Information
References
Contents
Download
[1]http://globocan.iarc.fr/Pages/fact_sheets_cancer.aspx
[2]http://inhance.iarc.fr/about.php
[3]R. Siegel, J. Ma, Z. Zou, A. Jemal. Cancer statistics, 2014. CA Cancer J Clin 64, 1, 9-29 (2014)
[4]C. Fakhry, M. L. Gillison. Clinical implications of human papillomavirus in head and neck cancers. Journal of Clinical Oncology. 24, 17, 2606-11 (2006)
[5]http://www.cdc.gov/std/HPV/STDFact-HPV.htm
[6]http://www.oralcancerfoundation.org
[7]V. Jayaprakash, M. Reid, E. Hatton,M. Merzianu, N. Rigual, J. Marshall, S. Gill, J. Frustino, G. Wilding, T. Loree, S. Popat, M. Sullivan. Human papillomavirus types 16 and 18 in epithelial dysplasia of oral cavity and oropharynx: a meta-analysis. Oral Oncology. 47, 11, 1048-54 (2011)
[8]A. K. Chaturvedi, E. A. Engels, R.M. Pfeiffer, B. Y. Hernandez, W. Xiao, E. Kim, B. Jiang, M.T. Goodman, M. Sibug-Saber, W. Cozen, L. Liu, C. F. Lynch, N. Wentzensen, R. C. Jordan, S. Altekruse, W. F. Anderson, P. S. Rosenberg, M. L. Gillison. Human papillomavirus and rising oropharyngeal cancer incidence in the United States. Journal of Clinical Oncology 29, 32, 4294-301 (2011)
[9]M. C. Wani, H. L. Taylor, M. E. Wall, P. Coggon, A. T. McPhail. Plant antitumor agents. VI. The isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia. J Am Chem Soc 93, 9, 2325-7 (1971)
[10]K. C. Nicolaou, W. M. Dai, R. K. Guy. Chemistry and biology of taxol. Angewandte Chemie-International Edition 33, 1, 15-44 (1994)
[11]D. Majumdar, S. Singhal. Medicinal chemistry and nanomedicine for reproductive cancer therapeutics. Frontiers in Bioscience (Elite Ed) 4, 2029-44 (2012)
[12]D. A. Fuchs, R. K. Johnson. Cytologic evidence that taxol, an antineoplastic agent from Taxus brevifolia, acts as a mitotic spindle poison. Cancer Treat Rep 62, 8,1219-22 (1978)
[13]P. B. Schiff, J. Fant, S. B. Horwitz. Nature 277, 5698, 665-7 (1979)
[14]P. B. Schiff, S. B. Horwitz. Proc Natl Acad Sci U S A 77, 3, 1561-5 (1980)
[15]H. Gelderblom, J. Verweij, K. Nooter, A. Sparreboom. Cremophor EL: the drawbacks and advantages of vehicle selection for drug formulation. Eur J Cancer 37, 13, 1590-8 (2001)
[16]Z. Li, R. Zhao, X. Wu, Y. Sun, M. Yao, J. Li, Y. Xu, J. Gu. Identification and characterization of a novel peptide ligand of epidermal growth factor receptor for targeted delivery of therapeutics. FASEB J 19, 14, 1978-85 (2005)
[17]L. Milane, Z. Duan, M. Amiji. Development of EGFR-targeted polymer blend nanocarriers for combination paclitaxel/lonidamine delivery to treat multi-drug resistance in human breast and ovarian tumor cells. Mol Pharm, 8, 1, 185-203 (2011)
[18]Y. Luo, G. D. Prestwich. Synthesis and selective cytotoxicity of a hyaluronic acid-antitumor bioconjugate. Bioconjug Chem 10, 5, 755-63 (1999)
