Recent advances in polymer drug conjugates

Mini-Reviews in Medicinal Chemistry

Volumn 15, Issue 9, 2015, Pages 751-761

  Sharma, Rajiv ^a,b   Singla, Nishu ^a   Mehta, Sahil ^a   Gaba, Tripti ^a   Rawal, Ravinder K ^a   Rao, H S ^b   Bhardwaj, T R ^a  

^a ISF COLLEGE OF PHARMACY   (India)

^b Sai Institute of Pharmaceutical Education and Research   (India)

Author keywords

Methotrexate; Polymer drug conjugates; Polymeric backbone; Polyphosphazene

Indexed keywords

AMIDE; ANESTHETIC AGENT; ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; CARBOXYLIC ACID; CISPLATIN; DOXORUBICIN; DRUG CARRIER; FUNCTIONAL GROUP; GEMCITABINE; GLUCOSYL SIDE GROUP; HEXACHLOROCYCLOTRIPHOSPHAZENE; IMIDAZOLE DERIVATIVE; IMIDAZOLYL DERIVATIVE; IMMUNOLOGICAL ADJUVANT; INFLUENZA VACCINE; LOCAL ANESTHETIC AGENT; METHOTREXATE; MOLECULAR SCAFFOLD; PACLITAXEL; PLATINUM COMPLEX; PLATINUM DERIVATIVE; POLY(DICHLOROPHOSPHAZENE); POLYMER; POLYPHOSPHAZENE; SCHIFF BASE; UNCLASSIFIED DRUG; VACCINE; BIOMATERIAL; ORGANOPHOSPHORUS COMPOUND; POLY(PHOSPHAZENE);

ARTICLE; CLINICAL TRIAL (TOPIC); CONJUGATE; CROSS LINKING; CYTOTOXICITY; DRUG DELIVERY SYSTEM; DRUG PENETRATION; DRUG RETENTION; HUMAN; HYDROGEL; NEOPLASM; POLYMER DRUG CONJUGATE; SUBSTITUTION REACTION; SYNTHESIS; TISSUE ENGINEERING; CHEMISTRY; NEOPLASMS;

ANTINEOPLASTIC AGENTS; BIOCOMPATIBLE MATERIALS; DRUG CARRIERS; HUMANS; NEOPLASMS; ORGANOPHOSPHORUS COMPOUNDS; POLYMERS;

EID: 84930511901     PISSN: 13895575     EISSN: 18755607     Source Type: Journal    
DOI: 10.2174/1389557515666150519104507     Document Type: Article

References (79)

