A novel in situ hydrophobic ion paring (HIP) formulation strategy for clinical product selection of a nanoparticle drug delivery system

Journal of Controlled Release

Volumn 229, Issue , 2016, Pages 106-119

  Song, Young Ho ^a   Shin, Eyoung ^a   Wang, Hong ^a   Nolan, Jim ^a   Low, Susan ^a   Parsons, Donald ^a   Zale, Stephen ^a   Ashton, Susan ^b   Ashford, Marianne ^b   Ali, Mir ^a   Thrasher, Daniel ^a   Boylan, Nicholas ^a   Troiano, Greg ^a  

^a BIND Therapeutics   (United States)

^b ASTRAZENECA   (United Kingdom)

Author keywords

Adjustable release rate; Counterions; Drug release kinetics; In situ hydrophobic ion paring; Nanoparticles; PLA PEG

Indexed keywords

CHROMATOGRAPHY; DRUG PRODUCTS; ENCAPSULATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROPHOBICITY; LIQUID CHROMATOGRAPHY; MAGNETIC RESONANCE SPECTROSCOPY; NANOPARTICLES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMER BLENDS;

1-HYDROXY-2-NAPHTHOIC ACID; ACTIVE PHARMACEUTICAL INGREDIENTS; COUNTERIONS; DRUG RELEASE KINETICS; ENCAPSULATION EFFICIENCY; NANOPARTICLE FORMULATION; PLA-PEG; RELEASE RATE;

IONS;

1 HYDROXY 2 NAPHTHOIC ACID; 2 NAPHTHOIC ACID DERIVATIVE; AURORA KINASE INHIBITOR; AZD 2811; BARASERTIB; BUFFER; CHOLIC ACID; COUNTERION; DEOXYCHOLIC ACID; DIOCTYLSULFOSUCCINIC ACID; EMBONIC ACID; MACROGOL; MONOETHANOLAMINE OLEATE; NANOCARRIER; NANOPARTICLE; OLANZAPINE; OLEIC ACID; POLYLACTIC ACID; POLYMER; SODIUM CHLORIDE; SUCCINIC ACID DERIVATIVE; UNCLASSIFIED DRUG; 1-HYDROXY-2-NAPHTHOIC ACID; 2-((3-((4-((5-(2-((3-FLUOROPHENYL)AMINO)-2-OXOETHYL)-1H-PYRAZOL-3-YL)AMINO)QUINAZOLIN-7-YL)OXY)PROPYL)(ETHYL)AMINO)ETHYL DIHYDROGEN PHOSPHATE; ACETANILIDE DERIVATIVE; ANTINEOPLASTIC AGENT; AZD2811; DOCUSATE SODIUM; MACROGOL DERIVATIVE; MONOMETHOXYPOLYETHYLENEGLYCOL-POLYLACTIDE BLOCK COPOLYMER; NAPHTHOL DERIVATIVE; ORGANOPHOSPHATE; PRODRUG; QUINAZOLINE DERIVATIVE;

ACID DISSOCIATION CONSTANT; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; CONTROLLED DRUG RELEASE; CONTROLLED STUDY; DRUG BLOOD LEVEL; DRUG DELIVERY SYSTEM; DRUG FORMULATION; DRUG SOLUBILITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; HYDROPHOBIC ION PAIRING FORMULATION; HYDROPHOBICITY; MALE; NANOEMULSION; NANOENCAPSULATION; NONHUMAN; PARTICLE SIZE; PH; PHARMACODYNAMICS; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; PRODUCT DEVELOPMENT; RAT; SMALL CELL LUNG CANCER; STOICHIOMETRY; SUSTAINED DRUG RELEASE; TUMOR XENOGRAFT; ANIMAL; BONE MARROW; CHEMICAL PHENOMENA; CHEMISTRY; DRUG EFFECTS; NEOPLASMS; NUDE MOUSE; NUDE RAT; PATHOLOGY; TUMOR CELL LINE; TUMOR VOLUME; WISTAR RAT;

ACETANILIDES; ANIMALS; ANTINEOPLASTIC AGENTS; BONE MARROW; CELL LINE, TUMOR; CHOLIC ACID; DEOXYCHOLIC ACID; DIOCTYL SULFOSUCCINIC ACID; DRUG DELIVERY SYSTEMS; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MALE; MICE, NUDE; NANOPARTICLES; NAPHTHOLS; NEOPLASMS; ORGANOPHOSPHATES; POLYETHYLENE GLYCOLS; PRODRUGS; QUINAZOLINES; RATS, NUDE; RATS, WISTAR; TUMOR BURDEN;

EID: 84961897444     PISSN: 01683659     EISSN: 18734995     Source Type: Journal    
DOI: 10.1016/j.jconrel.2016.03.026     Document Type: Article

