Parallel synthesis and biological evaluation of 837 analogues of procaspase-activating compound 1 (PAC-1)

ACS Combinatorial Science

Volumn 14, Issue 1, 2012, Pages 44-50

  Hsu, Danny C ^a   Roth, Howard S ^a   West, Diana C ^a   Botham, Rachel C ^a   Novotny, Chris J ^b   Schmid, Steven C ^a   Hergenrother, Paul J ^a,b  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^b UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

anticancer compounds; apoptosis; Cancer; procaspase 3; zinc

Indexed keywords

(4 BENZYLPIPERAZIN 1 YL)ACETIC ACID (3 ALLYL 2 HYDROXYBENZYLIDENE)HYDRAZINE; (4-BENZYLPIPERAZIN-1-YL)ACETIC ACID (3-ALLYL-2-HYDROXYBENZYLIDENE)HYDRAZINE; ANTINEOPLASTIC AGENT; CASPASE 3; HYDRAZONE DERIVATIVE; PIPERAZINE DERIVATIVE;

APOPTOSIS; ARTICLE; BIOSYNTHESIS; CELL STRAIN U937; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; CULTURE TECHNIQUE; DRUG ANTAGONISM; DRUG DEVELOPMENT; DRUG EFFECT; DRUG SCREENING; ENZYME INDUCTION; FLOW CYTOMETRY; HUMAN; METHODOLOGY; MOLECULAR LIBRARY; SYNTHESIS;

ANTINEOPLASTIC AGENTS; APOPTOSIS; CASPASE 3; CELL CULTURE TECHNIQUES; CELL SURVIVAL; CHEMISTRY TECHNIQUES, SYNTHETIC; DRUG DISCOVERY; DRUG SCREENING ASSAYS, ANTITUMOR; ENZYME INDUCTION; FLOW CYTOMETRY; HUMANS; HYDRAZONES; MOLECULAR STRUCTURE; PIPERAZINES; SMALL MOLECULE LIBRARIES; U937 CELLS;

EID: 84855580303     PISSN: 21568952     EISSN: None     Source Type: Journal    
DOI: 10.1021/co2001372     Document Type: Article

References (33)