1. [1] Ringsdorf, H.: Structure and properties of pharmacologically active polymers. J. Polym. Sci. Polym. Symp., 1975, 51, 135-153.
2. [2] Duncan, R. Polymer conjugates as anticancer nanaomedicines. Nature Rev., 2006, 6, 688-701.
3. [3] Duncan, R. The Drawing era of polymer therapeutics. Nat. Rev. Drug Discov., 2003, 25, 347-360.
4. [4] Vicent, M. J., Duncan, R. Polymer conjugates: nanosized medicines for treating cancer. Trends Biotechnol., 2006, 24(1), 39-47.
5. [5] Lakshmi, S., Katti, D. S., Laurencin, C. T. Biodegradable polyphosphazenes for drug delivery applications. Adv. Drug. Deliv. Rev., 2003, 55(4), 467-482.
6. [6] Neilson, H. R., Wisian-Neilson, P. Poly(alkyl/arylphosphazenes) and Their Precursors. Chem. Rev., 1988, 88, 541.
7. [7] Song, S. C., Sohn, Y. S.: Synthesis and hydrolytic properties of polyphosphazene/(diamine)platinum/saccharide conjugates. J. Control. Rel., 1998, 55(2-3), 161.
8. [8] Schenck, R., Romer, G. Uber die Phosphornitrilchloride und ihre Umsetzungen. Eur. J. Ing. Chem., 1924, 57(8), 1343-1355.
9. [9] Steinman, R., Schrimer, F. B., Audroeth, L.F. The Preparation and Physical Properties of Trimeric Phosphonitrilic Chloride. J. Am. Chem. Soc., 1942, 64(10), 2377-2378.
10. [10] Emsley, J., Udy, P. B. Factors influencing the preparation of the cyclic phosphonitrilic chlorides. J. Chem. Soc., 1971, 768-772.
11. [11] Krishnamurthi, S. S., Sau, A. C., Woods, M. Cyclophosphazene. Inorg. Chem. Radiochem., 1978, 21, 41-112.
12. [12] Allcock, H. R., Desorcie, J. L., Riding, G.H. The organometallic chemistry of phosphazenes. Polyhedron., 1987, 6, 119.
13. [13] Allcock, H. R., Kugel, R.L. Synthesis of High Polymeric Alkoxy and Aryloxyphosphonitriles. J. Am. Chem. Soc., 1965, 87, 4216-4217.
14. [14] Allcock, H. R., Kugel, R. L., Valan, K. J.: High Molecular Weight Poly(alkoxy- and aryloxyphosphazenes). Inorg. Chem., 1966, 5, 1709-1715.
15. [15] Allcock, H. R.: Phosphonitrilic Chemistry. Chem. Eng. News. 1968, 46, 68-81.
16. [16] Allcock, H.R.: Recent advances in phosphazene (phosphonitrilic) chemistry. Phosph. Nitro. Compound, 1972, 72(4), 315-356.
17. [17] Carroll, A. P., Shaw, R. A.: Phosphorus-nitrogen compounds. Part XXI. Alkylthio- and phenylthio-cyclotriphosphazatrienes. Chem. Ind., 1962, 1908.
18. [18] Carroll, A. P., Shaw, R. A. Phosphorus-nitrogen compounds. Part XXI. Alkylthio- and phenylthio-cyclotriphosphazatrienes. J. Chem. Soc., 1966, 914-921.
19. [19] Stokes, H. N. On the chloronitrides of phosphorus (II). Am. Chem. J., 1897, 19, 782.
20. [20] Stokes, H.N. On the chloronitrides of phosphorus. Am. Chem. J. 1895, 17, 275.
21. [21] Stokes, H. N. On trimetaphosphinic acid and its decomposition products. Am. Chem. J., 1896, 18, 629.
22. [22] Allcock, H. R.: Phosphazene polyelectrolytes as immunoadjuvants. Chem. Eng. News., 1988, 66, 142.
23. [23] Allcock, H. R.: Rational Design and Synthesis of New Polymeric Materials. M. Science, 1992, 255, 1106-1112.
24. [24] Hergrenrother, W.L., Fieldhouse, J.W., Halasa, A.F. Stabilizing complex for poly(dichlorophosphazene). U.S patent: 4,623,525. 1986.
25. [25] Rose, S. J. H.: Synthesis of phosphonitrilic fluoroelastomers. J. Polym. Sci., 1968, 6(12), 837-839.
26. [26] Allcock, H.R., Connolly, M. Polymerization and halogen scrambling behavior of phenyl-substituted cyclotriphosphazenes. Macromolecules. 1985, 18, 1330.
27. [27] Allcock, H. R., Cheg, J. Y. Strained Inorganic Heterocyclic Compounds and their Conversion to macrocycles and high Polymers. Macromolecules. 1989, 24, 993.
28. [28] Allcock, H.R., Brenan, D.J.J. General introduction of phosphagene. Organomet. Chem., 1998, 341, 231.
