Abstract
This paper presents a brief review of the methods for creating and diagnosing materials based on aliphatic polyesters used to create temporary prostheses and dosage forms of prolonged action. After a review of polymeric materials used in biomedicine, the special role of aliphatic polyesters in achieving these goals is substantiated. The need for impregnating polymeric biomedical products with biologically active compounds and the main approaches currently used for this are described. Particular attention is paid to green supercritical fluid (SCF) technologies for the formation of porous scaffolds with simultaneous impregnation, which makes it possible to control the structure, size, connectivity of pores, and the distribution of dopants. The possibilities of EPR spectroscopy (spin probe method) are discussed, which make it possible to obtain unique data that characterize the structure of polymer matrices and the features of their degradation with the release of paramagnetic additives. Modern ideas about the mechanisms of degradation of aliphatic polyesters and the release of biologically active substances from them are presented. Mathematical approaches to modeling qualitatively different experimental curves of the release of low molecular weight substances from poly-D,L-lactide (PDLLA) films of different thicknesses are discussed.
Similar content being viewed by others
REFERENCES
S. Ramakrishna, J. Mayer, E. Wintermantel, et al., Compos. Sci. Technol. 61, 1189 (2001).
M. Vert, Biomacromolecules 6, 538 (2005).
Y. Ji, K. Ghosh, X. Shu, et al., Biomaterials 27, 3782 (2006).
E. Piskin, J. Biomater. Sci. Polym. Ed. 6, 775 (1995).
F. Asghari, M. Samiei, K. Adibkia, et al., Artif. Cells Nanomed. Biotechnol. 45, 185 (2017).
N. Iqbal, A. S. Khan, A. Asif, et al., Int. Mater. Rev. 64, 91 (2019).
P. Gunatillake, R. Mayadunne, and R. Adhikari, Biotechnol. Ann. Rev. 12, 301 (2006).
B. Dhandayuthapani, Y. Yoshida, T. Maekawa, et al., Int. J. Polym. Sci. 2011, 1 (2011).
S. Commandeur, H. M. M. van Beusekom, and W. J. van der Giessen, J. Interv. Cardiol. 19, 500 (2006).
P. Gentile, V. Chiono, I. Carmagnola, et al., Int. J. Mol. Sci. 15, 3640 (2014).
J. Rich, H. Korhonen, R. Hakala, et al., Macromol. Biosci. 9, 654 (2009).
J.-W. Rhim, A. K. Mohanty, S. P. Singh, et al., J. Appl. Polym. Sci. 101, 3736 (2006).
V. A. Demina, N. G. Sedush, E. N. Goncharov, S. V. Krasheninnikov, A. E. Krupnin, N. G. Goncharov, and S. N. Chvalun, Nanotechnol. Russ. 16, 2 (2021).