[19]H. Ogura, S. Nagai, K. Takeda. A novel reagent (N_succinimidyl diphenylphosphate) for synthesis of active ester and peptide. Tetrahedron Letters 21, 15, 1467-68 (1980)
[20]P. E. Dawson, T. W. Muir, I. Clark-Lewis, S. B. Kent. Synthesis of proteins by native chemical ligation. Science 266, 5186, 776-9 (1994)
[21]Q. Wan, J. Chen, Y. Yuan, S. J. Danishefsky. Oxo-ester mediated native chemical ligation: concept and applications. J Am Chem Soc 130, 47, 15814-6 (2008)
[22]V. Vichai, K. Kirtikara. Sulforhodamine B colorimetric assay for cytotoxicity screening. Nat Protoc 1, 3, 1112-6 (2006)
[23]R. Duncan. The dawning era of polymer therapeutics. Nature Reviews Drug Discovery 2, 5, 347-60 (2003)
[24]M. Thanou, R. Duncan. Curr Opin Investig Drugs 4, 6, 701-9 (2003)
[25]M. J. Vicent, R. Duncan. Polymer-protein and polymer-drug conjugates in cancer therapy. Trends in Biotechnology 24, 1, 39-47 (2006)
[26]R. Duncan. Polymer conjugates as anticancer nanomedicines. Nature Reviews Cancer 6, 9, 688-701 (2006)
[27]C. D. Conover, H. Zhao, C. B. Longley, K. L. Shum, R. B. Greenwald. Utility of poly(ethylene glycol) conjugation to create prodrugs of amphotericin B. Bioconjugate Chemistry 14, 3, 661-6 (2003)
[28]R. B. Greenwald, A. Pendri, C. D. Conover, C. Lee, Y. H. Choe, C. Gilbert, A. Martinez, J. Xia, D. C. Wu, M. Hsue. Camptothecin-20-PEG ester transport forms: the effect of spacer groups on antitumor activity. Bioorganic & Medicinal Chemistry 6, 5, 551-62 (1998)
[29]P. C. A. Rodrigues, U. Beyer, P. Schumacher, T. Roth, H. H. Fiebig, C. Unger, L. Messori, P. Orioli, D. H. Paper, R. Mulhaupt, F. Kratz. Acid-sensitive polyethylene glycol conjugates of doxorubicin: preparation, in vitro efficacy and intracellular distribution. Bioorganic & Medicinal Chemistry 7, 11, 2517-24 (1999)
[30]E. K. Rowinsky, J. Rizzo, L. Ochoa, C. H. Takimoto, B. Forouzesh, G. Schwartz, L. A. Hammond, A. Patnaik, J. Kwiatek, A. Goetz, L. Denis, J. McGuire, A. W. Tolcher. A phase I and pharmacokinetic study of pegylated camptothecin as a 1-hour infusion every 3 weeks in patients with advanced solid malignancies. Journal of Clinical Oncology 21, 1, 148-57 (2003)
[31]H. Zhao, B. Rubio, P. Sapra, D. C. Wu, P. Reddy, P. Sai, A. Martinez, Y. Gao, Y. Lozanguiez, C. Longley, L. M. Greenberger, I. D. Horak. Novel prodrugs of SN38 using multiarm poly(ethylene glycol) linkers. Bioconjugate Chemistry 19, 4, 849-59 (2008)
[32]P. Sapra, H. Zhao, M. Mehlig, J. Malaby, P. Kraft, C. Longley, L. M. Greenberger, I. D. Horak. Novel delivery of SN38 markedly inhibits tumor growth in xenografts, including a camptothecin-11-refractory model. Clin Cancer Res. 14, 6, 1888-96 (2008)
[33]R. B. Greenwald, Y. H. Choe, J. McGuire, C. D. Conover. Effective drug delivery by PEGylated drug conjugates. Adv Drug Deliv Rev 55, 2, 217-50 (2003)
