Improved nonclinical pharmacokinetics and biodistribution of a new PPAR pan-agonist and COX inhibitor in nanocapsule formulation

Journal of Controlled Release

Volumn 209, Issue , 2015, Pages 207-218

  Garcia, Giani Martins ^a   Oliveira, Líliam Teixeira ^a   Pitta, Ivan Da Rocha ^b   De Lima, Maria Do Carmo Alves ^b   Vilela, José Mário Carneiro ^c   Andrade, Margareth Spangler ^c   Abdalla, Dulcinéia Saes Parra ^d   Mosqueira, Vanessa Carla Furtado ^a  

^a FEDERAL UNIVERSITY OF OURO PRETO   (Brazil)

^b FEDERAL UNIVERSITY OF PERNAMBUCO   (Brazil)

^c FUNDAÇÃO CENTRO TECNOLÓGICO DE MINAS GERAIS   (Brazil)

^d UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Bioanalytical method; Biodistribution; Nanocapsules; Peroxisome proliferator activated receptor agonist; Pharmacokinetics; Thiazolidinedione

Indexed keywords

CYTOLOGY; ENCAPSULATION; LACTIC ACID; NANOCAPSULES; PHARMACOKINETICS; RESIDENCE TIME DISTRIBUTION;

BIOANALYTICAL METHODS; BIODISTRIBUTIONS; ENCAPSULATION EFFICIENCY; INTRAVENOUS ADMINISTRATION; PEROXISOME PROLIFERATOR-ACTIVATED RECEPTOR; PHARMACOKINETIC PARAMETERS; POLY (D , L LACTIC ACID); THIAZOLIDINEDIONES;

LOADING;

5 [(5 BROMO 1H INDOL 3 YL)METHYLENE] 3 (4 CHLOROBENZYL)THIAZOLIDINE 2,4 DIONE; INSULIN SENSITIZING AGENT; NANOCAPSULE; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA AGONIST; PROSTAGLANDIN SYNTHASE INHIBITOR; UNCLASSIFIED DRUG; 2,4 THIAZOLIDINEDIONE DERIVATIVE; 5-((5-BROMO-1H-INDOL-3-YL)METHYLENE)-3-(4-CHLOROBENZYL)THIAZOLIDINE-2,4-DIONE; INDOLE DERIVATIVE; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA;

ANIMAL EXPERIMENT; AREA UNDER THE CURVE; ARTICLE; CONTROLLED STUDY; DIABETES MELLITUS; DRUG CLEARANCE; DRUG DISTRIBUTION; DRUG EFFECT; DRUG ELIMINATION; DRUG HALF LIFE; DRUG RELEASE; DRUG SOLUBILITY; HEART; IN VITRO STUDY; KIDNEY; LIVER; LUNG; MEAN RESIDENCE TIME; MOUSE; NANOENCAPSULATION; NONHUMAN; PLASMA CLEARANCE; PRIORITY JOURNAL; SINGLE DRUG DOSE; SPLEEN; VOLUME OF DISTRIBUTION; AGONISTS; ANIMAL; BLOOD; CHEMISTRY; DRUG EFFECTS; ERYTHROCYTE; FEMALE; HEART MUSCLE; HEMOLYSIS; METABOLISM; PARTICLE SIZE; SURFACE PROPERTY; TISSUE DISTRIBUTION; ULTRASTRUCTURE;

ANIMALS; CYCLOOXYGENASE INHIBITORS; ERYTHROCYTES; FEMALE; HEMOLYSIS; INDOLES; KIDNEY; LIVER; LUNG; MICE; MYOCARDIUM; NANOCAPSULES; PARTICLE SIZE; PPAR GAMMA; SPLEEN; SURFACE PROPERTIES; THIAZOLIDINEDIONES; TISSUE DISTRIBUTION;

EID: 84929463083     PISSN: 01683659     EISSN: 18734995     Source Type: Journal    
DOI: 10.1016/j.jconrel.2015.04.033     Document Type: Article

