Prediction of the solubility of cucurbitacin drugs in self-associating poly(ethylene oxide)-b-poly(α-benzyl carboxylate ε-caprolactone) block copolymer with different tacticities using molecular dynamics simulation

Biomaterials

Volumn 31, Issue 2, 2010, Pages 345-357

  Patel, Sarthak K ^a   Lavasanifar, Afsaneh ^a   Choi, Phillip ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Di block copolymer; Hydrophobic drugs; Interaction parameter; Molecular dynamics simulation; Solubility; Tacticity

Indexed keywords

DI-BLOCK COPOLYMER; HYDROPHOBIC DRUGS; INTERACTION PARAMETER; MOLECULAR DYNAMICS SIMULATION; TACTICITY;

BINARY MIXTURES; BLOCK COPOLYMERS; CARBOXYLATION; COPOLYMERIZATION; DISTRIBUTION FUNCTIONS; DYNAMICS; ETHYLENE; EXPERIMENTS; HYDROPHOBICITY; INSECTICIDES; MOLECULAR DYNAMICS; MOLECULAR MECHANICS; MOLECULAR STRUCTURE; PLASTIC PRODUCTS; POLYETHYLENE OXIDES; RING OPENING POLYMERIZATION; SIMULATORS; SOLUBILITY; TERNARY SYSTEMS;

DRUG INTERACTIONS;

COPOLYMER; CUCURBITACIN; CUCURBITACIN B; CUCURBITACIN I; LACTONE; OCTANOIC ACID; POLY(ETHYLENE OXIDE) B POLY(ALPHA BENZYL CARBOXYLATE EPSILON CAPROLACTONE) BLOCK COPOLYMER; STANNOUS OCTOATE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG SOLUBILITY; DRUG STRUCTURE; HYDROPHOBICITY; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; POLYMERIZATION; PREDICTION; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; RING OPENING; SIMULATION;

CUCURBITACINS; HEXANOIC ACIDS; ISOMERISM; LACTONES; MOLECULAR DYNAMICS SIMULATION; POLYESTERS; POLYETHYLENE GLYCOLS; SOLUBILITY; STATIC ELECTRICITY; THERMODYNAMICS; TORSION, MECHANICAL;

EID: 70350719134     PISSN: 01429612     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.biomaterials.2009.09.051     Document Type: Article

References (28)

