ε caprolactone ε cl

Manufactured by Merck Group

Sourced in United States, Spain

ε-caprolactone (ε-CL) is a cyclic ester compound. It is a colorless, viscous liquid. ε-CL is commonly used as a monomer for the production of polycaprolactone, a biodegradable polymer with various applications.

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20 protocols using ε caprolactone ε cl

Synthesis and Characterization of Polycaprolactone

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ε-Caprolactone (εCL) (98%, Sigma-Aldrich,
Sweden) was dried over calcium hydride for at least 24 h and subsequently
distilled at reduced pressure under an inert gas atmosphere prior
to use. All of the other chemicals were used as received. These chemicals
included initiators (i.e., benzyl alcohol (≥99%, Sigma-Aldrich,
Sweden) and 2-naphthalene ethanol (98%, Sigma-Aldrich, Sweden)), catalysts
(i.e., 1,5,7-triazabicyclo[4.4.0]-dec-5-ene (TBD) (98%, Sigma-Aldrich,
Sweden)), and a phosphazene base P₂-tBu
solution (P₂-tBu, ∼2 M in THF,
Sigma-Aldrich, Sweden). In addition, sodium hydride (NaH) (60% dispersion
in mineral oil, Sigma-Aldrich, Sweden), diethyl carbonate (99%, Sigma-Aldrich,
Sweden), trimethylolpropane allyl ether (98%, Sigma-Aldrich, Sweden),
acetic acid (technical, Fisher Scientific, Germany), acetic acid anhydride
(ReagentPlus, ≥ 99%, Sigma-Aldrich, Sweden),
triethylamine (TEA) (≥99%, Sigma-Aldrich, Sweden), dichloromethane
(anhydrous, ≥ 99.8%, Sigma-Aldrich, Sweden) chloroform (HPLC
grade, Fisher Scientific, Germany), chloroform-d (99.8%,
with silver foil, Cambridge Isotope Laboratories), and methanol (general
purpose grade, Fischer Scientific, Germany) were used.

Olsén P., Odelius K., Keul H, & Albertsson A.C. (2015). Macromolecular Design via an Organocatalytic, Monomer-Specific and Temperature-Dependent “On/Off Switch”. High Precision Synthesis of Polyester/Polycarbonate Multiblock Copolymers. Macromolecules, 48(6), 1703-1710.

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Stem Cell Culture and Differentiation

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Polyethylene oxide monomethyl ether (PEO₄₅, PEO₁₄₈, PEO₂₃₀, Sigma Aldrich), poly(ε-caprolactone) (PCL₃₉₄, average M_n 45,000 g/mol, Sigma Aldrich, St. Louis, MO, USA), ε-caprolactone (ε-CL, purity: 97%, Sigma Aldrich, St. Louis, MO, USA) (see Figure 1), stannous (II) octoate (SnOct₂, purity: 95%, Sigma Aldrich, St. Louis, MO, USA), tetrahydrofuran (THF, purity ≥99.5%, Merck, Darmstadt, Germany), n-hexane (purity ≥98.5%, Merck, Darmstadt, Germany), and dichloromethane (DCM, purity ≥99.8%, Merck, Darmstadt, Germany), were used as received. Culture medium (NeuroCult and NeuroCult NSA proliferation medium-rat, STEMCELL Technologies, Vancouver, BC, Canada) were used to culture stem cells. The following primary antibodies were used for immunofluorescence assays: (i) glial fibrillary acidic protein (GFAP, astrocyte marker), polyclonal raised in rabbit (1:750 dilution, Sigma, St. Louis, MO, USA); (ii) β-III tubulin (neuronal marker), monoclonal (1:750 dilution, Sigma, St. Louis, MO, USA); 1 mg/mL DAPI solution for nucleus staining (4′,6-diamidino-2-phenylindole dihydrochloride, Molecular Probes, Thermo Fisher Scientific, Waltham, MA, USA). Secondary antibodies conjugated with Alexa Fluor 488 or 594 (1:500 dilution, Invitrogen, Carlsbad, CA, USA) were also used.

Fernández D., Guerra M., Lisoni J.G., Hoffmann T., Araya-Hermosilla R., Shibue T., Nishide H., Moreno-Villoslada I, & Flores M.E. (2019). Fibrous Materials Made of Poly(ε-caprolactone)/Poly(ethylene oxide)-b-Poly(ε-caprolactone) Blends Support Neural Stem Cells Differentiation. Polymers, 11(10), 1621.

