Multifunctional lactobionic acid-modified dendrimers for targeted drug delivery to liver cancer cells: Investigating the role played by PEG spacer

ACS Applied Materials and Interfaces

Volumn 6, Issue 18, 2014, Pages 16416-16425

  Fu, Fanfan ^a   Wu, Yilun ^a   Zhu, Jingyi ^a   Wen, Shihui ^a   Shen, Mingwu ^a   Shi, Xiangyang ^a,b  

^a DONGHUA UNIVERSITY   (China)

^b UNIVERSITY OF MADEIRA   (Portugal)

Author keywords

Doxorubicin; Lactobionic acid; PAMAM dendrimers; PEG spacer; Targeted cancer therapy

Indexed keywords

ACETYLATION; AMINES; CELLS; CONTROLLED DRUG DELIVERY; CYTOLOGY; DENDRIMERS; DISEASES; FUNCTIONAL POLYMERS; ONCOLOGY; SHIMS;

DOXORUBICIN; LACTOBIONIC ACID; PAMAM DENDRIMER; PEG SPACERS; TARGETED CANCER THERAPY;

TARGETED DRUG DELIVERY;

ANTINEOPLASTIC AGENT; DENDRIMER; DISACCHARIDE; DOXORUBICIN; DRUG CARRIER; LACTOBIONIC ACID; MACROGOL DERIVATIVE; PAMAM STARBURST;

CELL SURVIVAL; CHEMISTRY; DRUG EFFECTS; HEPG2 CELL LINE; HUMAN; LIVER TUMOR;

ANTINEOPLASTIC AGENTS; CELL SURVIVAL; DENDRIMERS; DISACCHARIDES; DOXORUBICIN; DRUG CARRIERS; HEP G2 CELLS; HUMANS; LIVER NEOPLASMS; POLYETHYLENE GLYCOLS;

EID: 84912017642     PISSN: 19448244     EISSN: 19448252     Source Type: Journal    
DOI: 10.1021/am504849x     Document Type: Article

References (50)

