Cytotoxicity of three maleic anhydride copolymers and common solvents used for polymer solvation

Polymer Bulletin

Volumn 70, Issue 5, 2013, Pages 1591-1612

  Karakus, Gulderen ^a   Zengin, Haci Bayram ^a   Polat, Zubeyde Akin ^a   Yenidunya, Ali Fazil ^a   Aydin, Semiha ^b  

^a CUMHURIYET UNIVERSITY   (Turkey)

^b ERCIYES UNIVERSITY   (Turkey)

Author keywords

Body fluid; Copolymer cytotoxicity; Copolymer solubility; Free radical copolymerization; Solvent cytotoxicity

Indexed keywords

ACETONE; BENZOYL PEROXIDE; BODY FLUIDS; CELL CULTURE; COPOLYMERIZATION; ESTERS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; FREE RADICALS; MALEIC ANHYDRIDE; MORPHOLOGY; NUCLEAR MAGNETIC RESONANCE; ORGANIC SOLVENTS; SCANNING ELECTRON MICROSCOPY; SOLUBILITY; SOLVATION; STYRENE; SURFACE MORPHOLOGY; TOXICITY;

AZOBISISOBUTYRONITRILE; FOURIER TRANSFORM INFRARED; FREE RADICAL COPOLYMERIZATION; MALEIC ANHYDRIDE COPOLYMERS; MALEIC ANHYDRIDE/ STYRENES; METHYL ETHYL KETONES; METHYL METHACRYLATES; STRUCTURAL CHARACTERIZATION;

CYTOTOXICITY;

EID: 84892981882     PISSN: 01700839     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00289-012-0860-5     Document Type: Article

References (50)

