Biology and medicinal chemistry approaches towards various apoptosis inducers

Anti-Cancer Agents in Medicinal Chemistry

Volumn 13, Issue 3, 2013, Pages 433-455

  Vyas, Vivek K ^a   Chintha, Chetan ^a   Pandya, Mitul R ^a  

^a NIRMA UNIVERSITY   (India)

Author keywords

Anticancer agents; Apoptosis; Apoptosis inducers; Caspase; DNA damage

Indexed keywords

1, 2, 4 OXADIAZOLE DERIVATIVE; AMIDE; CARBAMIC ACID DERIVATIVE; CASPASE; CHROMENE DERIVATIVE; CLIOQUINOL; CROLIBULIN; EPIGALLOCATECHIN GALLATE; FLAVONE DERIVATIVE; GAMBOGIC ACID; GRANZYME A; GUANIDINE DERIVATIVE; HYDRAZIDE DERIVATIVE; MERCAPTOBENZOTHIAZOLE; NAPHTHALENE DERIVATIVE; NICOTINAMIDE ADENINE DINUCLEOTIDE ADENOSINE DIPHOSPHATE RIBOSYLTRANSFERASE 1; NICOTINAMIDE DERIVATIVE; PACLITAXEL; PERFORIN; PROTEIN BCL 2; PROTEIN KINASE C; PROTEIN P53; PYRIMIDINE DERIVATIVE; QUINOLINE DERIVATIVE; RESVERATROL; THIAZEPINE DERIVATIVE; TRANSFERRIN RECEPTOR; TUMOR NECROSIS FACTOR RELATED APOPTOSIS INDUCING LIGAND; UNCLASSIFIED DRUG; UNINDEXED DRUG; VINBLASTINE;

APOPTOSIS; BIOLOGY; CANCER THERAPY; CELL DEATH; CHEMICAL STRUCTURE; CLINICAL TRIAL (TOPIC); CYTOTOXICITY; DNA DAMAGE; DNA FRAGMENTATION; FLOW CYTOMETRY; GENE OVEREXPRESSION; HOMEOSTASIS; HUMAN; MITOCHONDRIAL GENE; NECROSIS; NEOPLASM; REVIEW; STRUCTURE ACTIVITY RELATION; TUMOR CELL;

ANTIBODIES, MONOCLONAL; ANTINEOPLASTIC AGENTS; APOPTOSIS; APOPTOSIS REGULATORY PROTEINS; DRUG DESIGN; DRUG RESISTANCE, NEOPLASM; GENE EXPRESSION REGULATION, NEOPLASTIC; HUMANS; MITOCHONDRIA; NEOPLASMS; OLIGONUCLEOTIDES, ANTISENSE; RECEPTORS, DEATH DOMAIN; RECOMBINANT PROTEINS; SIGNAL TRANSDUCTION; SMALL MOLECULE LIBRARIES;

EID: 84876708184     PISSN: 18715206     EISSN: 18755992     Source Type: Journal    
DOI: 10.2174/1871520611313030007     Document Type: Review

References (106)