1. Siegel, R.; Naishadham, D.; Jemal, A. Cancer Statistics, 2012. CACancer J. Clin. 2012, 62, 10-29.
2. Peer, D.; Karp, J. M.; Hong, S.; Farokhzad, O. C.; Margalit, R.; Langer, R. Nanocarriers as an Emerging Platform for Cancer Therapy. Nat. Nanotechnol. 2007, 2, 751-760.
3. Wang, Y.; Guo, R.; Cao, X.; Shen, M.; Shi, X. Encapsulation of 2-Methoxyestradiol within Multifunctional Poly(amidoamine) Dendrimers for Targeted Cancer Therapy. Biomaterials 2011, 32, 3322-3329.
4. Maeda, H.; Bharate, G. Y.; Daruwalla, J. Polymeric Drugs for Efficient Tumor-Targeted Drug Delivery Based on EPR-Effect. Eur. J. Pharm. Biopharm. 2009, 71, 409-419.
5. Malam, Y.; Loizidou, M.; Seifalian, A. M. Liposomes and Nanoparticles: Nanosized Vehicles for Drug Delivery in Cancer. Trends Pharmacol. Sci. 2009, 30, 592-599.
6. Prakash, S.; Malhotra, M.; Shao, W.; Tomaro-Duchesneau, C.; Abbasi, S. Polymeric Nanohybrids and Functionalized Carbon Nanotubes as Drug Delivery Carriers for Cancer Therapy. Adv. Drug Delivery Rev. 2011, 63, 1340-1351.
7. Adair, J. H.; Parette, M. P.; Altinoʇlu, E. I.; Kester, M. Nanoparticulate Alternatives for Drug Delivery. ACS Nano 2010, 4, 4967-4970.
8. Farokhzad, O. C.; Langer, R. Impact of Nanotechnology on Drug Delivery. ACS Nano 2009, 3, 16-20.
9. Hammond, P. T. Virtual Issue on Nanomaterials for Drug Delivery. ACS Nano 2011, 5, 681-684.
10. Shi, J.; Votruba, A. R.; Farokhzad, O. C.; Langer, R. Nanotechnology in Drug Delivery and Tissue Engineering: From Discovery to Applications. Nano Lett. 2010, 10, 3223-3230.
11. Lee, C. C.; Gillies, E. R.; Fox, M. E.; Guillaudeu, S. J.; Fréchet, J. M.; Dy, E. E.; Szoka, F. C. A Single Dose of Doxorubicin-Functionalized Bow-Tie Dendrimer Cures Mice Bearing C-26 Colon Carcinomas. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 16649-16654.
12. Zheng, L.; Zhu, J.; Shen, M.; Chen, X.; Baker, J. R., Jr.; Wang, S. H.; Zhang, G.; Shi, X. Targeted Cancer Cell Inhibition Using Multifunctional Dendrimer-Entrapped Gold Nanoparticles. Med. Chem. Commun. 2013, 4, 1001-1005.
13. Zheng, Y.; Fu, F.; Zhang, M.; Shen, M.; Zhu, M.; Shi, X. Multifunctional Dendrimers Modified With Alpha-Tocopheryl Succinate for Targeted Cancer Therapy. Med. Chem. Commun. 2014, 5, 879-885.
14. Zhu, J.; Shi, X. Dendrimer-Based Nanodevices for Targeted Drug Delivery Applications. J. Mater. Chem. 2013, 1, 4199-4211.
15. Zhu, J.; Zheng, L.; Wen, S.; Tang, Y.; Shen, M.; Zhang, G.; Shi, X. Targeted Cancer Theranostics Using Alpha-Tocopheryl Succinate-Conjugated Multifunctional Dendrimer-Entrapped Gold Nanoparticles. Biomaterials 2014, 35, 7635-7646.
16. Shi, X.; Lee, I.; Chen, X.; Shen, M.; Xiao, S.; Zhu, M.; Baker, J. R.; Wang, S. H. Influence of Dendrimer Surface Charge on the Bioactivity of 2-Methoxyestradiol Complexed with Dendrimers. Soft Matter 2010, 6, 2539-2545.
17. Wang, Y.; Cao, X.; Guo, R.; Shen, M.; Zhang, M.; Zhu, M.; Shi, X. Targeted Delivery of Doxorubicin into Cancer Cells Using a Folic Acid-Dendrimer Conjugate. Polym. Chem. 2011, 2, 1754-1760.
18. Zhang, M.; Guo, R.; Wang, Y.; Cao, X.; Shen, M.; Shi, X. Multifunctional Dendrimer/Combretastatin A4 Inclusion Complexes Enable in Vitro Targeted Cancer Therapy. Int. J. Nanomed. 2011, 6, 2337-2349.
19. Zhang, M.; Guo, R.; Kéri, M.; Bányai, I.; Zheng, Y.; Cao, M.; Cao, X.; Shi, X. Impact of Dendrimer Surface Functional Groups on the Release of Doxorubicin from Dendrimer Carriers. J. Phys. Chem. B 2014, 118, 1696-1706.