[34]Y. Yarden, M. X. Sliwkowski. Untangling the ErbB signalling network. Nat Rev Mol Cell Biol 2, 2, 127-37 (2001)
[35]J. Schlessinger. Ligand-induced, receptor-mediated dimerization and activation of EGF receptor. Cell 110, 6, 669-72 (2002)
[36]R. N. Jorissen, F. Walker, N. Pouliot, T. P. Garrett, C. W. Ward, A. W. Burgess. Epidermal growth factor receptor: mechanisms of activation and signalling. Exp Cell Res 284, 1, 31-53 (2003)
[37]S. V. Sharma, D. W. Bell, J. Settleman, D. A. Haber. Epidermal growth factor receptor mutations in lung cancer. Nat Rev Cancer 7, 3, 169-81 (2007)
[38]J. Bernier, S. M. Bentzen, J. B. Vermorken. Molecular therapy in head and neck oncology. Nat Rev Clin Oncol 6, 5, 266-77 (2009)
[39]K. Beaumont, R. Webster, I. Gardner, K. Dack. Design of ester prodrugs to enhance oral absorption of poorly permeable compounds: challenges to the discovery scientist. Current Drug Metabolism 4, 6, 461-85 (2003)
[40]R. B. Greenwald, A. Pendri, D. Bolikal. Highly Water Soluble Taxol Derivatives: 7-Polyethylene Glycol Carbamates and Carbonates. Journal of Organic Chemistry 60, 2, 331-36 (1995)
[41]R. B. Greenwald, C. W. Gilbert, A. Pendri, C. D. Conover, J. Xia, A. Martinez. Drug delivery systems: water soluble taxol 2’-poly(ethylene glycol) ester prodrugs-design and in vivo effectiveness. J Med Chem 39, 2, 424-31 (1996)
[42]C. Che, G. Yang, C. Thiot, M. C. Lacoste, J. C. Currie, M. Demeule, A. Regina, R. Beliveau, J. P. Castaigne. New Angiopep-modified doxorubicin (ANG1007) and etoposide (ANG1009) chemotherapeutics with increased brain penetration. J Med Chem 53, 7, 2814-24 (2010)
[43]R. V. Chari. Targeted cancer therapy: conferring specificity to cytotoxic drugs. Acc Chem Res 41, 1, 98-107 (2008)
[44]A. Meister, M. E. Anderson. Glutathione. Annu Rev Biochem 52, 711-60 (1983)
[45]H. Lee, K. Lee, T. G. Park. Hyaluronic acid-paclitaxel conjugate micelles: synthesis, characterization, and antitumor activity. Bioconjugate Chemistry 19, 6, 1319-25 (2008)
[46]L. Ducry, B. Stump. Antibody-drug conjugates: linking cytotoxic payloads to monoclonal antibodies. Bioconjugate Chemistry 21, 1, 5-13 (2010)
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Frontiers in Bioscience-Elite (FBE) is published by IMR Press from Volume 13 Issue 2 (2021). Previous articles were published by another publisher on a subscription basis, and they are hosted by IMR Press on imrpress.com as a courtesy and upon agreement with Frontiers in Bioscience.
Anticancer activity of drug conjugates in head and neck cancer cells
1 Department of Hematology and Medical Oncology, Winship Cancer Institute, Emory University School of Medicine, Emory University, 1365 C Clifton Road, Atlanta, GA 30322
2 Glycosyn LLC, Medford, MA 02155
*Author to whom correspondence should be addressed.