References (57)

1. H. Yki-Jarvinen Drug therapy - thiazolidinediones N. Engl. J. Med. 351 2004 1106 1118
2. M. Collin, and C. Thiemermann The PPAR-γ ligand 15-deoxy(δ12,14) prostaglandin J2 reduces the liver injury in endotoxic shock Eur. J. Pharmacol. 29 2003 257 258
3. Y. Yumei, L. Yu, M. Saraswathy, C.T. Brian, and B. Yochai Pioglitazone protects the myocardium against ischemia-reperfusion injury in eNOS and iNOS knockout mice Am. J. Physiol. Heart Circ. Physiol. 295 2008 2436 2446
4. A. Consoli, and G. Formoso Do thiazolidinediones still have a role in treatment of type 2 diabetes mellitus? Diabetes Obes. Metab. 11 2013 967 977
5. R.S. Rosenson, R.S. Wright, M. Farkouh, and J. Plutzky Modulating peroxisome proliferator-activated receptors for therapeutic benefit? Biology, clinical experience, and future prospects Am. Heart J. 164 2012 672 680
6. F.D.T. Uchôa, T.G. Silva, M.C.A. Lima, S.L. Galdino, I.R. Pitta, and T.D. Costa Preclinical pharmacokinetic and pharmacodynamic evaluation of thiazolidinone PG15: an anti-inflammatory candidate J. Pharm. Pharmacol. 61 2009 339 345
7. N.S. Murthy, and V. Srinivasa Screening of new synthetic thiazolidine-4-ones for anti-inflammatory activity in albino rats Indian J. Pharmacol. 35 2003 61 62
8. A.J.S. Góes, A.J. Alves, A.R. Faria, J.G. Lima, and M.B.S. Maia Synthesis and antiedematogenic activity of some N-trypthophyl-5-benzylidene-2,4-thiazolidinedione and N-trypthophyl-5-benzylidene-rhodanine derivatives Quim. Nova 27 2004 905 910
9. L.C. Santos, F.D.T. Uchôa, A.R.P.A. Canas, I.A. Sousa, R.O. Moura, M.C.A. Lima, S.L. Galdino, I.R. Pitta, and J. Barbe Synthesis and anti-inflammatory activity of new thiazolidine-2,4-diones, 4-thioxothiazolidinones and 2-thioxoimidazolidinones Heterocycl. Commun. 11 2005 121 128
10. J.R. Santin, F.D.T. Uchôa, M.C.A. Lima, M.M. Rabello, I.D. Machado, M.Z. Hernandes, A.A. Amato, F.A. Milton, P. Webb, F.A.R. Neves, S.L. Galdino, I.R. Pitta, and S.H.P. Farsky Chemical synthesis, docking studies and biological effects of a pan peroxisome proliferator-activated receptor agonist and cyclooxygenase inhibitor Eur. J. Pharm. Sci. 48 2013 689 697
11. J.R. Santin, I.D. Machado, S.F.P. Rodrigues, S. Teixeira, M.N. Muscará, S.L. Galdino, I.R. Pitta, and S.H.P. Farsky Role of an indole-thiazolidine molecule PPAR pan-agonist and COX inhibitor on inflammation and microcirculatory damage in acute gastric lesions PLoS One 8 2013 e76894
12. S. Stegemann, F. Leveiller, D. Franchi, H. de Jong, and H. Lindéne When poor solubility becomes an issue: from early stage to proof of concept Eur. J. Pharm. Sci. 31 2007 249 261
13. V.C.F. Mosqueira, P. Legrand, J.L. Morgat, M. Vert, E. Mysiakine, R. Gref, J.P. Devissaguet, and G. Barratt Biodistribution of long-circulating PEG-grafted nanocapsules in mice: effects of PEG chain length and density Pharm. Res. 18 2001 1411 1419
14. R. Nagahama, T. Matoba, K. Nakano, S. Kim-Mitsuyama, K. Sunagawa, and K. Egashira Nanoparticle-mediated delivery of pioglitazone enhances therapeutic neovascularization in a murine model of hindlimb ischemia Arterioscler. Thromb. Vasc. Biol. 32 2012 2427 2434
