Fujisawa S, Kadoma Y, Masuhara E
J Biomed Mater Res. 1984 Nov-Dec;18(9):1105-14. doi: 10.1002/jbm.820180912.
Mono-, di-, and trimethacrylates (monomers) are widely used in dentistry as restorative materials, adhesives, prosthetic devices, etc. It is known that the residual monomers released from the cured resin have been implicated in toxicological effects. In order to monitor the biological actions at the membrane level induced by monomers, we studied the changes in the phase transition temperature (T) and enthalpy (delta H) of dipalmitoyl-phosphatidylcholine liposomes induced by 37 different monomers using differential scanning calorimetry (DSC). The monomers that caused large changes in the T and delta H were vinyl monomers; acrylates; monomethacrylates that contain hydroxy, carbonyl, amino and phenyl groups; dimethacrylates with short-chain substituents; and aliphatic trimethacrylates. It is suggested that the changes in the T and delta H values may be due not only to hydrophobic interactions, but also to interactions induced by the double bonds or the functional groups in the monomers. On the other hand, methacrylates with simple alkyl ester linkage and dimethacrylates with bisphenol A groups exhibited the smallest changes. The changes in the T and delta H induced by highly hydrophobic methacrylates were small due to their slower interaction. These changes in transition properties of liposomes seem to be related to biological activities.
单甲基丙烯酸酯、二甲基丙烯酸酯和三甲基丙烯酸酯（单体）在牙科领域被广泛用作修复材料、粘合剂、假牙装置等。已知固化树脂释放的残留单体与毒理学效应有关。为了监测单体在膜水平上诱导的生物学作用，我们使用差示扫描量热法（DSC）研究了37种不同单体诱导的二棕榈酰磷脂酰胆碱脂质体的相变温度（T）和焓（ΔH）的变化。引起T和ΔH大幅变化的单体是乙烯基单体、丙烯酸酯、含有羟基、羰基、氨基和苯基的单甲基丙烯酸酯、具有短链取代基的二甲基丙烯酸酯以及脂肪族三甲基丙烯酸酯。有人认为，T和ΔH值的变化可能不仅归因于疏水相互作用，还归因于单体中的双键或官能团诱导的相互作用。另一方面，具有简单烷基酯键的甲基丙烯酸酯和具有双酚A基团的二甲基丙烯酸酯表现出最小的变化。高度疏水的甲基丙烯酸酯诱导的T和ΔH变化较小，因为它们的相互作用较慢。脂质体转变特性的这些变化似乎与生物活性有关。