Abstract
Sexually transmitted oral cancer/head and neck cancer is increasing rapidly. Human papilloma virus (HPV) is playing a role in the pathogenesis of a subset of squamous cell carcinoma of head and neck (SCCHN). Paclitaxel is a widely used anticancer drug for breast, ovarian, testicular, cervical, non-small cell lung, head and neck cancer. However, it is water insoluble and orally inactive. We report the synthesis of water soluble nanosize conjugates of paclitaxel, branched PEG, and EGFR-targeting peptide by employing native chemical ligation. We performed a native chemical ligation between the N-hydroxy succinimide (NHS) ester of paclitaxel succinate and cysteine at pH 6.5 to give the cysteine-conjugated paclitaxel derivative. The thiol functionality of cysteine was activated and subsequently conjugated to multiarm thiol-PEG to obtain the paclitaxel branched PEG conjugate. Finally, we conjugated an EGFR-targeting peptide to obtain conjugates of paclitaxel, branched PEG, and EGFR-targeting peptide. These conjugates show anticancer activity against squamous cell carcinoma of head and neck cells (SCCHN, Tu212).
Keywords
- Cancer
- Head
- Neck
- Cancer
- Squamous Cell Carcinoma
- SCCHN
- Paclitaxel
- Human Papillomavirus
- Oropharynx
- Epidermal Growth Factor Receptor
- EGFR
- Polyethylene Glycol Ether
- PEG
- Native Chemical Ligation
- Peptide
- Ligand
- Antibody
- Cancer Therapy
References
- [1] http://globocan.iarc.fr/Pages/fact_sheets_cancer.aspx
- [2] http://inhance.iarc.fr/about.php
- [3] R. Siegel, J. Ma, Z. Zou, A. Jemal. Cancer statistics, 2014. CA Cancer J Clin 64, 1, 9-29 (2014)
- [4] C. Fakhry, M. L. Gillison. Clinical implications of human papillomavirus in head and neck cancers. Journal of Clinical Oncology. 24, 17, 2606-11 (2006)
- [5] http://www.cdc.gov/std/HPV/STDFact-HPV.htm
- [6] http://www.oralcancerfoundation.org
- [7] V. Jayaprakash, M. Reid, E. Hatton,M. Merzianu, N. Rigual, J. Marshall, S. Gill, J. Frustino, G. Wilding, T. Loree, S. Popat, M. Sullivan. Human papillomavirus types 16 and 18 in epithelial dysplasia of oral cavity and oropharynx: a meta-analysis. Oral Oncology. 47, 11, 1048-54 (2011)
- [8] A. K. Chaturvedi, E. A. Engels, R.M. Pfeiffer, B. Y. Hernandez, W. Xiao, E. Kim, B. Jiang, M.T. Goodman, M. Sibug-Saber, W. Cozen, L. Liu, C. F. Lynch, N. Wentzensen, R. C. Jordan, S. Altekruse, W. F. Anderson, P. S. Rosenberg, M. L. Gillison. Human papillomavirus and rising oropharyngeal cancer incidence in the United States. Journal of Clinical Oncology 29, 32, 4294-301 (2011)
- [9] M. C. Wani, H. L. Taylor, M. E. Wall, P. Coggon, A. T. McPhail. Plant antitumor agents. VI. The isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia. J Am Chem Soc 93, 9, 2325-7 (1971)
- [10] K. C. Nicolaou, W. M. Dai, R. K. Guy. Chemistry and biology of taxol. Angewandte Chemie-International Edition 33, 1, 15-44 (1994)
- [11] D. Majumdar, S. Singhal. Medicinal chemistry and nanomedicine for reproductive cancer therapeutics. Frontiers in Bioscience (Elite Ed) 4, 2029-44 (2012)