1. Hengartner, M. O. The biochemistry of apoptosis Nature 2000, 407, 770-776
2. Elmore, S. Apoptosis: A review of programmed cell death Toxicol. Pathol. 2007, 35, 495-516 (Pubitemid 46911891)
3. Nicholson, D. W. Caspase structure, proteolytic substrates, and function during apoptotic cell death Cell Death Differ. 1999, 6, 1028-1042
4. Earnshaw, W. C.; Martins, L. M.; Kaufmann, S. H. Mammalian caspases: Structure, activation, substrates, and functions during apoptosis Annu. Rev. Biochem. 1999, 68, 383-424 (Pubitemid 29449198)
5. Slee, E. A.; Adrain, C.; Martin, S. J. Executioner caspase-3, -6, and -7 perform distinct, non-redundant roles during the demolition phase of apoptosis J. Biol. Chem. 2001, 276, 7320-6
6. Sakahira, H.; Enari, M.; Nagata, S. Cleavage of CAD inhibitor in CAD activation and DNA degradation during apoptosis Nature 1998, 391, 96-99 (Pubitemid 28079223)
7. Hanahan, D.; Weinberg, R. A. The hallmarks of cancer Cell 2000, 100, 57-70 (Pubitemid 30046295)
8. Hanahan, D.; Weinberg, R. A. Hallmarks of cancer: the next generation Cell 2011, 144, 646-74
9. Vassilev, L. T.; Vu, B. T.; Graves, B.; Carvajal, D.; Podlaski, F.; Filipovic, Z.; Kong, N.; Kammlott, U.; Lukacs, C.; Klein, C.; Fotouhi, N.; Liu, E. A. In vivo activation of the p53 pathway by small-molecule antagonists of MDM2 Science 2004, 303, 844-8 (Pubitemid 38174664)
10. Oltersdorf, T.; Elmore, S. W.; Shoemaker, A. R.; Armstrong, R. C.; Augeri, D. J.; Belli, B. A.; Bruncko, M.; Deckwerth, T. L.; Dinges, J.; Hajduk, P. J.; Joseph, M. K.; Kitada, S.; Korsmeyer, S. J.; Kunzer, A. R.; Letai, A.; Li, C.; Mitten, M. J.; Nettesheim, D. G.; Ng, S.; Nimmer, P. M.; O'Connor, J. M.; Oleksijew, A.; Petros, A. M.; Reed, J. C.; Shen, W.; Tahir, S. K.; Thompson, C. B.; Tomaselli, K. J.; Wang, B. L.; Wendt, M. D.; Zhang, H. C.; Fesik, S. W.; Rosenberg, S. H. An inhibitor of Bcl-2 family proteins induces regression of solid tumours Nature 2005, 435, 677-681 (Pubitemid 40825512)
11. Lu, J.; Bai, L.; Sun, H.; Nikolovska-Coleska, Z.; McEachern, D.; Qiu, S.; Miller, R. S.; Yi, H.; Shangary, S.; Sun, Y.; Meagher, J. L.; Stuckey, J. A.; Wang, S. SM-164: a novel, bivalent Smac mimetic that induces apoptosis and tumor regression by concurrent removal of the blockade of cIAP-1/2 and XIAP Cancer Res. 2008, 68, 9384-93
12. Putt, K. S.; Chen, G. W.; Pearson, J. M.; Sandhorst, J. S.; Hoagland, M. S.; Kwon, J. T.; Hwang, S. K.; Jin, H.; Churchwell, M. I.; Cho, M. H.; Doerge, D. R.; Helferich, W. G.; Hergenrother, P. J. Small-molecule activation of procaspase-3 to caspase-3 as a personalized anticancer strategy Nat. Chem. Biol. 2006, 2, 543-550 (Pubitemid 44413237)
13. Soini, Y.; Paakko, P. Apoptosis and expression of caspases 3, 6 and 8 in malignant non-Hodgkin's lymphomas APMIS 1999, 107, 1043-50
14. Estrov, Z.; Thall, P. F.; Talpaz, M.; Estey, E. H.; Kantarjian, H. M.; Andreeff, M.; Harris, D.; Van, Q.; Walterscheid, M.; Kornblau, S. M. Caspase 2 and caspase 3 protein levels as predictors of survival in acute myelogenous leukemia Blood 1998, 92, 3090-7 (Pubitemid 28492314)
15. Fink, D.; Schlagbauer-Wadl, H.; Selzer, E.; Lucas, T.; Wolff, K.; Pehamberger, H.; Eichler, H. G.; Jansen, B. Elevated procaspase levels in human melanoma Melanoma Res. 2001, 11, 385-93 (Pubitemid 32735229)
16. Virkajarvi, N.; Paakko, P.; Soini, Y. Apoptotic index and apoptosis influencing proteins bcl-2, mcl-1, bax and caspases 3, 6 and 8 in pancreatic carcinoma Histopathology 1998, 33, 432-9 (Pubitemid 28529777)
17. Persad, R.; Liu, C.; Wu, T. T.; Houlihan, P. S.; Hamilton, S. R.; Diehl, A. M.; Rashid, A. Overexpression of caspase-3 in hepatocellular carcinomas Mod. Pathol. 2004, 17, 861-7