A. J. R. Lasprilla, G. A. R. Martinez, B. H. Lunelli, et al., Biotechnol. Adv. 30, 321 (2012).
L. Chang, J. Liu, J. Zhang, et al., Polym. Chem. 4, 1430 (2013).
J. P. Vacanti and R. Langer, Lancet 354, S132 (1999).
P. X. Ma, Mater. Today 7 (5), 30 (2004).
M. N. Egorikhina, P. A. Mukhina, and I. I. Bronnikova, Kompleks. Probl. Serd.-Sosud. Zabolev. 9 (1), 92 (2020).
R. R. Chen and D. J. Mooney, Pharm. Res. 20, 1103 (2003).
D. Corry and J. Moran, Biomaterials 19, 1295 (1998).
M. A. González Corchón, M. Salvado, B. J. de la Torre, et al., Biomaterials 27, 1778 (2006).
T. M. Freyman, I. V. Yannas, and L. J. Gibson, Prog. Mater. Sci. 46, 273 (2001).
M. E. Gomes and R. L. Reis, Int. Mater. Rev. 49, 274 (2004).
V. Santos-Rosales, A. Iglesias-Mejuto, and C. A. Garc, Polymers (Basel) 12, 533 (2020).
M. V. Vedunova, P. S. Timashev, T. A. Mishchenko, et al., Cell Technol. Biol. Med. 161, 616 (2016).
C. A. García-González, A. Concheiro, and C. Alvarez-Lorenzo, Bioconjugate Chem. 26, 1159 (2014).
E. N. Golubeva, N. A. Chumakova, S. V. Kuzin, et al., J. Supercrit. Fluids 158, 104748 (2020).
S. M. Howdle, M. S. Watson, M. J. Whitaker, et al., Chem. Commun., No. 1, 109 (2001).
E. N. Antonov, A. G. Dunaev, S. A. Minaeva, et al., Pharm. Chem. J. 52, 69 (2018).
N. A. Chumakova, E. N. Golubeva, T. A. Ivanova, et al., Sverkhkrit. Flyuidy: Teor. Prakt. 13, 86 (2018).
H. Tai, M. L. Mather, D. Howard, et al., Eur. Cells Mater. 14, 64 (2007).
C. Song, J. Zhang, S. Li, et al., Chin. J. Chem. Eng. 29, 426 (2021).
M. Floren, S. Spilimbergo, A. Motta, et al., J. Biomed. Mater. Res., Part B 99, 338 (2011).
M. Z. Moghadam, S. Hassanajili, F. Esmaeilzadeh, et al., J. Mech. Behav. Biomed. Mater. 69, 115 (2017).
V. Santos-Rosales, M. Gallo, P. Jaeger, et al., J. Supercrit. Fluids 166, 105012 (2020).
M. Bhamidipati, A. M. Scurto, and M. S. Detamore, Tissue Eng., Part B 19, 221 (2013).
L. J. White, V. Hutter, H. Tai, et al., Acta Biomater. 8, 61 (2012).
E. Reverchon, R. Adami, S. Cardea, et al., J. Supercrit. Fluids 47, 484 (2009).
Application of Supercritical Fluids in Industrial Analysis, Ed. by J. R. Dean (Chapmann and Hall, London, 1993), p. 1.
D. Yu. Zalepugin, N. A. Til’kunova, I. V. Chernyshova, et al., Sverkhkrit. Flyuidy: Teor. Prakt. 1 (1), 27 (2006).
D. A. Zimnyakov, V. K. Popov, N. B. Minaev, et al., Sverkhkrit. Flyuidy: Teor. Prakt. 15 (2), 27 (2020).
L. I. Cabezas, V. Fernandez, R. Mazarro, et al., J. Supercrit. Fluids 63, 155 (2012).
L. I. Cabezas, I. Gracia, M. T. García, et al., J. Supercrit. Fluids 80, 1 (2013).
D. Yu. Zalepugin, N. A. Til’kunova, and I. V. Chernyshova, Sverkhkrit. Flyuidy: Teor. Prakt. 14 (3), 11 (2019).
C. Kroll, K. Mäder, R. Stößer, et al., Eur. J. Pharm. Sci. 3, 21 (1995).
K. Mäder, Biomaterials 17, 457 (1996).
A. Brunner, K. Mäder, and A. Göpferich, Pharm. Res. 16, 847 (1999).
I. Katzhendler, K. Mäder, and M. Friedman, Int. J. Pharm. 200, 161 (2000).
S. Kempe, H. Metz, and K. Mader, J. Control. Release 130, 220 (2008).
S. Kempe, H. Metz, P. G. C. Pereira, et al., Eur. J. Pharm. Biopharm. 74, 102 (2010).
S. Kempe, H. Metz, and K. Mäder, Eur. J. Pharm. Biopharm. 74, 55 (2010).
F. Eisenächer, A. Schädlich, and K. Mäder, Int. J. Pharm. 417, 204 (2011).
A. L. Buchachenko and A. M. Vasserman, Stable Radicals (Khimiya, Moscow, 1973) [in Russian].
A. M. Vasserman and A. L. Kovarskii, Spin Labels and Probes in Physical Chemistry of Polymers (Nauka, Moscow, 1986) [in Russian].