1. Marcello, D.; Elisa, T. The Apoptosome: Emerging insights and new potential targets. Pharm. Res., 2008, 25, 740-741.
2. Lockshin, R.A.; Zakeri, Z.F. Programmed cell death: new thoughts and relevance to aging. J. Gerontol., 1990, 45, 135-140.
3. Evan, G.; Littlewood, T.A. Matter of life and cell death. Science, 1998, 281, 1317-1322.
4. Denault, J.B.; Salvesen, G.S. Caspases: Keys in the ignition of cell death. Chem. Rev., 2002, 102, 4489-4499.
5. Kerr, J.F.R.; Willie, A.H.; Currie, A.R. Apoptosis: a basic biological phenomenon with wide-ranging implications in tissue kinetics. Br. J. Cancer, 1972, 26, 239-257.
6. Fischer, U.; Schulze, K. Apoptosis-based therapies and drug targets. Cell Death Differ., 2005, 12, 942-944.
7. David, F.E.; Gael, M.G. Apoptosis in tumorigenesis and cancer therapy. Front. Biosci., 1997, 2, 353-379.
8. Penaloza, C.; Lin L.; Richard, L.A.; Zahra, Z. Cell death in development: shaping the embryo. Histochem. Cell Biol., 2006, 126, 149-158.
9. Zheng, D.; Ming, Y.X. Essentials of Apoptosis: A guide for basic and clinical research, 2009, 2, 239-241.
10. rd ed.; Boehringer Mannheim GmbH: Biochemica, 1988.
11. Andreas, S.; Gemma, K. The essential role of evasion from cell death in cancer. Adv. Cancer Res., 2011, 111, 39-96.
12. Varmus, H. The new era in cancer research. Science, 2006, 312, 1162-1165.
13. Kingston, D.G.; Newman, D.J. Taxoids: cancer-fighting compounds from nature. Curr. Opin. Drug Discovery Dev., 2007, 10, 130-144.
14. Fesik, S.W. Promoting apoptosis as a strategy for cancer drug discovery. Nat. Rev. Cancer, 2000, 5, 876-885.
15. Grivicich, I.; Regner, A.; Rocha, A.B.; Grass, L.B.; Alves, P.A.; Kayser, G.B.; Schwartsmann, G.; Henriques, J.A. Irinotecan5-fluorouracil combination induces alterations in mitochondrial membrane potential and caspases on colon cancer cell lines. Oncol. Res., 2005, 15, 385-392.
16. Kolomeichuk, S.N.; Bene, A.; Upreti, M.; Dennis, R.A.; Lyle C.S; Rajasekaran, M.; Chambers TC Induction of apoptosis by vinblastine via c-Jun autoamplification and p53-independent down-regulation of p21WAF1/CIP1. Mol. Pharmacol., 2008, 73, 128-136.
17. Kolenko, V.M.; Uzzo, R.G.; Bukowski, R.; Finke, J.H. Caspase-dependent and -independent death pathways in cancer therapy. Apoptosis, 2000, 5, 17-20.
18. Gogvadze, V.; Orrenius, S. Mitochondrial regulation of apoptotic cell death. Chem.-Biol. Interact., 2006, 163, 4-14.
19. Tosa, N.; Iwai, A.; Tanaka, T.; Kumagai, T.; Nitta, T.; Chiba, S.; Maeda, M.; Takahama, Y.; Uede, T.; Miyazaki, T. Critical function of death-associated protein 3 in T cell receptor-mediated apoptosis induction. Biochem. Biophys. Res. Commun., 2010, 395, 356-360.
20. Martinvalet, D.; Zhu, P.; Lieberman, J. Granzyme A induces caspase independent mitochondrial damage: a required first step for apoptosis. Immunity, 2005, 22, 355-370.
21. Shi, Y.; Bao, Q. Apoptosome: a platform for the activation of initiator caspases. Cell Death Differ., 2007, 14, 56-65.
22. Yu, S.P.; Choi, D.W. Ions, cell volume and apoptosis. Proc. Natl. Acad. Sci. USA 2000, 97, 9360-9362.
23. Amelio, M.D.; Tino, E.; Cecconi, F. The apoptosome: emerging insights and new potential targets for drug design. Pharm. Res., 2008, 25, 740-751.
24. Elmore, S. Apoptosis: A Review of Programmed Cell Death. Toxicol. Pathol., 2007, 35, 495-516.
25. Scott, L.W.; Clemens, S.A. Apoptosis and therapy. J. Pathol., 1999, 187, 127-137.