29. [29] Allcock, H.R., Arcus, R.A. Crystalline Transitions and Related Physical Properties of Poly(dichloro-phosphazene). Macromolecules, 1979, 12, 1130-1136.
30. [30] Allcock, H. R., Paul, E.: Improved method for the synthesis of poly(organophosphazenes) and hindered cyclophosphazenes. Macromol. Chem. Suppl., 1981, 4, 3.
31. [31] Grolleman, W. J., Visser, A. C. D., Wolke, J. G. C., Timmerman, H. Studies on a bioerodible drug carrier system based on a polyphosphazene: Part II. Experiments in-vitro. J. Control. Rel., 1986, 4(2), 119-131.
32. [32] Goedemoed, J. H. Polyphosphazene Drug Delivery System for Antitumor Treatment. University Press, Amsterdam. 1990.
33. [33] Allcock, H. R., Pucher, S. R., Scopelianos, A. G. Synthesis of poly(orgnaophosphazenes) with glycolic acid ester and lactic acid ester side groups: prototypes for new bioerodible polymers. Macromolecules. 1994, 27(1), 1-4.
34. [34] Allcock, H. R., Pucher, S. R., Scopelianos, A. G. Poly[(amino acid ester)phosphazenes]: Synthesis, Crystallinity and Hydrolytic Sensitivity in Solution and the Solid State. Macromolecules, 1994, 27(5), 1071-1075.
35. [35] Crommen, J. H. L., Schacht, E. H., Mense, E. H. G. Biodegradable polymers: II. Degradation characteristics of hydrolysis-sensitive poly[(organo)phosphazenes]. Biomater, 1992, 13, 601-611.
36. [36] Laurensin, C., Koh, H. J., Neenan, T. X., Allcock, H. R., Langers, R. S. Controlled release using a new bioerodible polyphosphazene matrix system. J. Boimed. Mater. Res., 1987, 21, 1231-1246.
37. [37] Allcock, H. R., Austin, P. E., Neenan, T. X.: Phosphazene High Polymers with Bioactive Substituent Groups: Prospective Anesthetic Aminophosphazenes. Macromolecules, 1982, 15, 689-693.
38. [38] Allcock, H. R., Neenan, T. X., Kossa, W. C. Coupling of cyclic and high-polymeric [(aminoaryl)oxy]phosphazenes to carboxylic acids: prototypes for bioactive polymers. Macromolecules, 1982, 15 (3), 693-696.
39. [39] Allcock, H. R., Scopelianos, A. G. Synthesis of Sugar-Substituted Cyclic and Polymeric Phosphazenes, and their Oxidation, Reduction, and Acetylation Reactions. Macromolecules, 1983, 16, 715-719.
40. [40] Payne, L. G., Jenkins, S. A., Woods, A. L., Grund, E. M., Geribo, W. E., Loebelenz, J. R., Andrianov, A. K., Roberts, B. E. Poly[di(carboxylatophenoxy)phosphazene] (PCPP) is a potent immunoadjuvant for an influenza vaccine. Vaccine, 1998, 16(1), 92-98.
41. [41] Payne, L. G., Van Nest, G., Barchfeld, G. L., Siber, G. R., Gupta, R. K., Jenkins, S. A. PCPP as a parenteral adjuvant for diverse antigens. Dev. Biol. Stand, 1998, 92, 79-87.
42. [42] Mutwiri, G., Benjamin, P., Soita, H., Townsend, H., Yost, R., Roberts, B., Andrianov, A. K., Babiuk, L. A. Poly[di(sodium carboxylatoethylphenoxy)phosphazene] (PCEP) is a potent enhancer of mixed Th1/Th2 immune responses in mice immunized with influenza virus antigens. Vaccine, 2007, 25(7), 1204-1213.
43. [43] Andrianov, A. K., Marin, A., Roberts, B. E. Polyphosphazene polyelectrolytes: a link between the formation of noncovalent complexes with antigenic proteins and Immunostimulating activity. Biomacromolecules, 2005, 6, 1375-1379.
44. [44] Agnello, D., Herve, C.: Intrarectal immunization with rotavirus 2/6 virus-like particles induces an anti-rotavirus immune response localized in the Intestinal mucosa and protects against rotavirus infection in mice. J. Virol., 2006, 80(8), 3823-3832.
45. [45] Choi, A., Mc Neal, M. Intranasal or oral immunization of inbred and Outbred mice with murine of human rotavirus VP6 proteins protects against viral shedding after challenge with murine rotaviruses. Vaccine, 2002, 20, 3310-3321.