S. Stoll and A. Schweiger, J. Magn. Reson. 178, 42 (2006).
Nitroxides – Theory, Experiment and Applications, Ed. by A. I. Kokorin (InTech, Rijeka, Croatia, 2012).
N. A. Chumakova, T. A. Ivanova, E. N. Golubeva, et al., Appl. Magn. Reson. 49, 511 (2018).
N. A. Chumakova, S. V. Kuzin, and A. I. Grechishnikov, Appl. Magn. Reson. 50, 1125 (2019).
Nitroxides – Theory, Experiment and Applications, Ed. by A. I. Kokorin (InTech, Rijeka, Croatia, 2012).
D. Lurie and K. Mäder, Adv. Drug Deliv. Rev. 57, 1171 (2005).
A. Blank, J. H. Freed, N. P. Kumar, et al., J. Control. Release 111, 174 (2006).
K. Mäder, G. Bacic, A. Domb, et al., J. Pharm. Sci. 86, 126 (1997).
L. G. Griffith, Acta Mater. 48, 263 (2000).
A. Merkli, C. Tabatabay, R. Gurny, et al., Prog. Polym. Sci. 23, 563 (1998).
E. S. Morokov, V. A. Demina, N. G. Sedush, et al., Acta Biomater. 109, 61 (2020).
G. Schliecker, C. Schmidt, S. Fuchs, et al., Biomaterials 24, 3835 (2003).
G. Gorrasi and R. Pantani, Adv. Polym. Sci. 279, 119 (2018).
M. Vert, G. Schwarch, and J. Coudane, J. Macromol. Sci., Part A 32, 787 (1995).
Y. Aso, S. Yoshioka, A. Li Wan Po, et al., J. Control. Release 31, 33 (1994).
T. Heya, H. Okada, Y. Ogawa, et al., J. Pharm. Sci. 83, 636 (1994).
S. K. Saha and H. Tsuji, Polym. Degrad. Stab. 91, 1665 (2006).
S. K. Saha and H. Tsuji, Macromol. Mater. Eng. 291, 357 (2006).
L. I. Cabezas, I. Gracia, A. de Lucas, et al., Ind. Eng. Chem. Res. 53, 15374 (2014).
J. Siepmann, Adv. Drug Deliv. Rev. 48, 229 (2001).
S. J. Holland, A. M. Jolly, M. Yasin, et al., Biomaterials 8, 289 (1987).
K. Mäder, B. Bittner, Y. Li, et al., Pharm. Res. 15, 787 (1998).
N. A. Chumakova, E. N. Golubeva, S. V. Kuzin, T. A. Ivanova, et al., Polymers (Basel) 12 (12), 1 (2020).
C. S. Proikakis, N. J. Mamouzelos, P. A. Tarantili, et al., Polym. Degrad. Stab. 91, 614 (2006).
A. Frank, S. K. Rath, and S. S. Venkatraman, J. Control. Release 102, 333 (2005).
Y. Wan, Y. Fang, H. Wu, et al., J. Biomed. Mater. Res., Part A 80, 776 (2007).
T. Tarvainen, T. Karjalainen, M. Malin, et al., J. Control. Release 81, 251 (2002).
T. Tarvainen, M. Malin, I. Barragan, et al., Int. J. Pharm. 310, 162 (2006).
C. Witt, K. Mader, and T. Kissel, Biomaterials 21, 931 (2000).
J. Burke, R. Donno, R. D’Arcy, et al., Biomacromolecules 18, 728 (2017).
H. Tsuji and Y. Ikada, J. Polym. Sci., Part A 36, 59 (1998).
H. Tsuji, Polymer (Guildf.) 43, 1789 (2002).
D. Klose, F. Siepmann, K. Elkharraz, et al., Int. J. Pharm. 354, 95 (2008).
I. Grizzi, H. Garreau, S. Li, et al., Biomaterials 16, 305 (1995).
H. Tsuji and Y. Ikada, Polym. Degrad. Stab. 67, 179 (2000).
S. J. de Jong, E. R. Arias, D. T. S. Rijkers, et al., Polymer (Guildf.) 42, 2795 (2001).
Poly(factic acid): Synthesis, Structures, Properties, Processings and Applications, Ed. by R. Auras, L. Lim, S. Selke, and H. Tsnji (Wiley, Hoboken, NJ, 2010), Part 4, Chap. 21.
