Tumor-targeting drug delivery of new-generation taxoids

Future Medicinal Chemistry

Volumn 4, Issue 1, 2012, Pages 33-50

  Ojima, Iwao ^a   Zuniga, Edison S ^a   Berger, William T ^a   Seitz, Joshua D ^a  

^a STONY BROOK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BRENTUXIMAB VEDOTIN; DOCETAXEL; DOCOSAHEXAENOIC ACID; HUMAN SERUM ALBUMIN; ICOSAPENTAENOIC ACID; LINOLENIC ACID; MONOCLONAL ANTIBODY; ORTATAXEL; PACLITAXEL; SB T 11033; SB T 1213; SB T 121303; SB T 121313; SB T 1214; SB T 1216; SB T 121602; SERUM ALBUMIN; TAXOID; TOPOTECAN; UNCLASSIFIED DRUG; VITAMIN;

ANTINEOPLASTIC ACTIVITY; CANCER CELL; CANCER CELL CULTURE; CANCER CHEMOTHERAPY; CANCER STEM CELL; COLON CANCER; CYTOTOXICITY; DRUG DELIVERY SYSTEM; DRUG EFFICACY; DRUG POTENCY; DRUG RELEASE; DRUG SPECIFICITY; DRUG TARGETING; FLUORESCENCE MICROSCOPY; HUMAN; IC 50; MULTIDRUG RESISTANCE; NONHUMAN; PRIORITY JOURNAL; REVIEW; TUMOR TARGETING DRUG DELIVERY;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; DRUG DELIVERY SYSTEMS; HUMANS; NEOPLASMS; TAXOIDS;

EID: 83655198348     PISSN: 17568919     EISSN: 17568927     Source Type: Journal    
DOI: 10.4155/fmc.11.167     Document Type: Review

References (59)

