Synthesis and in vitro characterization of a dendrimer-MORF conjugate for amplification pretargeting

Bioconjugate Chemistry

Volumn 19, Issue 8, 2008, Pages 1518-1525

  Chen, Xiangji ^a   Dou, Shuping ^a   Liu, Guozheng ^a   Liu, Xinrong ^a   Wang, Yi ^a   Chen, Ling ^a   Rusckowski, Mary ^a   Hnatowich, Donald J ^a  

^a UNIVERSITY OF MASSACHUSETTS MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBODIES; DENDRIMERS; MOLECULAR IMAGING; MOLECULES; OLIGOMERS; TISSUE; TISSUE CULTURE;

ANTITUMOR ANTIBODIES; AVERAGE NUMBERS; CARBOXYL GROUPS; DENDRIMER GENERATION; IN-VITRO; PAMAM DENDRIMER; SINGLE PEAK; TARGET LOCALIZATION; TARGET TISSUES; VITRO CHARACTERIZATION;

AMPLIFICATION;

CANCER ANTIBODY; CANCER ANTIBODY CC49; CARBOXYL GROUP; DENDRIMER; DIHYDROLIPOAMIDE DEHYDROGENASE; GUANINE NUCLEOTIDE BINDING PROTEIN; OLIGOMER; POLYAMIDOAMINE; TECHNETIUM 99M; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CONTROLLED STUDY; DRUG CONJUGATION; DRUG PROTEIN BINDING; DRUG PURIFICATION; DRUG SYNTHESIS; DRUG TARGETING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; HYBRIDIZATION; IN VITRO STUDY; ISOTOPE LABELING; POLYACRYLAMIDE GEL ELECTROPHORESIS; RADIOACTIVITY; SIGNAL TRANSDUCTION; TISSUE CULTURE; TUMOR CELL;

EID: 50249133666     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc8001024     Document Type: Article

References (46)