15. V.C.F. Mosqueira, P. Legrand, and G. Barrat Surface-modified and conventional nanocapsules as novel formulations for parenteral delivery of halofantrine J. Nanosci. Nanotechnol. 6 2006 3193 3202
16. H. Fessi, F. Pusieux, J.P. Devissaguet, N. Ammoury, and S. Benita Nanocapsule formation by interfacial polymer deposition following solvent displacement Int. J. Pharm. 55 1989 R1 R4
17. C.S. de Paula, A.C. Tedesco, F.L. Primo, J.M. Vilela, M.S. Andrade, and V.C.F. Mosqueira Chloroaluminium phthalocyanine polymeric nanoparticles as photosensitisers: photophysical and physicochemical characterisation, release and phototoxicity in vitro Eur. J. Pharm. Sci. 49 2013 371 381
18. M.A. Dobrovolskaia, J.D. Clogston, B.W. Neun, J.B. Hall, A.K. Patri, and S.E. McNeil Method for analysis of nanoparticle hemolytic properties in vitro Nano Lett. 8 2008 2180 2187
19. ICH harmonised tripartite guideline International Conference on Harmonisation of Technical Requirements for Registration of Pharmaceuticals for Human Use, Validation of Analytical Procedures: Text and Methodology Q29(R1) 2005 ICH Steering Committee Geneva, Switzerland 1 13
20. U. Bhardwaj, and D.J.A. Burgess A novel USP apparatus 4 based release testing method for dispersed systems Int. J. Pharm. 388 2010 287 294
21. L.T. Oliveira, G.M. Garcia, E.K. Kano, A.C. Tedesco, and V.C.F. Mosqueira HPLC-FLD methods to quantify chloroaluminum phthalocyanine in nanoparticles, plasma and tissue: application in pharmacokinetic and biodistribution studies J. Pharm. Biomed. Anal. 56 2011 70 77
22. US Food and Drug Administration Guidance for Industry, Bioanalytical Method Validation 2001 Centre for Drug Evaluation and Research (CDER) Rockville
23. Y. Zhang, M. Huo, J. Zhou, and S. Xie PKSolver: an add-in program for pharmacokinetic and pharmacodynamic data analysis in Microsoft Excel Comput. Methods Prog. Biomed. 99 2010 306 314
24. E.A. Leite, J.M.C. Vilela, V.C.F. Mosqueira, and M.S. Andrade Poly-caprolactone nanocapsules morphological features by atomic force microscopy Microsc. Microanal. 11 2005 48 51
25. S.M. Moghimi, A.C. Hunter, C.M. Dadswell, S. Savay, C.R. Alving, and J. Szebeni Causative factors behind poloxamer 188 (Pluronic F65, Flocor™)-induced complement activation in human sera. A protective role against poloxamer-mediated complement activation by elevated serum lipoprotein levels Biochim. Biophys. Acta 1689 2004 103 113
26. P. Costa, and S.J.M. Lobo Modeling and comparison of dissolution profiles Eur. J. Pharm. Sci. 13 2001 123 133
27. C.E. Mora-Huertas, H. Fessi, and A. Elaissari Polymer-based nanocapsules for drug delivery Int. J. Pharm. 385 2010 113 142
28. A.L. Zampieri, F.S. Ferreira, E.C. Resende, M.P. Gaeti, D.G. Diniz, S.F. Taveira, and E.M. Lima Biodegradable polymeric nanocapsules based on poly(dl-lactide) for genistein topical delivery: obtention, characterization and skin permeation studies J. Biomed. Nanotechnol. 9 2013 527 534
