Using a build-and-click approach for producing structural and functional diversity in DNA-targeted hybrid anticancer agents

Journal of Medicinal Chemistry

Volumn 55, Issue 22, 2012, Pages 10198-10203

  Ding, Song ^a   Qiao, Xin ^a,c   Kucera, Gregory L ^b   Bierbach, Ulrich ^a  

^a WAKE FOREST UNIVERSITY   (United States)

^b WAKE FOREST UNIVERSITY HEALTH SCIENCES   (United States)

^c TIANJIN MEDICAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACRIDINE DERIVATIVE; AMINE; AMINOACRIDINE DERIVATIVE; ANTINEOPLASTIC AGENT; AZIDE; CARBOXYLIC ACID; CISPLATIN; CYTOTOXIC AGENT; DNA; HYDROXYL GROUP; METAL; NITRILE; PLATINUM; PLATINUM COMPLEX; PLATINUM DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; AUTOMATION; CELL PROLIFERATION; CELL VIABILITY; CHEMICAL COMPOSITION; CHEMICAL REACTION; CLICK CHEMISTRY; COMPLEX FORMATION; CONTROLLED STUDY; CROSS LINKING; CYTOTOXICITY; DNA LIBRARY; DNA STRUCTURE; DRUG SCREENING; DRUG TARGETING; ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; IC 50; QUANTITATIVE ANALYSIS; STRUCTURE ACTIVITY RELATION;

ACRIDINES; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DNA; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; NEOPLASMS; PLATINUM; SMALL MOLECULE LIBRARIES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84870031263     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm301278c     Document Type: Article

References (19)

1. Kelland, L. The resurgence of platinum-based cancer chemotherapy Nat. Rev. Cancer 2007, 7, 573-584
2. Graham, J.; Mushin, M.; Kirkpatrick, P. Oxaliplatin Nat. Rev. Drug Discovery 2004, 3, 11-12
3. Momekov, G.; Bakalova, A.; Karaivanova, M. Novel approaches towards development of non-classical platinum-based antineoplastic agents: design of platinum complexes characterized by an alternative DNA-binding pattern and/or tumor-targeted cytotoxicity Curr. Med. Chem. 2005, 12, 2177-2191
4. Guddneppanavar, R.; Bierbach, U. Adenine-N3 in the DNA minor groove - an emerging target for platinum containing anticancer pharmacophores Anti-Cancer Agents Med. Chem. 2007, 7, 125-138
5. Komeda, S.; Casini, A. Next-generation anticancer metallodrugs Curr. Top. Med. Chem. 2012, 12, 219-235
6. Komeda, S. Unique platinum-DNA interactions may lead to more effective platinum-based antitumor drugs Metallomics 2011, 3, 650-655
7. Baruah, H.; Wright, M. W.; Bierbach, U. Solution structural study of a DNA duplex containing the guanine-N7 adduct formed by a cytotoxic platinum-acridine hybrid agent Biochemistry 2005, 44, 6059-6070
8. Qiao, X.; Zeitany, A. E.; Wright, M. W.; Essader, A. S.; Levine, K. E.; Kucera, G. L.; Bierbach, U. Analysis of the DNA damage produced by a platinum-acridine antitumor agent and its effects in NCI-H460 lung cancer cells Metallomics 2012, 4, 645-652
9. Smyre, C. L.; Saluta, G.; Kute, T. E.; Kucera, G. L.; Bierbach, U. Inhibition of DNA synthesis by a platinum-acridine hybrid agent leads to potent cell kill in non-small cell lung cancer ACS Med. Chem. Lett. 2011, 2, 870-874
10. Graham, L. A.; Wilson, G. M.; West, T. K.; Day, C. S.; Kucera, G. L.; Bierbach, U. Unusual reactivity of a potent platinum-acridine hybrid antitumor agent ACS Med. Chem. Lett. 2011, 2, 687-691
11. Choudhury, J. R.; Rao, L.; Bierbach, U. Rates of intercalator-driven platination of DNA determined by a restriction enzyme cleavage inhibition assay J. Biol. Inorg. Chem. 2011, 16, 373-380
12. Ma, Z.; Choudhury, J. R.; Wright, M. W.; Day, C. S.; Saluta, G.; Kucera, G. L.; Bierbach, U. A non-cross-linking platinum-acridine agent with potent activity in non-small-cell lung cancer J. Med. Chem. 2008, 51, 7574-7580
13. Alley, S. C.; Okeley, N. M.; Senter, P. D. Antibody-drug conjugates: targeted drug delivery for cancer Curr. Opin. Chem. Biol. 2010, 14, 529-537
14. Srinivasan, R.; Li, J.; Ng, S. L.; Kalesh, K. A.; Yao, S. Q. Methods of using click chemistry in the discovery of enzyme inhibitors Nat. Protoc. 2007, 2, 2655-2664
15. Bahta, M.; Liu, F.; Kim, S. E.; Stephen, A. G.; Fisher, R. J.; Burke, T. R., Jr. Oxime-based linker libraries as a general approach for the rapid generation and screening of multidentate inhibitors Nat. Protoc. 2012, 7, 686-702
16. Kukushkin, V. Y.; Pombeiro, A. J. Additions to metal-activated organonitriles Chem. Rev. 2002, 102, 1771-1802
17. Baskin, J. M.; Prescher, J. A.; Laughlin, S. T.; Agard, N. J.; Chang, P. V.; Miller, I. A.; Lo, A.; Codelli, J. A.; Bertozzi, C. R. Copper-free click chemistry for dynamic in vivo imaging Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 16793-16797
18. Wang, R. E.; Costanza, F.; Niu, Y.; Wu, H.; Hu, Y.; Hang, W.; Sun, Y.; Cai, J. Development of self-immolative dendrimers for drug delivery and sensing J. Controlled Release 2012, 159, 154-163
19. Karver, M. R.; Weissleder, R.; Hilderbrand, S. A. Bioorthogonal reaction pairs enable simultaneous, selective, multi-target imaging Angew. Chem., Int. Ed. 2012, 51, 920-922