46. [46] Mc Neal, M., Rae, M., Ward R. L. Effects of different adjuvants on rotavirus antibody responses and protection in mice following intramuscular immunization with inactivated rotavirus. Vaccine, 1999, 17(11-12), 1573-1580.
47. [47] Perez, R. P., O'Dwyer, P. J., Handel, L. M., Ozols, R. F., Hamilton, T. C.: Comparative cytotoxicity of CI-973, cisplatin, carboplatin, and tetraplatin in human ovarian carcinoma cell lines. Inter. J. Cancer, 1991, 48, 265.
48. [48] Van Cott, J. L., Prada, A. L., Mc Neal, M. M., Stone, S. C., Basu, M., Jr., B.H. Smiley, K. L. Shao, M. Judy, A. Bean, J. A. Clements, J. D. Choi, A. H. C. Ward, R. L.: Mice develop effective but delayed protective immune responses when immunized as neonates either intranasally with nonliving VP6/LT(R192G) or orally with live rhesus rotavirus vaccine candidates. J. Virol., 2006, 80(10), 4949-4961.
49. [49] Alarcon, J.B., Hartley, A.W., Harvey, N.G., Mikszta, J.A. Preclinical evaluation of microneedle technology for intradermal delivery of influenza vaccines. Clin. Vaccine Immunol., 2007, 14 (4), 375-381.
50. [50] Kenney, R. T., Frech, S. A., Muenz, L. R., Villar, C. P., Glenn, G. M. Dose sparing with intradermal injection of influenza vaccine. N. Engl. J. Med., 2004, 351(22), 2295-2301.
51. [51] La Montagne Fauci, J. R.: Intradermal influenza vaccination: Can less be more? N. Engl. J. Med., 2004, 351(22), 2295-2301.
52. [52] Prausnitz, M. R. Microneedles for transdermal drug delivery. Adv. Drug Deliv. Rev., 2004, 56(5), 581-587.
53. [53] Andrianov, A. K.: Water-soluble polyphosphazenes for biomedical applications. J. Inorg. Organomet. Polym. Mater., 2006, 16(4), 397-406.
54. [54] Gill, H. S., Prausnitz, M. R. Coating formulations for microneedles. Pharm. Res., 2007, 24(7), 1369-1380.
55. [55] Laurencin, C. T., Morris, C. D., Pierre-Jacques, H., Schwartz, E. R., Keaton, A. R., Zou, L. Osteoblast culture on bioerodible polymers: studies of initial cell adhesion and spread. Polym. Adv. Tech., 1992, 3, 359-364.
56. [56] Deng, M., Nair, L. S., Nukavarapu, S. P., Kumbar, S. G., Jiang, T., Krogman, N. R., Singh, A., Allcock, H. R., Laurencin, C. T. Miscibility and in-vitro osteocompatibility of biodegradable blends of poly[(ethyl alanato)(P-phenyl phenoxy)phosphazene] and poly(lactic acid–glycolic acid). Biomater., 2008, 29, 337-349.
57. [57] Nair, L.S., Lee, D.A., Bender, J.D., Barrett, E.W., Greish, Y.E., Brown, P.W., Allcock, H.R., Laurencin, C.T.: Synthesis, characterization, and osteocompatibility evaluation of novel alanine-based polyphosphazenes. J. Biomed. Mater. Res., 2006, 76, 206-213.
58. [58] Brown, J. L., Nair, L. S., Bender, J. D., Allcock, H. R., Laurencin, C. T. The formation of an apatite coating on carboxylated polyphosphazenes via a biomimetic process. Mater. Lett., 2007, 61, 3692-3695.
59. [59] Sethuraman, S., Nair, L. S., El-Amin, S. F., Farrar, R., Nguyen, M. T., Singh, A., Allcock, H. R., Greish, Y. E., Brown, P. W., Laurencin, C. T.: In-vivo biodegradability and biocompatibility evaluation of novel alanine ester based polyphosphazenes in a rat model. J. Biomed. Mater. Res., 2006, 77, 679-687.
60. [60] Nukavarapu, S. P., Kumbar, S. G., Brown, J. L., Krogman, N. R., Weikel, A. L., Hindenlang, M. D., Nair, L. S., Allcock, H. R., Laurencin, C.T. Polyphosphazene/nano-hydroxyapatite composite microsphere scaffolds for bone tissue engineering. Biomacromolecules, 2008, 9, 1818-1825.
61. [61] Lee, S. B., Song, S. C., Jin, J. I., Sohn, Y. S. A new class of biodegradable Thermosensitive polymers. 2. Hydrolytic properties and salt effect on the lower critical solution temperature of poly(organophosphazenes) with methoxypoly(ethylene glycol) and amino acid esters as side groups. Macromolecules, 1999, 32, 7820-7827.
