Poly(L-glutamic acid)-anticancer drug conjugates

Advanced Drug Delivery Reviews

Volumn 54, Issue 5, 2002, Pages 695-713

  Li, Chun ^a  

^a UNIVERSITY OF TEXAS MD ANDERSON CANCER CENTER   (United States)

Author keywords

Anticancer drugs; Drug targeting; Enhanced permeability and retention effect; Poly(L glutamic acid); Polymer drug conjugates

Indexed keywords

CHEMOTHERAPY; MEDICAL IMAGING; POLYMERS; TOXICITY;

ANTICANCER DRUG CONJUGATES;

DRUG DOSAGE;

ANTINEOPLASTIC AGENT; CAMPTOTHECIN POLYGLUTAMIC ACID CONJUGATE; CYCLOPHOSPHAMIDE POLYGLUTAMIC ACID CONJUGATE; CYTARABINE POLYGLUTAMIC ACID CONJUGATE; DAUNORUBICIN POLYGLUTAMIC ACID CONJUGATE; DOXORUBICIN POLYGLUTAMIC ACID CONJUGATE; MELPHALAN POLYGLUTAMIC ACID CONJUGATE; MITOMYCIN C POLYGLUTAMIC ACID CONJUGATE; PACLITAXEL; PACLITAXEL POLYGLUTAMIC ACID CONJUGATE; POLYGLUTAMIC ACID; UNCLASSIFIED DRUG; URACIL POLYGLUTAMIC ACID CONJUGATE; URIDINE POLYGLUTAMIC ACID CONJUGATE;

ANTINEOPLASTIC ACTIVITY; BIOCOMPATIBILITY; BIODEGRADABILITY; CANCER; CANCER CHEMOTHERAPY; CELL MEMBRANE TRANSPORT; CLINICAL TRIAL; DRUG DELIVERY SYSTEM; DRUG EFFECT; DRUG HALF LIFE; DRUG MECHANISM; DRUG SYNTHESIS; HUMAN; NONHUMAN; PRIORITY JOURNAL; REVIEW;

ANTHRACYCLINES; ANTIMETABOLITES; ANTINEOPLASTIC AGENTS; CAMPTOTHECIN; CLINICAL TRIALS; DNA; DRUG CARRIERS; DRUG DELIVERY SYSTEMS; HUMANS; NEOPLASMS; PACLITAXEL; POLYGLUTAMIC ACID;

EID: 0037072529     PISSN: 0169409X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0169-409X(02)00045-5     Document Type: Review

References (82)

