Acetals as pH-sensitive linkages for drug delivery

Bioconjugate Chemistry

Volumn 15, Issue 6, 2004, Pages 1254-1263

  Gillies, Elizabeth R ^a   Goodwin, Andrew P ^a   Fréchet, Jean M J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CONTROLLED DRUG DELIVERY; HYDROLYSIS; PH; STRUCTURE (COMPOSITION); SYNTHESIS (CHEMICAL); TARGETED DRUG DELIVERY;

ACIDIC PH; DRUG MOLECULES; ENDOSOMES; HYDROLYSIS RATE; INFLAMMATORY TISSUES; MODEL DRUGS; PH SENSITIVE; PRIMARY ALCOHOLS; SECONDARY ALCOHOLS; TUMOUR TISSUE;

PH SENSORS;

ACETAL DERIVATIVE; POLYMER;

ACIDITY; CONFERENCE PAPER; DRUG CONJUGATION; DRUG DELIVERY SYSTEM; DRUG HALF LIFE; DRUG HYDROLYSIS; DRUG STRUCTURE; DRUG TARGETING; ENDOSOME; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFLAMMATION; LYSOSOME; MICELLE; PH; TUMOR;

EID: 9244219656     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc049853x     Document Type: Conference Paper

References (39)

1. Engin, K., Leeper, D. B., Cater, J. R., Thistlethwaite, A. J., Tupchong, L., and McFarlane, J. D. (1995) Extracellular pH distribution in human tumors. Int. J. Hypertherm. 11, 211-216.
2. Ojugo, A. S. E., Mesheehy, P. M. J., McIntyre, D. J. O., McCoy, C., Stubbs, M., Leach, M. O., Judson, I. R., and Griffiths, J. R. (1999) Measurement of the extracellular pH of solid tumors in mice by magnetic resonance spectroscopy: a comparison of exogenous 19F and 31P probes. NMR Biomed. 12, 495-504.
3. Gallin, J. I., Goldstein, I. M., and Snyderman, R. E. (1992) Inflammation - basic principles and clinical correlates, 2nd ed., pp 511-533.
4. Mellman, I., Fuchs, R., and Helenius, A. (1986) Acidification of the endocytic and exocytic pathways. Annu. Rev. Biochem. 55, 773-700.
5. Duncan, R. (2003) The dawning era of polymer therapeutics. Nature Rev. 2, 347-360.
6. Murthy, N., Xu, M., Schuck, S., Kunisawa, J., Shastri, N., and Fréchet, J. M. J. (2003) A macromolecular delivery vehicle for protein-based vaccines: acid-degradable protein-loaded microgels. Proc. Nat. Acad. Sci. 100, 4995-5000.
7. Davis, M. (2002) Nonviral gene delivery systems. Curr. Opin. Biotechnol. 13, 128-131.
8. Wiethoff, C. M., and Middaugh, C. R. (2003) Barriers to Nonviral Gene Delivery. J. Pharm. Sci. 92, 203-217.
9. Greenfield, R. S., Kaneko, T., Daues, A., Edson, M. A., Fitzgerald, K. A., Olech, L. J., Grattan, A., Spitalny, G. L., and Brawslawsky, G. R. (1990) In vitro evaluation of adriamycin immunoconjugates synthesized using an acid-sensitive hydrazone linker. Cancer Res. 50, 6600.
10. Kaneko, T., Willner, D., Monkovic, I., Knipe, J. O., Braslawsky, G. R., Greenfield, R. S., and Dolatrai, M. V. (1991) New hydrazone derivatives of Adriamycin and their immunoconjugates - a correlation between acid stability and cytotoxicity. Bioconjugate Chem. 2, 133-141.
11. Etrych, T., Jelínková, M., Rihová, B., and Ulbrich, K. (2001) New HPMA copolymers containing doxorubicin bound via pH-sensitive linkage: synthesis and preliminary in vitro and in vivo biological properties. J. Controlled Release 73, 89-102.
12. Kruger, M., Beyer, U., Schumacher, P., Unger, C., Zahn, H., and Kratz, F. (1997) Synthesis and stability of four maleimide derivatives of the anticancer drug doxorubicin for the preparation of chemoimmunoconjugates. Chem. Pharm. Bull. 45, 399-401.
13. Rodrigues, P. C. A., Beyer, U., Schumacher, P., Roth, T., Fiebig, H. H., Unger, C., Messori, L., Orioli, P., Paper, D. H., Mulhaupt, R., and Kratz, F. (1999) Acid-sensitive polyethylene glycol conjugates of doxorubicin: preparation, in vitro efficacy and intracellular distribution. Bioorg. Med. Chem. 7, 2517-2524.
14. Padilla De Jesús, O. L., Ihre, H. R., Gagne, L., Fréchet, J. M. J., and Szoka, F. C. J. (2002) Polyester Dendritic Systems for Drug Delivery Applications: In Vitro and In Vivo Evaluation. Bioconjugate Chem. 13, 453-461.
15. Shen, W. C., and Ryser, H. J. P. (1981) cis-Aconityl spacer between daunomycin and macromolecular carriers - a model of pH-sensitive linkage releasing drug from a lysosomotropic conjugate. Biochem. Biophys. Res. Commun. 102, 1048-1054.
16. Choi, W. M., Kopecková, P., Minko, T., and Kopecek, J. (1999) Synthesis of HPMA copolymer containing adriamycin bound via and acid-labile spacer and its activity toward human ovarian carcinoma cells. J. Bioact. Compat. Polym. 14, 447-456.
17. Hudecz, F., Ross, H., Price, M. R., and Baldwin, R. W. (1990) Immunoconjugate design: a predictive approach for coupling of daunomycin to monoclonal antibodies. Bioconjugate Chem. 1, 197-204.
