Partly PEGylated polyamidoamine dendrimer for tumor-selective targeting of doxorubicin: The effects of PEGylation degree and drug conjugation style

Biomaterials

Volumn 31, Issue 6, 2010, Pages 1360-1371

  Zhu, Saijie ^a   Hong, Minghuang ^a   Tang, Guotao ^a   Qian, Lili ^a   Lin, Jiayuan ^a   Jiang, Yanyan ^a   Pei, Yuanying ^a  

^a FUDAN UNIVERSITY   (China)

Author keywords

Acid sensitive linkage; Antitumor activity; Doxorubicin; Poly(amidoamine) dendrimer; Poly(ethylene glycol)

Indexed keywords

ANTI-TUMOR ACTIVITIES; ANTICANCER DRUG; B16 MELANOMA; CELLULAR UPTAKE; CIRCULATION TIME; CONCENTRATION OF; CONFOCAL LASER SCANNING MICROSCOPY; CYTOTOXIC; DOXORUBICIN; IN-VITRO; PEGYLATION; PH CONDITION; PHARMACOKINETIC AND BIODISTRIBUTION STUDIES; POLYAMIDOAMINE DENDRIMERS; POLYMERIC CARRIERS; SOLID TUMORS; TUMOR ACCUMULATION;

CONFOCAL MICROSCOPY; DENDRIMERS; ETHYLENE; ETHYLENE GLYCOL; POLYETHYLENE GLYCOLS; POLYETHYLENE OXIDES; TUMORS;

ACIDS;

DENDRIMER; DOXORUBICIN; DRUG CARRIER; MACROGOL; POLYAMIDOAMINE;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; AREA UNDER THE CURVE; ARTICLE; CONFOCAL LASER MICROSCOPY; CONTROLLED STUDY; CYTOTOXICITY; DISTRIBUTION VOLUME; DRUG CONJUGATION; DRUG DISTRIBUTION; DRUG ELIMINATION; DRUG HALF LIFE; DRUG RELEASE; DRUG TARGETING; DRUG TISSUE LEVEL; HEMOLYSIS; IN VITRO STUDY; LYSOSOME; MALE; MELANOMA; MELANOMA B16; MELANOMA CELL; MOUSE; NONHUMAN; PH; PRIORITY JOURNAL;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; DENDRIMERS; DOXORUBICIN; DRUG CARRIERS; DRUG COMPOUNDING; MATERIALS TESTING; MELANOMA; MICE; MICE, INBRED C57BL; POLYAMINES; POLYETHYLENE GLYCOLS; TREATMENT OUTCOME;

MURINAE;

EID: 72149091705     PISSN: 01429612     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.biomaterials.2009.10.044     Document Type: Article

References (45)

