[en] Poly(L-lactic acid) (PLLA) fibers were impregnated with the anti-inflammatory drug ketoprofen by supercritical CO2 (scCO2) assisted impregnation process, to develop drug-eluting absorbable sutures. This work indicates the possibility to tune not only the drug loading but also the release profile of ketoprofen from PLLA by modifying the impregnation (temperature and pressure) and depressurization (temperature and rate) conditions. Different PLLA sutures that release ketoprofen during 3 days up to 3 months were obtained. The release was shown to be governed by two parameters: the degradation rate of PLLA, that increases with the drug impregnation, and the sutures free volume, that was created due to scCO2 sorbed and was partially conserved during depressurization. The degradation rate and the tensile strength loss of the suture are accelerated by ketoprofen since it catalyzes PLLA acid hydrolysis.
Research center :
Center for Education and Research on Macromolecules (CERM) Complex and Entangled Systems from Atoms to Materials (CESAM) Research Unit
Disciplines :
Chemistry Materials science & engineering
Author, co-author :
Champeau, Mathilde; Federal University of ABC, Santo André, Center of Engineering, Modeling and Applied Social Sciences, Brazil
Trindade Coutinho, Isabela; Federal University of ABC, Santo André, Center of Engineering, Modeling and Applied Social Sciences, Brazil
Thomassin, Jean-Michel ; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM) Research Unit, Center for Education and Research on Macromolecules (CERM), Belgium
Tassaing, Thierry; University of Bordeaux, CNRS, Institute of Molecular Sciences, Talence, France
Jérôme, Christine ; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM) Research Unit, Center for Education and Research on Macromolecules (CERM), Belgium
Language :
English
Title :
Tuning the release profile of ketoprofen from poly(L-lactic acid) suture using supercritical CO2 impregnation process
Publication date :
February 2020
Journal title :
Journal of Drug Delivery Science and Technology
ISSN :
1773-2247
Publisher :
Éditions de Santé, France
Volume :
55
Pages :
101468
Peer reviewed :
Peer reviewed
Funders :
BELSPO - Politique scientifique fédérale [BE] F.R.S.-FNRS - Fonds de la Recherche Scientifique [BE] CAPES - Coordenação de Aperfeicoamento de Pessoal de Nível Superior [BR] FAPESP - Fundação de Amparo à Pesquisa do Estado de São Paulo [BR]
Champeau, M., Thomassin, J.-M., Tassaing, T., Jérôme, C., Drug loading of polymer implants by supercritical CO2 assisted impregnation: a review. J. Control. Release 209 (2015), 248–259, 10.1016/J.JCONREL.2015.05.002.
Bonavoglia, B., Storti, G., Morbidelli, M., Rajendran, A., Mazzotti, M., Sorption and swelling of semicrystalline polymers in supercritical CO 2. J. Polym. Sci., Part B: Polym. Phys. 44 (2006), 1531–1546, 10.1002/polb.20799.
Champeau, M., Thomassin, J.M., Jérôme, C., Tassaing, T., In situ FTIR micro-spectroscopy to investigate polymeric fibers under supercritical carbon dioxide: CO2sorption and swelling measurements. J. Supercrit. Fluids 90 (2014), 44–52, 10.1016/j.supflu.2014.03.006.
Škerget, M., Knez, Z., Knez-Hrnčič, M., Solubility of solids in sub- and supercritical fluids: a review. J. Chem. Eng. Data 56 (2011), 694–719, 10.1021/je1011373.
Kazarian, S.G., Supercritical fluid impregnation of polymers for drug delivery. York, P., Kompella, U.B., Shekunov, B.Y., (eds.) Supercritical Fluid Technology for Drug Product Development, 2004, CRC Press, Boca Raton, 322–343.
De Sousa, H.C., Gil, M.M., Duarte, C.M., Leite, E.B., Duarte, A.C., Method for preparing therapeutic ophthalmic articles using compressed fluids. US 20060008506, A1, 2006.
Costa, V.P., Braga, M.E.M., Guerra, J.P., Duarte, A.R.C., Duarte, C.M.M., Leite, E.O.B., Gil, M.H., de Sousa, H.C., Development of therapeutic contact lenses using a supercritical solvent impregnation method. J. Supercrit. Fluids 52 (2010), 306–316, 10.1016/j.supflu.2010.02.001.
Champeau, M., Thomassin, J.-M., Tassaing, T., Jerome, C., Drug loading of sutures by supercritical CO 2 impregnation: effect of polymer/drug interactions and thermal transitions. Macromol. Mater. Eng. 300 (2015), 596–610, 10.1002/mame.201400369.
Sugiura, K., Ogawa, S., Tabata, I., Hori, T., Impregnation of tranilast to the poly(lactic acid) fiber with supercritical carbon dioxide and the release behavior of tranilast. J. Fiber Sci. Technol. 61 (2005), 159–165, 10.2115/fiber.61.159.
