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Number of results

Journal

2014 | 12 | 10 | 1056-1066

Article title

Synthesis and characterization of poly [N-acryloyl-(D/L), (+/−)-phenylalanine-co-(D/L), (−/+)N-methacryloyloxyethyl-N′-2-hydroxybutyl(urea)] copolymers

Content

Title variants

Languages of publication

EN

Abstracts

EN
Two monomers of (D/L), (+/−)-N-methacryloyloxyethyl-N′-2-hydroxybutyl(urea) methacrylate (D/L-MABU) type were prepared and further polymerized through free radical polymerization with optically active monomers containing phenylalanine sequences such as N-acryloyl-(D/L), (−/+)-phenylalanine (A-D/L-Phe). The resulting copolymers, i.e., poly[N-acryloyl-(D/L), (−/+)-phenylalanine-co-(D/L), (+/−)-N-methacryloyloxyethyl-N′-2-hydroxybutyl(urea)], A-D/L-Phe-co-D/L-MABU, were characterized by FT-IR, 1D/2D NMR (1H and 13C), UV-vis, and circular dichroism (CD) spectroscopies, differential scanning calorimetry (DSC), and gel permeation chromatography (GPC). The copolymers obtained with a molar fraction of 0.76: 0.24 / 0.64: 0.36 monomer units had optical rotation values of −25° and +15°, respectively. Upon chemical modification of the phenylalanine-based copolymers with fluorescein-isothiocyanate, new fluorescent copolyacrylates (A-D/L-Phe-co-D/L-MABU-F) were synthesized and further studied for pH measurements in DMF solutions using HCl and NaOH 10−1M. It was found that sterioselectivity of the A-L-Phe-co-L-MABU-F copolymer is higher than of its dextro-form, especially at basic pH.

Publisher

Journal

Year

Volume

12

Issue

10

Pages

1056-1066

Physical description

Dates

published
1 - 10 - 2014
online
15 - 5 - 2014

Contributors

author
  • Petru Poni Institute of Macromolecular Chemistry
  • Petru Poni Institute of Macromolecular Chemistry
  • Petru Poni Institute of Macromolecular Chemistry

