Dipalmitoylphosphatidylcholine (DPPC) and DPPC/cholesterol liposomes as predictors of the cytotoxicity of bis-GMA related compounds

Journal of Liposome Research

Volumn 14, Issue 1-2, 2004, Pages 39-49

  Fajisawa, Seiichiro ^a   Kadoma, Yoshinori ^b   Ishihara, Mariko ^a   Atsumi, Toshiko ^a   Yokoe, Ichiro ^c  

^a MEIKAI UNIVERSITY SCHOOL OF DENTISTRY   (Japan)

^b TOKYO MEDICAL AND DENTAL UNIVERSITY   (Japan)

^c JOSAI UNIVERSITY   (Japan)

Author keywords

Dental material; DPPC liposomes; DSC; PM3 calculation

Indexed keywords

2,2 BIS[4 (1 HYDROXYMETHYL 2 METHACRYLOXY)PHENYL]PROPANE; BIOMATERIAL; BISPHENOL A BIS(2 HYDROXYPROPYL) ETHER DIMETHACRYLATE; CHOLESTEROL; DIPALMITOYLPHOSPHATIDYLCHOLINE; LIPOSOME; RESIN; TRIETHYLENE GLYCOL DIMETHACRYLATE; UNCLASSIFIED DRUG;

ARTICLE; CYTOTOXICITY; DIFFERENTIAL SCANNING CALORIMETRY; MOLECULAR SIZE; PHASE TRANSITION; PHYSICAL PARAMETERS; PRIORITY JOURNAL; TOOTH PROSTHESIS;

1,2-DIPALMITOYLPHOSPHATIDYLCHOLINE; BISPHENOL A-GLYCIDYL METHACRYLATE; CALORIMETRY, DIFFERENTIAL SCANNING; CHOLESTEROL; LIPOSOMES; MOLECULAR STRUCTURE; TEMPERATURE; THERMODYNAMICS; TOXICITY TESTS;

EID: 4744367309     PISSN: 08982104     EISSN: None     Source Type: Journal    
DOI: 10.1081/LPR-120039662     Document Type: Article

References (26)

1. Olea N. bisphenol A and dental sealants: Olea's response. Environ Health Perspect 2000; 108:A546.
2. Geutsen W, Spahl W, Muller K, Leyhausen G. Cytotoxicity of 35 composite monomers/additives in permanent 3T3-and three human oral primary fibroblast cultures. J Biomed Mater Res 1998; 41:474-480.
3. Laurence WH, Bass GE, Purcell WP, Autian J. Use of mathematical models in the study of structure-toxicity relationships of dental compounds: esters of acrylic and methacrylic acids. J Dent Res 1972; 51:526-535.
4. Yoshii Y. Cytotoxic effects of acrylates and methacrylates: relationships of monomer structures and cytotoxicity. Biomed Mater Res 1997; 37:517-524.
5. Sessa G, Weismann G. Phospholipid spherules (Liposomes) as a model for biological membranes. J Lipid Res 1968; 9:310-318.
6. Ohline SM, Campbell ML, Turnbull MT, Kohler SJ. Differential scanning calorimetric study of bilayer membrane phase transition. J Chem Educ 2001; 78:1251-1256.
7. Mabrey S, Sturtevant JM. High-Sensitivity Differential Scanning Calorimetry in the Study of Biomembranes and Related Model Systems. New York: Plenum Press, 1978:237-245.
8. Kodama M, Hashigami H, Seki S. Static and dynamic calorimetric studies on the three kinds of phase transition in the system of L- and DL-dipalmitoylphosphatidylcholine/water. Biochim Biophys Acta 1985; 814:300-306.
9. Samuni AM, Crommelin DJA, Zuidam NJ, Barenholz Y. Differential scanning calorimetry. A tool to assess physical and chemical alterations in liposomes. J. Thermal Analysis 1998; 51:37-48.
10. Fujisawa S, Atsumi T, Kadoma Y. Cytotoxicity and phospholipid-liposome phase-transition properties of 2-hydroxyethyl methacrylate (HEMA). Art Cells, Blood Subs Immob Biotech 2001; 29:245-261.
11. Fujisawa S, Atsumi T, Kadoma Y. Cytotoxicity of methyl methacrylate (MMA) and related compounds and their interaction with dipalmitoylphosphatidylcholine (DPPC) liposomes as a model for biomembranes. Oral Diseases 2000; 6:215-221.
12. Fujisawa S, Kadoma Y. Hemolytic activity of a dental adhesive monomer and its interaction with dipalmitoyl phosphatidylcholine liposomes. NMR and DSC measurements. J Thermal Analysis 1998; 51:151-160.
13. 1H-NMR chemical shifts of bis-GMA and its related methacrylates induced by their interaction with phosphatidylcholine/cholesterol liposomes. Dent Mater J 1991; 10:121-127.
14. Fujisawa S, Kadoma Y, Komoda Y. Nuclear magnetic resonance spectroscopic studies of interaction of bis-GMA analogues with phosphatidylcholine liposomes as a model for biomembranes. Biomaterials 1989; 10:269-272.
15. Fujisawa S, Kadoma Y, Masuhara E. A calorimetric study of the interaction of synthetic phospholipid liposomes with vinyl monomers, acrylates and methacrylates. J Biomed Mater Res 1984; 18:1105-1114.
16. Holder AJ. Rational design of dental materials using computational chemistry. Academic of dental materials and Japanese society for dental materials and devices. Transactions 2002; 16:55-75.
17. Fujisawa S. Nuclear magnetic resonance spectra of bis-GMA and iso-bis-GMA. Dent Mater J 1994; 13:251-255.
18. Rowe ES. Thermodynamic reversibility of phase transitions. Specific effects of alcohols on phosphatidylcholines. Biochim Biophys Acta 1985; 55:321-330.
19. Stutevant JM. A scanning calorimetric study of small molecule-lipid bilayer. Proc Natl Acad Sci U S A 1982; 79:3963-3967.
20. Lee AG. Lipid phase transitions and phase diagrams. I. Lipid phase transitions. Biochem Biophys Acta 1977; 472:237-281.
21. Fujisawa S, Masuhara E. Determination of partition coefficients of acrylates, methacrylates, and vinyl monomers using high performance liquid chromatography (HPLC). J Biomed Mater Res 1981; 15:787-793.
22. Yamazaki M, Miyazu M, Asano T, Yuba A, Kume N. Direct evidence of induction of interdigitated gel structure in large unilamellar vesicles of dipalmitoylphosphatidylcholine by ethanol: studies by excimer method and high resolution electron. Biophys J 1994; 66:729-733.
23. Simon SA, McIntosh TJ. Interdigitated hydrocarbon chain packing causes the biphasic transition behavior in lipid/alcohol suspensions. Biochim Biophys Acta 1983; 731:97-108.
24. Fujisawa S, Imai Y, Kojima K, Masuhara E. Studies of hemolytic activity of bisphenol a diglycidyl methacrylate (Bis-DMA). Dent Res 1978; 57:98-102.
25. Fujisawa S, Atsumi T, Ishihara M, Kadoma Y, Yokoe I. Cytotoxicity of bis-GMA and its interactions with dipalmitoylphosphatidylcholine (DPPC) liposomes. In Program and Abstracts of Papers, Japanese Association for Dental Reseach, 51st Annual Meeting. Japanese Association for Dental Research, 2003:123.
26. Betageri GV, Rogers JA. Correlation of partitioning of nitroimidazoles in the n-octanol/saline and liposome systems with pharmachokinetic parameters and quantitative structure-activity relationships (QSAR). Pharm Res 1989; 6:399-403.