Dipalmitoylphosphatidylcholine (DPPC) and DPPC Cholesterol Liposomes as Predictors of the Cytotoxicity of Bis-GMA Related Compounds

In light of recent development, dental materials such as 2, 2- bis [4-2(-hydroxy-3-methacryloyloxypropoxy)phenyl] propane, (bis-GMA); 2, 2- bis [4-(1-hydroxymethyl-2-methacryloxy)phenyl] propane, (iso- bis-GMA); and triethyleneglycol dimethacrylate, (TEGDMA) were investigated to determine whether th...

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Bibliographic Details
Published in:Journal of liposome research 2004, Vol.14 (1-2), p.39-49
Main Authors: Fujisawa, Seiichiro, Kadoma, Yoshinori, Ishihara, Mariko, Atsumi, Toshiko, Yokoe, Ichiro
Format: Article
Language:English
Subjects:
1,2-Dipalmitoylphosphatidylcholine - chemistry
Bisphenol A-Glycidyl Methacrylate - chemistry
Bisphenol A-Glycidyl Methacrylate - toxicity
Calorimetry, Differential Scanning
Cholesterol - chemistry
Dental material
DPPC liposomes
DSC
Liposomes
Molecular Structure
PM3 calculation
Temperature
Thermodynamics
Toxicity Tests
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Summary:In light of recent development, dental materials such as 2, 2- bis [4-2(-hydroxy-3-methacryloyloxypropoxy)phenyl] propane, (bis-GMA); 2, 2- bis [4-(1-hydroxymethyl-2-methacryloxy)phenyl] propane, (iso- bis-GMA); and triethyleneglycol dimethacrylate, (TEGDMA) were investigated to determine whether their phase transition properties (phase transition temperature, temperature width, cooperativity) could be induced in samples of DPPC or DPPC cholesterol (CHOL) liposomes using differential scanning calorimetry (DSC). The changes in phase transition properties of DPPC liposomes caused by addition of TEGDMA were greater than those caused by addition of bis-GMA or iso-bis-GMA, but the extent of changes in the properties of DPPC CHOL (10:1 or 4:1) liposomes declined in the order of bis-GMA > iso-bis-GMA > TEGDMA. The degree of alteration was related to the cytotoxicity of these compounds. DPPC CHOL liposomes were found to be better predictors of cytotoxicity than DPPC liposomes. Whether the computational approach to studying the molecular mechanism of alteration is applicable using descriptors such as reactivity of energy of the highest occupied molecular orbital (HOMO) and or lowest unoccupied molecular orbital (LUMO) was investigated, and the data suggested that these descriptors are useful for studying the interactive roles of dental materials.
ISSN:0898-2104
1532-2394
DOI:10.1081/LPR-120039662