1. Ringsdorf H. Structure and properties of pharmacologically active polymers. J. Polym. Sci. Symp. 51:1975;135-153.
2. Maeda H., Matsumura Y. Tumoritropic and lymphotropic principles of macromolecular drugs. Crit. Rev. Ther. Drug Carrier Syst. 6:1989;193-210.
3. Gerlowski L.E., Jain R.K. Microvascular permeability of normal and neoplastic tissues. Microvasc. Res. 31:1986;288-305.
4. Jain R.K. The next frontier of molecular medicine: delivery of therapeutics. Nature Med. 4:1998;655-657.
5. Roberts W.G., Palade G. Neovasculature induced by vascular endothelial growth factor is fenestrated. Cancer Res. 57:1997;765-772.
6. Fuertges F., Abuchowski A. The clinical efficacy of poly(ethylene glycol)-modified proteins. J. Control. Release. 11:1990;139-148.
7. Maeda H. SMANCS and polymer-conjugated macromolecular drugs: advantages in cancer chemotherapy. Adv. Drug Deliv. Rev. 6:1991;181-193.
8. Putnam D., Kopecek J. Polymer conjugates with anticancer activity. Adv. Polym. Sci. 122:1995;55-123.
9. Duncan R., Spreafico F. Polymer conjugates. Pharmacokinetic considerations for design and development. Clin. Pharmacokinet. 27:1994;290-306.
10. Drobnik J., Rypacek F. Soluble synthetic polymers in biological systems. Adv. Polym. Sci. 57:1984;2-50.
11. Idelson M., Blout E.R. High molecular weight poly(α-L-glutamic acid): preparation and physical rotation changes. J. Am. Chem. Soc. 80:1958;4631-4634.
12. Hanby W.E., Waley S.G., Watson J. Synthetic polypeptides. Part II. Polyglutamic acid. J. Chem. Soc. 1950;3239-3249.
13. Palacios P., Bussat P., Bichon D. Novel solid-phase synthesis of thio-terminated-poly(α-amino acid)-drug conjugate. J. Biochem. Biophys. Met. 23:1991;67-72.
14. Brack A., Spach G. New example of helical polymerization. Nature (Phys. Sci.). 229:1971;124-125.
15. Block H. Poly(γ-benzyl-L-glutamate) and Other Glutamic Acid Containing Polymers. 1983;Gordon and Breach, New York.
16. Peggion E., Scoffone E., Cosani A., Portolan A. Polymerization of γ-benzyl-L-glutamate N-carboxyanhydride: effects of conditions of polymer precipitation on the molecular weight distribution. Biopolymers. 4:1966;695-704.
17. Fuller W.D., Verlander M.S., Goodman M. A procedure for the facile synthesis of amino acid N-carboxyanhydrides. Biopolymers. 15:1976;1869-1871.
18. Katakai R., Iisuka Y. An improved method for the synthesis of N-carboxy α-amino acid anhydrides using trichloromethyl chloroformate. J. Org. Chem. 50:1985;715-716.
19. Deming T. Facile synthesis of block copolypeptides of defined architecture. Nature. 390:1997;386-389.
20. Zhang G., Fournier M.J., Mason T.L., Tirrell D.A. Biological synthesis of monodisperse derivatives of poly(α,L-glutamic acid): model rodlike polymers. Macromolecules. 25:1992;3601-3603.
21. Yu S.M., Conticello V.P., Zhang G., Kayser C., Fournier M.J., Mason T.L., Tirrell D.A. Smectic ordering in solutions and films of a rod-like polymer owing to monodispersity of chain length. Nature. 389:1997;167-170.
22. Leung D.W., Pietz G., Tompkins C., Bergman P. Expression of fusion proteins composed of polyglutamic acid linked to interferon or granulocyte colony stimulating factors. 5th International Symposium on Polymer Therapeutics: From Laboratory to Clinical Practice, Cardiff, UK, Jan. 3-5, 2002, p. 9.
23. Birrer G.A., Cromwick A.-M., Gross R.A. γ-Poly(glutamic acid) formation by Bacillus licheniformis 9945a: physiological and biochemical studies. Int. J. Biol. Macromol. 16:1994;265-275.
24. Weber J. Poly(γ-glutamic acid)s are the major constituents of nematocysts in Hydra (Hydrozoa, Cnidaria). J. Biol. Chem. 265:1990;9664-9669.
25. Morcellet M., Loucheux C. Viscosity/molecular weight relationship of poly(α-L-glutamic acid) in water and in water/dioxane mixtures. Biopolymers. 15:1976;1857-1862.
26. Rao S.P., Miller W.G. Effect of residual side chain blocking groups and side chain charge on polypeptide conformation in aqueous solution. Biopolymers. 12:1973;835-843.