References (41)

1. P.V. Devarajan Targeted Drug Delivery: Concepts and Design 2014 Springer New York
2. R.I. Mahato, and A.S. Narang Targeted Delivery of Small and Macromolecular Drugs 2010 CRC Press/Taylor & Francis Boca Raton, FL
3. D.F. Emerich, and C.G. Thanos Targeted nanoparticle-based drug delivery and diagnosis J. Drug Target. 15 2007 163 183
4. R. Singh, and J.W. Lillard Jr. Nanoparticle-based targeted drug delivery Exp. Mol. Pathol. 86 2009 215 223
5. X. Yu, and M.V. Pishko Nanoparticle-based biocompatible and targeted drug delivery: characterization and in vitro studies Biomacromolecules 12 2011 3205 3212
6. I.K. Kwon, S.C. Lee, B. Han, and K. Park Analysis on the current status of targeted drug delivery to tumors J. Control. Release 164 2012 108 114
7. T.M. Allen, and P.R. Cullis Drug delivery systems: entering the mainstream Science 303 2004 1818 1822
8. A. Budhian, S.J. Siegel, and K.I. Winey Controlling the in vitro release profiles for a system of haloperidol-loaded PLGA nanoparticles Int. J. Pharm. 346 2008 151 159
9. S.D. Li, and L. Huang Pharmacokinetics and biodistribution of nanoparticles Mol. Pharm. 5 2008 496 504
10. D.Y. Arifin, L.Y. Lee, and C.H. Wang Mathematical modeling and simulation of drug release from microspheres: implications to drug delivery systems Adv. Drug Deliv. Rev. 58 2006 1274 1325
11. A. Kumari, S.K. Yadav, and S.C. Yadav Biodegradable polymeric nanoparticles based drug delivery systems Colloids Surf. B: Biointerfaces 75 2010 1 18
12. M. Polakovic, T. Gorner, R. Gref, and E. Dellacherie Lidocaine loaded biodegradable nanospheres. II. Modelling of drug release J. Control. Release 60 1999 169 177
13. F. Alexis Factors affecting the degradation and drug-release mechanism of poly(lactic acid) and poly[(lactic acid)-co-(glycolic acid)] Polym. Int. 54 2005 36 46
14. G. Mittal, D.K. Sahana, V. Bhardwaj, and M.N. Ravi Kumar Estradiol loaded PLGA nanoparticles for oral administration: effect of polymer molecular weight and copolymer composition on release behavior in vitro and in vivo J. Control. Release 119 2007 77 85
15. S.M. Ansell, S.A. Johnstone, P.G. Tardi, L. Lo, S. Xie, Y. Shu, T.O. Harasym, N.L. Harasym, L. Williams, D. Bermudes, B.D. Liboiron, W. Saad, R.K. Prud'homme, and L.D. Mayer Modulating the therapeutic activity of nanoparticle delivered paclitaxel by manipulating the hydrophobicity of prodrug conjugates J. Med. Chem. 51 2008 3288 3296
16. C. Luo, J. Sun, B. Sun, and Z. He Prodrug-based nanoparticulate drug delivery strategies for cancer therapy Trends Pharmacol. Sci. 35 2014 556 566
17. J.J. Wang, K.S. Liu, K.C. Sung, C.Y. Tsai, and J.Y. Fang Lipid nanoparticles with different oil/fatty ester ratios as carriers of buprenorphine and its prodrugs for injection Eur. J. Pharm. Sci. 38 2009 138 146
18. S.D. Clas, R.I. Sanchez, and R. Nofsinger Chemistry-enabled drug delivery (prodrugs): recent progress and challenges Drug Discov. Today 19 2014 79 87
19. S. Ashton, Y.H. Song, J. Nolan, E. Cadogan, J. Murray, R. Odedra, J. Foster, P.A. Hall, S. Low, P. Taylor, R. Ellston, U.M. Polanska, J. Wilson, C. Howes, A. Smith, R.J.A. Goodwin, J.G. Swales, N. Stritmatter, Z. Takáts, A. Nilsson, P. Andren, D. Trueman, M. Walker, C.L. Reimer, G. Troiano, D. Parsons, D. De Witt, J. Ashford, J. Hrkach, S. Zale, P.J. Jewsbury, and S.T. Barry Aurora kinase inhibitor nanoparticles target tumors with favorable therapeutic index in vivo Sci. Transl. Med. 8 2016 325ra17
20. J. Hrkach, D. Von Hoff, M.M. Ali, E. Andrianova, J. Auer, T. Campbell, D. De Witt, M. Figa, M. Figueiredo, A. Horhota, S. Low, K. McDonnell, E. Peeke, B. Retnarajan, A. Sabnis, E. Schnipper, J.J. Song, Y.H. Song, J. Summa, D. Tompsett, G. Troiano, T. Van Geen Hoven, J. Wright, P. LoRusso, P.W. Kantoff, N.H. Bander, C. Sweeney, O.C. Farokhzad, R. Langer, and S. Zale Preclinical development and clinical translation of a PSMA-targeted docetaxel nanoparticle with a differentiated pharmacological profile Sci. Transl. Med. 4 2012 128ra139
