Methoxy-Functionalized Glycerol-Based Aliphatic Polycarbonate: Organocatalytic Synthesis, Blood Compatibility, and Hydrolytic Property,ACS Biomaterials Science & Engineering

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Methoxy-Functionalized Glycerol-Based Aliphatic Polycarbonate: Organocatalytic Synthesis, Blood Compatibility, and Hydrolytic Property
ACS Biomaterials Science & Engineering ( IF 5.4 ) Pub Date : 2021-01-05 , DOI: 10.1021/acsbiomaterials.0c01460
Valentina Montagna _{1,

2} , Junko Takahashi ₂ , Meng-Yu Tsai ₃ , Takayuki Ota ₃ , Nicolas Zivic ₁ , Seigou Kawaguchi ₂ , Takashi Kato ₄ , Masaru Tanaka ₅ , Haritz Sardon ₁ , Kazuki Fukushima _{2,

4}

Affiliation

Polymers that are biocompatible and degradable are desired for tissue engineering approaches in the treatment of vascular diseases, especially for those involving small-diameter blood vessels. Herein, we report the compatibility of a newly developed glycerol-based aliphatic polycarbonate possessing simple methoxy side groups, named poly(5-methoxy-1,3-dioxan-2-one) (PMDO), with blood cells and plasma proteins as well as its susceptibility to hydrolysis. As a consequence of the organocatalytic ring-opening polymerization (ROP) of a methoxy-functionalized cyclic carbonate derived from glycerol, PMDO with a sufficiently high molecular weight (M_n 14 kg/mol) and a narrow distribution (D̵_M 1.12) was obtained for evaluation as a bulk biomaterial. This study demonstrates for the first time the organocatalytic ROP of a glycerol-based cyclic carbonate in a controlled manner. Compared with the clinically applied aliphatic polycarbonate poly(trimethylene carbonate) (PTMC), PMDO inhibits platelet adhesion by 33% and denaturation of fibrinogen by 23%. Although the wettability of PMDO based on water contact angle was almost comparable to those of PTMC and poly(ethylene terephthalate), the reason for the inhibited platelet adhesion and protein denaturation appeared to be related to the presence of specific hydrated water formed in the hydrated polymer. The improved hydration of PMDO also enhanced the susceptibility to hydrolysis, with PMDO demonstrating a slightly higher hydrolytic property than PTMC. This simple glycerol-based aliphatic polycarbonate has the following benefits: bio-based characteristics of glycerol and improved blood compatibility and hydrolytic biodegradability stemming from moderate hydration of the methoxy side groups.

中文翻译：

甲氧基官能化甘油基脂肪族聚碳酸酯：有机催化合成，血液相容性和水解性能

具有生物相容性和可降解性的聚合物对于组织工程方法在血管疾病的治疗中是需要的，尤其是对于涉及小直径血管的那些。在此，我们报道了一种新开发的甘油基脂肪族聚碳酸酯，它具有简单的甲氧基侧基，称为聚（5-甲氧基-1,3-二恶烷-2-酮）（PMDO），与血细胞和血浆蛋白也具有相容性。由于其易水解。作为有机催化的开环聚合（ROP）的甲氧基官能环状碳酸酯衍生自甘油，PMDO具有足够高的分子量（的结果中号_Ñ 14公斤/ mol）和窄的分布（d_中号获得1.12）作为块状生物材料进行评估。这项研究首次证明了可控方式的甘油基环状碳酸酯的有机催化ROP。与临床应用的脂族聚碳酸酯聚碳酸三亚甲基酯（PTMC）相比，PMDO抑制血小板粘附33％，抑制纤维蛋白原变性23％。尽管基于水接触角的PMDO润湿性几乎可以与PTMC和聚对苯二甲酸乙二醇酯相媲美，但抑制血小板粘附和蛋白质变性的原因似乎与水合聚合物中形成的特定水合水有关。。PMDO更好的水合作用还增强了其对水解的敏感性，其中PMDO的水解性能略高于PTMC。

更新日期：2021-02-08

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