Reduction-sensitive tioguanine prodrug micelles

Molecular Pharmaceutics

Volumn 9, Issue 10, 2012, Pages 2812-2818

  Van Der Vlies, André J ^a   Hasegawa, Urara ^a   Hubbell, Jeffrey A ^a  

^a EPFL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CYSTEINE; POLY(ETHYLENE GLYCOL) BL POLY(PROPYLENE SULFIDE); POLYMER; PRODRUG; TIOGUANINE; UNCLASSIFIED DRUG; WATER;

AQUEOUS SOLUTION; ARTICLE; DISULFIDE BOND; DRUG RELEASE; ENDOCYTOSIS; MICELLE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING METATHESIS POLYMERIZATION;

EID: 84870216836     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp3001183     Document Type: Article

References (38)

1. Elion, G. B. Symposium on immunosuppressive drugs. Biochemistry and pharmacology of purine analogues Fed. Proc. 1967, 26 (3) 898-904
2. Elion, G. B. The Purine Path to Chemotherapy (Nobel Lecture) Angew. Chem., Int. Ed. Engl. 1989, 28 (7) 870-878
3. Ling, Y. H.; Chan, J. Y.; Beattie, K. L.; Nelson, J. A. Consequences of 6-Thioguanine Incorporation into DNA on Polymerase, Ligase, and Endonuclease Reactions Mol. Pharmacol. 1992, 42 (5) 802-807
4. Christie, N. T.; Drake, S.; Meyn, R. E.; Nelson, J. A. 6-Thioguanine-induced DNA Damage as a Determinant of Cytotoxicity in Cultured Chinese Hamster Ovary Cells Cancer Res. 1984, 44 (9) 3665-3671
5. Parker, W. B. Enzymology of Purine and Pyrimidine Antimetabolites Used in the Treatment of Cancer Chem. Rev. 2009, 109 (7) 2880-2893
6. Ootsu, K.; Matsumoto, T.; Aki, O.; Nakagawa, Y.; Sirakawa, K. Antitumor and immunosuppressive activities of alkyldithiopurine derivatives Gann 1972, 63 (5) 523-529
7. Elfarra, A. A.; Duescher, R. J.; Hwang, I. Y.; Sicuri, A. R.; Nelson, J. A. Targeting 6-thioguanine to the kidney with S-(guanin-6-yl)-L-cysteine J. Pharmacol. Exp. Ther. 1995, 274 (3) 1298-1304
8. Krenitsky, T. A.; Hall, W. W.; Selph, J. L.; Truax, J. F.; Vinegar, R. Nucleosides of azathioprine and thiamiprine as antiarthritics J. Med. Chem. 1989, 32 (7) 1471-1475
9. Kataoka, T.; Akahori, Y.; Sakurai, Y. 6-Mercaptopurine-induced potentiation of active immunotherapy in L1210-bearing mice treated with concanavalin A-bound leukemia cell vaccine Cancer Res. 1984, 44 (2) 519-524
10. Tomalik-Scharte, D.; Lazar, A.; Fuhr, U.; Kirchheiner, J. The clinical role of genetic polymorphisms in drug-metabolizing enzymes Pharmacogenomics J. 2008, 8 (1) 4-15
11. Aarbakke, J.; Janka-Schaub, G.; Elion, G. B. Thiopurine biology and pharmacology Trends Pharmacol. Sci. 1997, 18 (1) 3-7
12. Rautio, J.; Kumpulainen, H.; Heimbach, T.; Oliyai, R.; Oh, D.; Jarvinen, T.; Savolainen, J. Prodrugs: design and clinical applications Nat. Rev. Drug Discovery 2008, 7 (3) 255-270
13. Ringsdorf, H. Structure and properties of pharmacologically active polymers J. Polym. Sci.: Polym. Symp. 1975, 51 (1) 135-153
14. 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 (1-2) 271-284
15. Reddy, S. T.; van der Vlies, A. J.; Simeoni, E.; Angeli, V.; Randolph, G. J.; O'Neil, C. P.; Lee, L. K.; Swartz, M. A.; Hubbell, J. A. Exploiting lymphatic transport and complement activation in nanoparticle vaccines Nat. Biotechnol. 2007, 25 (10) 1159-1164
16. Reddy, S. T.; Rehor, A.; Schmoekel, H. G.; Hubbell, J. A.; Swartz, M. A. In vivo targeting of dendritic cells in lymph nodes with poly(propylene sulfide) nanoparticles J. Controlled Release 2006, 112 (1) 26-34
17. Napoli, A.; Valentini, M.; Tirelli, N.; Muller, M.; Hubbell, J. A. Oxidation-responsive polymeric vesicles Nat. Mater. 2004, 3 (3) 183-189
18. Cerritelli, S.; O'Neil, C. P.; Velluto, D.; Fontana, A.; Adrian, M.; Dubochet, J.; Hubbell, J. A. Aggregation Behavior of Poly(ethylene glycol-bl-propylene sulfide) Di- and Triblock Copolymers in Aqueous Solution Langmuir 2009, 25 (19) 11328-11335
19. O'Neil, C. P.; Suzuki, T.; Demurtas, D.; Finka, A.; Hubbell, J. A. A Novel Method for the Encapsulation of Biomolecules into Polymersomes via Direct Hydration Langmuir 2009, 25 (16) 9025-9029