18. Tormanen-Napankangas, U.; Soini, Y.; Kahlos, K.; Kinnula, V.; Paakko, P. Expression of caspases-3, -6 and -8 and their relation to apoptosis in non-small cell lung carcinoma Int. J. Cancer 2001, 93, 192-8 (Pubitemid 32574274)
19. Krepela, E.; Prochazka, J.; Liul, X.; Fiala, P.; Kinkor, Z. Increased expression of Apaf-1 and procaspase-3 and the functionality of intrinsic apoptosis apparatus in non-small cell lung carcinoma Biol. Chem. 2004, 385, 153-68 (Pubitemid 38461336)
20. O'Donovan, N.; Crown, J.; Stunell, H.; Hill, A. D.; McDermott, E.; O'Higgins, N.; Duffy, M. J. Caspase 3 in breast cancer Clin. Cancer Res. 2003, 9, 738-42 (Pubitemid 36182608)
21. Zapata, J. M.; Krajewska, M.; Krajewski, S.; Huang, R. P.; Takayama, S.; Wang, H. G.; Adamson, E.; Reed, J. C. Expression of multiple apoptosis-regulatory genes in human breast cancer cell lines and primary tumors Breast Cancer Res. Treat. 1998, 47, 129-40 (Pubitemid 28046084)
22. Roy, S.; Bayly, C. I.; Gareau, Y.; Houtzager, V. M.; Kargman, S.; Keen, S. L.; Rowland, K.; Seiden, I. M.; Thornberry, N. A.; Nicholson, D. W. Maintenance of caspase-3 proenzyme dormancy by an intrinsic "safety catch" regulatory tripeptide Proc. Natl. Acad. Sci. U. S. A. 2001, 98, 6132-7 (Pubitemid 32488205)
23. Wolan, D. W.; Zorn, J. A.; Gray, D. C.; Wells, J. A. Small-Molecule Activators of a Proenzyme Science 2009, 326, 853-858
24. Peterson, Q. P.; Hsu, D. C.; Goode, D. R.; Novotny, C. J.; Totten, R. K.; Hergenrother, P. J. Procaspase-3 activation as an anti-cancer strategy: Structure-activity relationship of procaspase-activating compound 1 (PAC-1) and its cellular co-localization with caspase-3 J. Med. Chem. 2009, 52, 5721-5731
25. Charkoudian, L. K.; Pham, D. M.; Franz, K. J. A pro-chelator triggered by hydrogen peroxide inhibits iron-promoted hydroxyl radical formation J. Am. Chem. Soc. 2006, 128, 12424-5 (Pubitemid 44476626)
26. Peterson, Q. P.; Goode, D. R.; West, D. C.; Ramsey, K. N.; Lee, J. J. Y.; Hergenrother, P. J. PAC-1 activates procaspase-3 in vitro through relief of zinc-mediated inhibition J. Mol. Biol. 2009, 388, 144-158
27. Truong-Tran, A. Q.; Grosser, D.; Ruffin, R. E.; Murgia, C.; Zalewski, P. D. Apoptosis in the normal and inflamed airway epithelium: role of zinc in epithelial protection and procaspase-3 regulation Biochem. Pharmacol. 2003, 66, 1459-1468 (Pubitemid 38373334)
28. Lucas, P. W.; Schmit, J. M.; Peterson, Q. P.; West, D. C.; Hsu, D. C.; Novotny, C. J.; Dirikolu, L.; Churchwell, M. I.; Doerge, D. R.; Garrett, L. D.; Hergenrother, P. J.; Fan, T. M. Pharmacokinetics and derivation of an anticancer dosing regimen for PAC-1, a preferential small molecule activator of procaspase-3, in healthy dogs Invest. New Drugs 2011, 29, 901-11
29. Peterson, Q. P.; Hsu, D. C.; Novotny, C. J.; West, D. C.; Kim, D.; Schmit, J. M.; Dirikolu, L.; Hergenrother, P. J.; Fan, T. M. Discovery and canine preclinical assessment of a nontoxic procaspase-3-activating compound Cancer Res. 2010, 70, 7232-41
30. Hergenrother, P. J.; Putt, K. S.; Sandhorst, J. S.; Peterson, Q. P.; Fako, V. Compositions and methods including cell death inducers and procaspase activation. International Patent Application WO 2008/134474.
31. Miller, C. E. Hydrogenation with diimide J. Chem. Educ. 1965, 42, 254-&
32. Chang, K. H.; Huang, C. C.; Liu, Y. H.; Hu, Y. H.; Chou, P. T.; Lin, Y. C. Synthesis of photo-luminescent Zn(II) Schiff base complexes and its derivative containing Pd(II) moiety Dalton Trans. 2004, 1731-8
33. Peterson, Q. P.; Goode, D. R.; West, D. C.; Botham, R. C.; Hergenrother, P. J. Preparation of the caspase-3/7 substrate Ac-DEVD-pNA by solution-phase peptide synthesis Nat. Protoc. 2010, 5, 294-302