26. Moreno, M.B.; Memon, S.A.; Zacharchuk, C.M. Apoptosis signaling pathways in normal T cells: differential activity of Bcl-2 and IL-1beta-converting enzyme family protease inhibitors on glucocorticoid- and Fas-mediated cytotoxicity. J. Immunol., 1996, 157, 3845-3849.
27. Gogvadze, V.; Orrenius, S.; Zhivotovsky, B. Multiple pathways of cytochrome c release from mitochondria in apoptosis. Biochimica. Et. Biophysica. Acta., 2006, 1757, 639-647.
28. Perez-Paya, E.; Orzaez, M.; Mondragon, L.; Wolan, D.; Wells, J.A.; Messeguer, A.; Vicent, M.J. Molecules that modulate Apaf-1 activity. Med. Res. Rev., 2011, 31, 649-675,
29. Petit, P.X.; Goubern, M.; Diolez, P.; Susin, S.A.; Zamzami, N.; Kroemer, G. Disruption of the outer mitochondrial membrane as a result of large amplitude swelling: the impact of irreversible permeability transition. FEBS Lett., 1998, 426, 111-116.
30. John, R.D.; Sten, O.; Boris, Z. Review: Nuclear events in apoptosis. J. Struct. Biol., 2000, 129, 346-358.
31. Cuconati, C.; Mukherjee, D.; Perez, D.; White, E. DNA damage response and MCL-1 destruction initiate apoptosis in adenovirus-infected cells. Genes Dev., 2003, 17, 2922-2932.
32. Haucker, G.; Vaux, D.L. The medical significance of physiological cell death. Med. Res. Rev., 1995, 15, 299-311.
33. Vladimir, G.; Sten, O. Mitochondrial regulation of apoptotic cell death. Chem.-Biol. Interact., 2006, 163, 4-14.
34. Bedi, A. On the TRAIL from death receptors to prostate cancer therapy. Cancer Biol. Ther., 2002, 1, 638-639.
35. Susin, A.S.; Queenan, B.; Bras, M. Programmed cell death via mitochondria: different modes of dying. Biochemistry (Moscow), 2005, 70, 231-239.
36. Ishibashi, M.; Ohtsuki, T. Studies on search for bioactive natural products targeting TRAIL signaling leading to tumor cell apoptosis. Med. Res. Rev., 2008, 28, 688-714.
37. Ashkenazi, A.; Dixit, V.M. Death receptors: signaling and modulation. Science, 1998, 281, 1305-13058.
38. Igney, F.H.; Krammer, P.H. Death and anti-death: tumour resistance to apoptosis. Nat. Rev. Cancer, 2002, 2, 277-288.
39. David, V.L.; Robert, G. Apoptosis in the development and treatment of cancer. Carcinogenesis, 2005, 26, 263-270.
40. Kenneth, N.; Philimon, G.; Guang, J.T.; Nordine, B.; Anas, C.; Mauro, E.D.; Roya, K.F. TRAIL induced mitochondrial pathway to apoptosis and caspase activation if potentiated by phospholipids scramblase-3. Apoptosis, 2008, 13, 845-856.
41. David V.; Gerry M. Cell Death, Wiley & Sons: New York, 2010.
42. Vivier, E.; Morin, P.M.; O'Brien, C.; Schlossman, SF.; Anderson, P. CD2 is functionally linked to the Zeta-Natural killer receptor complex. Eur. J. Immunol., 1991, 21, 1077-1080.
43. Duke, R.C.; Persechini, P.M.; Chang, S.; Liu, CC.; Cohen, J.J.; Young, J.D.E. Purified perforin induces target cell lysis but not DNA fragmentation. J. Exp. Med., 1989, 170, 1451-1456.
44. Schanne, F.A.X.; Kane, A.B.; Young, E.E.; Farber, J.L. Calcium dependence of toxic cell death: a final common pathway. Science, 1979, 206, 700-702.
45. Shieh, C.C.; Coghlan, M.; Sullivan, J.P.; Gopalakrishnan, M. Potassium channels: molecular defects, diseases and therapeutic opportunities. Pharmacol. Rev., 2000, 52, 557-594.
46. Yu, S.P.; Canzoniero, L.M.T.; Choi, D.W. Ion homeostasis and apoptosis. Curr. Opin. Cell Biol., 2001, 13, 405-411.
47. Hughes, F.M.; Cidlowski, J. Potassium is a critical regulator of apoptotic enzymes in vitro and in vivo. Adv. Enzyme Regul., 1999, 9, 157-171.