20. Lloyd, J. B. Disulphide reduction in lysosomes. The role of cysteine Biochem. J. 1986, 237 (1) 271-272
21. Pisoni, R. L.; Acker, T. L.; Lisowski, K. M.; Lemons, R. M.; Thoene, J. G.; Cysteine-Specific Lysosomal, A Transport-System Provides a Major Route for the Delivery of Thiol to Human Fibroblast Lysosomes-Possible Role in Supporting Lysosomal Proteolysis J. Cell Biol. 1990, 110 (2) 327-335
22. Meng, F.; Hennink, W. E.; Zhong, Z. Reduction-sensitive polymers and bioconjugates for biomedical applications Biomaterials 2009, 30 (12) 2180-2198
23. Doerr, I. L.; Wempen, I.; Clarke, D. A.; Fox, J. J. Thiation of Nucleosides. III. Oxidation of 6-Mercaptopurines1 J. Org. Chem. 1961, 26 (9) 3401-3409
24. Chávez-Gil, T. E.; Meléndez, E. Synthesis, spectroscopic and electrochemical characterization of water soluble [(5-C5H5) 2Mo(thionucleobase/thionucleoside)]Cl2 complexes Inorg. Chim. Acta 2004, 357 (4) 1092-1102
25. Segura, T.; Hubbell, J. A. Synthesis and in Vitro Characterization of an ABC Triblock Copolymer for siRNA Delivery Bioconjugate Chem. 2007, 18 (3) 736-745
26. Nishikawa, M.; Takakura, Y.; Hashida, M. Pharmacokinetic evaluation of polymeric carriers Adv. Drug Delivery Rev. 1996, 21 (2) 135-155
27. Inomata, M.; aFukuoka, F.; Hoshi, A.; Kuretani, K.; Saneyoshi, M. Antitumor activity of alkyldisulfide derivatives of 6 mercaptopurines against L-1210 leukemia J. Pharmacobiodyn. 1981, 4 (12) 928-932
28. Inomata, M.; Fukuoka, F.; Hoshi, A.; Kuretani, K.; Saneyoshi, M. Structure-antitumor activity relationship of purin-6-yl alkyl disulfides J. Pharmacobiodyn. 1981, 4 (1) 58-64
29. Gunnarsdottir, S.; Elfarra, A. A. Cytotoxicity of the novel glutathione-activated thiopurine prodrugs cis-AVTP [cis-6-(2-acetylvinylthio) purine] and trans-AVTG [trans-6-(2-acetylvinylthio)guanine] results from the National Cancer Institute's anticancer drug screen Drug Metab. Dispos. 2004, 32 (3) 321-327
30. Gunnarsdottir, S.; Rucki, M.; Elfarra, A. A. Novel glutathione-dependent thiopurine prodrugs: evidence for enhanced cytotoxicity in tumor cells and for decreased bone marrow toxicity in mice J. Pharmacol. Exp. Ther. 2002, 301 (1) 77-86
31. Thomson, P.; Naylor, M. A.; Stratford, M. R. L.; Lewis, G.; Hill, S.; Patel, K. B.; Wardman, P.; Davis, P. D. Hypoxia-driven elimination of thiopurines from their nitrobenzyl prodrugs Bioorg. Med. Chem. Lett. 2007, 17 (15) 4320-4322
32. Kirkpatrick, D. L. Modification of Antitumor Disulfide Cytotoxicity by Glutathione Depletion in Murine Cells Cancer Res. 1987, 47 (16) 4391-4395
33. Saneyoshi, M.; Inomata, M.; Sekine, T.; Hoshi, A.; Fukuoka, F. Synthetic nucleosides and nucleotides. X. Synthesis and biological activities of several purin-6-yl benzyl disulfides and their ribonucleosides J. Pharmacobiodyn. 1978, 1 (3) 168-174
34. Gunnarsdottir, S.; Elfarra, A. A. Glutathione-dependent metabolism of cis-3-(9H-purin-6-ylthio)acrylic acid to yield the chemotherapeutic drug 6-mercaptopurine: evidence for two distinct mechanisms in rats J. Pharmacol. Exp. Ther. 1999, 290 (3) 950-957
35. Eklund, B. I.; Gunnarsdottir, S.; Elfarra, A. A.; Mannervik, B. Human glutathione transferases catalyzing the bioactivation of anticancer thiopurine prodrugs Biochem. Pharmacol. 2007, 73 (11) 1829-1841
36. Choe, Y. H.; Greenwald, R. B. Preparation of polymeric thiol-linked prodrugs employing benzyl elimination systems. WO2003041642A2, 2003.
37. Hermanson, G. T. Bioconjugate techniques; Elsevier: 2008.
38. Kellogg, B. A.; Garrett, L.; Kovtun, Y.; Lai, K. C.; Leece, B.; Miller, M.; Payne, G.; Steeves, R.; Whiteman, K. R.; Widdison, W.; Xie, H.; Singh, R.; Chari, R. V.; Lambert, J. M.; Lutz, R. J. Disulfide-linked antibody-maytansinoid conjugates: optimization of in vivo activity by varying the steric hindrance at carbon atoms adjacent to the disulfide linkage Bioconjugate Chem. 2011, 22 (4) 717-727