1. Lide DR (1992) Handbook of chemistry and physics, 72nd edn. CRC Press, Boca Raton
2. Spridon D, Panaitescu L, Ursu D, Uglea CV (1997) Synthesis and biocompatibility of maleic anhydride copolymers: 1. Maleic anhydride-vinyl acetate, maleic anhydride methyl methacrylate and maleic anhydride-styrene. Polym Int 43:175-181
3. Hoste K, Winne KD, Schacht E (2004) Polymeric prodrug. Int J Pharm 277:119-131
4. Kaplan Can H, Dogan AL, Rzaev ZMO, Uner AH, Guner A (2005) Synthesis and antitumor activity of poly(3,4-dihydro-2H-pyran-co-maleic anhydride-co-vinyl acetate). J Appl Polym Sci 96: 2352-2359
5. Hoffmann F, Jr Cinatl, Kabickova H, Cinatl J, Kreuter J, Steineker F (1997) Preparation, characterization and cytotoxicity of methyl-methacrylate copolymer nanoparticles with a permanent positive surface charge. Int J Pharm 157:189-198
6. Krayukhina MA, Kozybakova SA, Samoilava NA, Babak VG, Karaeva SZ, Yamskov IA (2007) Synthesis and properties of amphiphilic maleic acid copolymers. Russ J Appl Chem 80:1145-1150. doi:10.1134/S1070427207070269
7. Ferruti P, Ranucci E, Trotta F, Gianasi E, Evagorou EG, Wasil M, Wilson G, Duncan R (1999) Synthesis, characterization and antitumour activity of platinum (II) complexes of novel functionalized poly(amido amine)s. Macromol Chem Phys 200:1644-1654
8. Garrec DL, Gori S, Luo L, Lessard D, Smith DC, Yessine M-A, Ranger M, Leroux J-C (2004) Poly(N-vinylpyrrolidone)-block-poly(D,L-lactide) as a new polymeric solubilizer for hydrophobic anticancer drugs: in vitro and in vivo evaluation. J Control Release 99:83-101
9. Greish K, Sawa T, Fang J, Akaika T, Maeda H (2004) SMA-doxorubicin, a new polymeric micellar drug for effective targeting to solid tumors. J Control Release 97:219-230
10. Patel H, Raval DA, Madamwar D, Patel SR (1998) Polymeric prodrug: synthesis, release study and antimicrobial property of poly(styrene-co-maleic anhydride)-bound acriflavine. Angew Makromol Chem 263:25-30
11. Oda T, Maeda H (1987) Binding to and internalization by cultured cells of neocarzinostatin and enhancement of its actions by conjugation with lipophilic styrene-maleic acid copolymer. Cancer Res 47:3206-3211
12. Greish K, Nagamitsu A, Fang J, Maeda H (2005) Copoly(styrene-maleic acid)-pirarubicin micelles: high tumor-targeting efficiency with little toxicity. Bioconjugate Chem 16:230-236
13. Fles D, Vukovic R, Kuzmic AE, Bogdanic G, Pilizota V, Karlovic D, Markus K, Wolsperger K, Vikic-Topic D (2003) Synthesis and spectroscopic evidences of N-arylmaleimides and N-aryl-2,3-dimethylmaleimides. Croat Chem Acta 76:69-74
14. Liu HY, Cao K, Yao Z, Li BG, Hu GH (2007) Variations of the glass-transition temperature in the imidization of poly(styrene-co-maleic anhydride). J Appl Polym Sci 104:2418-2422. doi:10.1002/ app.25917
15. 2. J Appl Polym Sci 103:3194-3205. doi: 10.1002/app.25131
16. Nguyen V, Yoshida W, Cohen Y (2003) Graft polymerization of vinyl acetate onto silica. J Appl Polym Sci 87:300-310
17. Ahmed RM (2009) Optical study on poly(methyl methacrylate)/poly(vinyl acetate) blends. Int J Photoenergy. Article ID 150389, 1-7. doi:10.1155/2009/ 150389
18. Solomon O, Gottesman FB (1967) Calculation of viscosity number from a single measurement. Makromol Chem 104:177p
19. Abdel-Azim A, Abdel-Azim M, Atta A, Farahat MS (1998) Boutros WY determination of intrinsic viscosity of polymeric compounds through a single specific viscosity measurement. Polymer 39:6827-6833
20. Kendrick BS, Kerwin BA, Chang BS, Philo JS (2001) Onlibe size-exclusion high-performance liquid chromatography light scattering and differential refractometry methods to determine degree of polymer conjugation to proteins and protein-protein or protein-ligand association states. Anal Biochem 299:136-146
21. Wen J, Arakawa T, Philo JS (1996) Size-exclusion chromatography with on-line light-scattering, absorbance, and refractive index detectors for studying proteins and their interactions. Anal Biochem 240:155-166. doi:10.1006/abio.1996.0345
22. Domazet-Damjanov D, Samayajulu-Nitu M, Pandey S (2009) Resistance of quiescent human diploid fibroblast to high dose of external oxidative stress and induction of senescence. Open Biol J 2:149-160
23. Michael HR, Pawlina W (2005) Histology a text and atlas. 5th edn, Lippincott Williams &Wilkins, Philadelphia
24. Pal J, Singh H, Ghosh AK (2004) Modification of LLDPE using esterified styrene maleic anhydride copolymer: Study of its properties and environmental degradability. J Appl Polym Sci 92:102-108
25. Popa I, Offenberg H, Beldie C, Uglea CV (1997) Benzocaine modified maleic anhydride copolymers-I. Synthesis and characterization of benzocaine modified poly(maleic anhydride-co-vinyl acetate), poly(maleic anhydride-co-methyl methacrylate) and poly(maleic anhydride-co-styrene). Eur Polym J 33:1511-1514
