Targeting and inhibition of cell growth by an engineered dendritic nanodevice

Journal of Medicinal Chemistry

Volumn 48, Issue 11, 2005, Pages 3729-3735

  Thomas, Thommey P ^a   Majoros, Istvan J ^a   Kotlyar, Alina ^a   Kukowska Latallo, Jolanta F ^a   Bielinska, Anna ^a   Myc, Andrzej ^a   Baker Jr , James R ^a  

^a UNIVERSITY OF MICHIGAN MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; DENDRIMER; ESTER; FLUORESCEIN; FOLATE RECEPTOR; FOLIC ACID; METHOTREXATE; NANOPARTICLE; POLYAMIDOAMINE; THIOUREA; UNCLASSIFIED DRUG;

ARTICLE; BIOENGINEERING; CANCER INHIBITION; CELL GROWTH; CELL STRAIN KB; CONFOCAL MICROSCOPY; CONJUGATION; CONTROLLED STUDY; CROSS LINKING; DEVICE; DOSE RESPONSE; DRUG CYTOTOXICITY; DRUG DELIVERY SYSTEM; DRUG TARGETING; DRUG UPTAKE; GENE OVEREXPRESSION; GROWTH INHIBITION; HUMAN; HUMAN CELL; IN VITRO STUDY; INTERNALIZATION;

ANTINEOPLASTIC AGENTS; CELL PROLIFERATION; DRUG CARRIERS; DRUG DELIVERY SYSTEMS; FLUORESCEIN-5-ISOTHIOCYANATE; FLUORESCENT DYES; FOLIC ACID; HUMANS; KB CELLS; METHOTREXATE; NANOSTRUCTURES; POLYAMINES;

EID: 20144380223     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm040187v     Document Type: Article

References (54)

