Design of interior-functionalized fully acetylated dendrimers for anticancer drug delivery

Biomaterials

Volumn 32, Issue 36, 2011, Pages 9950-9959

  Hu, Jingjing ^b   Su, Yunzhang ^a   Zhang, Hongfeng ^a   Xu, Tongwen ^b   Cheng, Yiyun ^a  

^a EAST CHINA NORMAL UNIVERSITY   (China)

^b UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

Acetylation; Dendrimer; Interior functionalized; NMR; Non toxic

Indexed keywords

ANTI-CANCER DRUG DELIVERY; ANTICANCER DRUG; CELL LINES; CLINICAL APPLICATION; GUEST MOLECULES; INTERIOR-FUNCTIONALIZED; NEW STRATEGY; NMR TECHNIQUES; NON-TOXIC; POLYMERIC NANOCARRIERS; SUSTAINED RELEASE;

ACETYLATION; CELL CULTURE; DENDRIMERS; DRUG DELIVERY; FUNCTIONAL GROUPS; SYNTHESIS (CHEMICAL); TOXIC MATERIALS;

FUNCTIONAL POLYMERS;

ANTINEOPLASTIC AGENT; DENDRIMER; METHOTREXATE; NANOCARRIER; POLY(PROPYLENE IMINE); POLYAMIDOAMINE; UNCLASSIFIED DRUG;

ARTICLE; BLOOD CELL COUNT; CANCER CELL CULTURE; CHEMICAL STRUCTURE; CYTOTOXICITY; DIARRHEA; DRUG ACETYLATION; DRUG DELIVERY SYSTEM; DRUG EFFICACY; DRUG ERUPTION; DRUG SYNTHESIS; ENCAPSULATION; EYE IRRITATION; FLUORESCENCE CORRELATION SPECTROSCOPY; HAIR LOSS; HUMAN; HUMAN CELL; IN VITRO STUDY; KIDNEY FAILURE; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; SUSTAINED DRUG RELEASE;

ACETYLATION; ANTINEOPLASTIC AGENTS; CELL DEATH; CELL LINE, TUMOR; DENDRIMERS; DRUG CARRIERS; DRUG DELIVERY SYSTEMS; HUMANS; HYDROGEN-ION CONCENTRATION; MAGNETIC RESONANCE SPECTROSCOPY; METHOTREXATE;

EID: 80054081012     PISSN: 01429612     EISSN: 18785905     Source Type: Journal    
DOI: 10.1016/j.biomaterials.2011.09.016     Document Type: Article

References (62)