48. +-ATPase may be one mechanism contributing to potassium efflux and cell shrinkage in CD95-induced apoptosis. Apoptosis, 2000, 5, 153-163.
49. Thompson, C.B. Apoptosis in the pathogenesis and treatment of disease. Science, 1995, 267, 1456-1462.
50. John, L.J.; Lihua, H.; Jaesung, K. Mitochondrial permeability transition: a common pathway to necrosis and apoptosis. Biochem. Biophy. Res. Comm., 2003, 304, 463-470.
51. Yutaka, E.; Shigeomi, S.; Yoshihide, T. Intracellular ATP levels determine cell death fate by apoptosis or necrosis. Cancer Res., 1997, 57, 1835-1840.
52. Emanuela, B.; Dimitri, K.; Maria, A.; Pierluigi, N.; Stuart, L.A. Apoptosis and necrosis: Two distinct events induced respectively by mild and intense insults with NMDA or nitric oxide/ superoxide in cortical cell cultures. Processings of National Academics of Science in USA, Neurobiology, 1995, 92, 7162-7166.
53. Amin, N.A.; Susanne, H.S. Alcohol, Health and Research World 1997, 21, 325-330.
54. Dive, C.; Hickman, J.A. Drug-target interactions: only the first step in the commitment to a programmed cell death. Br. J. Cancer, 1991, 64, 192-196.
55. Lowe, S.W.; Ruley, H.E.; Jacks, T.; Housman, D.E. p53-dependent apoptosis modulates the cytotoxicity of anticancer agents. Cell, 1993, 74, 957-967.
56. Lotem, J.; Sachs, L. Regulation by bcl-2.; c-myc.; and p53 of susceptibility to induction of apoptosis by heat shock and cancer chemotherapy compounds in differentiation competent and defective myeloid leukemic cells. Cell Growth Differ., 1993, 4, 41-47.
57. Rupnow, B.A.; Murtha, A.D.; Alarcon, R.M.; Giaccia, A.J.; Knox, S.J. Direct evidence that apoptosis enhances tumor responses to fractionated radiotherapy. Cancer Res., 1998, 58, 1779-1784.
58. Gideon, B. T-cell mediated cytotoxicity. Immunology, 1991, 3, 320-325.
59. Tom, B.; Joanna, S.; Subhadip, R. Bcl-2 inhibits apoptosis by increasing the time-to-death and intrinsic cell-to-cell variations in the mitochondrial pathway of cell death. Apoptosis, 2010, 15, 1223-1233.
60. Dario, A.C. Surviving: versatile modulation of cell division and apoptosis in cancer. Oncogene, 2003, 22, 8581-8589.
61. Cai, S.X.; Drewe, J.; Kasibhatla, S. A Chemical Genetics Approach for the Discovery of Apoptosis Inducers: From Phenotypic Cell Based HTS Assay and Structure-Activity Relationship Studies, to Identification of Potential Anticancer Agents and Molecular Targets. Curr. Med. Chem., 2006, 13, 2627-2644.
62. Cai, S.X.; Drewe, J.; Kemnitzer, W. Discovery of 4-Aryl-4H-Chromenes as Potent Apoptosis Inducers Using a Cell- and Caspase-Based Anti-Cancer Screening Apoptosis Program (ASAP): SAR Studies and the Identification of Novel Vascular Disrupting Agents. Anticancer Agents Med. Chem., 2009, 9, 437-456.
63. Zhang, H.Z.; Kasibhatla, S.; Wang, Y.; Herich, J.; Guastella, J.; Tseng, B.; Drewe, J.; Cai, S.X. Discovery, characterization and SAR of gambogic acid as a potent apoptosis inducer by a HTS assay. Bioorg. Med. Chem., 2004, 12, 309-317.
64. Kasibhatla, S.; Jessen, K.; Maliartchouk, S.; Wang, J.; English, N.; Drewe, J.; Qui, L.; Archer, S.; Ponce, A.; Sirisoma, N.; Jiang, S.; Zhang, H.Z.; Gehlsen, K.; Cai, S.X.; Green, D.R.; Tseng, B. A role for transferrin receptor in triggering apoptosis when targeted with gambogic acid. Proc. Natl. Acad. Sci. USA, 2005, 102, 12095-12100.
