An intramolecular cyclization reaction is responsible for the in vivo inefficacy and apparent pH insensitive hydrolysis kinetics of hydrazone carboxylate derivatives of doxorubicin

Bioconjugate Chemistry

Volumn 17, Issue 5, 2006, Pages 1364-1368

  Lee, Cameron C ^a   Cramer, Andrew T ^a   Szoka Jr , Francis C ^b   Fréchet, Jean M J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOMOLECULES; CONTROLLED DRUG DELIVERY; CYCLIZATION; DRUG PRODUCTS; HYDROLYSIS; KINETICS; REACTION KINETICS; TARGETED DRUG DELIVERY;

BIOCONJUGATES; CYCLIZATION REACTIONS; DOXORUBICIN; HYDRAZONES; HYDROLYSIS KINETICS; IN-VIVO; INTRAMOLECULAR CYCLIZATIONS; PH SENSITIVE; PH STABILITY; PH-STABILITY;

CARBOXYLATION;

CARBOXYLIC ACID DERIVATIVE; DOXORUBICIN; DRUG CARRIER; HYDRAZONE DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CYCLIZATION; DRUG CONJUGATION; DRUG HALF LIFE; DRUG RELEASE; DRUG STABILITY; DRUG STRUCTURE; HYDROLYSIS KINETICS; PH;

PADILLA;

EID: 33748999805     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc060117y     Document Type: Article

References (21)

1. Kratz, F., Warnecke, A., Schmid, B., Chung, D. E., and Gitzel, M. (2006) Prodrugs of anthracyclines in cancer chemotherapy. Curr. Med. Chem. 13, 477-523.
2. Tritton, T. R., and Yee, G. (1982) The anticancer agent adriamycin can be actively cytotoxic without entering cells. Science 217, 248-250.
3. Kratz, F., Beyer, U., and Schütte, M. T. (1999) Drug-polymer conjugates containing acid-cleavable bonds. Crit. Rev. Ther. Drug Carrier Syst. 16, 245-288.
4. Ulbrich, K., and Šubr, V. (2004) Polymeric anticancer drugs with pH-controlled activation. Adv. Drug Delivery Rev. 56, 1023-1050.
5. Greenfield, R. S., Kaneko, T., Daues, A., Edson, M. A., Fitzgerald, K. A., Olech, L. J., Grattan, J. A., Spitalny, G. L., and Braslawsky, G. R. (1990) Evaluation in vitro of adriamycin immunoconjugates synthesized using an acid-sensitive hydrazone linker. Cancer Res. 50, 6600-6607.
6. Kaneko, T., Willner, D., Monković, I., Knipe, J. O., Braslawsky, G. R., Greenfield, R. S., and Vyas, D. M. (1991) New hydrazone derivatives of adriamycin and their immunoconjugates - a correlation between acid stability and cytotoxicity. Bioconjugate Chem. 2, 133-141.
7. Rodrigues, P. C. A., Beyer, U., Schumacher, P., Roth, T., Fiebig, H. H., Unger, C., Messori, L., Orioli, P., Paper, D. H., Mülhaupt, R., and Kratz, F. (1999) Acid-sensitive polyethylene glycol conjugates of doxorubicin: Preparation, in vitro efficacy and intracellular distribution. Bioorg. Med. Chem. Lett. 7, 2517-2524.
8. Etrych, T., Chytil, P., Jelínková, M., Ríhová , B., and Ulbrich, K. (2002) Synthesis of HPMA copolymers containing doxorubicin bound via a hydrazone linkage. Effect of spacer on drug release and in vitro cytotoxicity. Macromol. Biosci. 2, 43-52.
9. Gerweck, L. E., and Seetharaman, K. (1996) Cellular pH gradient in tumor versus normal tissue: Potential exploitation for the treatment of cancer. Cancer Res. 56, 1194-1198.
10. Nori, A., and Kopecek, J. (2005) Intracellular targeting of polymerbound drugs for cancer chemotherapy. Adv. Drug Delivery Rev. 57, 609-636.
11. Ihre, H. R., Padilla de Jesús, O. L., Szoka, F. C., and Fréchet, J. M. J. (2002) Polyester dendritic systems for drug delivery applications: Design, synthesis, and characterization. Bioconjugate Chem. 13, 443-452.
12. Padilla de Jesús, O. L., Ihre, H. R., Gagne, L., Fréchet, J. M. J., and Szoka, F. C. (2002) Polyester dendritic systems for drug delivery applications: In vitro and in vivo evaluation. Bioconjugate Chem. 13, 453-461.
13. Padilla de Jesús, O. L. (2003) Ph.D. Dissertation, University of California, Berkeley, CA.
14. Gillies, E. R. (2004) Ph.D. Dissertation, University of California, Berkeley, CA.
15. Gillies, E. R., Dy, E., Fréchet, J. M. J., and Szoka, F. C. (2005) Biological evaluation of polyester dendrimer:poly(ethylene oxide) "bow-tie" hybrids with tunable molecular weight and architecture. Mol. Pharm. 2, 129-138.
16. Rosenblum, M., Nayak, V., DasGupta, S. K., and Longroy, A. (1963) Synthesis of dihydrooxadiazinones and study of geometrical isomerism in α-ketol carbethoxyhydrazones. J. Am. Chem. Soc. 85, 3874-3878.
17. Kamemitskii, A. V., Turuta, A. M., Korobov, A. A., and Istomina, Z. I. (1987) Transformation of corticoid side-chain of steroids into 1′,3′,4′-oxadiazine ring E. Russ. Chem. Bull. 36, 161-163.
18. Kamemitskii, A. V., Turuta, A. M., Istomina, Z. I., and Korobov, A. A. (1987) Alkaline cyclization of carboethoxyhydrazones of 21-hydroxy-20- ketosteroids to 17-β-(1′,3′,4′-oxadiazin-2′-ones) and its correlation with the geometry of the hydrazone fragment. Russ. Chem. Bull 36, 173-175.
19. McLennan, I. J., Lenkinski, R. E., and Yanuka, Y. (1985) A nuclear magnetic resonance study of the self-association of adriamycin and daunomycin in aqueous solution. Can. J. Chem. 63, 1233-1238.
20. Huang, S. K., Mayhew, E., Gilani, S., Lasic, D. D., Martin, F. J., and Papahadjopoulos, D. (1992) Pharmacokinetics and therapeutics of sterically stabilized liposomes in mice bearing C-26 colon carcinoma. Cancer Res. 52, 6774-6781.
21. Seymour, L. W., Ulbrich, K., Steyger, P. S., Brereton, M., Subr, V., Strohalm, J., and Duncan, R. (1994) Tumor tropism and anticancer efficacy of polymer-based doxorubicin prodrugs in the treatment of subcutaneous murine B16F10 melanoma. Br. J. Cancer 70, 636-641.