1. Tomalia D.A. Dendrons/dendrimers: quantized, nano-element like building blocks for soft-soft and soft-hard nano-compound synthesis. Soft Matter 2010, 6:456-474.
2. Fréchet J.M.J. Dendrimers and supramolecular chemistry. Proc Natl Acad Sci USA 2002, 99:4782-4787.
3. Gillies E.R., Fréchet J.M.J. Dendrimers and dendritic polymers in drug delivery. Drug Discov Today 2005, 10:35-43.
4. Caminade A.M., Laurent R., Majoral J.P. Characterization of dendrimers. Adv Drug Deliv Rev 2005, 57:2130-2146.
5. Cheng Y.Y., Zhao L.B., Li Y.W., Xu T.W. Design of biocompatible dendrimers for cancer diagnosis and therapy: current status and future perspectives. Chem Soc Rev 2011, 40:2673-2703.
6. Mintzer M.A., Grinstaff M.W. Biomedical applications of dendrimers: a tutorial. Chem Soc Rev 2011, 40:173-190.
7. Helms B., Meijer E.W. Dendrimers at work. Science 2005, 313:929-930.
8. Wang Y., Guo R., Cao X., Shen M., Shi X.Y. Encapsulation of 2-methoxyestradiol within multifunctional poly(amidoamine) dendrimers for targeted cancer therapy. Biomaterials 2011, 32:3322-3329.
9. Villaraza A.J., Bumb A., Brechbiel M.W. Macromolecules, dendrimers, and nanomaterials in magnetic resonance imaging: the interplay between size, function, and pharmacokinetics. Chem Rev 2010, 110:2921-2959.
10. Menjoge A.R., Kannan R.M., Tomalia D.A. Dendrimer-based drug and imaging conjugates: design considerations for nanomedical applications. Drug Discov Today 2010, 15:171-185.
11. Caminade A.M., Majoral J.P. Dendrimers and nanotubes: a fruitful association. Chem Soc Rev 2010, 39:2034-2047.
12. Spataro G., Malecaze F., Turrin C.O., Soler V., Duhayon C., Elena P.P., et al. Designing dendrimers for ocular drug delivery. Eur J Med Chem 2010, 45:326-334.
13. Tekade R.K., Kumar P.V., Jain N.K. Dendrimers in oncology: an expanding horizon. Chem Rev 2009, 109:49-87.
14. Svenson S. Dendrimers as versatile platform in drug delivery applications. Eur J Pharm Biopharm 2009, 71:445-462.
15. Lee C.C., Mackay J.A., Fréchet J.M.J., Szoka F.C. Designing dendrimers for biological applications. Nat Biotechnol 2005, 23:1517-1526.
16. van der Poll D.G., Kieler-Ferguson H.M., Floyd W.C., Guillaudeu S.J., Jerger K., Szoka F.C., et al. Design, synthesis, and biological evaluation of a robust, biodegradable dendrimer. Bioconjug Chem 2010, 21:764-773.
17. Almutairi A., Rossin R., Shokeen M., Hagooly A., Ananth A., Capoccia B., et al. Biodegradable dendritic positron-emitting nanoprobes for the noninvasive imaging of angiogenesis. Proc Natl Acad Sci USA 2009, 106:685-690.
18. Guillaudeu S.J., Fox M.E., Haidar Y.M., Dy E.E., Szoka F.C., Fréchet J.M.J. PEGylated dendrimers with core functionality for biological applications. Bioconjug Chem 2008, 19:461-469.
19. Almutairi A., Guillaudeu S.J., Berezin M.Y., Achilefu S., Fréchet J.M.J. Biodegradable pH-sensing dendritic nanoprobes for near-infrared fluorescence lifetime and intensity imaging. J Am Chem Soc 2008, 130:444-445.
20. Mynar J.L., Lowery T.J., Wemmer D.E., Pines A., Fréchet J.M.J. Xenon biosensor amplification via dendrimer-cage supramolecular constructs. J Am Chem Soc 2007, 128:6334-6335.
21. Gillies E.R., Dy E., Fréchet J.M.J., Szoka F.C. Biological evaluation of polyester dendrimer: poly(ethylene oxide) "bow-tie" hybrid with tunable molecular weight and architecture. Mol Pharm 2005, 2:129-138.
22. Gillies E.R., Fréchet J.M.J. Designing macromolecules for therapeutic applications: polyester dendrimer poly(ethylene oxide) "bow-tie" hybrids with tunable molecular weight and architecture. J Am Chem Soc 2002, 124:14137-14146.
23. Gillies E.R., Jonsson T.B., Fréchet J.M.J. Stimuli-responsive supramolecular assemblies of linear-dendritic copolymers. J Am Chem Soc 2004, 126:11936-11943.