65. Cai, S.X.; Zhang, H.Z.; Guastella, J.; Drewe, J.; Yang, W.; Weber, E. Design and synthesis of rhodamine 110 derivative and caspase-3 substrate for enzyme and cell-based fluorescent assay. Bioorg. Med. Chem. Lett., 2001, 11(1), 39-42.
66. Zhang, H.Z.; Kasibhatla, S.; Guastella, J.; Drewe, J.; Tseng, B.; Cai, S.X. N-Ac-DEVD-N¢-(Polyfluorobenzoyl)-R110: Novel Cell Permeable Fluorogenic Caspase Substrates for the Detection of Caspase Activity and Apoptosis. Bioconjugate Chem., 2003, 14, 458-463.
67. Cai, S.X.; Nguyen, B.; Jia, S.; Herich, J.; Guastella, J.; Reddy, S.; Tseng, B.; Drewe, J.; Kasibhatla, S. Discovery of Substituted N-Phenyl Nicotinamides as Potent Inducers of Apoptosis Using a Cell- and Caspase-Based High Throughput Screening Assay. J. Med. Chem., 2003, 46, 2474-2481.
68. Zhang, H.Z.; Tseng, B.; Drewe, J.; Kasibhatla, S.; Cai, S.X. Discovery and SAR of indole-2-carboxylic acid benzylidene-hydrazides as a new series of potent apoptosis inducers using a cell based HTS assay. Bioorg. Med. Chem., 2004, 12, 3649-3655.
69. Sirisoma, N.; Pervin, A.; Drewe, J.; Tseng, B.; Cai, S.X. Discovery of substituted N′-(2-oxoindolin-3-ylidene)benzohydrazides as new apoptosis inducers using a cell- and caspase-based HTS assay. Bioorg. Med. Chem. Lett., 2009; 19, 2710-2713.
70. Zhang, H.Z.; Kasibhatla, S.; Kuemmerle, J.; Kemnitzer, W.; Mason, K.O.; Qiu, L.; Grundy, C.C.; Tseng, B.; Drewe, J.; Cai, S.X. Discovery and Structure-Activity Relationship of 3-Aryl-5-aryl-1,2,4-oxadiazoles as a New Series of Apoptosis Inducers and Potential Anticancer Agents. J. Med. Chem., 2005, 48, 5215-5223.
71. Sirisoma, N.; Kasibhatla, S.; Nguyen, B.; Pervin, A.; Wang, Y.; Claassen, G.B.; Tseng, B.; Drewe, J.; Cai, S.X. Discovery of substituted 4-anilino-2-(2-pyridyl) pyrimidines as a new series of apoptosis inducers using a cell- and caspase-based high throughput screening assay. Part 1: Structure-activity relationships of the 4-anilino group. Bioorg. Med. Chem., 2006, 14, 7761-7773.
72. Sirisoma, N.; Pervin, A.; Nguyen, B.; Grundy, C.C.; Kasibhatla, S.; Tseng, B.; Drewe, J.; Cai, S.X. Discovery of substituted 4-anilino-2-arylpyrimidines as a new series of apoptosis inducers using a cell- and caspase-based high throughput screening assay. 2. Structure-activity relationships of the 2-aryl group. Bioorg. Med. Chem. Lett., 2009, 19, 2305-2309.
73. Kemnitzer, W.; Sirisoma, N.; May, C.; Tseng, B.; Drewe, J.; Cai, S.X. Discovery of 4-anilino-N-methylthieno[3.;2-d]pyrimidines and 4-anilino-N-methylthieno[2.;3-d]pyrimidines as potent apoptosis inducers. Bioorg. Med. Chem. Lett., 2009, 19, 3536-3540.
74. Drewe, J.; Kasibhatla, S.; Tseng, B.; Shelton, E.; Sperandio, D.; Yee, R.M.; Litvak, J.; Sendzik, M.; Spencer, J.R.; Cai, S.X. Discovery of 5-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-7-phenyl-(E)-2,3,6,7-tetrahydro-1,4-thiazepines as a new series of apoptosis inducers using a cell- and caspase-based HTS assay. Bioorg. Med. Chem. Lett., 2007, 17, 4987-4990.
75. Zhang, H.Z.; Claassen, G.; Grundy, C.C.; Tseng, B.; Drewe, J.; Cai, S.X. Discovery and structure-activity relationship of N-phenyl-1H-pyrazolo[3.;4-b]quinolin-4-amines as a new series of potent apoptosis inducers. Bioorg. Med. Chem., 2008, 16, 222-231.
76. Sirisoma, N.; Kasibhatla, S.; Pervin, A.; Zhang, H.; Jiang, S.; Willardsen, J.A.; Anderson, M.B.; Baichwal, V.; Mather, G.; Jessing, K.; Hussain, R.; Hoang, K.; Pleiman, C.M.; Tseng, B.; Drewe, J.; Cai, S.X. Discovery of 2-Chloro-N-(4-methoxyphenyl)-N-methylquinazolin-4-amine (EP128265, MPI-0441138) as a Potent Inducer of Apoptosis with High In Vivo Activity. J. Med. Chem., 2008, 51, 4771-4779.
