Synthesis and characterization of iodinated polyurethane with inherent radiopacity

Biomaterials

Volumn 30, Issue 29, 2009, Pages 5552-5559

  Kiran, S ^a   James, Nirmala R ^b   Joseph, Roy ^a   Jayakrishnan, A ^c  

^a SREE CHITRA TIRUNAL INSTITUTE FOR MEDICAL SCIENCES AND TECHNOLOGY   (India)

^b INDIAN INSTITUTE OF SPACE SCIENCE AND TECHNOLOGY   (India)

^c INDIAN INSTITUTE OF TECHNOLOGY MADRAS   (India)

Author keywords

Biocompatibility; Cytotoxicity; DMA; Iodination; Polyurethane; Radiopacity

Indexed keywords

BISPHENOL A; CHAIN EXTENDERS; CHEMICAL SYNTHESIS; CYTOTOXIC; CYTOTOXICITY TEST; DMA; ENERGY DISPERSIVE X-RAY ANALYSIS; GEL-PERMEATION-CHROMATOGRAPHY; IN-VITRO; IODINATION; MOLECULAR RATIOS; MOUSE-FIBROBLASTS; PHENYL ISOCYANATES; POLY(TETRAMETHYLENE GLYCOL); RADIOPACITY; SYNTHESIS AND CHARACTERIZATION; THERMOGRAVIMETRY; X-RADIOGRAPHY; X-RAY IMAGE;

BIOCOMPATIBILITY; CELL CULTURE; CHROMATOGRAPHIC ANALYSIS; DYNAMIC ANALYSIS; DYNAMIC MECHANICAL ANALYSIS; GELATION; GLYCOLS; INFRARED SPECTROSCOPY; PHENOLS; SPECTROSCOPIC ANALYSIS; SYNTHESIS (CHEMICAL); X RAY ANALYSIS;

X RAY RADIOGRAPHY;

4,4' ISOPROPYLIDENEDIPHENOL; 4,4' ISOPROPYLIDINEDI (2,6 DIIODOPHENOL); 4,4' METHYLENEBIS(PHENYLISOCYANATE); PHENYL ISOCYANATE; POLY(TETRAMETHYLENE GLYCOL); POLYMER; POLYURETHAN; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BIOCOMPATIBILITY; CONTROLLED STUDY; COVALENT BOND; CYTOTOXICITY; GEL PERMEATION CHROMATOGRAPHY; INFRARED SPECTROSCOPY; MOLECULAR DYNAMICS; NONHUMAN; PRIORITY JOURNAL; RADIOIODINATION; THERMOGRAVIMETRY; X RAY ANALYSIS;

ANIMALS; BIOCOMPATIBLE MATERIALS; CONTRAST MEDIA; IODINE; MATERIALS TESTING; MICE; POLYURETHANES; SCATTERING, RADIATION; X-RAYS;

EID: 68549134928     PISSN: 01429612     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.biomaterials.2009.06.049     Document Type: Article

References (40)

