (LA), (3S)-cis-3,6-Dimethyl-1,4-dioxane-2,5-dione (98%) and poly(vinyl alcohol) (PVA), Mw 31,000–50,000 Da (87%–89% hydrolyzed) were purchased from Sigma Aldrich Chemical Co (Steinheim, Germany). Rhizopus oryzae and Pseudomonas cepacia were purchased from BioChemika (Steinheim, Germany). Naltrexone base (99.9%) was kindly donated by Pharmathen S.A. (Athens, Greece). All other reagents and solvents used for the analytical methods were of analytical grade.
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6

Synthesis and Characterization of Doxorubicin-Loaded Polymeric Nanoparticles

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Poly(ethylene glycol) (PEG) methyl ether, molecular weight [MW] 5,000 Da), L-lactide (3,6-dimethyl-1,4-dioxite-2,5-dione), stannous octoate (Sn[Oct]2, Tin[II]2-ethylhexanoate), 4-(dimethylamino)pyridine (DMAP), pyren, succinic anhydride, pyridine, triethylamine (TEA), N-hydroxysuccinicimide (NHS), N,N′-dicyclohexylcarbodiimide (DCC), anhydrous 1,4-dioxane, N,N-dimethylformamide (DMF), D2O-d6, and CDCl3 were purchased from Sigma-Aldrich (St Louis, MO, USA). Triphosgene and branched PEI (MW 10,000 Da) were purchased from Alfa Aesar® Johnson Matthey Korea (Seoul, South Korea). Dichloromethane (DCM), methanol (MeOH), ethanol (EtOH), and toluene were purchased from Honeywell Burdick & Jackson® (Muskegon, MI, USA). Dox⋅HCl was purchased from Borung Co. (Seoul, South Korea). All other chemicals used were of analytical grade. For cell culture, human breast cancer MCF7 cells and cervical cancer KB cells were obtained from the Korean Cell Line Bank (KCLB, Seoul, South Korea). RPMI 1640 medium, fetal bovine serum (FBS), penicillin, and streptomycin were purchased from Welgene (Seoul, South Korea). Cell Counting Kit-8 (CCK-8) was obtained from Dojindo Molecular Technologies (Tokyo, Japan). P(Asp) was prepared as previously reported.20 The MW of P(Asp) was ~4,000 Da (degree of polymerization =35).
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7

Folate-Conjugated Doxorubicin Nanoparticles

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Doxorubicin was purchased from RPG Life Sciences limited (Mumbai, India). L-lactide, poly(ethylene glycol) (PEG) with MW 4000 g/mol, Hydrazine, N-hydroxysuccinimide (NHS), dicyclohexylcarbodiimde (DCC), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC ), stannous octoate, folate and MTT were obtained from Sigma (St Louis, MO, USA). p-Nitrophenyl chloroformate (p-NPC), acetonitrile, toluene, dichloromethane and acetone (analytical grade) were purchased from Merck (Darmstadt, Germany). RPMI 1640 medium and penicillin/streptomycin solution were obtained from Gibco Invitrogen (Carlsbad, CA, USA). All other chemicals were of analytical grade.
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8

Conjugation of Anti-EGFR mAb C225 with Photosensitizer Ce6

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The anti-EGFR monoclonal antibody (mAb) C225 was purchased from Merck KGaA (Darmstadt, Germany). The photosensitizer chlorin e6 (Ce6) was obtained from Frontier Scientific, Inc. (Logan, UT, USA). Hydroxyl poly(ethylene glycol)-maleimide (Mal-PEG-OH, Mal-PEG, MW 3400 Da) was purchased from JenKem Technology Co., Ltd. (Allen, TX, USA), and its chemical structure was confirmed by NMR. Monomethoxy poly(ethylene glycol) (CH3O-PEG-OH, MW 2000), l-lactide, pyrene, IgG, ZnEt2, 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT), toluene, methanol, n-hexane, tetrahydrofuran (THF), dimethylsulfoxide (DMSO), and dichloromethane (DCM) were purchased from Sigma-Aldrich (St. Louis, MO, USA). Traut’s reagent (2-iminothiolane) was obtained from Pierce (Rockfield, IL, USA).
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9

Synthesis and Characterization of Plasticizer Candidates

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1,4-Butanediol (BTD, 99%, Riedel-de Haën), d-isosorbide (ISB, 98%, Sigma-Aldrich), levulinic acid (LeA,
97%, Sigma-Aldrich), l-lactide (98%, Sigma-Aldrich), p-toluene sulfonic acid monohydrate (PTSA·H2O, 98.5%, Sigma-Aldrich), and tin(II) 2-ethylhexanoate (Sn(Oct)2, 92.5%, Sigma-Aldrich) were utilized for the synthesis of
plasticizer candidates. Ethyl acetate (EtOAc, analytical reagent grade,
Fisher Scientific) and potassium carbonate (analytical reagent grade,
Arcos) were employed in purifying and extracting the plasticizer candidates.
Dichloromethane (HPLC grade, Fisher Scientific) and polylactide (5200D,
Nature Works, Mn = 112,000 g/mol, Đ = 1.9) were used in solution casting to obtain neat
and blended PLA films. Chloroform-d (99.8%, Cambridge
Isotope Laboratories) and methanol (hypergrade for LC–MS, Merck)
were used as solvents in nuclear magnetic resonance (NMR) and electrospray
ionization mass spectrometry (ESI-MS) analyses, respectively. Water
(hypergrade for LC–MS, Merck) was utilized in the hydrolytic
aging experiments. Most chemicals were used as received, except BTD
and Sn(Oct)2, which were preserved with the activated molecular
sieves and l-lactide that was recrystallized in toluene twice
before use.
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10

Multifunctional Polyplexes for Gene Delivery

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Branched PEI (molecular weight 1800Da and 25kDa) were obtained from Alfa Aesar, USA. Isophorone di-isocyanate (IPDI), L-lactide, folic acid (FA), catalyst stannous octoate (Sn(Oct)2, 95%), 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC), N-Hydroxysuccinimide (NHS), 4′,6-Diamidino-2-phenylindole dihydrochloride (DAPI), Hoechst 33258, propidium iodide (PI), Dulbecoo’s Modified Eagle’s Medium (DMEM), Roswell Park Memorial Institute (RPMI)-1640 Medium (1640) and 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) were purchased from Sigma, USA. PECE hydrogel (PEG550-PCL2200-PEG550) was supplied by our group. Plasmid eGFP (green fluorescent protein) was offered by our group and after amplification was isolated and purified using a Qiagen plasmid purification kit following the protocol provided by manufacturer. Murine anti-oncogene WIF-1 (NM_011915.2) transformed into E.Coli JM109 was purchased as a sample from Biowit Technologies, China and after amplification was isolated and purified using a Qiagen plasmid purification kit. An Annexin V-FITC Apoptosis Detection Kit was supplied by Keygene biotech, China. Other chemicals were got from Chengdu KeLong Chemicals, China. They were all analytical pure grade and used as received.
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