29. S. Attili-Qadri, N. Karra, A. Nemirovski, O. Schwob, Y. Talmon, T. Nassar, and S. Benita Oral delivery system prolongs blood circulation of docetaxel nanocapsules via lymphatic absorption Proc. Natl. Acad. Sci. 110 2013 17498 17503
30. V.C.F. Mosqueira, P. Legrand, H.P. Alphandary, F. Puisieux, and G. Barratt Poly (d,l-lactide) nanocapsules prepared by a solvent displacement process: influence of the composition on physicochemical and structural properties J. Pharm. Sci. 89 2000 614 626
31. M. Hassellöv, J.W. Readman, J.F. Ranville, and K. Tiede Nanoparticle analysis and characterization methodologies in environmental risk assessment of engineered nanoparticles Ecotoxicology 17 2008 344 361
32. E.A. Brender, M.D. Adorne, L.M. Colomé, D.S.P. Abdalla, S.S. Guterres, and A.R. Pohlmann Hemocompatibility of poly(ε-caprolactone) lipid-core nanocapsules stabilized with polysorbate 80-lecithin and uncoated or coated with chitosan Int. J. Pharm. 426 2012 271 279
33. V.C.F. Mosqueira, P.M. Loiseau, C. Bories, P. Legrand, J.-P. Devissaguet, and G. Barratt Efficacy and pharmacokinetics of intravenous nanocapsule formulations of halofantrine in Plasmodium berghei-infected mice Antimicrob. Agents Chemother. 48 2004 1222 1228
34. E.A. Leite, A. Grabe-Guimarães, H.N. Guimarães, G.L.L. Machado-Coelho, G. Barratt, and V.C.F. Mosqueira Cardiotoxicity reduction induced by halofantrine entrapped in nanocapsule devices Life Sci. 80 2007 1327 1334
35. L. Shargel, S. Wu-Pong, and A. Yu Applied Biopharmaceutics & Pharmacokinetics Sixth edition 2012 McGraw-Hill
36. V. Saxena, M. Sadoqi, and J. Shao Polymeric nanoparticulate delivery system for indocyanine green: biodistribution in healthy mice Int. J. Pharm. 308 2006 200 204
37. M.A. Pereira, V.C.F. Mosqueira, V.A. Carmo, C.S. Ferrari, E.C. Reis, G.A. Ramaldes, and V.N. Cardoso Biodistribution study and identification of inflammatory sites using nanocapsules labeled with (99 m)Tc-HMPAO Nucl. Med. Commun. 30 2009 749 755
38. M. Hultin, C. Carneheim, K. Rosenqvist, and T. Olivecrona Intravenous lipid emulsions: removal mechanisms as compared to chylomicrons J. Lipid Res. 36 1995 2174 2184
39. M.N. Ton, C. Chang, Y.A. Carpentier, and R.J. Deckelbaum In vivo and in vitro properties of an intravenous lipid emulsion containing only medium chain and fish oil triglycerides Clin. Nutr. 24 2005 492 501
40. J. Ferezou, and A.C. Bach Structure and metabolic fate of triacylglycerol and phospholipid-rich particles of commercial parenteral fat emulsions Nutrition 15 1999 44 50
41. T. Sakaeda, and K. Hirano Effect of composition on biological fate of oil particles after intravenous injection of O/W lipid emulsions J. Drug Target. 6 1998 273 284
42. P.C. Calder, D.L. Waitzberg, and B. Koletzko Intravenous lipid emulsions World Rev. Nutr. Diet. 112 2015 57 62
43. A.L. Lainé, J. Gravier, M. Henry, L. Sancey, J. Béjaud, E. Pancani, M. Wiber, I. Texier, J.L. Coll, J.P. Benoit, and C. Passirani Conventional versus stealth lipid nanoparticles: formulation and in vivo fate prediction through FRET monitoring J. Control. Release 28 2014 1 8