24. D'Emanuele A., Attwood D. Dendrimer-drug interactions. Adv Drug Deliv Rev 2005, 57:2147-2162.
25. Boisselier E., Liang L., Dalko-Csiba M., Ruiz J., Astruc D. Interactions and encapsulation of vitamins C, B3, and B6 with dendrimers in Water. Chem Eur J 2010, 16:6056-6068.
26. Jain K., Kesharwani P., Gupta U., Jain N.K. Dendrimer toxicity: let's meet the challenge. Int J Pharm 2010, 394:122-142.
27. Duncan R., Izzo L. Dendrimer biocompatibility and toxicity. Adv Drug Deliv Rev 2005, 57:2215-2237.
28. Smith P.E.S., Brender J.R., Ulrich H., Durr N., Xu J.D., Mullen D.G., et al. Solid-state NMR reveals the hydrophobic-core location of poly (amidoamine) dendrimers in biomembranes. J Am Chem Soc 2010, 132:8087-8097.
29. Dufes C., Uchegbu I.F., Schatzlein A.G. Dendrimers in gene delivery. Adv Drug Deliv Rev 2005, 57:2177-2202.
30. Kim Y., Klutz A.M., Jacobson K.A. Systematic investigation of polyamidoamine dendrimers surface-modified with poly(ethylene glycol) for drug delivery applications: synthesis, characterization, and evaluation of cytotoxicity. Bioconjug Chem 2008, 19:1660-1672.
31. Stasko N.A., Johnson B., Schoenfisch M.H., Johnson T.A., Holmuhamedov E.L. Cytotoxicity of polypropylenimine dendrimer conjugates on cultured endothelial cells. Biomacromolecules 2007, 8:3853-3859.
32. Kolhatkar R.B., Kitchens K.M., Swaan P.W., Ghandehari H. Surface acetylation of polyamidoamine (PAMAM) dendrimers decreases cytotoxicity while maintaining membrane permeability. Bioconjug Chem 2007, 18:2054-2060.
33. Majoros I.J., Keszler B., Woehler S., Bull T., Baker J.R. Acetylation of poly(amidoamine) dendrimers. Macromolecules 2003, 36:5526-5529.
34. Wang H., Zheng L., Peng C., Guo R., Shen M., Shi X.Y., et al. Computed tomography imaging of cancer cells using acetylated dendrimer-entrapped gold nanoparticles. Biomaterials 2011, 32:2979-2988.
35. Shi X.Y., Bi X.D., Ganser T.R., Hong S., Myc L.A., Desai A., et al. HPLC analysis of functionalized poly(amidoamine) dendrimers and the interaction between a folate-dendrimer conjugate and folate binding protein. Analyst 2006, 131:842-848.
36. Cheng Y.Y., Wu Q.L., Li Y.W., Xu T.W. External electrostatic interaction versus internal encapsulation between cationic dendrimers and negatively charged drugs: which contributes more to solubility enhancement of the drugs?. J Phys Chem B 2008, 112:8884-8890.
37. Cheng Y.Y., Li Y.W., Wu Q.L., Zhang J.H., Xu T.W. Generation-dependent encapsulation/electrostatic attachment of phenobarbital molecules by poly(amidoamine) dendrimers: evidence from 2D-NOESY investigations. Eur J Med Chem 2009, 44:2219-2223.
38. 1H NMR, diffusion, and NOE analysis. J Phys Chem B 2010, 114:7265-7273.
39. Yang K., Weng L., Cheng Y.Y., Zhang H.F., Zhang J.H., Wu Q.L., et al. Host-guest chemistry of dendrimer-drug complexes. 6. Fully acetylated dendrimers as biocompatible drug vehicles using dexamethasone 21- phosphate as a model drug. J Phys Chem B 2011, 115:2185-2195.
40. Taratula O., Garbuzenko O.B., Kirkpatrick P., Pandya I., Savla R., Pozharov V.P., et al. Surface-engineered targeted PPI dendrimer for efficient intracellular and intratumoral siRNA delivery. J Control Release 2009, 140:284-293.
41. Patil M.L., Zhang M., Taratula O., Garbuzenko O.B., He H.X., Minko T. Internally cationic polyamidoamine PAMAM-OH dendrimers for siRNA delivery: effect of the degree of quaternization and cancer targeting. Biomacromolecules 2009, 10:258-266.
42. Patil M.L., Zhang M., Betigeri S., Taratula O., He H.X., Minko T. Surface-modified and internally cationic polyamidoamine dendrimers for efficient siRNA delivery. Bioconjug Chem 2008, 19:1396-1403.
43. Housni A., Zhao Y. Gold nanoparticles functionalized with block copolymers displaying either LCST or UCST thermosensitivity in aqueous solution. Langmuir 2010, 26:12933-12939.
