Cytotoxicity of methyl methacrylate (MMA) and related compounds and their interaction with dipalmitoylphosphatidylcholine (DPPC) liposomes as a model for biomembranes.
Cytotoxicity of methyl methacrylate (MMA) and related compounds and their interaction with dipalmitoylphosphatidylcholine (DPPC) liposomes as a model for biomembranes.
复制标题
甲基丙烯酸甲酯（MMA）和相关化合物的细胞毒性及其与作为生物膜模型的二棕榈酰磷脂酰胆碱（DPPC）脂质体的相互作用。
DOI：
10.1111/j.1601-0825.2000.tb00116.x
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发表时间：
2008
期刊：
影响因子：
3.8
通讯作者：
Y. Kadoma
中科院分区：
文献类型：
--
作者：
S. Fujisawa;T. Atsumi;Y. Kadoma
目标
旨在阐明甲基丙烯酸甲酯 (MMA) 和相关化合物对活细胞膜的潜在作用机制，并与它们与作为生物膜模型的二棕榈酰磷脂酰胆碱 (DPPC) 脂质体的相互作用进行比较。
材料和方法
对于（甲基）丙烯酸酯，使用MMA、丙烯酸乙酯（EA）、丙烯酸正丁酯（BA）和甲基丙烯酸正丁酯（BMA），对于活细胞，使用原代人牙龈成纤维细胞（HGF）、人颌下腺腺癌细胞系（HSG）和人红细胞。使用差示扫描量热法 (DSC) 和核磁共振波谱 (NMR) 研究了 (甲基) 丙烯酸酯诱导的 DPPC 脂质体的物理化学变化。
结果
细胞毒性降低如下：BA > BMA > EA > MMA。相变特性的变化（DSC峰的温度Tm、焓δH和高度/半高宽（H/HHW）降低如下：BA>EA>MMA。BMA增强H/HHW并略微增加Tm。NMR屏蔽效应降低如下：BMA>MMA>BA、EA。
结论
与 EA 或 MMA 相比，BA 和 BMA 由于其亲脂性而表现出较大的细胞毒性和较高的 DPPC 相互作用。 MMA表现出很小的细胞毒性并且在DPPC脂质体中变化很小，而BA表现出很大的细胞毒性并且在以膜扰动为特征的脂质体中变化很大。丙烯酸酯的溶血活性和细胞毒性均高于甲基丙烯酸酯。 (甲基)丙烯酸酯的物理化学性质（Log P 或 Q sigma）影响生物膜中的脂质双层。
OBJECTIVE
To clarify the potential mechanism of action of methyl methacrylate (MMA) and related compounds to membranes of living cells, compared with their interaction with dipalmitoylphosphatidylcholine (DPPC) liposomes as a model for biological membranes.
MATERIALS AND METHODS
For (meth)acrylates, MMA, ethyl acrylate(EA), n-butyl acrylate (BA) and n-butyl methacrylate (BMA) and for living cells, primary human gingival fibroblast (HGF), human submandibular gland adenocarcinoma cell line (HSG) and human erythrocytes were used. The physicochemical changes in DPPC liposomes induced by (meth)acrylates were studied using differential scanning calorimetry (DSC) and nuclear magnetic resonance spectroscopy (NMR).
RESULTS
Cytotoxicity decreased as follows: BA > BMA > EA > MMA. Changes in phase transition properties (temperature Tm, enthalpy delta H and Height/Half-Height Width (H/HHW) of DSC peak were decreased as follows: BA > EA > MMA. BMA enhanced H/HHW and increased Tm slightly. NMR-shielding effect decreased as follows: BMA > MMA > BA, EA.
CONCLUSION
BA and BMA exhibited large cytotoxicity and high DPPC-interaction due to their lipophilicity, compared to EA or MMA. MMA showed little cytotoxicity and small changes in DPPC liposomes, whereas BA showed large cytotoxicity and large changes in the liposomes characterized by the membrane disturbance. Haemolytic activity and cytotoxicity of acrylates were higher than those of methacrylates. The physico-chemical properties (Log P or Q sigma) of (meth)acrylates affect the lipid bilayer in biological membranes.