Synthesis and biological evaluation of an albumin-binding prodrug of doxorubicin that is cleaved by prostate-specific antigen (PSA) in a PSA-positive orthotopic prostate carcinoma model (LNCaP)

International Journal of Cancer

Volumn 122, Issue 5, 2008, Pages 1145-1154

  Graeser, Ralph ^a   Chung, Da Eun ^b   Esser, Norbert ^a   Moor, Sandra ^a   Schächtele, Christoph ^a   Unger, Clemens ^b   Kratz, Felix ^b  

^a PROQINASE GMBH   (Germany)

^b TUMOR BIOLOGY CENTER   (Germany)

Author keywords

Doxorubicin; Human serum albumin; in vivo bioluminescence; LNCaP; Luciferase; Macromolecular prodrug; Orthotopic animal model; PSA

Indexed keywords

ALBUMIN; ARGININE; CYSTEINE; DIPEPTIDE; DOXORUBICIN; EPSILON MALEIMIDOCAPROIC ACID; LUCIFERASE; PRODRUG; PROSTATE SPECIFIC ANTIGEN; PSA 5; SERINE PROTEINASE; THIOL; UNCLASSIFIED DRUG; ALBUMINOID; ANTINEOPLASTIC ANTIBIOTIC;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER MODEL; CELL STRAIN LNCAP; CHEMICAL BOND; CONTROLLED STUDY; DRUG EFFICACY; DRUG SCREENING; DRUG SYNTHESIS; DRUG TOLERABILITY; ENZYME ASSAY; HUMAN; HUMAN CELL; LUNG METASTASIS; MACROMOLECULE; MALE; MORTALITY; MOUSE; NONHUMAN; ORTHOTOPIC TRANSPLANTATION; PRIORITY JOURNAL; PROSTATE CARCINOMA; PROTEIN EXPRESSION; SCID MOUSE; SOLUBILITY; TUMOR VOLUME; WEIGHT REDUCTION; ANIMAL; DISEASE MODEL; METABOLISM; MOUSE MUTANT; PROSTATE TUMOR; SYNTHESIS;

ALBUMINS; ANIMALS; ANTIBIOTICS, ANTINEOPLASTIC; DISEASE MODELS, ANIMAL; DOXORUBICIN; HUMANS; MALE; MICE; MICE, SCID; PRODRUGS; PROSTATE-SPECIFIC ANTIGEN; PROSTATIC NEOPLASMS; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 38749154289     PISSN: 00207136     EISSN: 10970215     Source Type: Journal    
DOI: 10.1002/ijc.23050     Document Type: Article

References (24)