44. R. Savonen, M. Hiden, M. Hultin, R. Zechner, S. Levak-Frank, G. Olivecrona, and T. Olivecrona The tissue distribution of lipoprotein lipase determines where chylomicrons bind J. Lipid Res. 56 2015 588 598
45. G. Olivecrona, and T. Olivecrona Triglyceride lipases and atherosclerosis Curr. Opin. Lipidol. 21 2010 409 415
46. J.K. Kim, J.J. Fillmore, Y. Chen, C. Yu, I.K. Moore, M. Pypaert, E.P. Lutz, Y. Kako, W. Velez-Carrasco, I.J. Goldberg, J.L. Breslow, and G.I. Shulman Tissue-specific overexpression of lipoprotein lipase causes tissue-specific insulin resistance Proc. Natl. Acad. Sci. 98 2001 7522 7527
47. L. Fajas, M.B. Debril, and J. Auwerx PPAR gamma: an essential role in metabolic control Nutr. Metab. Cardiovasc. Dis. 11 2001 64 69
48. F.A. César, M. Rudnicki, B. de las Heras, L. Boscá, M.C.A. Lima, I.R. Pitta, and D.S.P. Abdalla New indole-thiazolidine attenuates atherosclerosis in LDLr -/- mice Vasc. Pharmacol. 2015 http://dx.doi.org/10.1016/j.vph.2015.03.009
49. T. Ruge, M. Bergö, M. Hultin, G. Olivecrona, and T. Olivecrona Nutritional regulation of binding sites for lipoprotein lipase in rat heart Am. J. Physiol. Endocrinol. Metab. 278 2000 E211 E218
50. J.P.H. Wilding PPAR agonists for the treatment of cardiovascular disease in patients with diabetes Diabetes Obes. Metab. 14 2012 973 982
51. L.C. Poulsen, M. Siersbæk, and S. Mandrup PPARs: fatty acid sensors controlling metabolism Semin. Cell Dev. Biol. 23 2012 613 639
52. O. Braissant, F. Foufelle, C. Scotto, M. Dauca, and W. Wahli Differential expression of peroxisome proliferator-activated receptors (PPARs): tissue distribution of PPAR-alpha, -beta and -gamma in the adult rat Endocrinology 137 1996 354 366
53. M. Ahmadian, J.M. Suh, N. Hah, C. Liddle, A.R. Atkins, M. Downes, and R.M. Evans PPARγ signaling and metabolism: the good, the bad and the future Nat. Med. 19 2013 557 566
54. E.R. Blasi, J. Heyen, M. Hemkens, A. McHarg, C.M. Ecelbarger, and S. Tiwari Effects of chronic PPAR-agonist treatment on cardiac structure and function, blood pressure, and kidney in healthy Sprague-Dawley rats PPAR Res. 2009 1-13, http://dx.doi.org/10.1155/2009/237865. (237865)
55. M.Y. Lee, R. Choi, H.M. Kim, E.J. Cho, B.H. Kim, Y.S. Choi, J. Naowaboot, E.Y. Lee, Y.C. Yang, and J.Y. Shin Peroxisome proliferator-activated receptor δ agonist attenuates hepatic steatosis by anti-inflammatory mechanism Exp. Mol. Med. 44 2012 578 585
56. P.A. Sarafidis, and G.L. Bakris Protection of the kidney by thiazolidinediones: an assessment from bench to bedside Kidney Int. 70 2006 1223 1233
57. S.P. Lakshmi, A.T. Reddy, Y. Zhang, F.C. Sciurba, R.K. Mallampalli, S.R. Duncan, and R.C. Reddy Down-regulated peroxisome proliferator-activated receptor γ (PPARγ) in lung epithelial cells promotes a PPARγ agonist-reversible pro-inflammatory phenotype in chronic obstructive pulmonary disease (COPD) J. Biol. Chem. 289 2013 6383 6393