Disulfide-Based Multifunctional Conjugates for Targeted Theranostic Drug Delivery

Accounts of Chemical Research

Volumn 48, Issue 11, 2015, Pages 2935-2946

  Lee, Min Hee ^a   Sessler, Jonathan L ^b   Kim, Jong Seung ^c  

^a Sookmyung Women's University   (South Korea)

^b University of Texas at Austin   (United States)

^c Korea University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; DISULFIDE; FLUORESCENT DYE;

ANIMAL; CHEMISTRY; DRUG DELIVERY SYSTEM; HUMAN; METABOLISM; MOUSE; RAT; THERANOSTIC NANOMEDICINE; TUMOR CELL LINE;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; DISULFIDES; DRUG DELIVERY SYSTEMS; FLUORESCENT DYES; HUMANS; MICE; RATS; THERANOSTIC NANOMEDICINE;

EID: 84947213707     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/acs.accounts.5b00406     Document Type: Article

References (34)

1. Corrie, P. G.; Pippa, G. Cytotoxic chemotherapy: clinical aspects Medicine 2008, 36, 24-28 10.1016/j.mpmed.2007.10.012
2. Garnett, M. C. Targeted drug conjugates: principles and progress Adv. Drug Delivery Rev. 2001, 53, 171-216 10.1016/S0169-409X(01)00227-7
3. Mahato, R.; Tai, W.; Cheng, K. Prodrugs for improving tumor targetability and efficiency Adv. Drug Delivery Rev. 2011, 63, 659-670 10.1016/j.addr.2011.02.002
4. Allen, T. M. Ligand-targeted therapeutics in anticancer therapy Nat. Rev. Cancer 2002, 2, 750-763 10.1038/nrc903
5. Lim, E. K.; Kim, T.; Paik, S.; Haam, S.; Huh, Y.-M.; Lee, K. Nanomaterials for theranostics: Recent advances and future challenges Chem. Rev. 2015, 115, 327-394 10.1021/cr300213b
6. Lee, M. H.; Yang, Z.; Lim, C. W.; Lee, Y. H.; Dongbang, S.; Kang, C.; Kim, J. S. Disulfide-cleavage-triggered chemosensors and their biological applications Chem. Rev. 2013, 113, 5071-5109 10.1021/cr300358b
7. Wong, P. T.; Choi, S. K. Mechanisms of drug release in nanotherapeutic delivery systems Chem. Rev. 2015, 115, 3388-3432 10.1021/cr5004634
8. Chen, S.; Zhao, X.; Chen, J.; Chen, J.; Kuznetsova, L.; Wong, S. S.; Ojima, I. Mechanism-based tumor-targeting drug delivery system. Validation of efficient vitamin receptor-mediated endocytosis and drug release Bioconjugate Chem. 2010, 21, 979-987 10.1021/bc9005656
9. Lee, M. H.; Kim, J. Y.; Han, J. H.; Bhuniya, S.; Sessler, J. L.; Kang, C.; Kim, J. S. Direct fluorescence monitoring of the delivery and cellular uptake of a cancer-targeted RGD peptide-appended naphthalimide theragnostic prodrug J. Am. Chem. Soc. 2012, 134, 12668-12674 10.1021/ja303998y
10. Lee, M. H.; Han, J. H.; Kwon, P.-S.; Bhuniya, S.; Kim, J. Y.; Kang, C.; Kim, J. S.; Seessler, J. L. Hepatocyte-targeting single galactose-appended naphthalimide: a tool for intracellular thiol imaging in vivo J. Am. Chem. Soc. 2012, 134, 1316-1322 10.1021/ja210065g
11. Pierschbacher, M. D.; Ruoslathi, E. Cell attachment activity of fibronectin can be duplicated by small synthetic fragments of the molecule Nature 1984, 309, 30-33 10.1038/309030a0
12. Hertzberg, R. P.; Caranfa, M. J.; Hecht, S. M. On the mechanism of topoisomerase I inhibition by camptothecin: evidence for binding to an enzyme-DNA complex Biochemistry 1989, 28, 4629-4638 10.1021/bi00437a018
13. 3 Cancer Res. 2006, 66, 9673-9681 10.1158/0008-5472.CAN-06-1480
14. 18F-FRGD2 J. Nucl. Med. 2006, 47, 113-121
15. Wang, H.; Chen, X. Applications for site-directed molecular imaging agents coupled with drug delivery potential Expert Opin. Drug Delivery 2009, 6, 745-768 10.1517/17425240902889751
16. Saksena, S.; Shao, Y.; Braunagel, S. C.; Summers, M. D.; Johnson, A. E. Cotranslational integration and initial sorting at the endoplasmic reticulum translocon of proteins destined for the inner nuclear membrane Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 12537-12542 10.1073/pnas.0404934101