20. Liu, W.; Wen, S.; Jiang, L.; An, X.; Zhang, M.; Wang, H.; Zhang, Z.; Zhang, G.; Shi, X. PLGA Hollow Microbubbles Loaded with Iron Oxide Nanoparticles and Doxorubicin for Dual-mode US/MR Imaging and Drug Delivery. Curr. Nanosci. 2014, 10, 543-552.
21. Liu, W.; Wen, S.; Shen, M.; Shi, X. Doxorubicin-Loaded Poly(lactic-co-glycolic acid) Hollow Microcapsules for Targeted Drug Delivery to Cancer Cells. New J. Chem. 2014, 38, 3917-3924.
22. Farokhzad, O. C.; Cheng, J. J.; Teply, B. A.; Sherifi, I.; Jon, S.; Kantoff, P. W.; Richie, J. P.; Langer, R. Targeted Nanoparticle-Aptamer Bioconjugates for Cancer Chemotherapy in Vivo. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 6315-6320.
23. Niu, C.; Wang, Z.; Lu, G.; Krupka, T. M.; Sun, Y.; You, Y.; Song, W.; Ran, H.; Li, P.; Zheng, Y. Doxorubicin Loaded Superparamagnetic PLGA-Iron Oxide Multifunctional Microbubbles for Dual-Mode US/ MR Imaging and Therapy of Metastasis in Lymph Nodes. Biomaterials 2013, 34, 2307-2317.
24. Cheng, J.; Teply, B. A.; Sherifi, I.; Sung, J.; Luther, G.; Gu, F. X.; Levy-Nissenbaum, E.; Radovic-Moreno, A. F.; Langer, R.; Farokhzad, O. C. Formulation of Functionalized PLGA-PEG Nanoparticles for in Vivo Targeted Drug Delivery. Biomaterials 2007, 28, 869-876.
25. Díaz, A.; Saxena, V.; González, J.; David, A.; Casañas, B.; Carpenter, C.; Batteas, J. D.; Colón, J. L.; Clearfield, A.; Hussain, M. D. Zirconium Phosphate Nano-Platelets: A Novel Platform for Drug Delivery in Cancer Therapy. Chem. Commun. 2012, 48, 1754-1756.
26. Wang, S.; Wu, Y.; Guo, R.; Huang, Y.; Wen, S.; Shen, M.; Wang, J.; Shi, X. Laponite Nanodisks as an Efficient Platform for Doxorubicin Delivery to Cancer Cells. Langmuir 2013, 29, 5030-5036.
27. Liu, Z.; Fan, A. C.; Rakhra, K.; Sherlock, S.; Goodwin, A.; Chen, X.; Yang, Q.; Felsher, D. W.; Dai, H. Supramolecular Stacking of Doxorubicin on Carbon Nanotubes for in Vivo Cancer Therapy. Angew. Chem., Int. Ed. 2009, 48, 7668-7672.
28. Wen, S.; Liu, H.; Cai, H.; Shen, M.; Shi, X. Targeted and pHResponsive Delivery of Doxorubicin to Cancer Cells Using Multi-functional Dendrimer-Modified Multi-Walled Carbon Nanotubes. Adv. Healthcare Mater. 2013, 2, 1267-1276.
29. Perche, F.; Patel, N. R.; Torchilin, V. P. Accumulation and Toxicity of Antibody-Targeted Doxorubicin-Loaded PEG-PE Micelles in Ovarian Cancer Cell Spheroid Model. J. Controlled Release 2012, 164, 95-102.
30. Mohan, P.; Rapoport, N. Doxorubicin as a Molecular Nanotheranostic Agent: Effect of Doxorubicin Encapsulation in Micelles or Nanoemulsions on the Ultrasound-Mediated Intracellular Delivery and Nuclear Trafficking. Mol. Pharmaceutics 2010, 7, 1959-1973.
31. Szebeni, J.; Bedǒcs, P.; Urbanics, R.; Bünger, R.; Rosivall, L.; Tóth, M.; Barenholz, Y. Prevention of Infusion Reactions to Pegylated Liposomal Doxorubicin via Tachyphylaxis Induction by Placebo Vesicles: A Porcine Model. J. Controlled Release 2012, 160, 382-387.
32. Tomalia, D. A.; Naylor, A. M.; Goddard, W. A. Starburst Dendrimers: Molecular-Level Control of Size, Shape, Surface Chemistry, Topology, and Flexibility from Atoms to Macroscopic Matter. Angew. Chem., Int. Ed. 1990, 29, 138-175.
33. Esfand, R.; Tomalia, D. A. Poly(amidoamine) (PAMAM) Dendrimers: From Biomimicry to Drug Delivery and Biomedical Applications. Drug Discovery Today 2001, 6, 427-436.
34. Kukowska-Latallo, J. F.; Candido, K. A.; Cao, Z.; Nigavekar, S. S.; Majoros, I. J.; Thomas, T. P.; Balogh, L. P.; Khan, M. K.; Baker, J. R. Nanoparticle Targeting of Anticancer Drug Improves Therapeutic Response in Animal Model of Human Epithelial Cancer. Cancer Res. 2005, 65, 5317-5324.