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Synthesis of Stereochemically Pure PLA

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l-Lactide (Purac,
Singapore) was recrystallized from dry ethyl acetate, sublimed under
reduced pressure, and stored in a glovebox. ε-Caprolactone (ε-CL)
(Sigma-Aldrich, USA) was dried over calcium hydride for 24 h and vacuum-distilled
before use. 1, 8-Diazabicyclo [5.4.0] undec-7-ene (DBU) and diphenyl
phosphate (DPP) (from Sigma-Aldrich, USA) were used as received. Dipentaerythritol
(DPE, Sigma-Aldrich) was dried at 30 °C under vacuum (1 mm of
Hg) for 5 h before use. All monomers, initiators, and catalysts were
stored in a glovebox (MBRAUN UNilab TM). Injection molding grade poly(l-lactide) (PLA, Ingeo 3052D, NatureWorks, USA) with M_n = 95,000 g/mol and Đ = 1.5 was used as received. The T_m of
the PLA is 160 °C. Based on this, it is estimated that the enantiomeric
purity of the PLA is above ∼95%.⁵⁶ Other laboratory grade reagents and solvents were used as received.

Deokar M.D., Garnaik B, & Sivaram S. (2022). Toughening Poly(l-lactide) Blends: Effectiveness of Sequence-Controlled Six-Arm Star-Branched Block Copolymers of Poly(l-lactide) and Poly(ε-caprolactone). ACS Omega, 7(11), 9118-9129.

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Synthesis of Polyurethane Biomaterials

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DHBA (3,4-Dihydroxybenzoic acid), 1,1′-carbonyldiimidazole (CDI), thionyl chloride (SOCl₂), triethyl orthoformate (TEOF), resin Amberlyst 15, polycaprolactone diol with molecular weight of 2037 (PCL-2000), 1,4-butanediol (BD), ε-caprolactone (ε-CL), tin(II) 2-ethylhexanoate (Sn(Oct)₂), N,N-dimethyl-acetamide (DMAc), and 1,6-diisocyanatohexane (HDI) were purchased from Sigma-Aldrich (Madrid, Spain). The diisocyanate product was freshly distilled at low pressure before use, and the rest of the products were used as received. AMPD (2-Amino-2-methyl-1,3-propanediol) and N,N-diethanolamine (DEA) were purchased from Merck (Madrid, Spain) and used as received.

Briz-López E.M., Navarro R., Martínez-Hernández H., Téllez-Jurado L, & Marcos-Fernández Á. (2020). Design and Synthesis of Bio-Inspired Polyurethane Films with High Performance. Polymers, 12(11), 2727.

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Synthesis of Biobased Polymeric Materials

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ε-caprolactone (ε-CL, purity: 97%, MW = 114.14 g/mol), p-coumaric acid (PCA, purity: ≥98.0%, MW = 164.16 g/mol), and 4-dodecylbenzenesulfonic acid (DBSA, purity: ≥95%, MW = 326.49 g/mol) were purchased from Sigma-Aldrich and used without further purification.

Contardi M., Alfaro-Pulido A., Picone P., Guzman-Puyol S., Goldoni L., Benítez J.J., Heredia A., Barthel M.J., Ceseracciu L., Cusimano G., Brancato O.R., Di Carlo M., Athanassiou A, & Heredia-Guerrero J.A. (2019). Low molecular weight ε-caprolactone-p-coumaric acid copolymers as potential biomaterials for skin regeneration applications. PLoS ONE, 14(4), e0214956.

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Multivalent Mannose-Functionalized Nanoparticles

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4-Cyano-4-[(dodecylsulfanylthiocarbonyl)sulfanyl]pentanol (CDSP, containing 15 wt % ethyl acetate as residual solvent), tin(II) 2-ethylhexanoate (Sn(Oct)₂, 95%), ε-caprolactone (ε-CL, 99%), concanavalin A (ConA, Type VI, lyophilized powder) lectin, mucin from porcine stomach (type II) and 2,2′-azoisobutyronitrile (AIBN, 98%) were purchased from Sigma-Aldrich Chemical Co (St. Louis, MO, USA), Doxorubicin (DOX) hydrochloric acid salt (DOX·HCl, 99%) was purchased from LC Laboratories (Woburn, MA, USA). All other regents were purchased from Sigma-Aldrich or Merck Chem. Co. (Darmstadt, Germany), and were used without further purification. Pentafluorophenyl acrylate (PFA) and 2-aminoethyl-α-d-mannopyranoside were synthesized according to the methods reported in the literature [18 (link),19 (link)].

Li N.N., Cai X.Y., Chen J.C., Hu X.F, & Xu L.Q. (2016). Conjugation of Lectin to Poly(ε-caprolactone)-block-glycopolymer Micelles for In Vitro Intravesical Drug Delivery. Polymers, 8(11), 379.