27. Dupta P.K., Gillespie D., Hammons K., Haney M.A. Characterization of polyamino acids by use of GPC-viscometry technology. J. Pharm. Biomed. Anal. 9:1991;865-870.
28. Tsutsumi A., Perly B., Forchioni A., Chachaty C. A magnetic resonance study of the segmental motion and local conformations of poly(L-glutamic acid) in aqueous solutions. Macromolecules. 11:1978;977-986.
29. Dolnik V., Novotny M., Chmelik J. Electronmigration behavior of poly-(L-glutamate) conformers in concentrate polyacrylamide gels. Biopolymers. 33:1993;1299-1306.
30. Miller W.G. Degradation of poly(α-L-glutamic acid). I. Degradation of high molecular weight PGA by papain. J. Am. Chem. Soc. 83:1961;259-265.
31. Miller W.G. Degradation of synthetic polypeptides. II. Degradation of poly-α-L-glutamic acid by proteolytic enzymes in 0.20 M sodium chloride. J. Am. Chem. Soc. 86:1964;3913-3918.
32. 5-(2-hydroxylethyl)-L-glutamine and L-glutamic acid homopolymers and copolymers by papain. Int. J. Biol. Macromol. 12:1990;241-246.
33. Hayashi T., Iwatsuki M. Biodegradation of copoly(L-aspartic acid/L-glutamic acid) in vitro. Biopolymer. 29:1990;549-557.
34. Chiu H.-C., Kopeckova P., Deshmane S.S., Kopecek J. Lysosomal degradability of poly(alpha-amino acids). J. Biomed. Mater. Res. 34:1997;381-392.
35. Hoes C.J.T., Potman W., van Heeswijk W.A.R., Mud J., de Grooth B.G., Greve J., Feijen J. Optimization of macromolecular prodrugs of the antitumor antibiotic Adriamycin. J. Control. Release. 2:1985;205-213.
36. McCormick-Thomson L.A., Duncan R. Poly(amino acid) copolymers as a potential soluble drug delivery system. 1. Pinocytotic uptake and lysosomal degradation measured in vitro. J. Bioact. Compat. Polym. 4:1989;242-251.
37. Kishore B.K., Lambricht P., Laurent G., Maldague P., Wagner R., Tulkens P.M. Mechanism of protection afforded by polyaspartic acid against gentamicin-induced phospholipidosis. II. Comparative in vitro and in vivo studies with poly-L-aspartic, poly-L-glutamic and poly-D-glutamic acids. J. Pharmacol. Exp. Ther. 255:1990;875-885.
38. Singer J.W., Nudelman E., de Vries P., Shaffer S. Metabolism of poly-L-glutamic acid (PG) paclitaxel (CT-2103): intratumoral peptide cleavage followed by esterolysis. 5th International Symposium on Polymer Therapeutics: From Laboratory to Clinical Practice, Cardiff, UK, Jan. 3-5, 2002, p. 52.
39. Akamatsu K., Yamasaki Y., Nishikawa M., Takakura Y., Hashida M. Development of a hepatocyte-specific prostaglandin E1 polymeric prodrug and its potential for preventing carbon tetrachloride-induced fulminant hepatitis in mice. J. Pharmacol. Exp. Ther. 290:1999;1242-1249.
40. McCormick-Thomson L.A., Sgouras D., Duncan R. Poly(amino acid) copolymers as a potential soluble drug delivery system. 2. Body distribution and preliminary biocompatibility testing in vitro and in vivo. J. Bioact. Compat. Polym. 4:1989;252-268.
41. 5-hydroxyethyl-L-glutamine-co-L-glutamic acid copolymers in rats. J. Bioact. Compat. Polym. 8:1993;51-68.
42. Sumi H., Kawabe K., Nakajima N. Effect of various polyamino acids and D- and L-amino acids on the blood fibrinolytic system. Comp. Biochem. Physiol. 102B:1992;159-162.
43. Li C., Yu D.F., Newman R.A., Cabral F., Stephens L.C., Hunter N., Milas L., Wallace S. Complete regression of well-established tumors using novel water-soluble poly(L-glutamic acid)-paclitaxel conjugates. Cancer Res. 58:1998;2404-2409.
44. Li C., Price J.E., Milas L., Hunter N.R., Ke S., Yu D.F., Charnsagavej C., Wallace S. Antitumor activity of poly(L-glutamic acid)-paclitaxel on syngeneic and xenografted tumors. Clin. Cancer Res. 5:1999;891-897.
45. Kenny A.D. Evaluation of sodium poly(α-L-glutamic acid) as a plasma expander. Proc. Soc. Exp. Biol. Med. 100:1959;778-780.
46. Hoes C.J.T., Grootoonk J., Duncan R., Hume I.C., Bhakoo M., Bouma J.M.W., Feijen J. Biological properties of Adriamycin bound to biodegradable polymeric carriers. J. Control. Release. 23:1993;37-54.