Dias, A.M.A., Braga, M.E.M., Seabra, I.J., Ferreira, P., Gil, M.H., De Sousa, H.C., Development of natural-based wound dressings impregnated with bioactive compounds and using supercritical carbon dioxide. Int. J. Pharm. 408 (2011), 9–19, 10.1016/j.ijpharm.2011.01.063.
Duarte, A.R.C., Mano, J.F., Reis, R.L., Dexamethasone-loaded scaffolds prepared by supercritical-assisted phase inversion. Acta Biomater. 5 (2009), 2054–2062, 10.1016/j.actbio.2009.01.047.
Fanovich, M.A., Ivanovic, J., Misic, D., Alvarez, M.V., Jaeger, P., Zizovic, I., Eggers, R., Development of polycaprolactone scaffold with antibacterial activity by an integrated supercritical extraction and impregnation process. J. Supercrit. Fluids 78 (2013), 42–53, 10.1016/j.supflu.2013.03.017.
Gamse, T., Marr, R., Wolf, C., Lederer, K., Supercritical CO2 impregnation of polyethylene components for medical purposes. Hem. Ind. 61 (2007), 229–232, 10.2298/hemind0704229g.
Greiner, R.W., Pharmaceutically impregnated catheters. EP 0405284 A2, 1991.
Bouledjouidja, A., Masmoudi, Y., Sergent, M., Badens, E., Effect of operational conditions on the supercritical carbon dioxide impregnation of anti-inflammatory and antibiotic drugs in rigid commercial intraocular lenses. J. Supercrit. Fluids 130 (2017), 63–75, 10.1016/J.SUPFLU.2017.07.015.
Gong, K., Darr, J.A., Rehman, I.U., Supercritical fluid assisted impregnation of indomethacin into chitosan thermosets for controlled release applications. Int. J. Pharm. 315 (2006), 93–98, 10.1016/j.ijpharm.2006.02.030.
Yu, J.P., Guan, Y.X., Yao, S.J., Zhu, Z.Q., Preparation of roxithromycin-loaded poly(l-lactic Acid) films with supercritical solution impregnation. Ind. Eng. Chem. Res. 50 (2011), 13813–13818, 10.1021/ie201294u.
Torres, A., Ilabaca, E., Rojas, A., Rodríguez, F., Galotto, M.J., Guarda, A., Villegas, C., Romero, J., Effect of processing conditions on the physical, chemical and transport properties of polylactic acid films containing thymol incorporated by supercritical impregnation. Eur. Polym. J. 89 (2017), 195–210, 10.1016/J.EURPOLYMJ.2017.01.019.
Rojas, A., Cerro, D., Torres, A., Galotto, M.J., Guarda, A., Romero, J., Supercritical impregnation and kinetic release of 2-nonanone in LLDPE films used for active food packaging. J. Supercrit. Fluids 104 (2015), 76–84, 10.1016/j.supflu.2015.04.031.
Rojas, A., Torres, A., Martínez, F., Salazar, L., Villegas, C., Galotto, M.J., Guarda, A., Romero, J., Assessment of kinetic release of thymol from LDPE nanocomposites obtained by supercritical impregnation: effect of depressurization rate and nanoclay content. Eur. Polym. J. 93 (2017), 294–306, 10.1016/j.eurpolymj.2017.05.049.
Milovanovic, S., Stamenic, M., Markovic, D., Ivanovic, J., Zizovic, I., Supercritical impregnation of cellulose acetate with thymol. J. Supercrit. Fluids 97 (2015), 107–115, 10.1016/J.SUPFLU.2014.11.011.
Anderson, J.M., Inflammation, wound healing, and the foreign-body response. Ratner, B.D., Hoffman, A.S., Schoen, F.J., Lemons, J.E., (eds.) Biomaterials Science: an Introduction to Biomaterials in Medicine, 2013, Elsevier Academic Press, San Diego, 503–512.
Champeau, M., Thomassin, J.M., Jérôme, C., Tassaing, T., Solubility and speciation of ketoprofen and aspirin in supercritical CO2 by infrared spectroscopy. J. Chem. Eng. Data 61 (2016), 968–978, 10.1021/acs.jced.5b00812.
Li, S., Girod-Holland, S., Vert, M., Hydrolytic degradation of poly(dl-lactic acid) in the presence of caffeine base. J. Control. Release 40 (1996), 41–53, 10.1016/0168-3659(95)00138-7.