62. [62] Lee, B.H., Lee, Y.M., Sohn, Y.S., Song, S.C. A thermosensitive poly(organophosphazene) gel. Macromolecules, 2002, 35, 3876-3879.
63. [63] Lee, B. H., Park, J. S., Song, S. C.: Synthesis and biocompatibility of Thermosensitive poly(organophosphazene)gels. Biomater. Res. 2003, 7, 182-187.
64. [64] Lee, B.H., Song S.C. Synthesis and characterization of biodegradable Thermosensitive poly(organophosphazene) gels. Macromolecules, 2004, 37, 4533-4537.
65. [65] Chun, C., Lee, S. M., Kim, C. W., Hong, Ki, Y. Kim, S. Y. Yang, H.K. Song, S.C. Doxorubicin-polyphosphazene conjugate hydrogels for locally controlled delivery of cancer therapeutics. Biomater., 2009, 30, 4752-4762.
66. [66] Chun, C., Lee, S.M., Kim, S.Y., Yang, H.K., Song, S.C. Thermosensitive poly(organophosphazene)-paclitaxel conjugate gels for antitumor applications. Biomater., 2009, 30, 2349-2360.
67. [67] Carter, S. K. Platinum Coordination Complexes in Cancer Chemotherapy, Boston, Martinus Nijhoff Press. 1984.
68. [68] Von Hoff, D. D., Schilsky, R., Reichert, C. M., Reddick, R. L., Rozencweig, M., Young, R., Muggia, F. M. Toxic effects of cis dichlorodiammineplatinum (II) in man. Cancer Treat. Rep., 1979, 63, 1527-1535.
69. [69] Maeda, H., Wu, J., Sawa, T., Matsumura, Y., Hori, K. Tumor vascular permeability and the EPR effect in macromolecular therapeutics: a review. J. Control. Rel., 2000, 65, 271-284.
70. [70] Son, Y. J., Jang, J. S., Cho, Y. W., Chung, H., Park, R. W., Kwon, I. C., Kim, I. S., Park, J. Y., Seo, S. B., Park, C. R., Jeong, S. Y.: Biodistribution and anti-tumor efficacy of doxorubicin loaded glycol-chitosan nanoaggregates by EPR effect. J. Control. Rel., 2003, 91(1-2), 135-145.
71. [71] Poddubnaja, I., Kruglova, G. PEG-l-asparaginase: New anticancer agent for treatment of relapses or resistant malignant non- Hodgkin’s lymphoma in adults. Eur. J. Cancer, 1993. 29(6), 176.
72. [72] Klibanov, A. L., Maruyama, K., Beckerleg, A. M., Torchilin, V. P., Huang, L.: Activity of amphipathic poly(ethylene glycol)5000 to prolong the circulation time of liposomes depends on the liposome size and is unfavorable for immunoliposome binding to target. Biochim. Biophys. Acta., 1991, 1062(2), 142-148.
73. [73] Allcock, H. R., Allen, R. W., O’Brien, J. P.: Synthesis of Platinum derivatives of polymeric and cyclic phosphazenes. J. Am. Chem. Soc., 1977, 99, 3984-3987.
74. [74] Allen, R. W., O’Brien, J. P., Allcock, H. R. Crystal and molecular structure of a platinum-cyclophosphazene complex: cis- dichloro [octa(methylamino)cyclotetraphosphazene-N’,N”] platinum (II). J. Am. Chem. Soc., 1977, 99, 3987-3991.
75. [75] Sohn, Y. S., Baek, H. G., Cho, Y. H., Lee, Y. A., Jung, O. S., Lee, C. O., Kim, Y. S.: Synthesis and antitumor activity of novel polyphosphazene (diamine) platinum (II) conjugates. Int. J. Pharm., 1997, 153, 79-91.
76. [76] Jung, Y. J., Lee, J. S., Kim, Y. M.: Synthesis and in-vitro/in-vivo evaluation of 5-aminosalicyl-glycine as a colon-specific prodrug of 5-aminosalicylic acid. J. Pharm. Sci., 2000, 89, 594-602.
77. [77] Song, R., Jun, Y. J., Kim, J. I., Jin, C. B., Sohn, Y. S.: Synthesis, characterization and tumor selectivity of a polyphosphazeneplatinum (II) conjugate. J. Control. Rel., 2005, 105, 142-150.
78. [78] Sharma, R., Rawal, R.K., Malhotra, M., Sharma, A.K., Bhardwaj, T.R.: Design, synthesis and ex-vivo release studies of colon-specific polyphosphazene–anticancer drug conjugates. Bioorg. Med. Chem. 2014, 22, 1104-1114.
79. [79] Singla, N., Sharma, R., Bhardwaj, T.R.: Design, Synthesis and Invitro Evaluation of Polymer-linked Prodrug of Methotrexate for the Targeted Delivery to the Colon. Lett. Drug Design Discov., 2014, 11, 601-610.