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2 protocols using carbodiimidazole

1

Synthesis and Characterization of Polymer Biomaterials

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Calcium hydroxide (Ca(OH)2, 98%) and orthophosphoric acid (H3PO4, 85%) were purchased
by Carlo Erba Reagents (Carlo Erba Reagents, Milano, Italy). ε-Caprolactone
(CL, 99%) and 1,5,7triazabicyclo[4.4.0]dec-5-ene (TBD, 95%) were purchased by Sigma-Aldrich, Germany. Arabic gum (AG) was
kindly gifted from the research group of Prof. Ciofani from Scuola
Superiore di Studi Universitari e Perfezionamento Sant’Anna,
CRIM Lab-Center for Applied Research in Micro and Nano Engineering.
Jeffamine (Elastamine RE-2000) was sold by Huntsman Corporation (Woodlands,
Texas, USA). Polyethylene glycol 8000 (PEG8000, MW = 8 kDa), carbodiimidazole
(CDI, 98%), deuterium oxide (99.9 atom %
D), PBS (Dulbecco’s phosphate-buffered saline solution pH =
7.4, 0.1 M), ethosuximide (Etho, MW = 141.168 g/mol),
and dimethyl fumarate (DMF, MW = 144.127 g/mol) were purchased from
Sigma-Aldrich, Germany. Fluorescein sodium salt (SF, MW = 412.3 g/mol)
and rhodamine B (RhB, MW = 479.02 g/mol) were purchased from Merck
(Deisenhofen, Germany). All reagents and solvents were used without
further purification. Solvents were of analytical laboratory grade.
Synthetized products were stored at 4 °C in the dark until used.
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2

Multifunctional Polymer Conjugate Synthesis

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Lithium diisopropylamide
(LDA), propargyl bromide, hexamethylphosphoramide (HMPA), sodium azide,
copper(II) sulfate, tin(II)-trifluoromethanesulfonate (Sn(OTf)2), ε-caprolactone, anhydrous tetrahydrofuran (THF),
monomethoxy poly(ethylene glycol) (molecular weight [Mn] = 1450 g/mol), doxorubicin hydrochloride, 4-aminobenzoic
acid, tert-butyl carbazate, carbo-di-imidazole, 2-hydroxyethyl
disulfide, 1,8-diazobicyclo[5,4,0]undec-7-ene (DBU), dicyclohexylcarbodiimide
(DCC), 4-dimethylaminopyridine (DMAP), 1-hydroxybenzotriazole (HOBt), N-(3-dimethylaminopropyl)-N-ethylcarbodiimide
hydrochloride (EDC-HCl), trifluoroacetic acid, deuterated methanol
(CD3OD), deuterated chloroform (CDCl3), and
dimethyl sulfoxide-d6 (DMSO-d6) were purchased from Sigma-Aldrich. Sodium nitrate,
potassium bromide, sodium sulfate, ammonium chloride, sodium chloride,
sodium bicarbonate, toluene, ethanol, methanol, dimethyl formamide
(DMF), ethyl acetate, dioxane, hexane, chloroform, acetone, hydrochloric
acid (HCl), acetonitrile, and dichloromethane were purchased from
Merck and used as received without further purification. All other
solvents were of highest purity and purchased from Sigma-Aldrich.
ε-caprolactone, ethanol, and THF were distilled over calcium
hydride under an inert atmosphere before use.
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