Cholic acid-modified dendritic multimolecular micelles and enhancement of anticancer drug therapeutic efficacy

Bioconjugate Chemistry

Volumn 21, Issue 9, 2010, Pages 1596-1601

  Zhang, Kun ^a   Wang, Yongjian ^a   Yu, Ao ^a   Zhang, Yue ^a   Tang, Hao ^a   Zhu, X X ^a,b  

^a NANKAI UNIVERSITY   (China)

^b UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

DENDRIMERS; DRUG DELIVERY; DRUG DOSAGE; LIGHT SCATTERING; MEDICAL APPLICATIONS; MOLECULES; SOLUTIONS; TITRATION;

ACID MOLECULES; ACID-BASE TITRATION; ANTICANCER DRUG; BIOMEDICAL APPLICATIONS; CHOLIC ACIDS; DENDRITICS; NMR STUDIES; POLYAMIDOAMINE DENDRIMERS; POLYAMIDOAMINES; THERAPEUTIC EFFICACY;

MICELLES;

CAMPTOTHECIN; CHOLIC ACID; POLYAMIDOAMINE;

ANIMAL CELL; ARTICLE; CYTOTOXICITY; DENDRITE; DRUG DELIVERY SYSTEM; DRUG EFFICACY; HUMAN; HUMAN CELL; MICELLE; MOUSE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 77956632011     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc900490u     Document Type: Article

References (46)