1. Lee C.C., MacKay J.A., Fréchet J.M., and Szoka F.C. Designing dendrimers for biological applications. Nat Biotechnol 23 (2005) 1517-1526
2. Svenson S. Dendrimers as versatile platform in drug delivery applications. Eur J Pharm Biopharm 71 (2009) 445-462
3. Kolhe P., Khandare J., Pillai O., Kannan S., Lieh-Lai M., and Kannan R.M. Preparation, cellular transport, and activity of polyamidoamine-based dendritic nanodevices with a high drug payload. Biomaterials 27 (2006) 660-669
4. Kurtoglu Y.E., Navath R.S., Wang B., Kannan S., Romero R., and Kannan R.M. Poly(amidoamine) dendrimer-drug conjugates with disulfide linkages for intracellular drug delivery. Biomaterials 30 (2009) 2112-2121
5. Kono K., Kojima C., Hayashi N., Nishisaka E., Kiura K., Watarai S., et al. Preparation and cytotoxic activity of poly(ethylene glycol)-modified poly(amidoamine) dendrimers bearing adriamycin. Biomaterials 29 (2008) 1664-1675
6. Gillies E.R., Dy E., Fréchet J.M., and Szoka F.C. Biological evaluation of polyester dendrimer: poly(ethylene oxide) "bow-tie" hybrids with tunable molecular weight and architecture. Mol Pharmacol 2 (2005) 129-138
7. Chandrasekar D., Sistla R., Ahmad F.J., Khar R.K., and Diwan P.V. The development of folate-PAMAM dendrimer conjugates for targeted delivery of anti-arthritic drugs and their pharmacokinetics and biodistribution in arthritic rats. Biomaterials 28 (2007) 504-512
8. Patri A.K., Myc A., Beals J., Thomas T.P., Bander N.H., and Baker J.R. Synthesis and in vitro testing of J591 antibody-dendrimer conjugates for targeted prostate cancer therapy. Bioconjug Chem 15 (2004) 1174-1181
9. Nam H.Y., Nam K., Hahn H.J., Kim B.H., Lim H.J., Kim H.J., et al. Biodegradable PAMAM ester for enhanced transfection efficiency with low cytotoxicity. Biomaterials 30 (2009) 665-673
10. Boswell C.A., Eck P.K., Regino C.A., Bernardo M., Wong K.J., Milenic D.E., et al. Synthesis, characterization, and biological evaluation of integrin alphavbeta3-targeted PAMAM dendrimers. Mol Pharmacol 5 (2008) 527-539
11. Luo D., Haverstick K., Belcheva N., Han E., and Saltzman W.M. Poly(ethylene glycol)-conjugated PAMAM dendrimer for biocompatible, high-efficiency DNA delivery. Macromolecules 35 (2002) 3456-3462
12. Ulbrich K., and Subr V. Polymeric anticancer drugs with pH-controlled activation. Adv Drug Deliv Rev 56 (2004) 1023-1050
13. Shen W.T., and Ryser H.J.P. Cis-aconityl spacer between daunomycin and macromolecular carriers: a model of pH-sensitive linkage releasing drug from a lysosomotropic conjugate. Biochem Biophys Res Commun 102 (1981) 1048-1054
14. Chytil P., Etrych T., Konák C., Sírová M., Mrkvan T., Ríhová B., et al. Properties of HPMA copolymer-doxorubicin conjugates with pH-controlled activation: effect of polymer chain modification. J Control Release 115 (2006) 26-36
15. Kakinoki A., Kaneo Y., Ikeda Y., Tanaka T., and Fujita K. Synthesis of poly(vinyl alcohol)-doxorubicin conjugates containing cis-aconityl acid-cleavable bond and its isomer dependent doxorubicin release. Biol Pharm Bull 31 (2008) 103-110
16. Yoo H.S., Lee E.A., and Park T.G. Doxorubicin-conjugated biodegradable polymeric micelles having acid-cleavable linkages. J Control Release 82 (2002) 17-27
17. Chytil P., Etrych T., Konák C., Sírová M., Mrkvan T., and Boucek J. New HPMA copolymer-based drug carriers with covalently bound hydrophobic substituents for solid tumour targeting. J Control Release 127 (2008) 121-130
18. Furuhata M., Izumisawa T., Kawakami H., Toma K., Hattori Y., and Maitani Y. Decaarginine-PEG-liposome enhanced transfection efficiency and function of arginine length and PEG. Int J Pharm 371 (2009) 40-46
19. Thöle M., Nobmanna S., Huwyler J., Bartmann A., and Fricker G. Uptake of cationzied albumin coupled liposomes by cultured porcine brain microvessel endothelial cells and intact brain capillaries. J Drug Target 10 (2002) 337-344
20. Bender M.L. General acid-base catalysis in the intramolecular hydrolysis of phthalamic acid. J Am Chem Soc 79 (1957) 1258-1259
21. Luo Y., Bernshaw N.J., Lu Z.R., Kopecek J., and Prestwich G.D. Targeted delivery of doxorubicin by HPMA copolymer-hyaluronan bioconjugates. Pharm Res 19 (2002) 396-402
22. Saovapakhiran A., D'Emanuele A., Attwood D., and Penny J. Surface modification of PAMAM dendrimers modulates the mechanism of cellular internalization. Bioconjug Chem 20 (2009) 693-701
23. Tomlinson R., Heller J., Brocchini S., and Duncan R. Polyacetal-doxorubicin conjugates designed for pH-dependent degradation. Bioconjug Chem 14 (2003) 1096-1106