1. Jemal A, Bray F, Center MM, Ferlay J, Ward E, Forman D. Global cancer statistics. CA Cancer J. Clin. 61, 69-90 (2011).
2. Siegel R, Ward E, Brawley O, Jemal A. Cancer statistics, 2011. CA Cancer J. Clin. 61, 212-236 (2011).
3. Jaracz S, Chen J, Kuznetsova LV, Ojima I. Recent advances in tumor-targeting anticancer drug conjugates. Bioorg. Med. Chem. 13(17), 5043-5054 (2005). (Pubitemid 41039965)
4. Ducry L, Stump B. Antibody-drug conjugates: linking cytotoxic payloads to monoclonal antibodies. Bioconjugate Chem. 21, 5-13 (2010).
5. Xia W, Low PS. Folate-targeted therapies for cancer. J. Med. Chem. 53, 6811-6824 (2010).
6. Farokhzad C, Cheng J, Teply BA et al. Targeted nanoparticle-aptamer bioconjugates for cancer chemotherapy in vivo. Proc. Natl Acad. Sci. USA 103, 6315-6320 (2006).
7. Ojima I. Use of fluorine in the medicinal chemistry and chemical biology of bioactive compounds: a case study on fluorinated taxane anticancer agents. Chem. Biochem. 5, 628-635 (2004). (Pubitemid 39257084)
8. Ojima I. Guided molecular missiles for tumor-targeting chemotherapy: case studies using the second-generation taxoid as warheads. Acc. Chem. Res. 41(1), 108-119 (2008).
9. Chen S, Zhao X, Chen J et al. Mechanism-based tumor-targeting drug delivery system. Validation of efficient vitamin receptor-mediated endocytosis and drug release. Bioconjugate Chem. 21, 979-987 (2010).
10. Vredenburg MR, Ojima I, Veith J et al. Effects of orally active taxanes on P-glycoprotein modulation and colon and breast carcinoma drug resistance. J. Natl Cancer Inst. 93, 1234-1245 (2001). (Pubitemid 32816198)
11. Ojima I, Slater JC, Michaud E et al. Syntheses and structure-activity relationships of the second-generation antitumor taxoids: exceptional activity against drug-resistant cancer cells. J. Med. Chem. 39, 3889-3896 (1996). (Pubitemid 26327426)
12. Ojima I, Slater JC, Kuduk SD et al. Syntheses and structure-activity relationships of taxoids derived from 14-b-hydroxy-10- deacetylbaccatin III. J. Med. Chem. 40(3), 267-278 (1997). (Pubitemid 27081961)
13. Ojima I, Wang T, Miller ML et al. Syntheses and structure-activity relationships of new second-generation taxoids. Bioorg. Med. Chem. Lett. 9, 3423-3428 (1999).
14. Ojima I, Lin S, Wang T. The recent advances in the medicinal chemistry of taxoids with novel b-amino acid side chains. Curr. Med. Chem. 6, 927-954 (1999). (Pubitemid 29455182)
15. Ferlini C, Distefano M, Pignatelli F et al. Antitumor activity of novel taxanes that act as cytotoxic agents and P-glycoprotein inhibitors at the same time. Brit. J. Cancer 83, 1762-1768 (2000). (Pubitemid 32001726)
16. Geney R, Chen J, Ojima I. Recent advance in the new generation taxane anticancer agents. Med. Chem. 1, 125-139 (2005).
17. Ehrlichova M, Vaclavikova R, Ojima I et al. Transport and cytotoxicity of paclitaxel, docetaxel and novel taxanes in human breast cancer cells. Arch. Pharmacol. 372, 95-105 (2005). (Pubitemid 41414050)
18. Ojima I, Chen J, Sun L et al. Design, synthesis and biological evaluation of new-generation taxoids. J Med. Chem. 51, 3203-3221 (2008). (Pubitemid 351821880)
19. Kovar J, Ehrlichova M, Smejkalova B, Zanardi I, Ojima I, Gut I. Comparison of cell death-inducing effect of novel taxane SB-T-1216 and paclitaxel in breast cancer cells. Anticancer Res. 29, 2951-2960 (2009).
20. Beer M, Lenaz L, Amadori D. Phase II study of ortataxel in taxane-resistant breast cancer. J. Clin. Oncol. (Suppl.) 26, 1066 (2008).
21. Kamb A, Wee S, Lengauer C. Why is cancer drug discovery so difficult? Nat. Rev. Drug Discov. 6, 115-120 (2007). (Pubitemid 46745339)
22. Dalerba P, Cho RW, Clarke MF. Cancer stem cells: models and concepts. Annu. Rev. Med. 58, 267-284 (2007). (Pubitemid 46706514)
23. Botchkina GI, Zuniga ES, Das M et al. New-generation taxoid SB-T-1214 inhibits stem cell-related gene expression in 3D cancer spheriods induced by purified colon tumor-initiating cells. Mol. Cancer 9, 192-204 (2010).
24. Sauer LA, Dauchy RT, Blask DE. Mechanism for the antitumor and anticachectic effects of n-3 fatty acids. Cancer Res. 60, 5289-5295 (2000).
25. Wigmore SJ, Ross JA, Falconer JS et al. The effect of polyunsaturated fatty acids on the progress of cachexia in patients with pancreatic cancer. Nutrition 12, S27-S30 (1996).
26. Hawkins RA, Sangster K, Arends MJ. Apoptotic death of pancreatic cancer cells induced by polyunsaturated fatty acids varies with double bond number an involves an oxidative mechanism. J. Pathol. 185, 61-70 (1998). (Pubitemid 28266718)
27. Grammatikos SI, Subbaiah PV, Victor TA, Miller WM. n-3 and n-6 fatty acid processing and growth effects in neoplastic and noncancerous human mammary epithelial cell lines. Br. J. Cancer 70, 219-227 (1994). (Pubitemid 24247140)
28. Diomede L, Colotta F, Piovani B, Re F, Modest EJ, Salmona M. Induction of apoptosis in human leukemic cells by the ether lipid 1-octadecyl-2-methyl- racglycero-3- phosphocholine. A possible basis for its selective action. Int. J. Cancer Res. 53, 124-130 (1993). (Pubitemid 23018434)
29. Bradley MO, Webb NL, Anthony FH et al. Tumor targeting by covalent conjugation of a natural fatty acid to taxol. Clin. Cancer Res. 7, 3229-3238 (2001). (Pubitemid 32963848)
30. Sparreboom A, Wolff AC, Verweij J et al. Dispostition of docosahexaenoic acid: paclitaxel, a novel taxane, in blood. Clin. Cancer Res. 9, 151-159 (2003).