1. Goodwin, D. A., Meares, C. F., McCall, M. J., McTigue, M., and Chaovapong, W. (1988) Pre-targeted immunoscintigraphy of murine tumors with indium-111-labeled bifunctional haptens. J. Nucl. Med. 29, 226-234.
2. Hnatowich, D. J., Virzi, F., and Rusckowski, M. (1987) Investigations of avidin and biotin for imaging applications. J. Nucl. Med. 28, 1294-1302.
3. Bos, E. S., Kuijpers, W. H. A., Meesterswinters, M., Pham, D. T., Dehaan, A. S., Vandoornmalen, A. M., Kaspersen, F. M., Vanboeckel, C. A. A., and Gougeonbertrand, F. (1994) In-vitro evaluation of DNA-DNA hybridization as a 2-step approach in radioimmunotherapy of cancer. Cancer Res. 54, 3479-3486.
4. Chang, C. H., Sharkey, R. M., Rossi, E. A., Karacay, H., McBride, W., Hansen, H. J., Chatal, J. F., Barbet, J., and Goldenberg, D. M. (2002) Molecular advances in pretargeting radioimunotherapy with bispecific antibodies. Mol. Cancer Ther. 1, 553-563.
5. Rusckowski, M., Qu, T., Chang, F., and Hnatowich, D. J. (1997) Pretargeting using peptide nucleic acid. Cancer 80, 2699-2705.
6. Wang, Y., Chang, F., Zhang, Y., Liu, N., Liu, G., Gupta, S., Rusckowski, M., and Hnatowich, D. J. (2001) Pretargeting with amplification using polymeric peptide nucleic acid. Bioconjugate Chem. 12, 807-816.
7. He, J., Liu, G., Zhang, S., Rusckowski, M., and Hnatowich, D. J. (2003) Pharmacokinetics in mice of four oligomer-conjugated polymers for amplification targeting. Cancer Biother. Radiopharm. 18, 941-947.
8. He, J., Liu, G., Gupta, S., Zhang, Y., Rusckowski, M., and Hnatowich, D. J. (2004) Amplification targeting: A modified pretargeting approach with potential for signal amplification - Proof of a concept. J. Nucl. Med. 45, 1087-1095.
9. Sharkey, R. M., Cardillo, T. M., Rossi, E. A., Chang, C. H., Karacay, H., McBride, W. J., Hansen, H. J., Horak, I. D., and Goldenberg, D. M. (2005) Signal amplification in molecular imaging by pretargeting a multivalent, bispecific antibody. Nat. Med. 11, 1250-1255.
10. Bogdanov, A., Kang, H. W., Querol, M., Pretorius, P. H., and Yudina, A. (2007) Synthesis and testing of a binary catalytic system for imaging of signal amplification in vivo. Bioconjugate Chem. 18, 1123-1130.
11. Malik, N., and Duncan, R. (2002) Dendritic-platinate drug delivery system, U. S. Patent 6,585,956.
12. Kolhe, P., Misra, E., Kannan, R. M., Kannan, S., and Lieh-Lai, M. (2003) Drug complexation, in vitro release and cellular entry of dendrimers and hyperbranched polymers. Int. J. Pharm. 259, 143-160.
13. Kannan, S., Kolhe, P., Raykova, V., Glibatec, M., Kannan, R. M., Lieh-Lai, M., and Bassett, D. (2004) Dynamics of cellular entry and drug delivery by dendritic polymers into human lung epithelial carcinoma cells. J. Biomater. Sci.-Polym. Ed. 15, 311-330.
14. Patri, A. K., Kukowska-Latallo, J. F., and Baker, J. R. (2005) Targeted drug delivery with dendrimers: Comparison of the release kinetics of covalently conjugated drug and non-covalent drug inclusion complex. Adv. Drug Delivery Rev. 57, 2203-2214.
15. Kukowska-Latallo, J. F., Candido, K. A., Cao, Z., Nigavekar, S. S., Majoros, I. J., Thomas, T. P., Balogh, L. P., Khan, M. K., and Baker, J. R. (2005) Nanoparticle targeting of anticancer drug improves therapeutic response in animal model of human epithelial cancer. Cancer Res. 65, 5317-5324.
16. Bai, S., Thomas, C., Rawat, A., and Ahsan, F. (2006) Recent progress in dendrimer-based nanocarriers. Crit. Rev. Ther. Drug Carrier Syst. 23, 437-495.
17. Kolhe, P., Khandare, J., Pillai, O., Kannan, S., Lieh-Lal, M., and Kannan, R. M. (2006) Preparation, cellular transport, and activity of polyamidoamine-based dendritic nanodevices with a high drug payload. Biomaterials 27, 660-669.
18. Chandrasekar, D., Sistla, R., Ahmad, F. J., Khar, R. K., and Diwan, P. V. (2007) The development of folate-PAMAM dendrimer conjugates for targeted delivery of anti-arthritic drugs and their pharmacokinetics and biodistribution in arthritic rats. Biomaterials 28, 504-512.
19. Chandrasekar, D., Sistla, R., Ahmad, F. J., Khar, R. K., and Diwan, P. V. (2007) Folate coupled poly(ethyleneglycol) conjugates of anionic poly(amidoamine) dendrimer for inflammatory tissue specific drug delivery. J. Biomed. Mater. Res.: Part A 82A, 92-103.
20. Quintana, A., Raczka, E., Piehler, L., Lee, I., Myc, A., Majoros, I., Patri, A. K., Thomas, T., Mule, J., and Baker, J. R. (2002) Design and function of a dendrimer-based therapeutic nanodevice targeted to tumor cells through the folate receptor. Pharm. Res. 19, 1310-1316.
21. Nakanishi, H., Mazda, O., Satoh, E., Asada, H., Morioka, H., Kishida, T., Nakao, M., Mizutani, Y., Kawauchi, A., Kita, M., Imanishi, J., and Miki, T. (2003) Nonviral genetic transfer of Fas ligand induced significant growth suppression and apoptotic tumor cell death in prostate cancer in vivo. Gene Ther. 10, 434-442.
22. Thomas, T. P., Patri, A. K., Myc, A., Myaing, M. T., Ye, J. Y., Norris, T. B., and Baker, J. R. (2004) In vitro targeting of synthesized anti body-conjugated dendrimer nanoparticles. Biomacromolecules 5, 2269-2274.
23. Khandare, J., Kolhe, P., Pillai, O., Kannan, S., Lieh-Lai, M., and Kannan, R. M. (2005) Synthesis, cellular transport, and activity of polyamidoamine dendrimer-methylprednisolone conjugates. Bioconjugate Chem. 16, 330-337.