24. Duncan R., Bakoo M., and Riley M.L. Soluble drug carriers: haemocompatibility. In: Gomez-Fernandez J.C., Chapman D., and Packer L. (Eds). Progress in membrane biotechnology (1991), Birkhauser Verlag, Basel, Switzerland 253-265
25. Greco F., Vicent M.J., Gee S., Jones A.T., Gee J., and Nicholson I.R. Investigating the mechanism of enhanced cytotoxicity of HPMA copolymer-DOX-AGM in breast cancer cells. J Control Release 117 (2007) 28-39
26. Sorensen M., Sehested M., and Jensen P.B. Effect of cellular ATP depletion on topoisomerase II poisons. Abrogation of cleavable-complex formation by etoposide but not by amsacrine. Mol Pharmacol 55 (1999) 424-431
27. Loadman P.M., Bibby M.C., Double J.A., Al-Shakhaa W.M., and Duncan R. Pharmacokinetics of PK1 and doxorubicin in experimental colon tumor models with differing responses to PK1. Clin Cancer Res 5 (1999) 3682-3688
28. Nicholls G.M., Clark B.J., and Brown J.E. Solid phase extraction and optimised separation of doxorubicin, epirubicin and their metabolites using reversed-phase high performance liquid-chromatography. J Pharm Biomed Anal 10 (1992) 949-957
29. Xiong X.B., Huang Y., Lu W.L., Zhang X., Zhang H., Nagai T., et al. Enhanced intracellular delivery and improved antitumor efficacy of doxorubicin by sterically stabilized liposomes modified with a synthetic RGD mimetic. J Control Release 107 (2005) 262-275
30. Liu J., and Shapiro J.I. Endocytosis and signal transduction: basic science update. Biol Res Nurs 5 (2003) 117-128
31. Krogstad D.J., and Schlesinger P.H. The basis of antimalarial action: non-weak base effects of chloroquine on acid vesicle pH. Am J Trop Med Hyg 36 (1987) 213-220
32. Yang H.M., and Reisfeld R.A. Doxorubicin conjugated with a monoclonal antibody directed to a human melanoma-associated proteoglycan suppresses the growth of established tumor xenografts in nude mice. Proc Natl Acad Sci U S A 85 (1988) 1189-1193
33. Glodde M., Sirsi S.R., and Lutz G.J. Physiochemical properties of low and high molecular weight poly(ethylene glycol)-grafted poly(ethylene imine) copolymers and their complexes with oligonucleotides. Biomacromolecules 7 (2006) 347-356
34. Papagiannaros A., Dimas K., Papaioannou G.T., and Demetzos C. Doxorubicin-PAMAM dendrimer complex attached to liposomes: cytotoxic studies against human cancer cell lines. Int J Pharm 302 (2005) 29-38
35. Ke W., Zhao Y., Huang R., Jiang C., and Pei Y. Enhanced oral bioavailability of doxorubicin in a dendrimer drug delivery system. J Pharm Sci 97 (2008) 2208-2216
36. Leonardi D., Barrera M.G., Lamas M.C., and Salomón C.J. Development of prednisone:polyethylene glycol 6000 fast-release tablets from solid dispersions: solid-state characterization, dissolution behavior, and formulation parameters. AAPS Pharm Sci Tech 8 (2007) E108
37. Liu C., and Desai K.G. Characteristics of rofecoxib-polyethylene glycol 4000 solid dispersions and tablets based on solid dispersions. Pharm Dev Technol 10 (2005) 467-477
38. Gewirtz D.A. A critical evaluation of the mechanisms of action proposed for the antitumor effects of the anthracycline antibiotics adriamycin and daunorubicin. Biochem Pharmacol 57 (1999) 727-734
39. Li S.D., and Huang L. Pharmacokinetics and biodistribution of nanoparticles. Mol Pharmacol 5 (2008) 496-504
40. Owens III D.E., and Peppas N.A. Opsonization, biodistribution, and pharmacokinetics of polymeric nanoparticles. Int J Pharm 307 (2006) 93-102
41. Kobayashi H., Kawamoto S., Saga T., Sato N., Hiraga A., Ishimori T., et al. Positive effects of polyethylene glycol conjugation to generation-4 polyamidoamine dendrimers as macromolecular MR contrast agents. Magn Reson Med 46 (2001) 781-788
42. Sheng Y., Liu C., Yuan Y., Tao X., Yang F., Shan X., et al. Long-circulating polymeric nanoparticles bearing a combinatorial coating of PEG and water-soluble chitosan. Biomaterials 30 (2009) 2340-2348
43. Shiah J.G., Dvorák M., Kopecková P., Sun Y., Peterson C.M., and Kopecek J. Biodistribution and antitumour efficacy of long-circulating N-(2-hydroxypropyl)methacrylamide copolymer-doxorubicin conjugates in nude mice. Eur J Cancer 37 (2001) 131-139
44. Blum R.H., and Carter S.H. Adriamycin: a new anticancer drug with significant clinical activity. Ann Intern Med 80 (1974) 249-259
45. Takakura Y., Mahato R.I., Nishikawa M., and Hashida M. Control of pharmacokinetic profiles of drug-macromolecule conjugates. Adv Drug Deliv Rev 19 (1996) 377-399