17. Bhuniya, S.; Maiti, S.; Kim, E.-J.; Lee, H.; Sessler, J. L.; Hong, K. S.; Kim, J. S. An activatable theranostic for targeted cancer therapy and imaging Angew. Chem., Int. Ed. 2014, 53, 4469-4474 10.1002/anie.201311133
18. Russell-Jones, G.; McTavish, K.; McEwan, J.; Rice, J.; Nowotnik, D. Vitamin-mediated targeting as a potential mechanism to increase drug uptake by tumors J. Inorg. Biochem. 2004, 98, 1625-1633 10.1016/j.jinorgbio.2004.07.009
19. Brown, K. D.; Blakeley, D. M.; Roberts, P.; Avery, R. J. Loss of epidermal growth factor receptors and release of transforming growth factors do not correlate with sarcoma virus-transformation in clonally-related NIH/3T3-derived cell lines Biochem. J. 1985, 229, 119-125 10.1042/bj2290119
20. Heo, D. N.; Yang, D. H.; Moon, H. J.; Lee, J. B.; Bae, M. S.; Lee, S. C.; Lee, W. J.; Sun, I. C.; Kwon, I. K. Gold nanoparticles surface-functionalized with paclitaxel drug and biotin receptor as theranostic agents for cancer therapy Biomaterials 2012, 33, 856-866 10.1016/j.biomaterials.2011.09.064
21. Maiti, S.; Park, N.; Han, J. H.; Jeon, H. M.; Lee, J. H.; Bhuniya, S.; Kang, C.; Kim, J. S. Gemcitabine-coumarin-biotin conjugates: a target specific theranostic anticancer prodrug J. Am. Chem. Soc. 2013, 135, 4567-4572 10.1021/ja401350x
22. Gregory, J. D. The stability of N-ethylmaleimide and its reaction with sulfhydryl groups J. Am. Chem. Soc. 1955, 77, 3922-3923 10.1021/ja01619a073
23. Cerqueira, N. M. F. S. A.; Fernandes, P. A.; Ramos, M. J. Understanding ribonucleotide reductase inactivation by gemcitabine Chem.-Eur. J. 2007, 13, 8507-8515 10.1002/chem.200700260
24. Bhuniya, S.; Lee, M. H.; Jeon, H. M.; Han, J. H.; Lee, J. H.; Park, N.; Maiti, S.; Kang, C.; Kim, J. S. A fluorescence off-on reporter for real time monitoring of gemcitabine delivery to the cancer cells Chem. Commun. 2013, 49, 7141-7143 10.1039/c3cc42653j
25. Weissleder, R.; Ntziachristos, V. Shedding light onto live molecular targets Nat. Med. 2003, 9, 123-128 10.1038/nm0103-123
26. Yang, Z.; Lee, J. H.; Jeon, H. M.; Han, J. H.; Park, N.; He, Y.; Lee, H.; Hong, K. S.; Kang, C.; Kim, J. S. Folate-based near-infrared fluorescent theranostic gemcitabine delivery J. Am. Chem. Soc. 2013, 135, 11657-11662 10.1021/ja405372k
27. Parker, N.; Turk, M. J.; Westrick, E.; Lewis, J. D.; Low, P. S.; Leamon, C. P. Folate receptor expression in carcinomas and normal tissues determined by a quantitative radioligand binding assay Anal. Biochem. 2005, 338, 284-293 10.1016/j.ab.2004.12.026
28. Takeuchi, H.; Yamamoto, H.; Kawashima, Y. Mucoadhesive nanoparticulate systems for peptide drug delivery Adv. Drug Delivery Rev. 2001, 47, 39-54 10.1016/S0169-409X(00)00120-4
29. Kato, T.; Sato, N.; Hayama, S.; Yamabuki, T.; Ito, T.; Miyamoto, M.; Kondo, S.; Nakamura, Y.; Daigo, Y. Activation of Holliday junction-recognizing protein involved in the chromosomal stability and immortality of cancer cells Cancer Res. 2007, 67, 8544-8553 10.1158/0008-5472.CAN-07-1307
30. Kim, T.; Jeon, H. M.; Le, H. T.; Kim, T. W.; Kang, C.; Kim, J. S. A biotin-guided fluorescent-peptide drug delivery system for cancer treatment Chem. Commun. 2014, 50, 7690-7693 10.1039/c4cc02878c
31. Curtin, N. J. DNA repair dysregulation from cancer driver to therapeutic target Nat. Rev. Cancer 2012, 12, 801-817 10.1038/nrc3399
32. Boldt, J. L.; Pinilla, C.; Segall, A. Reversible inhibitors of λ integrase-mediated recombination efficiently trap Holliday junction intermediates and form the basis of a novel assay for junction resolution J. Biol. Chem. 2004, 279, 3472-3483 10.1074/jbc.M309361200
33. Gunderson, C. W.; Segall, A. DNA repair, a novel antibacterial target: Holliday junction-trapping peptides induce DNA damage and chromosome segregation defects Mol. Microbiol. 2006, 59, 1129-1148 10.1111/j.1365-2958.2005.05009.x
34. Holliday, R. A mechanism for gene conversion in fungi Genet. Res. 1964, 5, 282-304 10.1017/S0016672300001233