1. Lavasanifar A., Samuel J., Sattari S., and Kwon G.S. Block copolymer micelles for the encapsulation and delivery of amphotericin B. Pharm Res 19 (2002) 418-422
2. Yokoyama M., Satoh A., Sakurai Y., Okano T., Matsumura Y., Kakizoe T., et al. Incorporation of water-insoluble anticancer drug into polymeric micelles and control of their particle size. J Control Release 55 (1998) 219-229
3. Lee J., Cho E.C., and Cho K. Incorporation and release behavior of hydrophobic drug in functionalized poly(d,l-lactide)-block-poly(ethylene oxide) micelles. J Control Release 94 (2004) 323-335
4. Liu J., Xiao Y., and Allen C. Polymer-drug compatibility: a guide to the development of delivery systems for the anticancer agent, ellipticine. J Pharm Sci 93 (2004) 132-143
5. Forrest M.L., Zhao A., Won C.Y., Malick A.W., and Kwon G.S. Lipophilic prodrugs of Hsp90 inhibitor geldanamycin for nanoencapsulation in poly(ethylene glycol)-b-poly(epsilon-caprolactone) micelles. J Control Release 116 (2006) 139-149
6. Latere Dwan'Isa J.P., Rouxhet L., Preat V., Brewster M.E., and Arien A. Prediction of drug solubility in amphiphilic di-block copolymer micelles: the role of polymer-drug compatibility. Pharmazie 62 (2007) 499-504
7. Mahmud A., Patel S., Molavi O., Choi P., Samuel J., and Lavasanifar A. Self-associating poly(ethylene oxide)-b-poly(α-cholesteryl carboxylate-ε-caprolactone) block copolymer for the solubilization of STAT-3 inhibitor cucurbitacin I. Biomacromolecules 9 (2009) 471-478
8. Mahmud A., Xiong X., and Lavasanifar A. Novel self-associating poly(ethylene oxide)-block-poly(ε-caprolactone) block copolymers with functional side groups on the polyester block for drug delivery. Macromolecules 39 (2006) 9419-9428
9. Molavi O., Ma Z., Mahmud A., Alshamsan A., Samuel J., Lai R., et al. Polymeric micelles for the solubilization and delivery of STAT3 inhibitor cucurbitacins in solid tumors. Int J Pharm 347 (2008) 118-127
10. Flory P.J. Statistical mechanics of chain molecules (1989), Hanser, New York
11. Sun H. COMPASS: an ab initio force-field optimized for condensed-phase applications - overview with details on alkane and benzene compounds. J Phys Chem B 102 (1998) 7338-7364
12. Theodorou D.N., and Suter U.W. Atomistic modeling of mechanical properties of polymeric glasses. Macromolecules 19 (1986) 139-154
13. Patel S., Lavasanifar A., and Choi P. Application of molecular dynamics simulation to predict the compatibility between water-insoluble drugs and self-associating poly(ethylene oxide)-b-poly(ε-caprolactone) block copolymers. Biomacromolecules 9 (2008) 3014-3023
14. Patel S.K., Lavasanifar A., and Choi P. Roles of nonpolar and polar intermolecular interactions in the improvement of the drug loading capacity of PEO-b-PCL with increasing PCL content for two hydrophobic cucurbitacin drugs. Biomacromolecules 10 (2009) 2584-2591
15. Andersen H.C. Molecular dynamics simulations at constant pressure and/or temperature. J Chem Phys 72 (1980) 2384-2393
16. Nose S. A unified formulation of the constant-temperature molecular dynamics methods. J Chem Phys 81 (1984) 511-519
17. Flory P.J. Foundations of rotational isomeric state theory and general methods for generating configurational averages. Macromolecules 7 (1974) 381-392
18. Mattice W.L., and Suter U.W. Conformational theory of large molecules: the rotational isomeric state model in macromolecular systems (1994), J. Wiley, New York
19. Sagui C., and Darden T.A. Molecular dynamics simulations of biomolecules: long-range electrostatic effects. Annu Rev Biophys Biomol Struct 28 (1999) 155-179
20. Bai F., Li F., Calhoun B.H., Quirk R.P., and Cheng S. Physical constant of poly(propylene). In: Brandrup J., Immergut E.H., and Grulke E.A. (Eds). Polymer handbook. 4th ed. (1999), A Wiley Interscience Publications, New York V/21-V/30
21. Kricheldorf H.R., Boettcher C., and Tönnes K. Polylactones: 23. Polymerization of racemic and meso d, l-lactide with various organotin catalysts - stereochemical aspects. Polymer 33 (1992) 2817-2824
22. Kricheldorf H.R., Kreiser-Saunders I., and Boettcher C. Polylactones: 31. Sn(II)octoate-initiated polymerization of l-lactide: a mechanistic study. Polymer 36 (1995) 1253-1259
23. 1H solution NMR study of poly(lactide). Macromolecules 30 (1997) 2422-2428
24. 1H NMR: a case of changing stereospecificity. Macromolecules 31 (1998) 1487-1494
25. Burley S.K., and Petsko G.A. Aromatic-aromatic interaction: a mechanism of protein structure stabilization. Science 229 (1985) 23-28
26. Barlow J.W., and Paul D.R. Polymer blends and alloys - a review of selected considerations. Polym Eng Sci 21 (1981) 985-996
27. Cruz C.A., Barlow J.W., and Paul D.R. The basis for miscibility in polyester-polycarbonate blends. Macromolecules 12 (1979) 726-731
28. Li G., Cowie J.M.G., and Arrighi V. Miscibility of polymer blends of poly(styrene-co-4-hydroxystyrene) with bisphenol-A polycarbonate. J Appl Polym Sci 74 (1999) 639-646