18. Patel, V. F., Hardin, J. N., Mastro, J. M., Law, K. L., Zimmerman, J. L., Ehlhardt, W. J., Woodland, J. M., and Starling, J. J. (1996) Novel acid labile COL1 trityl-linked difluoronucleoside immunoconjugate: synthesis, characterization, and biological activity. Bioconjugate Chem. 7, 497-510.
19. Patel, V. F., Hardin, J. N., Starling, J. J., and Mastro, J. M. (1995) Novel trityl linked drug immunoconjugates for cancer-therapy. Bioorg. Med. Chem. Lett. 5, 507-512.
20. Heller, J., Barr, J., Ng, S. Y., Abdellauoi, K. S., and Gurny, R. (2002) Poly(ortho esters): synthesis, characterization, properties and uses. Adv. Drug Delivery Rev. 54, 1015-1039.
21. Guo, X., and Szoka, F. C. J. (2001) Steric stabilization of fusogenic liposomes by a low-pH sensitive PEG-diortho ester-lipid conjugate. Bioconjugate Chem. 12, 291-300.
22. Srinivasachar, K., and Neville, D. M. (1989) New protein cross-linking reagents that are cleaved by mild acid. Biochemistry 28, 2501-2509.
23. Fife, T., and Jao, L. (1965) Substituent effects in acetal hydrolysis. J. Org. Chem. 30, 1492-1495.
24. Neville, D. M., Srinivasachar, K., Stone, R., and Scharff, J. (1989) Enhancement of immunotoxin efficacy by acid-cleavable cross-linking agents utilizing diphtheria-toxin and toxin mutants. J. Biol. Chem. 264, 14653-14661.
25. Tietze, L. F., Neumann, M., Möllers, T., Fischer, R., Glüsenkamp, K.-H., Rajewsky, M. F., and Jähde, E. (1989) Proton-mediated liberation of aldophosphamide from a nontoxic prodrug: a strategy for tumor-selective activation of cytocidal drugs. Cancer Res. 49, 4179-4184.
26. Jähde, E., Glüsenkamp, K.-H., Klünder, I., Hülser, D. F., Tietze, L. F., and Rajewsky, M. F. (1989) Hydrogen ion-mediated enhancement of cytotoxicity of bis-chloroethylating drugs in rat mammary carcinoma cells in vitro. Cancer Res. 49, 4179-4184.
27. Tietze, L. F., Heller, M., Fischer, R., Lögers, M., Jähde, E., Glüsenkamp, K.-H., and Rajewsky, M. F. (1990) Development of tailor-made cytostatics activable by acid-catalyzed hydrolysis for selective tumor therapy. Angew. Chem., Int. Ed. Engl. 29, 782-783.
28. Tan, H., and Espenson, J. H. (1999) Regioselective hydroxylactonization of γ,δ-unsaturated carboxylic acids with hydrogen peroxide catalyzed by methyltrioxorhenium. J. Mol. Catal. A 142, 333-338.
29. Mihelic, D., Jakse, R., Svete, J., Stanovnik, B., and Grdadolnik, S. G. (2001) Synthesis of (S)-3-heteroaryl-2-hydroxy-1-propylbenzoates by "ring switching" methodology. J. Heterocycl. Chem. 38, 1307-1312.
30. Lee-Ruff, E., Xi, F., and Qie, J. H. (1996) Enantioselective preparation of 2′,3′-dideoxynucleosides and their analogues from ring expansion of cyclobutanones. 2. Synthesis of 2′,3′-dideoxyribosides and (1S, 3R)-1-amino-3-(hydroxymethyl)-cyclopentane. J. Org. Chem. 61, 1547-1550.
31. Coulson, R. D. (1964) New synthesis of methyl ketones. Tetrahedron Lett. 3323-3326.
32. 4 metabolites. Tetrahedron Lett. 43, 6063-6066.
33. Loth, H., and Foltin, U. (1998) Methoxy-polyethoxy side-chain silastomers as materials controlling drug delivery by diffusion flux. J. Controlled Release 54, 273-282.
34. Albericio, F., Kneib-Cordonier, N., Biancalana, S., Gera, L., Masada, R. I., Hudson, D., and Barany, G. (1990) Preparation and application of the 5-(4-(9-fluorenylmethyloxycarbonyl)aminomethyl-3,5-dimethoxyphenoxy)-valeric acid (PAL) handle for the solid-phase synthesis of C-terminal peptide amides under mild conditions. J. Org. Chem. 55, 3730-3743.
35. Greene, T. W., and Wuts, P. G. M. (1999) Protective groups in organic synthesis, 3rd ed., pp 57-58.
36. Kruse, C. G., Jonkers, F. L., Dert, V., and van der Gen, A. (1979) Synthetic applications of 2-chlorotetrahydrofuran: protection of alcohols as tetrahydro-2-furanyl (THF) ethers. Recl. Trav. Chim. Pays-Bas. 98, 371-380.
37. Greenwald, R. B., Conover, C. D., and Choe, Y. H. (2000) Poly(ethylene glycol) conjugated drugs and prodrugs: a comprehensive review. Crit. Rev. Ther. Drug 17, 101-161.
38. Kreevoy, M. M., and Taft, R. W. J. (1955) The evaluation of inductive and resonance effects on reactivity. I. Hydrolysis rates of acetals of nonconjugated aldehydes and ketones. J. Am. Chem. Soc. 77, 5590-5595.
39. Gillies, E. R., and Fréchet, J. M. J. (2003) A new approach towards acid sensitive copolymer micelles for drug delivery. Chem. Commun. 1640-1641.