47. Kato Y., Saito M., Fukushima H., Takeda Y., Hara T. Antitumor activity of 1-β-D-arabinofuranosylcytosine conjugated with polyglutamic acid and its derivative. Cancer Res. 44:1984;25-30.
48. Hurwitz E., Wilchek M., Pitha J. Soluble macromolecules as carriers for daunorubicin. J. Appl. Biochem. 2:1980;25-35.
49. Marre A.D., Soyez H., Schacht E. Synthesis of macromolecular mitomycin C derivatives. J. Control. Release. 32:1994;129-137.
50. Nichifor M., Schacht E.H., Seymour L.W. Macromolecular prodrug of 5-fluorouracil. 2. Enzymatic degradation. J. Control. Release. 39:1996;79-92.
51. van Heeswijk W.A.R., Hoes C.J.T., Stoffer T., Eenink M.J.D., Potman W., Feijen J. The synthesis and characterization of polypeptide-adriamycin conjugates and its complexes with Adriamycin. Part 1. J. Control. Release. 1:1985;301-315.
52. Zunino F., Pratesi G., Micheloni A. Poly(carboxylic acid) polymers as carriers for anthracyclines. J. Control. Release. 10:1989;65-73.
53. Mochizuki E., Inaki Y., Takemoto K. Synthesis of poly-L-glutamates containing 5-substituted uracil moieties. Nucleic Acids Res. Symp. 16:1985;121-124.
54. Batz H.G., Ringsdorf H., Ritter H. Pharmacologically active polymers. 7. Cyclophosphamide- and steroid hormone-containing polymers as potential anticancer compounds. Makromol. Chem. 175:1974;2229-2239.
55. Moromoto Y., Sugibayashi K., Sugihara S., Hosoya K.-I., Nozake S., Ogawa Y. Antitumor agent poly(amino acid) conjugates as a drug carrier in chemotherapy. J. Pharm. Dyn. 7:1984;688-698.
56. Roos C.F., Matsumoto S., Takarura Y., Hashida M., Sezaki H. Physicochemical and antitumor characteristics of some polyamino acid prodrugs of mitomycin C. Int. J. Pharm. 22:1984;75-87.
57. Oldham E.A., Li C., Ke S., Wallace S., Huang P. Comparison of action of paclitaxel and poly(L-glutamic acid)-paclitaxel conjugate in human breast cancer cells. Int. J. Oncol. 16:2000;125-132.
58. Multani A., Li C., Ozen M., Imam A.S., Wallace S., Pathak S. Cell-killing by paclitaxel in a metastatic murine melanoma cell line is mediated by extensive telomere erosion with no decrease in telomerase activity. Oncol. Rep. 6:1999;39-44.
59. Li C., Newman R.A., Wu Q.-P., Ke S., Chen W., Hutto T., Charnsangavej C., Wallace S. Biodistribution of paclitaxel and poly(L-glutamic acid)-paclitaxel conjugates in mice with ovarian OCa-1 tumor. Cancer Chemother. Pharmacol. 46:2000;416-422.
60. Sat Y.N., Burger A.M., Fiebig H.H., Sausville E.A., Duncan R. Comparison of vascular permeability and enzymatic activation of the polymeric prodrug HPMA copolymer-doxorubicin (PK1) in human tumor xenografts. Proc. Am. Assoc. Cancer Res. 40:1999;419.
61. R. Todd, J. Sludden, A.V. Boddy, M.J. Griffin, L. Robson, J. Cassidy, D. Bissett, M. Main, M.D. Brannan, S. Elliott, K. Fishwick, M. Verrill, H. Calvert, Phase I and Pharmacological Study of CT-2103, a Poly(L-glutamic acid)-paclitaxel Conjugate, ASCO, 2001 (abstract 439).
62. Sabbatini P., Aghajanian C., Hensley M., Pezzulli S., Oflaherty C., Soignet S., Lovegren M., Esch J., Funt S., Odujinrin O., Warner M., Bolton M.G., Spriggs D. Early findings in a Phase I study of PG-paclitaxel (CT-2103) in recurrent ovarian or primary peritoneal cancer. Proceedings of the AACR-NCI-EORTC International Conference on Molecular Targets and Cancer Therapeutics, 2001, p. 96, abstract 470.
63. Kudelka A.P., Verschraegen C.F., Loyer E.M., Wallace S., Gershenson D.M., Vincent M.C., Alden C., Ho L., Bolton M.G., Warner M., Garzone P., Kavanagh J.J. Preliminary report of a Phase I study of escalating dose PG-paclitaxel (CT-2103) and fixed dose cisplatin in patients with various solid tumors. Proceedings of the AACR-NCI-EORTC International Conference on Molecular Targets and Cancer Therapeutics, 2001, p. 59, abstract 287.
64. Zou Y., Wu Q.-P., Tansey W., Chow D., Hung M.-C., Charnsangavej C., Wallace S., Li C. Effectiveness of water soluble poly(L-glutamic acid)-camptothecin conjugate against resistant human lung cancer xenografted in nude mice. Int. J. Oncol. 18:2001;331-336.