E. W. Fischer, H. J. Sterzel, and G. Wegner, Kolloid-Zeitschr. Zeitschr. Polym. 251, 980 (1973).
H. V. Maulding, T. R. Tice, D. R. Cowsar, et al., J. Control. Release 3, 103 (1986).
A. A. Bobko, I. A. Kirilyuk, I. A. Grigor’ev, et al., Free Radical. Biol. Med. 42, 404 (2007).
Q. Xu, S. E. Chin, C.-H. Wang, et al., Biomaterials 34, 3902 (2013).
C. Strobel, N. Bormann, A. Kadow-Romacker, et al., J. Control. Release 156, 37 (2011).
E. Zhang, C. Zhu, J. Yang, et al., Mater. Sci. Eng. C 58, 278 (2016).
A. S. Determan, B. G. Trewyn, V. S. Y. Lin, et al., J. Control. Release 100, 97 (2004).
B. S. Kim, J. M. Oh, K. S. Kim, et al., Biomaterials 30, 902 (2009).
J. C. Kang and S. P. Schwendeman, Macromolecules 36, 1324 (2003).
L. Brannon-Peppas and N. A. Peppas, J. Control. Release 8, 267 (1989).
A. Fayzullin, S. Churbanov, N. Ignatieva, et al., Biomedicines 9, 853 (2021).
S. Jonnalagadda and D. H. Robinson, J. Appl. Polym. Sci. 93, 2025 (2004).
Y. Wang, P. Challa, D. L. Epstein, et al., Biomaterials 25, 4279 (2004).
C. Wu, Y. Ramaswamy, Y. Zhu, et al., Biomaterials 30, 2199 (2009).
A. Mashak, H. Mobedi, and H. Mahdavi, Pharm. Sci. (Iran.) 21, 77 (2015).
Y. Dong, Z. Zhang, and S.-S. Feng, Int. J. Pharm. 350, 166 (2008).
G. R. Owen, J. K. Jackson, B. Chehroudi, et al., J. Biomed. Mater. Res., Part A 95, 857 (2010).
K. Lee, E. A. Silva, and D. J. Mooney, J. R. Soc. Interface 8, 153 (2011).
D. Ma and A. J. McHugh, Int. J. Pharm. 388, 1 (2010).
S. Fredenberg, M. Wahlgren, M. Reslow, et al., Int. J. Pharm. 415, 34 (2011).
S. Cardea, L. Baldino, M. Scognamiglio, et al., J. Mater. Sci. - Mater. Med. 25, 989 (2014).
V. E. Santo, A. R. C. Duarte, E. G. Popa, et al., J. Control. Release 162, 19 (2012).
M. Nof and L. D. Shea, J. Biomed. Mater. Res. 59, 349 (2002).
T. P. Richardson, M. C. Peters, A. B. Ennett, et al., Nat. Biotechnol. 19, 1029 (2001).
A. R. C. Duarte, V. E. Santo, A. Alves, et al., J. Supercrit. Fluids 79, 177 (2013).
D. Velasco, L. Benito, M. Fernández-Gutiérrez, et al., J. Supercrit. Fluids 54, 335 (2010).
T. A. Ivanova, N. A. Chumakova, E. N. Golubeva, et al., Sverkhkrit. Flyuidy: Teor. Prakt. 14 (1), 67 (2019).
S. S. Shah, Y. Cha, and C. G. Pitt, J. Control. Release 18, 261 (1992).
Y. Xu, C. S. Kim, D. M. Saylor, et al., J. Biomed. Mater. Res., Part B 105, 1692 (2017).
C. Raman, C. Berkland, K. Kim, et al., J. Control. Release 103, 149 (2005).
C. Wischke and S. P. Schwendeman, Int. J. Pharm. 364, 298 (2008).
J. Siepmann and F. Siepmann, J. Control. Release 161, 351 (2012).