1. Moghimi, S. M.; Hunter, A. C.; Murray, J. C. Long-circulating and target-specific nanoparticles: Theory to practice. Pharm. Rev. 2001, 53, 283-318.
2. Brigger, I.; Dubernet, C.; Couvreur, P. Nanoparticles in cancer therapy and diagnosis. Adv. Drug Delivery Rev. 2002, 54, 631-651.
3. Luo, Y.; Prestwich, G. D. Cancer-targeted polymeric drugs. Curr. Cancer Drug Targets 2002, 2, 209-226.
4. Jensen, K. D.; Nori, A.; Tijerina, M.; Kopeckova, P.; Kopecek, J. Cytoplasmic delivery and nuclear targeting of synthetic macromolecules. J. Controlled Release 2003, 87, 89-105.
5. Majoros, I. J.; Thomas, T. P.; Baker, J. R., Jr. Molecular engineering in Nanotechnology: Engineered Drug Delivery. In Handbook of Theoretical and Computational Nanotechnology; Rieth, M., Schommers, W., Eds.; in press.
6. Ulbrich, K.; Sur, V.; Stohalm, J.; Plocova, D.; Jelinkova, M.; Rihova, B. Polymeric drugs based on conjugates of synthetic and natural macromolecules. 1. Synthesis and physicochemical characterization. J. Controlled Release 2000, 64, 63-79.
7. Thanou, M.; Duncan, R. Polymer-protein and polymer-drug conjugates in cancer therapy. Curr. Opin. Invest. Drugs 2003, 4, 701-709.
8. Tomalia, D. A.; Taylor, A. M.; Goddard, W. A., III. Starburst dendrimers: Control of size, shape, surface chemistry, topology. Angnew Chem. Int. Ed. Engl. 1990, 102, 119-157.
9. Esfand, R.; Tomalia, D. A. Polyamidoamine (PAMAM) dendrimers: From biomimicry to drug delivery and biomedical application. Drug Discovery Today 2001, 6, 427-436.
10. Stiribara, S. E.; Frey, H.; Haag, R. Dendritic polymers in biomedical applications: From potential to clinical use in diagnosis and therapy. Angnew Chem. Int. Ed. 2002, 41, 1329-1334.
11. Patri, A. K.; Majoros, I. J.; Baker, J. R., Jr. Dendritic polymer macromolecular carriers for drug delivery. Current Opin. Chem. Biol. 2002, 6, 466-471.
12. Kojima, C.; Kono, K.; Maruyama, K.; Tkagishi, T. Synthesis of polyamidoamine dendrimers having poly-(ethylene glycol) grafts and their ability to encapsulate anticancer drugs. Bioconjugate Chem. 2000, 11, 910-917.
13. Bielinska, A.; J. Kukowska-Latallo, J. F.; Johnson, J.; Tomalia, D. A.; Baker, J. R., Jr. Regulation of in vitro gene expression using antisense oligonucleotides or antisense expression plasmids transfected using starburst PAMAM dendrimers. Nucleic Acid Res. 1996, 24, 2176-2182.
14. Kukowska-Latallo, J. F.; Bielinska, A.; Johnson, J.; Spindler, R.; Tomalia, D. A.; Baker, J. R., Jr. Efficient transfer of genetic material into mammalian cells using Starburst polyamidoamine dendrimers. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 4897-4902.
15. Kobayashi, H.; Wu, C.; Kim, M. K.; Paik, C. H.; Carasquillo, J. A.; Brechbiel, M. W. Evaluation of the in vivo biodistribution of indium-111 and yttrium-88 labeled dendrimer-1B4M-DTPA and its conjugation with anti-tac monoclonal antibody. Bioconjugate Chem. 1999, 10, 103-111.
16. 153Gd-folate dendrimer, generation R, in mice with folate-receptor positive and negative ovarian tumor xenografts. Invest. Radiol. 2002, 37, 199-204.
17. Shukla, S.; Wu, G.; Chatterjee, M.; Yang, W.; Sekido, M.; Diop, L. A.; Muller, R.; Sudimack, J. J.; Lee, R. J.; Barth, R. F.; Tjarks, W. Synthesis and biological evaluation of folate receptor-targeted boronated PAMAM dendrimers as potential agents for neutron capture therapy. Bioconjugate Chem. 2003, 14, 158-167.
18. Weitman, D.; Lark, R. H.; Coney, L. R.; Fort, D. W.; Frasca, V.; Surawski, V. R.; Kamen, B. A. Distribution of the folate receptor GP38 in normal and malignant cell lines and tissues. Cancer Res. 1992, 52, 3396-3401.