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Abamectin-Loaded Polymeric Nanoparticles for Nematode Control

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Abamectin (95.5%) was supplied by Hebei Veyong Bio-Chemical Co., Ltd. (Shijiazhuang, China). Poly(lactic-co-glycolic acid)-b-poly(ethylene glycol) (PLGA-b-PEG, 10k-b-5k) and poly(d,l-lactide)-b-poly(ethylene glycol) (PLA-b-PEG, 10k-b-5k) were purchased from Jinan Daigang Biomaterial Co., Ltd. (Jinan, China); ε-Caprolactone (ε-CL), stannous octoate, anhydrous toluene, and monomethoxy poly(ethylene glycol) (MW = 5000) were purchased from Sigma-Aldrich; diethyl ether was purchased from Shanghai Tianlian Fine Chemical Co., Ltd. (Shanghai, China), and tetrahydrofuran (THF) was purchased from Beijing Chemical Reagents Company (Beijing, China). Poly(caprolactone)-b-poly(ethylene glycol) (PCL-b-PEG, 10k-b-5k) was synthesized according to a previously reported method [32 (link)].
A population of root-knot nematodes (Meloidogyne incognita) was originally obtained from a greenhouse in the Beijing Academy of Agriculture and Forestry, Beijing, China.

Fu Z., Chen K., Li L., Zhao F., Wang Y., Wang M., Shen Y., Cui H., Liu D, & Guo X. (2018). Spherical and Spindle-Like Abamectin-Loaded Nanoparticles by Flash Nanoprecipitation for Southern Root-Knot Nematode Control: Preparation and Characterization. Nanomaterials, 8(6), 449.

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Polymeric Nanoformulation for Genistein Delivery

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PCL (MW, 14,000 Da), ε-caprolactone (ε-CL), TPGS, stannous octoate (Sn(Oct)₂), methanol (HPLC [high-performance liquid chromatography]-grade), genistein powder with about 98% purity (HPLC-grade), coumarin-6, 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT), and 4′,6-diamidino-2-phenylindole (DAPI) were purchased from Sigma-Aldrich (St Louis, MO, USA). Dulbecco’s Modified Eagle’s Medium (DMEM) and fetal bovine serum were obtained from Gibco BRL (Invitrogen Co, Carlsbad, CA, USA). Human cervical carcinoma cell line HeLa cells were kept by our laboratory.

Zhang H., Liu G., Zeng X., Wu Y., Yang C., Mei L., Wang Z, & Huang L. (2015). Fabrication of genistein-loaded biodegradable TPGS-b-PCL nanoparticles for improved therapeutic effects in cervical cancer cells. International Journal of Nanomedicine, 10, 2461-2473.

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Synthesis of Polycaprolactone-Based Polyurethanes

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Anhydrous pyridine, 4-(N,N-dimethylamino)pyridine (DMPA), dichloromethane, sodium bisulphate, ε-caprolactone (ε-CL), stannous octoate SnOct₂ and polycaprolactone diol of nominal molecular weight of 522 g mol⁻¹ were supplied by Sigma Aldrich Química S.L. (Madrid, Spain) and used as received. 1,4-Butanediol (BD) was supplied by Sigma Aldrich Química S.L. and dried over magnesium sulphate, distilled and stored with nitrogen atmosphere before use. N,N-Dimethylacetamide (DMAc) was dried by distillation over commercial polymeric MDI.^{24 (link)} Amino-4-methylcoumarin (AMC) was provided by Carbosynth and used as received. Isophorone diisocyanate (IPDI) was a gift by Evonik Industries and used as received.

Navarro R., Seoane-Rivero R., Cuevas J.M, & Marcos-Fernandez Á. (2020). A novel strategy to polyurethanes with improved mechanical properties by photoactivation of amidocoumarin moieties. RSC Advances, 10(50), 29935-29944.

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Synthesis of Biodegradable Polymeric Nanoparticles

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Vitamin E TPGS (TPGS; purum 99.5%), ε-caprolactone (ε-CL; purum 99%), stannous octoate (Sn(Oct)₂; purum 95.0%) and poly(vinyl alcohol) (PVA; hydrolyzed 87%-89%, having Mw between 13,000 and 23,000) were purchased from Sigma-Aldrich (Sigma-Aldrich Corporation, St Louis, MO). ε-CL was distilled at 94 °C–95 °C under reduced pressure at about 5 mmHg prior to use in order to remove the inhibitor contained within. Rhizopus delemar and Pseudomonas cepacia lipases were purchased from BioChemika. AL API was kindly donated by Pharmathen S.A. All other chemicals and reagents were of analytical grade.

Koulouktsi C., Nanaki S., Barmpalexis P., Kostoglou M, & Bikiaris D. (2019). Preparation and characterization of Alendronate depot microspheres based on novel poly(-ε-caprolactone)/Vitamin E TPGS copolymers. International Journal of Pharmaceutics: X, 1, 100014.

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