1. Silberman-Hazony R. In: Mark H.F., Bikales N.M., Overberger C.G., and Menges G. (Eds). Radiopaque polymers. 2nd ed. Encyclopedia of polymer science and engineering vol. 14 (1988), Wiley, New York 1-8
2. Jayakrishnan A., and Thanoo B.C. Barium sulphate loaded poly(2-hydroxyethyl methacrylate) microspheres as artificial emboli: preparation and properties. Biomaterials 11 (1990) 477-481
3. Thanoo B.C., Sunny M.C., and Jayakrishnan A. Tantalum loaded polyurethane microspheres for particulate embolization: preparation and properties. Biomaterials 12 (1991) 525-528
4. Williams D.F., and Roaf R. Implants in surgery (1973), WB Saunders, London
5. Davy K.W.M., and Causton B.E. Radio-opaque denture base: a new acrylic co-polymer. J Dent 10 (1982) 254-264
6. Cassabo I., Smid J., and Sahni S.K. Radiopaque miscible systems composed of poly(methyl methacrylate) and transition and nontransition metal salts: spectroscopic, thermal, and radiographic characterization. J Appl Polym Sci 38 (1989) 1653-1666
7. Cassabo I., Smid J., and Sahni S.K. Radiopaque polymers based on acrylated phosphonate esters derived from polyols. J Appl Polym Sci 41 (1990) 3025-3042
8. Horak D., Metalova M., Svec F., Drobnik J., Kalal J., Borovicka M., et al. Hydrogels in endovascular embolization. III. Radiopaque spherical particles, their preparation and properties. Biomaterials 8 (1987) 142-145
9. Jayakrishnan A., Thanoo B.C., Rathinam K., and Mohanty M. Preparation and evaluation of radiopaque hydrogel microspheres based on PHEMA/iothalamic acid and PHEMA/iopanoic acid as particulate emboli. J Biomed Mater Res 24 (1990) 993-1004
10. Mottu F., Rufenacht D.A., Laurent A., and Doelker E. Iodine-containing cellulose mixed esters as radiopaque polymers for direct embolization of cerebral aneurysms and arteriovenous malformations. Biomaterials 23 (2002) 121-131
11. James N.R., and Jayakrishnan A. Polyurethanes with radiopaque properties. Biomaterials 27 (2006) 160-166
12. James N.R., and Jayakrishnan A. On imparting radiopacity to a poly(urethane urea). Biomaterials 28 (2007) 3182-3187
13. Rusu M.C., Rusu M., Popa M., Delaite C., and Riess G. New radio-opaque acrylic bone cements. I. The synthesis of bromine containing methacrylates. Polym Bull 59 (2007) 25-30
14. Rusu M.C., Ichim I.C., Popa M., and Rusu M. New radiopaque acrylic bone cement. II. Acrylic bone cement with bromine-containing monomer. J Mater Sci Mater Med 19 (2008) 2609-2617
15. Nottelet B., Coudane J., and Vert M. Synthesis of an X-ray opaque biodegradable copolyester by chemical modification of poly(ε-caprolactone). Biomaterials 27 (2006) 4948-4954
16. Dawlee S., Jayakrishnan A., and Jayabalan M. Studies on novel radiopaque methyl methacrylate: glycidyl methacrylate based polymer for biomedical applications. J Mater Sci Mater Med (2008) 10.1007/s10856-008-3557-4
17. Jayakrishnan A., and Thanoo B.C. Synthesis and polymerization of some iodine-containing monomers for biomedical applications. J Appl Polym Sci 44 (1992) 743-748
18. Kruft M.-A.B., Benzina A., Bar F., van der Veen F.H., Bastiaansen C.W., Blezer R., et al. Studies on two new radiopaque polymeric biomaterials. J Biomed Mater Res 28 (1994) 1259-1266
19. Benzina A., Kruft M.-A.B., van der Veen F.H., Bar F.H.M.W., Blezer R., Lindhout T., et al. A versatile three-iodine molecular building block leading to new radiopaque polymeric materials. J Biomed Mater Res 32 (1996) 459-466
20. van Hooy-Corstjens C.S.J., Aldenhoff Y.B.J., Knetsch M.L.W., Govaert L.E., Arin E., Erli H., et al. Radiopaque polymeric spinal cages: a prototype study. J Mater Chem 14 (2004) 3008-3013
21. Okamura M., Uehara H., Yamanobe T., Komoto T., Hosoi S., and Kumazaki T. Synthesis and properties of radiopaque polymer hydrogels: polyion complexes of copolymers of acrylamide derivatives having triiodophenyl and carboxyl groups and p-styrene sulfonate and polyallylamine. J Mol Struct 554 (2000) 35-45
22. Davy K.W., Anseau M.R., and Berry C. Iodinated methacrylate copolymers as X-ray opaque denture base acrylics. J Dent 25 (1997) 499-505
23. Vasquez B., Ginebra M.P., Gil F.J., Planell J.A., Bravo A.L., and Roman J.S. Radiopaque acrylic cements prepared with a new acrylic derivative of iodo-quinoline. Biomaterials 20 (1999) 2047-2053
24. Lakshmi S., James N.R., Nisha V.S., and Jayakrishnan A. Synthesis and polymerization of a new iodine-containing monomer. J Appl Polym Sci 88 (2003) 2580-2584
25. Boelen E.J.H., Lewis G., Xu J., Slots T., Koole L.H., and van Hooy-Corstjens C.S.J. Evaluation of a highly-radiopaque iodine-containing acrylic bone cement for use in augmentation of vertebral compression fractures. J Biomed Mater Res 86A (2008) 76-88
26. Carbone A.L., Song M., and Uhrich K.E. Iodinated salicylate-based poly(anhydride-esters) as radiopaque biomaterials. Biomacromolecules 9 (2008) 1604-1612
27. Mawad D., Poole-Warren L.A., Martens P., Koole L.H., Slots T.L.B., and van Hooy-Corstjens C.S.J. Synthesis and characterization of radiopaque iodine-containing degradable PVA hydrogels. Biomacromolecules 9 (2008) 263-268
28. Flynn VJ. Radiopaque polyurethane-silicone network resin compositions and medical surgical tubings prepared there from US Patent No. 4579879; 1986.
29. Flynn VJ. Radiopaque polyurethane resin compositions. US Patent No. 4250072; 1981.
30. Cambron RE, Dempsy DJ, Mills KM, Silverwood AH. Radiopaque polyurethanes and catheters formed there from US Patent No. 4722344; 1988.
31. Onwumere FC. Radiopaque polymer coating. US Patent No. 6623823; 2003.
32. Markush PH, Sarpeshkar AM. Radiopaque polyurethanes. US Patent No. 5177170; 1993.
33. Markush PH, Sarpeshkar AM. Radiopaque polyurethanes. US Patent No. 5346981; 1994.
34. Edgar K.J., and Falling S.N. An efficient method for the preparation of iodophenols. J Org Chem 55 (1990) 5287-5291
35. Balakrishnan B., and Jayakrishnan A. Self-cross-linking biopolymers as injectable in situ forming biodegradable scaffolds. Biomaterials 26 (2005) 3941-3951
36. Pouchert C.J. The Aldrich library of NMR spectra. 2nd ed. vol. 1 (1983), Aldrich Chemical Co, Milwaukee
37. Spectrum available at. www.sigmaaldrich.com/spectra/fnmr/FNMR006985.PDF [last accessed on 30.03.09].
38. Salinas-Castillo A., Sanchez-Barragan I., Costa-Fernadez J.M., Pereiro R., Ballesteros A., Gonzalez J.M., et al. Iodinated molecularly imprinted polymer for room temperature phosphorescence optosensing of fluoranthene. Chem Commun (2005) 3224-3226
39. Sanchez-Barragan I., Costa-Fernandez J.M., Pereiro R., Sanz-Medel A., Salinas A., Segura A., et al. Molecularly imprinted polymers based on iodinated monomers for selective room-temperature phosphorescence optosensing of fluoranthene in water. Anal Chem 77 (2005) 7005-7011
40. Liaw D.-J. The relative physical and thermal properties of polyurethane elastomers: effect of chain extenders of bisphenols, diisocyanate, and polyol structures. J Appl Polym Sci 66 (1997) 1251-1265