A doxorubicin prodrug activated by the staudinger reaction

Bioconjugate Chemistry

Volumn 19, Issue 3, 2008, Pages 714-718

  Van Brakel, Remco ^a   Vulders, Roland C M ^a   Bokdam, Rembrandt J ^a   Grüll, Holger ^a   Robillard, Marc S ^a  

^a PHILIPS RESEARCH LABORATORIES   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CELL PROLIFERATION; CHEMICAL ACTIVATION; DRUG DELIVERY; MOLECULAR BIOLOGY;

CHEMICAL ACTIVATORS; DOXORUBICIN; DRUG RELEASE; ENZYMATIC ACTION; GROWTH MEDIUM; PRODRUG ACTIVATION; PRODRUG SYSTEMS; PRODRUGS; STAUDINGER REACTIONS; TRIPHENYL PHOSPHINES;

CELL CULTURE;

4 AZIDOBENZYL; AZIDOBENZYLCARBAMATE DOXORUBICIN; BENZYL DERIVATIVE; DOXORUBICIN; PRODRUG; TRIPHENYLPHOSPHINE; UNCLASSIFIED DRUG;

ARTICLE; CARCINOMA CELL; CELL GROWTH; CELL PROLIFERATION; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG ACTIVATION; DRUG CONJUGATION; DRUG STRUCTURE; DRUG TOLERABILITY; ENZYME ACTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; SKIN CARCINOMA; STAUDINGER REACTION; VULVA CARCINOMA;

EID: 41149116085     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc700394s     Document Type: Article

References (13)

1. Minotti, G., Menna, P., Salvatorelli, E., Cairo, G., and Gianni, L. (2004) Anthracyclines: molecular advances and pharmacologic developments in antitumor activity and cardiotoxicity. Pharmacol. Rev. 56, 185-229.
2. 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.
3. Bagshawe, K. D. (2006) Antibody-directed enzyme prodrug therapy (ADEPT) for cancer. Exp. Rev. Anticancer Ther. 6, 1421-1431.
4. de Groot, F. M. H., Albrecht, C., Koekkoek, R., Beusker, P. H., and Scheeren, H. W. (2003) "Cascade-release dendrimers" liberate all end groups upon a single triggering event in the dendritic core. Angew. Chem., Int. Ed. 42, 4490-4494.
5. Papot, S., Tranoy, I., Tillequin, F., Florent, J.-C., and Gesson, J.-P. (2002) Design of selectively activated anticancer prodrugs: elimination and cyclization strategies. Curr. Med. Chem. - AntiCancer Agents 2, 155-185.
6. Duncan, R. (2006) Polymer conjugates as anticancer nanomedicines. Nat. Rev. Cancer 6, 688-701.
7. Köhn, M., and Breinbauer, R. (2004) The Staudinger Ligation - a gift to chemical biology. Angew. Chem., Int. Ed. 43, 3106-3116.
8. Dube, D. H., Prescher, J. A., Quang, C. N., and Bertozzi, C. R. (2006) Probing mucin-type O-linked glycosylation in living animals. Proc. Natl. Acad. Sci. U.S.A. 103, 4819-4824.
9. Shabat, D., Amir, R. J., Gopin, A., Pessah, N., and Shamis, M. (2004) Chemical adaptor systems. Chem. Eur. J. 10, 2626-2634.
10. Doronina, S. O., Mendelsohn, B. A., Bovee, T. D., Cerveny, C. G., Alley, S. C., Meyer, D. L., Oflazoglu, E., Toki, B. E., Sanderson, R. J., Zabinski, R. F., Wahl, A. F., and Senter, P. D. (2006) Enhanced activity of monomethylauristatin F through monoclonal antibody delivery: effects of linker technology on efficacy and toxicity. Bioconjugate Chem. 17, 114-124.
11. Mossman, T. (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods 65, 55-63.
12. Griffin, R. J., and Irwin, W. J. (1996) The 4-azidoberazyloxycarbonyl function; application as a novel protecting group and potential prodrug modification for amines. J. Chem. Soc., Perkin Trans. 1, 1205-1211.
13. Recently, a phosphine-doxorubicin conjugate was reported that effects drug release via the traceless Staudinger ligation in aqueous THF: Azoulay, M., Tuffin, G., Sallem, W., and Florent, J.-C. (2006) A new drug-release method using the Staudinger ligation. Bioorg. Med. Chem. Lett. 16, 3147-3149.