Preview

Nanosystems: Physics, Chemistry, Mathematics

Advanced search

Toward paclitaxel-[60]fullerene immunoconjugates as a targeted prodrug against cancer

Abstract

Two newly synthesized water-soluble conjugates of Paclitaxel with malonodiserinolamide-derivatized [60]fullerene (C60-ser) undergo hydrolysis and release their medical payload under biological conditions. In vivo testing of one of these compounds in a murine model showed tumor volume reduction similar to the FDA-approved drug Abraxane, but without the associated weight-loss, indicating better tolerance of this new formulation.

About the Authors

Y. Mackeyev
Rice University
United States

Department of Chemistry and The Smalley Institute for Nanoscale Science & Technology

Houston



M. Raoof
The University of Texas M. D. Anderson Cancer Center
United States

Department of Surgical Oncology

Houston



B. Cisneros
Rice University; The University of Texas M. D. Anderson Cancer Center
United States

Department of Chemistry and The Smalley Institute for Nanoscale Science & Technology; Department of Surgical Oncology

Houston



N. Koshkina
The University of Texas M. D. Anderson Cancer Center
United States

Department of Surgical Oncology

Houston



C. S. Berger
Rice University
United States

Department of Chemistry and The Smalley Institute for Nanoscale Science & Technology

Houston



L. J. Wilson
Rice University
United States

Department of Chemistry and The Smalley Institute for Nanoscale Science & Technology

Houston



S. A. Curley
One Baylor Plaza
United States

Baylor College of Medicine

MS390, Houston, TX 77030



References

1. Schiff P.B., Fant J., Horwitz S.B. Promotion of microtubule assembly in vitro by taxol. Nature, 277, P. 665– 667 (1979).

2. Sparreboom A., Van Tellingen O., Nooijen W.J., Beijnen J.H. Nonlinear Pharmacokinetics of Paclitaxel in Mice Results from the Pharmaceutical Vehicle Cremophor EL. Cancer Res., 56, P. 2112–2115 (1996).

3. Gradishar W.J. Albumin-bound Paclitaxel: a next-generation taxane. Expert Opinion on Pharmacotherapy, 7 (8), P. 1041–1053 (2006).

4. Cascinu S., Ficarelli R., et al. A phase I study of Paclitaxel and 5-fluorouracil in advanced gastric cancer. European J. Cancer, 33 (10), P. 1699–1702 (1997).

5. Postma T.J., Vermorken J.B., et al. Paclitaxel-induced neuropathy. Annals of Oncology, 5, P. 489–494 (1995).

6. Schiller J.H., Storer B., et al. Phase I trial of 3-hour Paclitaxel with or without granulocyte colony-stimulating factor in patients with advanced cancer. J. Clinical Oncology, 12, P. 241–248 (1994).

7. Dugan L.L., Turetsky D.M., et al. Carboxyfullerenes as neuroprotective agents. Proc. Natl. Acad. Sci. USA, 94, P. 9434–9439 (1997).

8. Dugan L.L., Lovett E., et al. Carboxyfullerenes as neuroprotective agents. Proc. Electrochem. Soc., 98, P. 1236–1245 (1998).

9. Quick K.L., Ali S.S., et al. A carboxyfullerene SOD mimetic improves cognition and extends the lifespan of mice. Neurobiology of Aging, 29, P. 117–128 (2008).

10. Raoof M., Mackeyev Y., et al. Internalization of C60 fullerenes into cancer cells with accumulation in the nucleus via the nuclear pore complex. Biomaterials, 33, P. 2952–2960 (2012).

11. Huang F., Mackeyev Y., et al. Evidence for nuclear internalisation of biocompatible [60]fullerene. European Journal of Nanomedicine, 5 (1), P. 51–55 (2013).

12. Ashcroft J.M., Tsyboulski D.A., et al. Fullerene (C60) immunoconjugates: interaction of water-soluble C60 derivatives with the murine anti-gp240 melanoma antibody. Chem. Commun., 28, P. 3004–3006 (2006).

13. Gannon C.J., Cherukuri P., et al. Carbon nanotube-enhanced thermal destruction of cancer cells in a noninvasive radiofrequency field. Cancer, 110, P. 2654–2665 (2007).

14. Sitharaman B., Zakharian T.Y., et al. Water-soluble fullerene (C60) derivatives as nonviral gene-delivery vectors. Molecular Pharmaceutics, 5 (4), P. 567–578 (2008).

15. Greenwald R.B., Pendri A., Bolikal D., Gilbert C.W. Highly water soluble taxol derivatives: 2 polyethylene glycol esters as potential prodrugs. Bioorg. Med. Chem. Lett., 4, P. 2465–2470 (1994).

16. Camps X., Hirsch A., Efficient cyclopropanation of C60 starting from malonates. J. Chem. Soc. Perkin Trans., 1, P. 1595 (1997).

17. Cho M., Lee J., et al. Visible light sensitized inactivation of MS-2 bacteriophage by a cationic aminefunctionalized C60 derivative. Environmental Sci. & Technol., 44 (17), P. 6685–6691 (2010).

18. Wharton T., Wilson L.J. Highly-iodinated fullerene as a contrast agent for X-ray imaging. Bioorganic & Medicinal Chem., 10 (11), P. 3545–3554 (2002).

19. Zakharian T.Y., Seryshev A., et al. A Fullerene-Paclitaxel Chemotherapeutic: Synthesis, Characterization, and Study of Biological Activity in Tissue Culture. J. Am. Chem. Soc., 127, P. 12508–12509 (2005).

20. Laus S., Sitharaman B., et al. Destroying Gadofullerene Aggregates by Salt Addition in Aqueous Solution of Gd@C60(OH)x and Gd@C60[C(COOH2)]10. J. Am. Chem. Soc., 127, P. 9368–1969 (2005).

21. Desai N., Trieu V., 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. Clinical Cancer Research, 12, P. 1317–1324 (2006).


Review

For citations:


Mackeyev Y., Raoof M., Cisneros B., Koshkina N., Berger C.S., Wilson L.J., Curley S.A. Toward paclitaxel-[60]fullerene immunoconjugates as a targeted prodrug against cancer. Nanosystems: Physics, Chemistry, Mathematics. 2014;5(1):67-75.

Views: 4


Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 License.


ISSN 2220-8054 (Print)
ISSN 2305-7971 (Online)