J. Yoo and Y. Won, ACS Biomater. Sci. Eng. 6, 6053 (2020).
A. Mochizuki, T. Niikawa, I. Omura, et al., J. Appl. Polym. Sci. 108, 3353 (2008).
W. L. Webber, F. Lago, C. Thanos, et al., J. Biomed. Mater. Res. 41, 18 (1998).
S. Fredenberg, M. Wahlgren, M. Reslow, et al., J. Control. Release 150, 142 (2011).
T. G. Park, Biomaterials 16, 1123 (1995).
L. J. Ford, K. Mitchell, P. Rowe, et al., Int. J. Pharm. 71, 95 (1991).
C. Kao, S. Chen, and M. Sheu, J. Control. Release 44, 263 (1997).
W. D. Lindner and B. C. Lippold, Pharm. Res. 12, 1781 (1995).
N. A. Peppas and J. J. Sahlin, Int. J. Pharm. 57, 169 (1989).
L. L. Lao, S. S. Venkatraman, and N. A. Peppas, Eur. J. Pharm. Biopharm. 70, 796 (2008).
P. R. Batycky, J. Hanes, R. Langer, et al., J. Pharm. Sci. 86, 1464 (1997).
X. Zhu and R. D. Braatz, J. Biomed. Mater. Res., Part A 103, 2269 (2015).
A. Charlier, B. Leclerc, and G. Couarraze, Int. J. Pharm. 200, 115 (2000).
N. Faisant, J. Akiki, F. Siepmann, et al., Int. J. Pharm. 314, 189 (2006).
T. Casalini, F. Rossi, S. Lazzari, et al., Mol. Pharm. 11, 4036 (2014).
R. Wada, S. Hyon, and Y. Ikada, J. Control. Release 37, 151 (1995).
A. Joshi and K. J. Himmelstein, J. Control. Release 15, 95 (1991).
F. Baino, Acta Biomater. 7, 3248 (2011).
Y. You, B.-M. Min, S. J. Lee, et al., J. Appl. Polym. Sci. 95, 193 (2005).
Y. You, S. W. Lee, J. H. Youk, et al., Polym. Degrad. Stab. 90, 441 (2005).
J. Bergsma et al., Biomaterials 16, 25 (1995).
C. M. Agrawal and R. B. Ray, J. Biomed. Mater. Res. 55, 141 (2001).
P. Sarazin, X. Roy, and B. D. Favis, Biomaterials 25, 5965 (2004).
M. Vert, S. Li, H. Garreau, et al., Angew. Macromol. Chem. 247, 239 (1997).
Y. A. Hussain and C. S. Grant, J. Supercrit. Fluids 71, 127 (2012).
M. Ramchandani and D. Robinson, J. Control. Release 54, 167 (1998).
A. R. C. Duarte, J. F. Mano, and R. L. Reis, Acta Biomater. 5, 2054 (2009).
R. Yoganathan, R. Mammucari, and N. R. Foster, J. Phys.: Conf. Ser. 215, 012087 (2010).
ACKNOWLEDGMENTS
The authors thank P.S. Timashev and N.A. Chumakova for their valuable comments and discussions during the study.
Funding
This study was performed as part of a state order (registration number АААА-А21-121011590090-7).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Ivanova, T.A., Golubeva, E.N. Aliphatic Polyesters for Biomedical Purposes: Design and Kinetic Regularities of Degradation in vitro. Russ. J. Phys. Chem. B 16, 426–444 (2022). https://doi.org/10.1134/S1990793122030162
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1990793122030162