1. Medina, S. H. and El-Sayed, M. E. H. (2009) Dendrimers as carriers for delivery of chemotherapeutic agents Chem. Rev. 109, 3141-3157
2. Tekade, R. K., Kumar, P. V., and Jain, N. K. (2009) Dendrimers in oncology: an expanding horizon Chem. Rev. 109, 49-87
3. Boas, U. and Heegaard, P. M. H. (2004) Dendrimers in drug research Chem. Soc. Rev. 33, 43-63
4. Esfand, R. and Tomalia, D. A. (2001) Poly(amidoamine) (PAMAM) dendrimers: from biomimicry to drug delivery and biomedical applications Drug Discovery Today 6, 427-436
5. Wang, Y., Kong, W., Song, Y., Duan, Y., Wang, L., Steinhoff, G., Kong, D., and Yu, Y. (2009) Polyamidoamine dendrimers with a modified pentaerythritol core having high efficiency and low cytotoxicity as gene carriers Biomacromolecules 10, 617-622
6. de Jong, G., Telenius, A., Vanderbyl, S., Meitz, A., and Drayer, J. (2001) Efficient in-vitro transfer of a 60-Mb mammalian artificial chromosome into murine and hamster cells using cationic lipids and dendrimers Chromosome Res. 9, 475-485
7. Eichman, J. D., Bielinska, A. U., Kukowska-Latallo, J. F., and Baker, J. R. (2000) The use of PAMAM dendrimers in the efficient transfer of genetic material into cells Pharm. Sci. Technol. Today 3, 232-245
8. Konda, S. D., Wang, S., Brechbiel, M., and Wiener, E. C. (2002) Biodistribution of a 153Gd-folate dendrimer, generation = 4, in mice with folate-receptor positive and negative ovarian tumor xenografts Invest. Radiol. 37, 199-204
9. Kobayashi, H., Kawamoto, S., Jo, S. K., Bryant, H. L., Brechbiel, M. W., and Star, R. A. (2003) Macromolecular MRI contrast agents with small dendrimers: pharmacokinetic differences between sizes and cores Bioconjugate Chem. 14, 388-394
10. Balagurusamy, V. S. K., Ungar, G., Percec, V., and Johansson, G. (1997) Rational design of the first spherical supramolecular dendrimers self-organized in a novel thermotropic cubic liquid-crystalline phase and the determination of their shape by X-ray analysis J. Am. Chem. Soc. 119, 1539-1555
11. Goran, U., Virgil, P., Marian, N. H., Gary, J., and James, A. H. (2000) Heat-shrinking spherical and columnar supramolecular dendrimers: their interconversion and dependence of their shape on molecular taper angle Chem. - Eur. J. 6, 1258-1266
12. Pitois, C., Hult, A., and Lindgren, M. (2005) Lanthanide-cored fluorinated dendrimer complexes: synthesis and luminescence characterization J. Lumin. 111, 265-283
13. D'Ambruoso, G. D. and McGrath, D. V. (2008) Energy harvesting in synthetic dendrimer materials, Advances in Polymer Science. Vol. 214: Photoresponsive Polymers II, (Marder, S. R., Lee, and K.- S., Eds.) pp 87 - 147, Chapter 2, Springer-Verlag Berlin, Berlin.
14. Archut, A., Azzellini, G. C., Balzani, V., De Cola, L., and Vogtle, F. (1998) Toward photoswitchable dendritic hosts. Interaction between azobenzene-functionalized dendrimers and eosin J. Am. Chem. Soc. 120, 12187-12191
15. Kollner, C., Pugin, B., and Togni, A. (1998) Dendrimers containing chiral ferrocenyl diphosphine ligands for asymmetric catalysis J. Am. Chem. Soc. 120, 10274-10275
16. Twyman, L. J., King, A. S. H., and Martin, I. K. (2002) Catalysis inside dendrimers Chem. Soc. Rev. 31, 69-82
17. D'Emanuele, A. and Attwood, D. (2005) Dendrimer-drug interactions Adv. Drug Delivery Rev. 57, 2147-2162
18. Tomalia, D. A., Naylor, A. M., and Goddard, W. A. (1990) Starburst dendrimers: molecular-level control of size, shape, surface chemistry, topology, and flexibility from atoms to macroscopic matter Angew. Chem., Int. Ed. Engl. 29, 138-175
19. Scherrenberg, R., Coussens, B., van Vliet, P., Edouard, G., Brackman, J., de Brabander, E., and Mortensen, K. (1998) The molecular characteristics of poly(propyleneimine) dendrimers as studied with small-angle neutron scattering, viscosimetry, and molecular dynamics Macromolecules 31, 456-461
20. Gullotti, E. and Yeo, Y. (2009) Extracellularly activated nanocarriers: a new paradigm of tumor targeted drug delivery Mol. Pharmaceutics 6, 1041-1051
21. Criscione, J. M., Le, B. L., Stern, E., Brennan, M., Rahner, C., Papademetris, X., and Fahmy, T. M. (2009) Self-assembly of pH-responsive fluorinated dendrimer-based particulates for drug delivery and noninvasive imaging Biomaterials 30, 3946-3955
22. Vutukuri, D. R., Basu, S., and Thayumanavan, S. (2004) Dendrimers with both polar and apolar nanocontainer characteristics J. Am. Chem. Soc. 126, 15636-15637
23. Gomez-Escudero, A., Azagarsamy, M. A., Theddu, N., Vachet, R. W., and Thayumanavan, S. (2008) Selective peptide binding using facially amphiphilic dendrimers J. Am. Chem. Soc. 130, 11156-11163