65. Singer J.W., Devries P., Bhatt R., Tulinsky J., Klein P., Li C., Milas L., Lewis R.A., Wallace S. Conjugation of camptothecins to poly(L-glutamic acid). Ann. NY Acad. Sci. 922:2000;136-150.
66. Singer J.W., Bhatt R., Tulinsky J., Buhler K.R., Heasley E., Klein P., de Vries P. Water-soluble poly(L-glutamic acid)-Gly-camptothecin conjugates enhance camptothecin stability and efficacy in vivo. J. Control. Release. 74:2001;243-247.
67. de Vries P., Bhatt R., Stone I., Klein P., Singer J. Optimization of CT-2106: a water-soluble poly-L-glutamic acid (PG)-camptothecin conjugate with enhanced in vivo anti-tumor efficacy. Proceedings of the AACR-NCI-EORTC International Conference on Molecular Targets and Cancer Therapeutics, 2001, p. 21, abstract 100.
68. Rowland G.F., O'Neill G.J., Davies D.A.L. Suppression of tumor growth in mice by drug-antibody conjugate using a novel approach to linkage. Nature. 255:1975;487-488.
69. Greenfield R.S., Senter P.D., Daues A.T., Fitzgerald K.A., Gawlak S., Manger W., Braslawsky G.R. In vitro evaluation of immunoconjugates prepared by linking mitomycin C to monoclonal antibodies via polyglutamic acid carriers. Antibody Immunoconjug. Radiopharm. 2:1989;201-216.
70. Xu F., Jiang X.T. Preparation and in vitro activity of monoclonal antibody-pharmorubicin immunoconjugates. Acta Pharm. Sin. 31:1996;632-636.
71. Galun E., Shouval D., Adler R., Shahaar M., Wilchek M., Hurwitz E., Sela M. The effect of anti-α-fetoprotein-Adriamycin conjugate on a human hepatoma. Hepatology. 11:1990;578-584.
72. Goff B.A., Bamberg M., Hasan T. Photoimmunotherapy of human ovarian carcinoma cells ex vivo. Cancer Res. 51:1991;4762-4767.
73. Kato Y., Umemoto N., Kayama Y., Fukushima H., Takeda Y., Hara T., Tsukada Y. A novel method of conjugation of daunomycin with antibody with a poly-L-glutamic acid derivative as intermediate drug carrier. An anti-α-fetoprotein antibody-daunomycin conjugate. J. Med. Chem. 27:1984;1602-1607.
74. Tsukada Y., Kato Y., Umemoto N., Takeda Y., Hara T., Hirai H. An anti-alpha-fetoprotein antibody-daunorubicin conjugate with a novel poly-L-glutamic acid derivative as intermediate drug carrier. J. Natl. Cancer Inst. 73:1984;721-729.
75. Palacios P., Bussat P., Bichon D. Novel solid-phase synthesis of thio-terminated-poly(α-amino acid)-drug conjugate. J. Biochem. Biophys. Met. 23:1991;67-72.
76. Vega J., Ke S., Fan Z., Wallace S., Charsangavej C., Li C. Targeting Adriamycin to EGF receptors by site-specific conjugation of monoclonal antibody to poly(L-glutamic acid). 5th International Symposium on Polymer Therapeutics: From Laboratory to Clinical Practice, Cardiff, UK, Jan. 3-5, 2002, p. 63.
77. Li C., Ke S., Wu Q.-P., Tansey W., Hunter N., Buchmiller L.M., Milas L., Charnsangavej C., Wallace S. Potentiation of ovarian OCA-1 tumor radioresponse by poly(L-glutamic acid)-paclitaxel conjugate. Int. J. Radiat. Oncol. Biol. Phys. 48:2000;1119-1126.
78. L. Milas, N. Hunter, K. Mason, C. Li, S. Wallace, Poly(L-glutamic acid)-paclitaxel conjugate is a potent enhancer of tumor radiocurability, J. Natl. Cancer Inst. (submitted for publication).
79. Li C., Ke S., Wu Q.-P., Tansey W., Hunter N., Buchmiller L.M., Milas L., Charnsangavej C., Wallace S. Tumor irradiation enhances the tumor-specific distribution of poly(l-glutamic acid) conjugated paclitaxel and its antitumor efficacy. Clin. Cancer Res. 6:2000;2829-2834.
80. Ke S., Milas L., Charnsangavej C., Wallace S., Li C. Potentiation of radioresponse by polymer-drug conjugates. J. Control. Release. 74:2001;237-242.
81. Pechar M., Ulbrich K., Subr V. Poly(ethylene glycol) multiblock copolymer as a carrier of the anti-cancer drug doxorubicin. Bioconjug. Chem. 11:2000;131-139.
82. Li C., Tansey W., Vega J., Wallace S., Charsangavej C. Synthesis and characterization of dendritic polyamino acids as potential carriers for targeted drug delivery. 5th International Symposium on Polymer Therapeutics: From Laboratory to Clinical Practice, Cardiff, UK, Jan. 3-5, 2002, p. 31.