21. J.D. Meyer, and M.C. Manning Hydrophobic ion pairing: altering the solubility properties of biomolecules Pharm. Res. 15 1998 188 193
22. R. Gaudana, A. Parenky, R. Vaishya, S.K. Samanta, and A.K. Mitra Development and characterization of nanoparticulate formulation of a water soluble prodrug of dexamethasone by HIP complexation J. Microencapsul. 28 2011 10 20
23. N.M. Pinkerton, A. Grandeury, A. Fisch, J. Brozio, B.U. Riebesehl, and R.K. Prud'homme Formation of stable nanocarriers by in situ ion pairing during block-copolymer-directed rapid precipitation Mol. Pharm. 10 2013 319 328
24. C.S. Lengsfeld, D. Pitera, M. Manning, and T.W. Randolph Dissolution and partitioning behavior of hydrophobic ion-paired compounds Pharm. Res. 19 2002 1572 1576
25. S.H. Choi, and T.G. Park Hydrophobic ion pair formation between leuprolide and sodium oleate for sustained release from biodegradable polymeric microspheres Int. J. Pharm. 203 2000 193 202
26. W.G. Dai, and L.C. Dong Characterization of physiochemical and biological properties of an insulin/lauryl sulfate complex formed by hydrophobic ion pairing Int. J. Pharm. 336 2007 58 66
27. A. Patel, R. Gaudana, and A.K. Mitra A novel approach for antibody nanocarriers development through hydrophobic ion-pairing complexation J. Microencapsul. 31 2014 542 550
28. S. Sun, N. Liang, H. Piao, H. Yamamoto, Y. Kawashima, and F. Cui Insulin-S.O (sodium oleate) complex-loaded PLGA nanoparticles: formulation, characterization and in vivo evaluation J. Microencapsul. 27 2010 471 478
29. L. Yang, F. Cui, K. Shi, D. Cun, and R. Wang Design of high payload PLGA nanoparticles containing melittin/sodium dodecyl sulfate complex by the hydrophobic ion-pairing technique Drug Dev. Ind. Pharm. 35 2009 959 968
30. D.T. Manallack The pK(a) distribution of drugs: application to drug discovery Perspect Medicin Chem. 1 2008 25 38
31. V.V. Ambardekar, and S.T. Stern NBCD pharmacokinetics and bioanalytical methods to measure drug release D.J.A. Crommelin, J.S.B. de Vlieger, Non-Biological Complex Drugs 2015 Springer International Publishing 261 287
32. P.H. Stahl, and C.G. Wermuth Handbook of Pharmaceutical Salts: Properties, Selection, and Use 2011 Verlag Helvetica Chimica Acta Zürich
33. A.T. Serajuddin Salt formation to improve drug solubility Adv. Drug Deliv. Rev. 59 2007 603 616
34. A.T. Serajuddin, P.C. Sheen, D. Mufson, D.F. Bernstein, and M.A. Augustine Physicochemical basis of increased bioavailability of a poorly water-soluble drug following oral administration as organic solutions J. Pharm. Sci. 77 1988 325 329
35. W.Q. Tong, and G. Whitesell In situ salt screening - a useful technique for discovery support and preformulation studies Pharm. Dev. Technol. 3 1998 215 223
36. R.J. Bastin, M.J. Bowker, and B.J. Slater Salt selection and optimisation procedures for pharmaceutical new chemical entities Org. Process Res. Dev. 4 2000 427 435
37. G. Garrido, V. de Nogales, C. Ràfols, and E. Bosch Acidity of several polyprotic acids, amiodarone and quetiapine hemifumarate in pure methanol Talanta 73 2007 115 120
38. H. Kim, C.R. Babu, and D.J. Burgess Quantification of protonation in organic solvents using solution NMR spectroscopy: implication in salt formation Int. J. Pharm. 448 2013 123 131
39. P. Ruenraroengsak, J.M. Cook, and A.T. Florence Nanosystem drug targeting: facing up to complex realities J. Control. Release 141 2010 265 276
40. Y.H. Bae, and K. Park Targeted drug delivery to tumors: myths, reality and possibility J. Control. Release 153 2011 198 205
41. A. Kumar, L.A. Dailey, and B. Forbes Lost in translation: what is stopping inhaled nanomedicines from realizing their potential? Ther. Deliv. 5 2014 757 761