Moy, R.L., Waldman, B., Hein, D.W., A review of sutures and suturing techniques. J. Dermatol. Surg. Oncol. 18 (1992), 785–795 http://www.ncbi.nlm.nih.gov/pubmed/1512311. (Accessed 21 March 2019)
Li, S.M., Garreau, H., Vert, M., Structure-property relationships in the case of the degradation of massive aliphatic poly-(α-hydroxy acids) in aqueous media - Part 1: poly(dl-lactic acid). J. Mater. Sci. Mater. Med. 1 (1990), 123–130, 10.1007/BF00700871.
Hochberg, J., Meyer, K.M., Marion, M.D., Suture choice and other methods of skin closure. Surg. Clin. N. Am. 89 (2009), 627–641, 10.1016/j.suc.2009.03.001.
Pineros-Fernandez, A., Drake, D.B., Rodeheaver, P.A., Moody, D.L., Edlich, R.F., Rodeheaver, G.T., CAPROSYN*, another major advance in synthetic monofilament absorbable suture. J. Long Term Eff. Med. Implant. 14 (2004), 359–368, 10.1615/JLongTermEffMedImplants.v14.i5.30.
Braga, M.E.M., Pato, M.T.V., Silva, H.S.R.C., Ferreira, E.I., Gil, M.H., Duarte, C.M.M., de Sousa, H.C., Supercritical solvent impregnation of ophthalmic drugs on chitosan derivatives. J. Supercrit. Fluids 44 (2008), 245–257, 10.1016/J.SUPFLU.2007.10.002.
Ma, X., Tomasko, D.L., Coating and impregnation of a nonwoven fibrous polyethylene material with a nonionic surfactant using supercritical carbon dioxide. Ind. Eng. Chem. Res. 36 (1997), 1586–1597, 10.1021/ie960566p.
Singhal, D., Curatolo, W., Drug polymorphism and dosage form design: a practical perspective. Adv. Drug Deliv. Rev. 56 (2004), 335–347, 10.1016/j.addr.2003.10.008.
Brittain, H.G., Grant, D.J.R., Myrdal, P.B., Effects of polymorphism and solid-state solvation on solubility and dissolution rate. Brittain, H.G., (eds.) Polymorphism in Pharmaceutical Solids, 2009, CRC Press, Boca Raton, 436–480.
Pasquali, I., Bettini, R., Giordano, F., Supercritical fluid technologies: an innovative approach for manipulating the solid-state of pharmaceuticals. Adv. Drug Deliv. Rev. 60 (2008), 399–410, 10.1016/J.ADDR.2007.08.030.
Macnaughton, S.J., Kikic, I., Foster, N.R., Alessi, P., Cortesi, A., Colombo, I., Solubility of anti-inflammatory drugs in supercritical carbon dioxide. J. Chem. Eng. Data 41 (1996), 1083–1086, 10.1021/je960103q.
Florey, K., Analytical Profiles of Drug Substances and Excipients. first ed., 1981, Elsevier Science, New York.
Dixit, M., Kulkarni, P.K., Vaghela, R.S., Effect of different crystallization techniques on the dissolution behavior of ketoprofen. Trop. J. Pharm. Res. 12 (2013), 317–322, 10.4314/tjpr.v12i3.7.
Yu, J., Tang, C., Guan, Y., Yao, S., Zhu, Z., Sorption and diffusion behavior of carbon dioxide into poly(l-lactic acid) films at elevated pressures. Chin. J. Chem. Eng. 21 (2013), 1296–1302, 10.1016/S1004-9541(13)60623-0.
Kiran, E., Foaming strategies for bioabsorbable polymers in supercritical fluid mixtures. Part I. Miscibility and foaming of poly(l-lactic acid) in carbon dioxide + acetone binary fluid mixtures. J. Supercrit. Fluids 54 (2010), 296–307, 10.1016/j.supflu.2010.05.004.
Kazarian, S.G., Vincent, M.F., Bright, F.V., Liotta, C.L., Eckert, C.A., Specific intermolecular interaction of carbon dioxide with polymers. J. Am. Chem. Soc. 118 (1996), 1729–1736, 10.1021/ja950416q.
Fanovich, M.A., Jaeger, P., Sorption and diffusion of compressed carbon dioxide in polycaprolactone for the development of porous scaffolds. Mater. Sci. Eng. C 32 (2012), 961–968, 10.1016/j.msec.2012.02.021.
Champeau, M., Thomassin, J.-M., Jérôme, C., Tassaing, T., In situ investigation of supercritical CO2 assisted impregnation of drugs into a polymer by high pressure FTIR micro-spectroscopy. Analyst 140 (2015), 869–879, 10.1039/C4AN01130A.
Ritger, P.L., Peppas, N.A., A simple equation for description of solute release I. Fickian and non-fickian release from non-swellable devices in the form of slabs, spheres, cylinders or discs. J. Control. Release 5 (1987), 23–36, 10.1016/0168-3659(87)90034-4.