References

  • [1] E.G. Bellomo, M.D. Wyrsta, L. Pakstis, D.J. Pochan, T.J. Deming, Nat. Mater. 3, 244 (2004) http://dx.doi.org/10.1038/nmat1093[Crossref]
  • [2] S. Fukushima, K. Miyata, N. Nishiyama, N. Kanayama, Y. Yamasaki, K. Kataoka, J. Am. Chem. Soc. 127, 2810 (2005) http://dx.doi.org/10.1021/ja0440506[Crossref]
  • [3] S. Lakshmi, T.C.T Laurencin, Prog. Polym. Sci. 32, 762 (2007) http://dx.doi.org/10.1016/j.progpolymsci.2007.05.017[Crossref]
  • [4] K.S. Stakleff, F. Lin, L.A.S. Callahan, M.B. Wade, A. Esterle, J. Miller, M. Graham, M.L. Becker, Acta Biomaterialia 9, 5132 (2013) http://dx.doi.org/10.1016/j.actbio.2012.08.035[Crossref]
  • [5] M.H. El-Newehy, A.S. Elsherbiny, H. Mori, J. Appl. Polym. Sci. 127, 4918 (2013) http://dx.doi.org/10.1002/app.37611[Crossref]
  • [6] H. Wu, L. Zhu, V.P. Torchilin, Biomaterials 34, 1213 (2013) http://dx.doi.org/10.1016/j.biomaterials.2012.08.072[Crossref]
  • [7] Y.A. Diaz-Fernandez, E. Mottini, L. Pasotti, E.F. Craparo, G. Cavallaro, P. Pallavicini, Biosens Bioelectron 26, 29 (2010) http://dx.doi.org/10.1016/j.bios.2010.04.048[Crossref]
  • [8] S. Gingter, E. Bezdushna, H. Ritter, Beilstein J. Org. Chem. 7, 204 (2011) http://dx.doi.org/10.3762/bjoc.7.27[Crossref]
  • [9] S. Gingter, B. Mondrzik, R. Ritter, Macromolecules 45, 1753 (2012) http://dx.doi.org/10.1021/ma3002164[Crossref]
  • [10] K. Matyjaszewschi, J. Xiao, Chem. Rev. 101, 2921 (2001) http://dx.doi.org/10.1021/cr940534g[Crossref]
  • [11] C. Boyer, V. Bulmus, T.P. Davis, V. Ladmival, J. Liu, S. Perrier, Chem. Rev. 109, 5402 (2009) http://dx.doi.org/10.1021/cr9001403[Crossref]
  • [12] S. Mallakpour, Z. Rafiee, H. Polym. Sci.: Polym. Phys. 124, 4512 (2012)
  • [13] I.-D. Chung, P. Britt, D. Xie, E. Harth, J. Mays, Chem. Comm. 1046 (2005)
  • [14] J. Skey, R. O’Reilly, J. Polym. Sci, Part A: Polym. Chem. 46, 3690 (2008) http://dx.doi.org/10.1002/pola.22710[Crossref]
  • [15] K. Bauri, S.G. Roy, S. Pant, P. De, Langmuir 29, 2764 (2013) http://dx.doi.org/10.1021/la304918s[Crossref]
  • [16] H. Mori, H. Iwaya, A. Nagai, T. Endo, Chem. Commun. 4872 (2005)
  • [17] H. Mori, I. Kato, S. Saito, T. Endo, Macromolecules 43, 1289 (2010) http://dx.doi.org/10.1021/ma902002b[Crossref]
  • [18] Z. Liu, J. Hu, J. Sun, G. He, Y. Li, G. Zhang, J. Polym. Sci. Part A: Polym. Chem. 48, 3573 (2010) http://dx.doi.org/10.1002/pola.24137[Crossref]
  • [19] H. Mori, S. Okabayashi, React. Funct. Polym. 69, 441 (2009) http://dx.doi.org/10.1016/j.reactfunctpolym.2009.01.012[Crossref]
  • [20] S. Kumar, P. De, Polymer, DOI: 10.1016/j.polymer.2013.12.054 [Crossref]
  • [21] H. Mori, E. Takahashi, K. Nakabayashi, Macromolecules 46, 6451 (2013) http://dx.doi.org/10.1021/ma400596r[Crossref]
  • [22] M. Yoshida, A. Safranj, H. Omichi, R. Katakai, Macromolecules 29, 2321 (1996) http://dx.doi.org/10.1021/ma9510193[Crossref]
  • [23] A. Bentolila, I. Vlodavsky, R. Isahai-Michaeli, O. Kovalchuk, C. Haloun, A.J. Domb, J. Med. Chem. 43, 2591 (2000) http://dx.doi.org/10.1021/jm000089j[Crossref]
  • [24] M. Casolaro, Macromolecules 28, 2351 (1995) http://dx.doi.org/10.1021/ma00111a031[Crossref]
  • [25] S. Gingter, B. Mondrzik, H. Ritter, Macromolecules 45, 1753 (2012) http://dx.doi.org/10.1021/ma3002164[Crossref]
  • [26] W. Wu, D. Xie, A. Pucket, J.W. Mays, Eur. Polym. J. 39, 959, (2003) http://dx.doi.org/10.1016/S0014-3057(02)00308-7[Crossref]
  • [27] E.C. Buruiana, T. Buruiana, L. Hahui, J. Photochem. Photobiol. A: Chem. 189, 65 (2007) http://dx.doi.org/10.1016/j.jphotochem.2007.01.008[Crossref]
  • [28] E.C. Buruiana, M. Zamfir, T. Buruiana, J. Photochem. Photobiol. A: Chem. 205, 161 (2009) http://dx.doi.org/10.1016/j.jphotochem.2009.04.023[Crossref]
  • [29] R. Sjoback, J. Nygren, M. Kubista, Spectrochim. Acta Part. A 51, 7 (1995) http://dx.doi.org/10.1016/0584-8539(95)01421-P[Crossref]
  • [30] A. Song, J. Zhang, M. Zhang, T. Shen, J. Tang, Colloid. Surface. Physicochem. Eng. Aspect. 167, 253 (1999) http://dx.doi.org/10.1016/S0927-7757(99)00313-1[Crossref]
  • [31] M. Alvarez-Pez, L. Ballesteros, E. Talavera, J. Yguerabide, J. Phys. Chem. A 105, 6320 (2001) http://dx.doi.org/10.1021/jp010372+[Crossref]

Document Type

Publication order reference

Identifiers

YADDA identifier

bwmeta1.element.-psjd-doi-10_2478_s11532-014-0556-9
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