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5 protocols using sn oct 2

1

Synthesis and Characterization of Biodegradable Polymers

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l-Lactide 99.5% (Green Square Materials Inc), pentaerythritol tri and tetraacrylate (Photomer 4335), tin(ii) 2-ethylhexanoate 96% (Sn(Oct)2,Alfa Aesar®), 4-methoxyphenol (SHORA), 2-hydroxy-2-methyl-1-phenylpropanone (I.G.M Omnirad 1173), PBS Tablets (MP Biomedicals), tetrahydrofuran (TEDIA), ethyl acetate (TEDIA), acetone (TEDIA), high-purity grade silica gel, pore size 60 Å, 70–230 mesh (AACASH Exports).
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2

Synthesis of Polylactic Acid Precursors

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l-Lactide, a product of PURAC, kindly supplied by Thyssen-Uhde AG (Berlin, Germany) was recrystallized from “toluene 99.89% extra dry” purchased from ACROS Chem. (Geel, Belgium). l-Lactylamide, ethyl l-lactate (EtLac), n-butanol, 10-undecenol (10-UND), benzyl alcohol (BnOH), benzylamine (BnNH2), 2-hydroxymethyl naphthalene (2-HMN), 1,12-dodecanediol (DOD) and SnOct2 were all purchased from Alfa Aesar (Karlsruhe, Germany) and used as received. The catalysts DSTL,12 (link) BuSnBuca,13 (link) BuSnBiph,13 (link) BuSnSal,14 (link) SnSal,14 (link) BuSnNaph,13 (link) SnBiph15 (link) and SnNaph15 (link) were those already used in the cited previous publications.
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3

Synthesis of Poly(ε-caprolactone-co-lactide)

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Predetermined amounts of ε-caprolactone (ε-CL, Alfa Aesar, USA; 500 mmol), L-lactide (LA, Medichem, South Korea; 500 mmol), stannous octoate (Sn(Oct)2, Alfa Aesar, USA; 5 mmol), and 1-dodecanol (Alfa Aesar, USA; 0.2, 0.1, and 0.05 mmol for molecular weights of 60k, 140k, and 200k, respectively) were added into a dried glass ampule equipped with a magnetic stirring bar. The ampule was sealed under vacuum after purging three times with N2 at 90 °C and heated in an oil bath at 150 °C. After the reaction for 24 h, the product was dissolved in chloroform and microfiltered through a membrane filter with a pore size of 0.45 μm. It was then precipitated by pouring the polymer solution into excess methanol to remove the catalyst and unreacted monomers, filtered, and dried in a vacuum oven at 50 °C for 24 h. The products were analyzed by 1H nuclear magnetic resonance (NMR) and gel permeation chromatography (GPC) (Supplementary Fig. S1).
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Multifunctional Bioactive Chitosan Hydrogel

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Poly(ε-caprolactone) diol (PCL, Mn 2000 Da, Sigma-Aldrich, St. Louis, MO, USA), isophorone diisocyanate (IPDI, Acros, Geel, Belgium), Sn(Oct)2 (Alfa Aesar, Haverhill, MA, USA), 2,2-bis(hydroxymethyl) propionic acid (DMPA, Sigma-Aldrich, St. Louis, MO, USA), triethylamine (TEA, J.T. Baker, Phillipsburg, NJ, USA), ethylenediamine (EDA, Tedia, Fairfield, OH, USA), glyoxal (Alfa Aesar, Haverhill, MA, USA), chitosan (170 kDa, 97% deacetylation, Kiotec, Hsinchu, Taiwan), acrylic acid (Showa, Gyoda, Japan), NaOH (Sigma-Aldrich, St. Louis, MO, USA), methacrylic anhydride (MAA, Sigma-Aldrich, St. Louis, MO, USA), acetic acid (Fluka, Buchs, Switzerland), pyrrole (Alfa Aesar, Haverhill, MA, USA), oxidant ammonium persulfate (APS, Sigma-Aldrich, St. Louis, MO, USA), HCl (Showa, Gyoda, Japan), high glucose Dulbecco’s modified Eagle’s medium (HG-DMEM, Gibco, Waltham, MA, USA), fetal bovine serum (FBS, Gibco, Waltham, MA, USA), Ham’s F-12 (Gibco, Waltham, MA, USA), G418 (Invitrogen, Waltham, MA, USA), penicillin-streptomycin-amphotericin (PSA, Caisson Laboratories, Inc., Smithfield, UT, USA), cell counting Kit-8 (CCK-8, Sigma-Aldrich, St. Louis, MO, USA), and KAPA SYBR Green qPCR kit (Kapa Biosystems, Inc., Wilmington, MA, USA) were applied in commercial form.
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5

Synthesis and Characterization of Poly(Lactide-co-Caprolactone)

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L,L-Dilactide (Purasorb L), D,D-dilactide (Purasorb D), and Poly(D-lactide, Mw = 147 kg·mol−1, Purasorb PD24) were bought from Corbion, Amsterdam, the Netherlands. ε-caprolactone (99%), 1-hexanol (99%, anhydrous), and 1-dodecanol were purchased from Acros Organics, Geel Belgium. Sn(Oct)2 (96%) was received from Alfa Aesar, Kandel, Germany. THF (anhydrous, >99.9%, 250 ppm BHT), DMSO-d6, and CDCl3 were from Sigma Aldrich, Munich, Germany, and chloroform (>99%) and methanol from Roth, Karlsruhe, Germany.
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