19. Ross, F.; Chaudhauri, P. K.; Ratnam, M. Differential regulation of folate receptor isoforms in normal and malignant tissues in vivo and in established cell lines. Physiologic and clinical implications. Cancer 1994, 73, 2432-2443.
20. Antony, A. C. Folate receptors. Annu. Rev. Nutr. 1996, 16, 501-521.
21. Wang, H.; Zheng, X.; Behm, F.; Ratnam, M. Differentiation-independent retinoid induction of folate receptor type β, a potential tumor target in myeloid leukemia. Blood 2000, 15, 3529-3536.
22. Lu, Y.; Low, P. S. Folate-mediated delivery of macromolecular anticancer therapeutic agents. Adv. Drug. Delivery Rev. 2003, 54, 675-693.
23. Leamon, C. P.; Pastan, I.; Low, P. S. Cytotoxicity of folate-Pseudomonas exotoxin conjugates toward tumor cells. Contribution of translocation domain. J. Biol. Chem. 1993, 268, 24847-24854.
24. Gabizon, A.; Horowitz, A.; Goren, D.; Tzemach, D.; Mandelbaum-Shavit, F.; Qazen, M.; Zalipsky, S. Targeting Folate Receptor with Folate Linked to Extremities of Poly(ethylene glycol)-Grafted Liposomes: In Vitro Studies. Bioconjugate Chem. 1999, 10, 289-298.
25. Kranz, D. M.; Patrick, T. A.; Brigle, K. E.; Spinella, M. J.; Roy, E. J. Conjugates of Folate and Anti-T-Cell-Receptor Antibodies Specifically Target Folate-Receptor-Positive Tumor Cells for Lysis. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 9057-9061.
26. Goren, D.; Horowitz, A. T.; Tzemach, D.; Tarshish, M.; Zalipsky, S.; Gabizon, A. Nuclear Delivery of Doxorubicin via Folate-targeted Liposomes with Bypass of Multidrug-resistance Efflux Pump. Clin. Cancer Res. 2000, 6, 1949-1957.
27. Stella, B.; Arpicco, S.; Peracchia, M. T.; Desmaele, D.; Hoebeke, J.; Renoir, M.; d'Angelo, J.; Cattel, L.; Couvreur, P. Design of folic acid-conjugated nanoparticles for drug targeting. J. Pharm. Sci. 2000, 89, 1452-1464.
28. Ravindranath, Y. Recent advances in pediatric acute lymphoblastic and myeloid leukemia. Curr. Opin. Oncol. 2003, 15, 23-35.
29. 99mTc-Based Radiopharmaceutical. Bioconjugate Chem. 2002, 13, 1200-1210.
30. Calvert, H. Folate status and the safety proile of antifolates. Semin. Oncol. 2002, 29, 3-7.
31. Goldman, I. D.; Matherly, L. H. The cellular pharmacology of methotrexate. Pharmacol. Ther. 1985, 28, 77-102.
32. Majoros, I. J.; Thomas, T. P.; Mehta, C. B.; Baker, J. R., Jr. PAMAM dendrimer-based multif-functional engineered nano-device for cancer therapy. J. Med. Chem. 2005, in press.
33. Quintana, A.; Raczka, E.; Piehler, L.; Lee, I.; Myc, A.; Majoros, I.; Patri, A.; Thomas, T.; Mulé, J.; Baker, J. R., Jr. Design and function of a dendrimer-based therapeutic nanodevice targeted to tumor cells through the folate receptor. Pharm. Res. 2002, 19, 1310-1316.
34. Kane, M. A.; Waxman, S. Role of folate binding proteins in folate metabolism. Lab Invest. 1989, 60, 737-746.
35. Oyewumi, M. O.; Mumber, R. J. Engineereing tumor-targeted gadolinium hexanedione nanoparticles for potential application in neutron capture therapy. Bioconjugate Chem. 2002, 13, 1328-1335.
36. Sobrero, A. F.; Bertino, J. R. Endogenous thymidine and hypoxanthine are a source of error in evaluating methotrexate cytotoxicity by clonogenic assays using undialyzed fetal bovine serum. Int. J. Cell Cloning 1986, 4, 51-62.
37. Roehm, N. W. Rodgers, G.; Hatfield, S.; Glasebrook, A. An improved colorimetric assay for cell proliferation and viability utilizing the tetrazolium salt XTT. J. Immunol. Methods 1991, 142, 257-265.
38. Deutsch, J. C.; Elwood, P. C.; Portillo, R. M.; Macey, M. G.; Kolhouse, J. F. Role of the membrane-associated folate binding protein (folate receptor) in methotrexate transport by human KB cells. Arch. Biochem. Biophys. 1989, 274, 327-337.
39. Saikawa, Y.; Knight, C. B.; Saikawa, T.; Page, S. T.; Chabner, B. A.; Elwood, P. C. Decreased expression of the human folate receptor mediates transport-defective methotrexate resistance in KB cells. J. Biol. Chem. 1993, 268, 5293-5301.