- [12] D. A. Fuchs, R. K. Johnson. Cytologic evidence that taxol, an antineoplastic agent from Taxus brevifolia, acts as a mitotic spindle poison. Cancer Treat Rep 62, 8,1219-22 (1978)
- [13] P. B. Schiff, J. Fant, S. B. Horwitz. Nature 277, 5698, 665-7 (1979)
- [14] P. B. Schiff, S. B. Horwitz. Proc Natl Acad Sci U S A 77, 3, 1561-5 (1980)
- [15] H. Gelderblom, J. Verweij, K. Nooter, A. Sparreboom. Cremophor EL: the drawbacks and advantages of vehicle selection for drug formulation. Eur J Cancer 37, 13, 1590-8 (2001)
- [16] Z. Li, R. Zhao, X. Wu, Y. Sun, M. Yao, J. Li, Y. Xu, J. Gu. Identification and characterization of a novel peptide ligand of epidermal growth factor receptor for targeted delivery of therapeutics. FASEB J 19, 14, 1978-85 (2005)
- [17] L. Milane, Z. Duan, M. Amiji. Development of EGFR-targeted polymer blend nanocarriers for combination paclitaxel/lonidamine delivery to treat multi-drug resistance in human breast and ovarian tumor cells. Mol Pharm, 8, 1, 185-203 (2011)
- [18] Y. Luo, G. D. Prestwich. Synthesis and selective cytotoxicity of a hyaluronic acid-antitumor bioconjugate. Bioconjug Chem 10, 5, 755-63 (1999)
- [19] H. Ogura, S. Nagai, K. Takeda. A novel reagent (N_succinimidyl diphenylphosphate) for synthesis of active ester and peptide. Tetrahedron Letters 21, 15, 1467-68 (1980)
- [20] P. E. Dawson, T. W. Muir, I. Clark-Lewis, S. B. Kent. Synthesis of proteins by native chemical ligation. Science 266, 5186, 776-9 (1994)
- [21] Q. Wan, J. Chen, Y. Yuan, S. J. Danishefsky. Oxo-ester mediated native chemical ligation: concept and applications. J Am Chem Soc 130, 47, 15814-6 (2008)
- [22] V. Vichai, K. Kirtikara. Sulforhodamine B colorimetric assay for cytotoxicity screening. Nat Protoc 1, 3, 1112-6 (2006)
- [23] R. Duncan. The dawning era of polymer therapeutics. Nature Reviews Drug Discovery 2, 5, 347-60 (2003)
- [24] M. Thanou, R. Duncan. Curr Opin Investig Drugs 4, 6, 701-9 (2003)
- [25] M. J. Vicent, R. Duncan. Polymer-protein and polymer-drug conjugates in cancer therapy. Trends in Biotechnology 24, 1, 39-47 (2006)
- [26] R. Duncan. Polymer conjugates as anticancer nanomedicines. Nature Reviews Cancer 6, 9, 688-701 (2006)
- [27] C. D. Conover, H. Zhao, C. B. Longley, K. L. Shum, R. B. Greenwald. Utility of poly(ethylene glycol) conjugation to create prodrugs of amphotericin B. Bioconjugate Chemistry 14, 3, 661-6 (2003)
- [28] R. B. Greenwald, A. Pendri, C. D. Conover, C. Lee, Y. H. Choe, C. Gilbert, A. Martinez, J. Xia, D. C. Wu, M. Hsue. Camptothecin-20-PEG ester transport forms: the effect of spacer groups on antitumor activity. Bioorganic & Medicinal Chemistry 6, 5, 551-62 (1998)Cited within: 0Google Scholar
- [29] P. C. A. Rodrigues, U. Beyer, P. Schumacher, T. Roth, H. H. Fiebig, C. Unger, L. Messori, P. Orioli, D. H. Paper, R. Mulhaupt, F. Kratz. Acid-sensitive polyethylene glycol conjugates of doxorubicin: preparation, in vitro efficacy and intracellular distribution. Bioorganic & Medicinal Chemistry 7, 11, 2517-24 (1999)Cited within: 0Google Scholar