24. Radowski, M. R., Shukla, A., von Berlepsch, H., Bottcher, C., Pickaert, G., Rehage, H., and Haag, R. (2007) Supramolecular aggregates of dendritic multishell architectures as universal nanocarriers Angew. Chem., Int. Ed. 46, 1265-1269
25. Zhang, D. H., Hamilton, P. D., Kao, J. L. F., Venkataraman, S., Wooley, K. L., and Ravi, N. (2007) Formation of nanogel aggregates by an amphiphilic cholesteryl-poly(amidoamine) dendrimer in aqueous media J. Polym. Sci., Part A: Polym. Chem. 45, 2569-2575
26. Wang, B. B., Zhang, X., Jia, X. R., Li, Z. C., Ji, Y., Yang, L., and Wei, Y. (2004) Fluorescence and aggregation behavior of poly(amidoamine) dendrimers peripherally modified with aromatic chromophores: the effect of dendritic architectures J. Am. Chem. Soc. 126, 15180-15194
27. Zhao, Y., Song, Y., Jiang, W., Zhang, B., Li, Y., Sha, K., Wang, S., Chen, L., Ma, L., and Wang, J. (2008) Synthesis of a novel star polymer consisting of a dendritic polyamidoamine core and polystyrene arms and its self-assembly to form large multimolecular micelles J. Appl. Polym. Sci. 109, 1039-1047
28. Yang, W., Cheng, Y., Xu, T., Wang, X., and Wen, L.-p. (2009) Targeting cancer cells with biotin-dendrimer conjugates Eur. J. Med. Chem. 44, 862-868
29. Majoros, I. J., Myc, A., Thomas, T., Mehta, C. B., and Baker, J. R. (2006) PAMAM dendrimer-based multifunctional conjugate for cancer therapy: synthesis, characterization, and functionality Biomacromolecules 7, 572-579
30. Boswell, C. A., Eck, P. K., Regino, C. A. S., Bernardo, M., Wong, K. J., Milenic, D. E., Choyke, P. L., and Brechbiel, M. W. (2008) Synthesis, characterization, and biological evaluation of integrin αvβ3-targeted PAMAM dendrimers Mol. Pharmaceutics 5, 527-539
31. Hafez, I. M., Maurer, N., and Cullis, P. R. (2001) On the mechanism whereby cationic lipids promote intracellular delivery of polynucleic acids Gene Ther. 8, 1188-1196
32. Gautrot, J. E. and Zhu, X. X. (2006) Biodegradable polymers based on bile acids and potential biomedical applications J. Biomater. Sci., Polym. Ed. 17, 1123-1139
33. Luo, J., Chen, Y., and Zhu, X. X. (2009) Invertible amphiphilic molecular pockets made of cholic acid Langmuir 25, 10913-10917
34. Zhang, J., Luo, J., Zhu, X. X., Junk, M. J. N., and Hinderberger, D. (2010) Molecular pockets derived from cholic acid as chemosensors for metal ions Langmuir 26, 2958-2962
35. Li, Y., Li, G. T., Wang, X. Y., Lin, C. X., Zhang, Y. H., and Ju, Y. (2008) Poly(p-phenylene ethynylene)s with facially amphiphilic pendant groups: solvatochromism and supramolecular assemblies Chem. - Eur. J. 14, 10331-10339
36. Mukhopadhyay, S. and Maitra, U. (2004) Chemistry and biology of bile acids Curr. Sci. 87, 1666-1683
37. Enhsen, A., Kramer, W., and Wess, G. (1998) Bile acids in drug discovery Drug Discovery Today 3, 409-418
38. Hazra, B. G., Pore, V. S., Dey, S. K., Datta, S., Darokar, M. P., Saikia, D., Khanuja, S. P. S., and Thakur, A. P. (2004) Bile acid amides derived from chiral amino alcohols: novel antimicrobials and antifungals Bioorg. Med. Chem. Lett. 14, 773-777
39. Han, S. O., Mahato, R. I., and Kim, S. W. (2001) Water-soluble lipopolymer for gene delivery Bioconjugate Chem. 12, 337-345
40. Chen, W., Tomalia, D. A., and Thomas, J. L. (2000) Unusual pH-dependent polarity changes in PAMAM dendrimers: evidence for pH-responsive conformational changes Macromolecules 33, 9169-9172
41. Gouin, S. and Zhu, X. X. (1998) Fluorescence and NMR studies of the effect of a bile acid dimer on the micellization of bile salts Langmuir 14, 4025-4029
42. Lin, W., Galletto, P., and Borkovec, M. (2004) Charging and aggregation of latex particles by oppositely charged dendrimers Langmuir 20, 7465-7473
43. DeLong, R. K., Yoo, H., Alahari, S. K., Fisher, M., Short, S. M., Kang, S. H., Kole, R., Janout, V., Regan, S. L., and Juliano, R. L. (1999) Novel cationic amphiphiles as delivery agents for antisense oligonucleotides Nucleic Acids Res. 27, 3334-3341
44. Shuai, X. T., Merdan, T., Unger, F., and Kissel, T. (2005) Supramolecular gene delivery vectors showing enhanced transgene expression and good biocompatibility Bioconjugate Chem. 16, 322-329
45. Prokop, A. and Davidson, J. M. (2008) Nanovehicular intracellular delivery systems J. Pharm. Sci. 97, 3518-3590
46. Fan, L., Li, F., Zhang, H., Wang, Y., Cheng, C., Li, X., Gu, C.-h., Yang, Q., Wu, H., and Zhang, S. (2010) Co-delivery of PDTC and doxorubicin by multifunctional micellar nanoparticles to achieve active targeted drug delivery and overcome multidrug resistance Biomaterials 31, 5634-5642