44. Hu J.J., Cheng Y.Y., Ma Y.R., Wu Q.L., Xu T.W. Host-guest chemistry and physicochemical properties of the dendrimer-mycophenolic acid complex. J Phys Chem B 2009, 113:64-74.
45. Yang W.J., Cheng Y.Y., Xu T.W., Wang X.Y., Wen L.P. Targeting cancer cells with biotin-dendrimer conjugates. Eur J Med Chem 2008, 44:862-868.
46. Majoros I.J., Myc A., Thomas T., Mehta C.B., Baker J.R. PAMAM dendrimer-based multifunctional conjugate for cancer therapy: synthesis, characterization, and functionality. Biomacromolecules 2006, 7:572-579.
47. Majoros I.J., Thomas T.P., Mehta C.B., Baker J.R. Poly(amidoamine) dendrimer-based multifunctional engineered nanodevice for cancer therapy. J Med Chem 2005, 48:5892-5899.
48. Thomas T.P., Majoros I.J., Kotlyar A., Kukowska-Latallo J.F., Bielinska A., Myc A., et al. Targeting and inhibition of cell growth by an engineered dendritic nanodevice. J Med Chem 2005, 48:3729-3735.
49. Thomas T.P., Majoros I.J., Kotlyar A., Mullen D., Holl M.M.B., Baker J.R. Cationic poly(amidoamine) dendrimer induces lysosomal apoptotic pathway at therapeutically relevant concentrations. Biomacromolecules 2009, 10:3207-3214.
50. Weaver J.V.M., Armes S.P., Butun V. Synthesis and aqueous solution properties of a well-defined thermo-responsive schizophrenic diblock copolymer. Chem Comm 2002, 2122-2133.
51. Wu Q.L., Cheng Y.Y., Hu J.J., Zhao L.B., Xu T.W. Insights into the interactions between dendrimers and bioactive surfactants: 3. Size-dependent and hydrophobic property-dependent encapsulation of bile salts. J Phys Chem B 2009, 113:12934-12943.
52. Zhao L.B., Wu Q.L., Cheng Y.Y., Zhang J.H., Wu J.H., Xu T.W. High-throughput screening of dendrimer-binding drugs. J Am Chem Soc 2010, 132:13182-13184.
53. Chai M.H., Niu Y.H., Youngs W.J., Rinaldi P.L. 3D NMR studies of DAB-16 dendrimer. Macromolecules 2000, 33:5395-5398.
54. Chai M.H., Niu Y.H., Youngs W.J., Rinaldi P.L. Structure and conformation of DAB dendrimers in solution via multidimensional NMR techniques. J Am Chem Soc 2001, 123:4670-4678.
55. Chai M.H., Holley A.K., Kruskamp M. Encapsulating fluorescein using adipic acid self-assembly on the surface of PPI-3 dendrimer. Chem Commun 2007, 168-170.
56. Yang W.J., Li Y.W., Cheng Y.Y., Wu Q.L., Wen L.P., Xu T.W. Evaluation of phenylbutazone and poly(amidoamine) dendrimers interactions by a combination of solubility, 2D-NOESY NMR, and isothermal titration calorimetry studies. J Pharm Sci 2009, 98:1075-1085.
57. Cheng Y.Y., Wu Q.L., Li Y.W., Hu J.J., Xu T.W. New insights into the interactions between dendrimers and surfactants: 2. Design of new drug formulations based on dendrimer-surfactant aggregates. J Phys Chem B 2009, 113:8339-8346.
58. Zhao L.B., Cheng Y.Y., Hu J.J., Wu Q.L., Xu T.W. Host-guest chemistry of dendrimer-drug complexes. 3. Competitive binding of multiple drugs by a single dendrimer for combination therapy. J Phys Chem B 2009, 113:14172-14179.
59. Kojima C., Kono K., Maruyama K., Takagishi T. Synthesis of polyamidoamine dendrimers having poly(ethylene glycol) grafts and their ability to encapsulate anticancer drugs. Bioconjug Chem 2000, 11:910-917.
60. Dhanikula R.S., Hildgen P. Influence of molecular architecture of polyether-co-polyester dendrimers on the encapsulation and release of methotrexate. Biomaterials 2007, 28:3140-3152.
61. Liu J.Y., Pang Y., Huang W., Zhu X.Y., Zhou Y.F., Yan D.Y. Self-assembly of phospholipid- analogous hyperbranched polymers nanomicelles for drug delivery. Biomaterials 2010, 31:1334-1341.
62. Lee C.C., Gillies E.R., Fox M.E., Guillaudeu S.J., Fréchet J.M.J., Dy E.E., et al. A single dose of doxorubicin-functionalized bow-tie dendrimer cures mice bearing C-26 colon carcinomas. Proc Natl Acad Sci USA 2006, 103:16649-16654.