- [30] E. K. Rowinsky, J. Rizzo, L. Ochoa, C. H. Takimoto, B. Forouzesh, G. Schwartz, L. A. Hammond, A. Patnaik, J. Kwiatek, A. Goetz, L. Denis, J. McGuire, A. W. Tolcher. A phase I and pharmacokinetic study of pegylated camptothecin as a 1-hour infusion every 3 weeks in patients with advanced solid malignancies. Journal of Clinical Oncology 21, 1, 148-57 (2003)
- [31] H. Zhao, B. Rubio, P. Sapra, D. C. Wu, P. Reddy, P. Sai, A. Martinez, Y. Gao, Y. Lozanguiez, C. Longley, L. M. Greenberger, I. D. Horak. Novel prodrugs of SN38 using multiarm poly(ethylene glycol) linkers. Bioconjugate Chemistry 19, 4, 849-59 (2008)
- [32] P. Sapra, H. Zhao, M. Mehlig, J. Malaby, P. Kraft, C. Longley, L. M. Greenberger, I. D. Horak. Novel delivery of SN38 markedly inhibits tumor growth in xenografts, including a camptothecin-11-refractory model. Clin Cancer Res. 14, 6, 1888-96 (2008)
- [33] R. B. Greenwald, Y. H. Choe, J. McGuire, C. D. Conover. Effective drug delivery by PEGylated drug conjugates. Adv Drug Deliv Rev 55, 2, 217-50 (2003)
- [34] Y. Yarden, M. X. Sliwkowski. Untangling the ErbB signalling network. Nat Rev Mol Cell Biol 2, 2, 127-37 (2001)
- [35] J. Schlessinger. Ligand-induced, receptor-mediated dimerization and activation of EGF receptor. Cell 110, 6, 669-72 (2002)
- [36] R. N. Jorissen, F. Walker, N. Pouliot, T. P. Garrett, C. W. Ward, A. W. Burgess. Epidermal growth factor receptor: mechanisms of activation and signalling. Exp Cell Res 284, 1, 31-53 (2003)
- [37] S. V. Sharma, D. W. Bell, J. Settleman, D. A. Haber. Epidermal growth factor receptor mutations in lung cancer. Nat Rev Cancer 7, 3, 169-81 (2007)
- [38] J. Bernier, S. M. Bentzen, J. B. Vermorken. Molecular therapy in head and neck oncology. Nat Rev Clin Oncol 6, 5, 266-77 (2009)
- [39] K. Beaumont, R. Webster, I. Gardner, K. Dack. Design of ester prodrugs to enhance oral absorption of poorly permeable compounds: challenges to the discovery scientist. Current Drug Metabolism 4, 6, 461-85 (2003)
- [40] R. B. Greenwald, A. Pendri, D. Bolikal. Highly Water Soluble Taxol Derivatives: 7-Polyethylene Glycol Carbamates and Carbonates. Journal of Organic Chemistry 60, 2, 331-36 (1995)
- [41] R. B. Greenwald, C. W. Gilbert, A. Pendri, C. D. Conover, J. Xia, A. Martinez. Drug delivery systems: water soluble taxol 2’-poly(ethylene glycol) ester prodrugs-design and in vivo effectiveness. J Med Chem 39, 2, 424-31 (1996)
- [42] C. Che, G. Yang, C. Thiot, M. C. Lacoste, J. C. Currie, M. Demeule, A. Regina, R. Beliveau, J. P. Castaigne. New Angiopep-modified doxorubicin (ANG1007) and etoposide (ANG1009) chemotherapeutics with increased brain penetration. J Med Chem 53, 7, 2814-24 (2010)
- [43] R. V. Chari. Targeted cancer therapy: conferring specificity to cytotoxic drugs. Acc Chem Res 41, 1, 98-107 (2008)
- [44] A. Meister, M. E. Anderson. Glutathione. Annu Rev Biochem 52, 711-60 (1983)
- [45] H. Lee, K. Lee, T. G. Park. Hyaluronic acid-paclitaxel conjugate micelles: synthesis, characterization, and antitumor activity. Bioconjugate Chemistry 19, 6, 1319-25 (2008)
- [46] L. Ducry, B. Stump. Antibody-drug conjugates: linking cytotoxic payloads to monoclonal antibodies. Bioconjugate Chemistry 21, 1, 5-13 (2010)