31. Ibrahim NK, Desai N, Legha S et al. Phase I and pharmacokinetic study ABI-007, a cremophor-free, protein-stabilized nanoparticle formulation of paclitaxel. Clin. Cancer Res. 8, 1038-1044 (2002). (Pubitemid 34517637)
32. Desai N, Trieu V, Yao Z et al. Increased antitumor activity, intratumor paclitaxel concentrations, and endothelial cell transport of cremophor-free, albumin-bound paclitaxel, ABI-007, compared with cremophor-based paclitaxel. Clin. Cancer Res. 12, 1317-1324 (2006). (Pubitemid 43342524)
33. Seitz JD, Ojima I. Drug conjugates with polyunsaturated fatty acids. In: Drug Delivery in Oncology: From Basic Research to Cancer Therapy. Kratz F, Senter P, Steinhagen H (Eds). Wiley-VCH, Weinheim, Germany 1323-1360 (2011).
34. Rose DP, Connolly JM. Omega-3 fatty acids as cancer chemopreventive agents. Pharmacol. Ther. 83, 217-244 (1999). (Pubitemid 29430123)
35. Whelan J. Targeted taxane therapy for cancer. Drug Discov. Today 7, 90-92 (2002). (Pubitemid 34088128)
36. Kuznetsova L, Chen J, Sun X et al. Syntheses and evaluation of novel fatty acid: 2nd-generation taxoid conjugates as promising anticancer agents. Bioorg. Med. Chem. Lett. 16, 974-977 (2006). (Pubitemid 43059863)
37. Chari RVJ. Targeted delivery of chemotherapeuitcs: tumor-activated prodrug therapy. Adv. Drug Deliv. Rev. 31, 89-104 (1998). (Pubitemid 28191877)
38. Doronina SO, Mendelsohn BA, Bovee TD et al. Enhanced activity of monomethylauristatin F through monoclonal antibody delivery: effects of linker technology on efficacy and toxicity. Bioconjugate Chem. 17, 114-124 (2006). (Pubitemid 43157592)
39. Beck A, Haeuw JF, Wurch T, Goetsch L, Bailly C, Corvaia N. The next generation of antibody-drug conjugates comes of age. Discov. Med. 10, 329-339 (2010).
40. Kigawa J, Minagawa Y, Kanamori Y et al. Glutathione concentration may be a useful predictor of response to second-line chemotherapy in patients with ovarian cancer. Cancer 82, 697-702 (1998). (Pubitemid 28090281)
41. Ojima I, Geng X, Wu X et al. Tumor-specific novel taxoid-monoclonal antibody conjugates. J Med. Chem. 45, 5620-5623 (2002). (Pubitemid 35453753)
42. Chen J, Chen S, Zhao X, Kuznetsova L, Wong SS, Ojima I. Functionalized single-walled carbon nanotubes as rationally designed vehicles for tumor-targeted drug delivery. J. Am. Chem. Soc. 130, 16778-16785 (2008).
43. Weinstein SJ, Hartman TJ, Stolzenberg- Solomon R et al. Null association between prostate cancer and serum folate, vitamin B6, vitamin B12 and homocysteine. Cancer Epidemiol. Biomarkers Prev. 12, 1271-1272 (2003). (Pubitemid 37499457)
44. Reddy JA, Leamon CP. Folate receptor targeted cancer chemotherapy. In: Targeted Drug Strategies for Cancer and Inflammation. Jackman AL, Leamon CP (Eds). Springer Science+Business Media, LLC, NY, USA 135-150 (2011).
45. Leamon CP, Reddy JA. Folate-targeted chemotherapy. Adv. Drug Deliv. Rev. 56, 1127-1141 (2004). (Pubitemid 38496512)
46. Lu Y, Low PS. Folate-mediated delivery of macromolecular anticancer therapeutic agents. Adv. Drug Deliv. Rev. 54, 675-693 (2002). (Pubitemid 35247522)
47. Lu Y, Sega E, Leamon CP, Low PS. Folate receptor-targeted immunotherapy of cancer: mechanism and therapeutic potential. Adv. Drug Deliv. Rev. 56, 1161-1176 (2004). (Pubitemid 38496513)
48. Leamon CP, Reddy JA, Vlahov IR et al. Synthesis and biological evaluation of EC72: a new folate-targeted chemotherapeutic. Bioconjugate Chem. 16(16), 803-811 (2005). (Pubitemid 41026166)
49. Reddy JA, Westrick E, Vlahov I, Howard SJ, Santhapuram HK, Leamon CP. Folate receptor specific anti-tumor activity of folate-mitomycin conjugates. Cancer Chemother. Pharmacol. 58, 229-236 (2006).
50. Zempleni J, Wijeratne SS, Hassan YI. Biotin. Biofactors 35(1), 36-46 (2009).
51. Russell-Jones G, McTavish K, McEwan J, Rice J, Nowotnik D. Vitamin-mediated targeting as a potential mechanism to increase drug uptake by tumours. J. Inorg. Biochem. 98(10), 1625-1633 (2004). (Pubitemid 39349188)
52. Mukherjee S, Ghosh RN, Masfield FR. Endocytosis. Physiol. Rev. 77, 759-803 (1997).
53. Zuniga E, Ojima I. Design, synthesis and biological evaluation of tumor-targeting drug conjugates bearing dual warheads. Presented at: The American Chemical Society National Meeting. Denver, CO, USA, 28 August-1 September 2011.
54. Prato M, Kostarelos K, Bianco A. Functionalized carbon nanotubes in drug design and discovery. Acc. Chem. Res. 41(1), 60-68 (2008).
55. Bianco A, Kostarelos K, Prato M. Applications of carbon nanotubes in drug delivery. Curr. Opin Chem. Biol. 9(6), 674-679 (2005). (Pubitemid 41612196)
56. Kam NWS, Jessop TC, Wender PA, Dai H. Nanotube molecular transporters internalization of carbon-nanotube-protein conjugates into mammalian cells. J. Am. Chem. Soc. 126, 6850-6851 (2004). (Pubitemid 38855367)
57. Duncan R. The dawning era of polymer therapeutics. Nat. Rev. Drug Discov. 2, 347-360 (2003). (Pubitemid 37361705)
58. Bottini M, Cerignoli F, Dawson MI, Magrini A, Rosato N, Mustelin T. Full-length single-walled carbon nanotubes decorated with streptavidin- conjugated quantum dots as multivalent intracellular fluorescent nanoprobes. Biomacromolecules 7, 2259-2263 (2006). (Pubitemid 44336335)
59. Kostarelos K, Lacerda L, Pastorin G et al. Cellular uptake of functionalized carbon nanotubes is independent of functional group and cell type. Nat. Nanotechnol. 2(2), 108-113 (2007). (Pubitemid 46230832)