40. Wang, X., Shen, F., Fresheim, J. H., Gentry, L. E.; Ratnak, M. Differential stereospecificities and affinities of folate receptor isoforms for folate compounds and antifolates. Biochem. Pharmcol. 1992, 44, 1898-1901.
41. Westerhof, G. R.; Rinjboutt, S.; Schornagel, J. H.; Pinedo, H. S.; Peters, G. J.; Jansern, G. Functional activity of the reduced folate carrier in KB, MA104, and IGROV-1 cells expressing folate-binding protein. Cancer Res. 1995, 55, 3795-3802.
42. Corona, G.; Giannini, F.; Fabris, M.; Toffoli, G.; Boiocchi, M. Role of folate receptor and reduced folate carrier in the transport of 5-methyltetrahydrofolic acid in human ovarian carcinoma cells. Int. J. Cancer 1998, 75, 125-133.
43. Sierra, E. E.; Goldman, D. Recent advances in the understanding of the mechanism of membrane transport of folates and anti-folates. Semin. Oncol. 1999, 26, 11-23.
44. Henderson, G. B. Folate-Binding Proteins. Annu. Rev. Nutr. 1990, 10, 319-335.
45. Assaraf, Y. G.; Schimke, R. T. Identification of methotrexate transport deficiency in mammalian cells using fluoresceinated methotrexate and flow cytometry. Proceed. Nat. Acad. Sci. U.S.A. 1987, 84, 7154-7158.
46. Elwood, P. C.; Kane, M. A.; Portillo, R. M.; Kolhouse, J. F. The isolation, characterization, and comparison of the membrane-associated and soluble folate-binding proteins from human KB cells. J. Biol. Chem. 1986, 261, 15416-15423.
47. Antony, A. C.; Kane, M. A.; Portillo, R. M.; Elwood, P. C.; Kolhouse, J. F. Studies of the role of a particulate folate-binding protein in the uptake of 5-methyltetrahydrofolate by cultured human KB cells. J. Biol. Chem. 1985, 260, 14911-14917.
48. Levasseur, L. M.; Slocum, H. K.; Rustum, Y. M.; Greco, W. R.; Modeling of the time-dependency of in vitro drug cytotoxicity and resistance. Cancer Res. 1998, 58, 5749-5761.
49. Zhao, R.; Seither, R.; Brigle, K. E.; Sharina, I. G.; Wag, P. J.; Goldman, D. I. Impact of overexpression of the reduced folate carrier (RFC1), an anion exchanger, on concentrative transport in murine L1210 cells. Am. Soc. Biochem. Mol. Biol. 1997, 272, 21207-21212.
50. White, J. C.; Goldman, I. D. Methotrexate resistance in an L1210 cell line resulting from increased dihydrofolate reductase, decreased thymidylate synthetase activity, and normal membrane transport. Computer simulations based on network thermodynamics. J. Biol. Chem. 1981, 256, 5722-5727.
51. Kamen, B. A.; Wang, M.; Streckfuss, A. J.; Peryea, X.; Anderson, R. G. Delivery of folates to the cytoplasm of MA104 cells is mediated by a surface membrane receptor that recycles. J. Biol. Chem. 1988, 263, 13602-13609.
52. Westerhof, G. R.; Schoranagel, J. H.; Rijnboutt, S.; Pinedo, H. M.; Janser, G. Identification of a reduced folate/methotrexate carrier in human Kb cells expressing high levels of membrane associated folate binding protein. In Chemistry and Biology of Pteridines and Folates. Aying, J. E., et al., Eds.; Plenum Press: New York, 1993; pp 771-774.
53. Gorlick, R.; Goker, E.; Trippett, T.; Steinherz, P.; Elisseyeff, Y.; Mazumdar, M.; Flintoff, W. F.; Bertino, J. R. Defective transport is a common mechanism of acquired methotrexate resistance in acute lymphoblastic leukemia and is associated with decreased reduced folate carrier expression. Blood 1997, 89, 1013-1018.
54. Liani, E.; Rothem, L.; Bunni, M. A.; Smith, C. A.; Jansen, G.; Assaraf, Y. G. Loss of folylpoly-gamma-glutamate synthetase activity is a dominant mechanism of resistance to polyglutamylation-dependent novel antifolates in multiple human leukemia sublines. Int. J. Cancer 2003, 103, 587-599.