26. 2 nanocomposites. J Mater Sci Lett 18:2009-2012
27. Coskun M, Seven P (2011) Synthesis, characterization and investigation of dielectric properties of two-armed graft copolymers prepared with methyl methacrylate and styrene onto PVC using atom transfer radical polymerization. React Funct Polym 71:395-401
28. Rajput RS, Rupainwar DC, Singh RK, Singh A (2009) Study on characterization and degree of esterification of styrene maleic anhydride by some medicines. Indian J Chem B 48:1597-1600
29. Qiao Z, Xie Y, Chen M, Xu J, Zhu Y, Qian Y (2000) Synthesis of lead sulfide/(polyvinyl acetate) nanocomposites with controllable morphology. Chem Phys Lett 321:504-507
30. Barakat MF, Abdelkerim FM (1973) Investigation of the polymers formed in reactor irradiated aniline and pyridine. Can J Chem 51:3860-3865
31. Elliott J, Hamerton I, Hay JN, Shaw SJ (2003) Synthesis and characterization of novel methyl methacrylate-2-(dimethylamino)ethyl methacrylate copolymer salts containing polymerisable anions. Polymer 44:3775-3784. doi:10.1016/S0032-3861(03)00355-0
32. Liu Y, Lee JY, Hong L (2002) Synthesis, characterization and electrochemical properties of poly(methyl methacrylate)-grafted-poly(vinylidene fluoride-hexafluoropropylene) gel electrolytes. Solid State Ionics 150:317-326
33. Celik M, Sacak M (2002) Synthesis and characterization of starch-poly(methyl methacrylate) graft copolymers. J Appl Polym Sci 86:53-57
34. Balaji R, Nanjundan S (1999) Copolymerization of 3-methoxy-4- methacryloyloxybenzal phenylimine with methyl methacrylate. Eur Polym J 35:1133-1138
35. Sanmathi CS, Prasannakumar S, Sherigara BS (2004) Terpolymerization of 2-ethoxy ethylmethacrylate, styrene and maleic anhydride: determination of the reactivity ratios. Bull Mater Sci 27: 243-249
36. Atici-Galioglu O, Akar A, Rahimian R (2001) Modification of poly(maleic anhydride-co-styrene) with hydroxyl containing compounds. Turk J Chem 25:259-266
37. Bruch M, Mader D, Bauers F, Loontjens T, Mulhaupt R (2000) Melt modification of poly(styrene-comaleic anhydride) with alcohols in the presence of 1,3-oxazolines. J Polym Sci 38:1222-1231. doi: 10.1002/(SICI)1099- 0518(20000415)38:8\1222:AID-POLA5[3.0.CO;2-Z
38. Saad GR, Morsi RE, Mohammady SZ, Elsabee MZ (2008) Dielectric relaxation of monoesters based poly(styrene-co-maleic anhydride) copolymer. J Polym Res 15:115-123. doi:10.1007/s10965-007-9150-6
39. Yoon KJ, Woo JH, Seo YS (2003) Formaldehyde free cross-linking agents based on maleic anhydride copolymers. Fiber Polym 4:182-187
40. Nemtoi G, Beldie C, Tircolea C, Popa I, Cretescu I, Humelnicu I, Humelnicu D (2001) Behaviour of the poly(maleic anhydride-co-vinyl acetate) copolymer in aqueous solutions. Eur Polym J 37: 729-735
41. Hwang S, Lee CH, Ahn IS (2008) Product identification of guaiacol oxidation catalyzed by manganese peroxidase. J Ind Eng Chem 14:487-492. doi:10.1016/j.jiec.2008.02.008
42. Lee E, Moon BH, Park Y, Hong S, Lee S, Lee Y, Lim Y (2008) Effects of hydroxyl and methoxy substituents on NMR data in flavonols. Bull Korean Chem Soc 29:507-510
43. Sanchez CO, Alvarado F, Bustos CJ, Schott E, Gatica N, Valdebenito K (2007) Synthesis, characterization, thermal stability and fluorescence of hybrid polymers prepared from amino-phenyl esters. Polym Bull 59:19-330. doi:10.1007/S00289-007-0776-7
44. Mustata F, Bicu I (2006) P-aminobenzoic acid/cyclohexanone/formaldehyde resins as hardener for epoxy resins. Synthesis and characterization. J Optoelectron Adv M 8:871-875
45. Barron PF, Hill DJT, O'Donnell JH, O'Sullivan PW (1984) Applications of DEPT experiments to the 13C NMR of copolymers: poly(styrene-co-maleic anhydride) and poly(styrene-co-acrylonitrile). Macromol 17:1967-1972
46. Ocampo-Fernández M, Herrera AM, Méndez-Bautista T, Garcia-Serrano J (2009) Synthesis and characterization of diethyl-p-vinylbenzyl phosphonate monomer: precursor of ion exchange polymers for fuel cells. Superficies y Vacío 22:6-10
47. Winter H, van der Velden GPM (1992) 13C NMR analysis of the polymer microstructure of a cured bis(maleimide)-styrene thermoset resin. Macromolecules 25:4285-4289
48. Zafar F, Sharmin E, Ashraf SM, Ahmad S (2004) Studies on poly(styrene-co-maleic anhydride)-modified polyesteramide-based anticorrosive coatings synthesized from a sustainable resource. J Appl Polym Sci 92:2538-2544
49. Lai MF, Li J, Liu JJ (2005) Thermal and dynamic mechanical properties of poly(propylene carbonate). J Therm Anal Calorim 82:293-298
50. Rahman MH, Chen HL, Chen SA, Chu PPJ (2010) 1H NMR spectroscopic study of the solution structure of a conjugated polymer. J Chin Chem Soc 57:490-495