35. 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.
36. 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.
37. Medina, S. H.; Tekumalla, V.; Chevliakov, M. V.; Shewach, D. S.; Ensminger, W. D.; El-Sayed, M. E. N-Acetylgalactosamine-Functionalized Dendrimers as Hepatic Cancer Cell-Targeted Carriers. Biomaterials 2011, 32, 4118-4129.
38. Thomas, T. P.; Majoros, I. J.; Kotlyar, A.; Kukowska-Latallo, J. F.; Bielinska, A.; Myc, A.; Baker, J. R. Targeting and Inhibition of Cell Growth by an Engineered Dendritic Nanodevice. J. Med. Chem. 2005, 48, 3729-3735.
39. Dhanikula, R. S.; Argaw, A.; Bouchard, J.-F.; Hildgen, P. Methotrexate Loaded Polyether-Copolyester Dendrimers for the Treatment of Gliomas: Enhanced Efficacy and Intratumoral Transport Capability. Mol. Pharmaceutics 2008, 5, 105-116.
40. Morgan, M. T.; Nakanishi, Y.; Kroll, D. J.; Griset, A. P.; Carnahan, M. A.; Wathier, M.; Oberlies, N. H.; Manikumar, G.; Wani, M. C.; Grinstaff, M. W. Dendrimer-Encapsulated Camptothecins: Increased Solubility, Cellular Uptake, and Cellular Retention Affords Enhanced Anticancer Activity in Vitro. Cancer Res. 2006, 66, 11913-11921.
41. Kojima, C.; Kono, K.; Maruyama, K.; Takagishi, T. Synthesis of Polyamidoamine Dendrimers Having Poly (ethylene glycol) Grafts and Their Ability to Encapsulate Anticancer Drugs. Bioconjugate Chem. 2000, 11, 910-917.
42. Morgan, M. T.; Carnahan, M. A.; Immoos, C. E.; Ribeiro, A. A.; Finkelstein, S.; Lee, S. J.; Grinstaff, M. W. Dendritic Molecular Capsules for Hydrophobic Compounds. J. Am. Chem. Soc. 2003, 125, 15485-15489.
43. Wen, S.; Li, K.; Cai, H.; Chen, Q.; Shen, M.; Huang, Y.; Peng, C.; Hou, W.; Zhu, M.; Zhang, G.; Shi, X. Multifunctional Dendrimer-Entrapped Gold Nanoparticles for Dual Mode CT/MR Imaging Applications. Biomaterials 2013, 34, 1570-1580.
44. Peng, C.; Zheng, L.; Chen, Q.; Shen, M.; Guo, R.; Wang, H.; Cao, X.; Zhang, G.; Shi, X. PEGylated Dendrimer-Entrapped Gold Nanoparticles for in Vivo Blood Pool and Tumor Imaging by Computed Tomography. Biomaterials 2012, 33, 1107-1119.
45. Chen, Q.; Li, K.; Wen, S.; Liu, H.; Peng, C.; Cai, H.; Shen, M.; Zhang, G.; Shi, X. Targeted CT/MR Dual Mode Imaging of Tumors Using Multifunctional Dendrimer-Entrapped Gold Nanoparticles. Biomaterials 2013, 34, 5200-5209.
46. Liu, H.; Wang, H.; Xu, Y.; Shen, M.; Zhao, J.; Zhang, G.; Shi, X. Synthesis of PEGylated Low Generation Dendrimer-Entrapped Gold Nanoparticles for CT Imaging Applications. Nanoscale 2014, 6, 4521-4526.
47. Zhang, Y.; Sun, Y.; Xu, X.; Zhang, X.; Zhu, H.; Huang, L.; Qi, Y.; Shen, Y.-M. Synthesis, Biodistribution, and Microsingle Photon Emission Computed Tomography (SPECT) Imaging Study of Technetium-99m Labeled PEGylated Dendrimer Poly(amidoamine) (PAMAM)-Folic Acid Conjugates. J. Med. Chem. 2010, 53, 3262-3272.
48. Guo, R.; Yao, Y.; Cheng, G.; Wang, S. H.; Li, Y.; Shen, M.; Zhang, Y.; Baker, J. R.; Wang, J.; Shi, X. Synthesis of Glycoconjugated Poly (amindoamine) Dendrimers for Targeting Human Liver Cancer Cells. RSC Adv. 2012, 2, 99-102.
49. Liu, H.; Wang, H.; Xu, Y.; Guo, R.; Wen, S.; Huang, Y.; Liu, W.; Shen, M.; Zhao, J.; Zhang, G.; Shi, X. Lactobionic Acid-Modified Dendrimer-Entrapped Gold Nanoparticles for Targeted CT Imaging of Human Hepatocellular Carcinoma. ACS Appl. Mater. Interfaces 2014, 6, 6944-6953.
50. Liao, H.; Liu, H.; Li, Y.; Zhang, M.; Tomás, H.; Shen, M.; Shi, X. Antitumor Efficacy of Doxorubicin Encapsulated within PEGylated Poly(amidoamine) Dendrimers. J. Appl. Polym. Sci. 2014, 131, 40358.