1. Arlen PM, Gulley JL. Docetaxel-based regimens, the Standard of care for metastatic androgen-insensitive prostate cancer. Future Oncol 2005;1:19-22.
2. Lilja H, Abrahamsson PA, Lundwall A. Semenogelin, the predominant protein in human semen. Primary structure and identification of closely related proteins in the male accessory sex glands and on the spermatozoa. J Biol Chem 1989;264:1894-900.
3. Akiyama K, Nakamura T, Iwanaga S, Hara M. The chymotrypsin-like activity of human prostate-specific antigen, gamma-seminoprotein. FEBS Lett 1987;225:168-72.
4. Yu H, Diamandis EP, Levesque M, Sismondi P, Zola P, Katsaros D. Ectopic production of prostate specific antigen by a breast tumor metastatic to the ovary. J Clin Lab Anal 1994;8:251-3.
5. Diamandis EP, Yu H, Sutherland DJ. Detection of prostate-specific antigen immunoreactivity in breast tumors. Breast Cancer Res Treat 1994;32:301-10.
6. Yu H, Diamandis EP, Sutherland DJ. Immunoreactive prostate-specific antigen levels in female and male breast tumors and its association with steroid hormone receptors and patient age. Clin Biochem 1994;27:75-9.
7. Levesque M, Hu H, D'Costa M, Diamandis EP. Prostate-specific antigen expression by various tumors. J Clin Lab Anal 1995;9:123-8.
8. Diamandis EP. New diagnostic applications and physiological functions of prostate specific antigen. Scand J Clin Lab Invest Suppl 1995;221:105-12.
9. Kratz F, Mansour A, Soltau J, Warnecke A, Fichtner I, Unger C, Drevs J. Development of albumin-binding doxorubicin prodrugs that are cleaved by prostate-specific antigen. Arch Pharm (Weinheim) 2005;338:462-72.
10. Kratz F, Mueller-Driver R, Hofmann I, Drevs J, Unger C. A novel macromolecular prodrug concept exploiting endogenous serum albumin as a drug carrier for cancer chemotherapy. J Med Chem 2000;43:1253-6.
11. Kratz F, Warnecke A, Scheuermann K, Stockmar C, Schwab J, Lazar P, Druckes P, Esser N, Drevs J, Rognan D, Bissantz C, Hinderung C, et al. Probing the cysteine-34 position of endogenous serum albumin with thiol-binding doxorubicin derivatives: improved efficacy of an acid-sensitive doxorubicin derivative with specific albumin-binding properties compared to that of the parent compound. J Med Chem 2002;45:5523-33.
12. Mansour AM, Drevs J, Esser N, Hamada FM, Badary OA, Unger C, Fichtner I, Kratz F. A new approach for the treatment of malignant melanoma: enhanced antitumor efficacy of an albumin-binding doxorubicin prodrug that is cleaved by matrix metalloproteinase 2. Cancer Res 2003;63:4062-6.
13. Chung DE, Kratz F. Development of a novel albumin-binding prodrug that is cleaved by urokinase-type-plasminogen activator (uPA). Bioorg Med Chem Lett 2006;16:5157-63.
14. El Hilali N, Rubio N, Blanco J. Different effect of paclitaxel on primary tumor mass, tumor cell contents, and metastases for four experimental human prostate tumors expressing luciferase. Clin Cancer Res 2005;11:1253-8.
15. Bornmann C, Graeser R, Esser N, Zirolr V, Jantscheff P, Keck T, Unger C, Hopt UT, Adam U, Schaechtele C, Massing U, von Dobschuetz E. A new liposomal formulation of Gemcitabine is active in an orthotopic mouse model of pancreatic cancer accessible to bioluminescence imaging. Cancer Chemother. Pharmacol., 2007, in press (epub available).
16. Sato N, Gleave ME, Bruchovsky N, Rennte PS, Beraldi E, Sullivan LD. A metastatic and androgen-sensitive human prostate cancer model using intraprostatic inoculation of LNCaP cells in SCID mice. Cancer Res 1997;57:1584-9.
17. Stephenson RA, Dinney CP, Gohji K, Ordonez NG, Killion JJ, Fidler IJ. Metastatic model for human prostate cancer using orthotopic implantation in nude mice. J Natl Cancer Inst 1992;84:951-7.
18. Workman P, Balmain A, Hickman JA, McNally NJ, Rohas AM, Mitchison NA, Pierrepoint CG, Raymond R, Rowlatt C, Stephens TC, et al. UKCCCR guidelines for the welfare of animals in experimental neoplasia. Lab Anim 1988;22:195-201.
19. Kratz F, Warnecke A, Schmid B, Chung DE, Gitzel M. Prodrugs of anthracyclines in cancer chemotherapy. Curr Med Chem 2006,13, 477-523.
20. Kratz F. DOXO-EMCH (INNO-206), the first albumin-binding pro-drug of doxorubicin to enter clinical trials. Expert Opin Investig Drugs 2007;16:855-866.
21. Maeda H, Wu J, Sawa T, Matsumura Y, Hori K. Tumor vascular permeability and the EPR effect in macromolecular therapeutics: a review. J Controlled Release 2000;65:271-84.
22. Denmeade SR, Nagy A, Gao J, Lilja H, Schally AV, Isaacs JT. Enzymatic activation of a doxorubicin-peptide prodrug by prostate-specific antigen. Cancer Res 1998;58:2537-40.
23. Khan SR, Denmeade SR. In vivo activity of a PSA-activated doxorubicin prodrug against PSA-producing human prostate cancer xenografts. Prostate 2000;45:80-3.
24. DeFeo-Jones D, Garsky VM, Wong BK, Feng DM, Bolyar T, Haskell K, Kiefer DM, Leander K, McAvoy E, Lumma P, Wai J, Senderak ET, et al. A peptide-doxorubicin 'prodrug' activated by prostate-specific antigen selectively kills prostate tumor cells positive for prostate-specific antigen in vivo. Nat Med 2000;6:1248-52.