24. Thomas, T. P., Majoros, I. J., Kotlyar, A., Kukowska-Latallo, J. F., Bielinska, A., Myc, A., and Baker, J. R. (2005) Targeting and inhibition of cell growth by an engineered dendritic nanodevice. J. Med. Chem. 48, 3729-3735.
25. Arima, H., Chihara, Y., Arizono, M., Yamashita, S., Wada, K., Hirayama, F., and Uekama, K. (2006) Enhancement of gene transfer activity mediated by mannosylated dendrimer/alpha-cyclodextrin conjugate (generation 3, G3). J. Controlled Release 116, 64-74.
26. Khandare, J. J., Jayant, S., Singh, A., Chandna, P., Wang, Y., Vorsa, N., and Minko, T. (2006) Dendrimer versus linear conjugate: Influence of polymeric architecture on the delivery and anticancer effect of paclitaxel. Bioconjugate Chem. 17, 1464-1472.
27. Ke, T., Feng, Y., Guo, J., Parker, D. L., and Lu, Z. R. (2006) Biodegradable cystamine spacer facilitates the clearance of Gd(III) chelates in poly(glutamic acid) Gd-DO3A conjugates for contrast-enhanced MR imaging. Magn. Reson. Imaging 24, 931-940.
28. Shukla, R., Thomas, T. P., Peters, J. L., Desai, A. M., Kukowska-Latallo, J., Patri, A. K., Kotlyar, A., and Baker, J. R. (2006) HER2 specific tumor targeting with dendrimer conjugated anti-HER2 mAb. Bioconjugate Chem. 17, 1109-1115.
29. Rudovsky, J., Botta, M., Hermann, P., Hardcasde, K. I., Lukes, I., and Aime, S. (2006) PAMAM dendrimeric conjugates with a Gd-DOTA phosphinate derivative and their adducts with polyaminoacids: The interplay of global motion, internal rotation, and fast water exchange. Bioconjugate Chem. 17, 975-987.
30. Fu, Y., Nitecki, D. E., Maltby, D., Simon, G. H., Berejnoi, K., Raatschen, H. J., Yeh, B. M., Shames, D. M., and Brasch, R. C. (2006) Dendritic iodinated contrast agents with PEG-cores for CT imaging: Synthesis and preliminary characterization. Bioconjugate Chem. 17, 1043-1056.
31. Wang, X., Inapagolla, R., Kannan, S., Lieh-Lai, M., and Kannan, R. M. (2007) Synthesis, characterization, and in vitro activity of dendrimer-streptokinase conjugates. Bioconjugate Chem. 18, 791-799.
32. Tsutsumi, T., Hirayama, F., Uekama, K., and Arima, H. (2007) Evaluation of polyamidoamine dendrimer/alpha-cyclodextrin conjugate (generation 3, G3) as a novel carrier for small interfering RNA (siRNA). J. Controlled Release 119, 349-359.
33. Battah, S., Balaratnam, S., Casas, A., O'Neill, S., Edwards, C., Batlle, A., Dobbin, P., and MacRobert, A. J. (2007) Macromolecular delivery of 5-aminolaevulinic acid for photodynamic therapy using dendrimer conjugates. Mol. Cancer Ther. 6, 876-885.
34. Myc, A., Majoros, I. J., Thomas, T. P., and Baker, J. R. (2007) Dendrimer-based targeted delivery of an apoptotic sensor in cancer cells. Biomacromolecules 8, 13-18.
35. Liu, G., He, J., Dou, S., Gupta, S., Vanderheyden, J., Rusckowski, M., and Hnatowich, D. J. (2004) Pretargeting in tumored mice with radiolabeled morpholino oligomer showing low kidney uptake. Eur. J. Nucl. Med. Mol. Imaging 31, 417-424.
36. Liu, G., He, J., Dou, S., Gupta, S., Rusckowski, M., and Hnatowich, D. J. (2005) Further investigations of morpholino pretargeting in mice-establishing quantitative relations in tumor. Eur. J. Nucl. Med. Mol. Imaging 32, 1115-1123.
37. 3 for technetium-99m labeling of DNA. Nucl. Med. Biol. 24, 425-432.
38. 188Re at high labeling efficiency and specific radioactivity for tumor pretargeting. Appl. Radiat. Isot. 64, 971-978.
39. Sharma, A., Desai, A., Ali, R., and Tomalia, D. (2005) Polyacrylamide gel electrophoresis separation and detection of polyamidoamine dendrimers possessing various cores and terminal groups. J. Chromatogr., A 1081, 238-244.
40. Shi, X., Patri, A. K., Lesniak, W., Islam, M. T., Zhang, C., Baker, J. R., and Balogh, L. P. (2005) Analysis of poly(amidoamine)-succinamic acid dendrimers by slab-gel electrophoresis and capillary zone electrophoresis. Electrophoresis 26, 2960-2967.
41. He, J., Liu, G., Dou, S., Gupta, S., Rusckowski, M., and Hnatowich, D. J. (2007) An improved method for covalently conjugating morpholino oligomers to antitumor antibodies. Bioconjugate Chem. 18, 983-988.
42. Liu, G., Zhang, S., He, J., Liu, N., Gupta, S., Rusckowski, M., and Hnatowich, D. J. (2002) The influence of chain length and base sequence on the pharmacokinetic behavior of Tc-99m-morpholinos in mice. Q. J. Nucl. Med. 46, 233-243.
43. Malik, N., Wiwattanapatapee, R., Klopsch, R., Lorenz, K., Frey, H., Weener, J. W., Meijer, E. W., Paulus, W., and Duncan, R. (2000) Dendrimers: Relationship between structure and biocompatibility in vitro, and preliminary studies on the biodistribution of I-125-labelled polyamidoamine dendrimers in vivo. J. Controlled Release 65, 133-148.
44. Jevprasesphant, R., Penny, J., Jalal, R., Attwood, D., McKeown, N. B., and D'Emanuele, A. (2003) The influence of surface modification on the cytotoxicity of PAMAM dendrimers. Int. J. Pharm. 252, 263-266.
45. Duncan, R., and Izzo, L. (2005) Dendrimer biocompatibility and toxicity. Adv. Drug Delivery Rev. 57, 2215-2237.
46. Svenson, S., and Tomalia, D. A. (2005) Commentary - Dendrimers in biomedical applications - reflections on the field. Adv. Drug Delivery Rev. 57, 2106-2129.