77. Sirisoma, N.; Pervin, A.; Zhang, H.; Jiang, S.; Willardsen, J.A.; Anderson, M.B.; Mather, G.; Pleiman, C.M.; Kasibhatla, S.; Tseng, B.; Drewe, J.; Cai, S.X. Discovery of N-(4-Methoxyphenyl)-N,2-dimethylquinazolin-4-amine, a Potent Apoptosis Inducer and Efficacious Anticancer Agent with High Blood Brain Barrier Penetration. J. Med. Chem., 2009, 52, 2341-2351.
78. Cai, S.X.; Sirisoma, N.; Pervin, A.; Jiang, S.; Williardsen, A.; Anderson, B.M.; Mather, G.; Pleiman, C.M.; Kasibhatla, S.; Tseng, B.; Drewe, J. Discovery of N-methyl-4-(4-methoxyanilino) quinazolines as potent apoptosis inducers. Structure-activity relationship of quinazoline ring. Bioorg. Med. Chem. Lett., 2010, 20, 2330-2334.
79. Jiang, S.; Grundy, C.C.; Drewe, J.; Tseng, B.; Cai, S.X. Discovery of (naphthalen-4-yl) (phenyl)methanones and N-methyl-N-phenylnaphthalen-1-amines as new apoptosis inducers using a cell-and caspase-based HTS assay. Bioorg. Med. Chem. Lett., 2008, 18, 5725-5728.
80. Kemnitzer, W.; Kuemmerle, J.; Jiang, S.; Zhang, H.Z.; Sirisoma, N.; Kasibhatla, S.; Grundy, C.; Tseng, B.; Drewe, J.; Cai, S.X. Discovery of 1-benzoyl-3-cyanopyrrolo[1,2-α]quinolines as a new series of apoptosis inducers using a cell- and caspase-based high-throughput screening assay. Part 1: Structure-activity relationships of the 1- and 3-positions. Bioorg. Med. Chem. Lett., 2008, 18, 6259-6264.
81. Kemnitzer, W.; Kuemmerle, J.; Jiang, S.; Zhang, H.Z.; Sirisoma, N.; Kasibhatla, S.; Grundy, C.; Tseng, B.; Drewe, J.; Cai, S.X. Discovery of 1-benzoyl-3-cyanopyrrolo[1.;2- α]quinolines as a new series of apoptosis inducers using a cell- and caspase-based high-throughput screening assay. 2: Structure-activity relationships of the 4-, 5-, 6-, 7- and 8-positions. Bioorg. Med. Chem. Lett., 2009, 19, 3481-3484.
82. Kemnitzer, W.; Sirisoma, N.; Nguyen, B.; Jiang, S.; Kasibhatla, S.; Grundy, C.; Tseng, B.; Drewe, J.; Cai, S.X. Discovery of N-aryl-9-oxo-9H-fluorene-1-carboxamides as a new series of apoptosis inducers using a cell- and caspase-based high-throughput screening assay. 1. Structure-activity relationships of the carboxamide group. Bioorg. Med. Chem. Lett., 2009; 19, 3045-3049.
83. Cai, S.X.; Kemnitzer, W.; Sirisoma, N.; Jiang, S.; Kasibhatla, S.; Grundy, C.; Tseng, B.; Drewe, J. Discovery of N-aryl-9-oxo-9H-fluorene-1-carboxamides as a new series of apoptosis inducers using a cell-and caspase-based high-throughput screening assay. 2. Structure-activity relationships of the 9-oxo-9H-fluorene ring. Bioorg. Med. Chem. Lett., 2010; 20, 1288-1292.
84. Cai, S.X.; Sirisoma, N.; Pervin, A.; Jiang, S.; Williardsen, A.; Anderson, M.B.; Gary, M.; Pleiman, C.M.; Kasibhatla, S.; Tseng, B.; Drewe, J. Discovery of N-methyl-4-(4-methoxyanilino) quinazolines as potent apoptosis inducers. Structure-activity relationship of quinazoline ring. Bioorg. Med. Chem. Lett., 2010; 20, 2330-2334.
85. Zhang, H.Z.; Grundy, C.; May, C.; Drewe, J.; Tseng, B.; Cai S.X. Discovery and structure-activity relationships of (2-(arylthio)-benzylideneamino)guanidines as a novel series of potent apoptosis inducers. Bioorg. Med. Chem., 2009, 17, 2852-2858.
86. Kemnitzer, W.; Kasibhatla, S.; Jiang, S.; Zhang, H.; Zhao, J.; Jia, S.; Xu, L.; Grundy, C.; Denis, R.; Barriault, N.; Vaillancourt, L.; Charron, S.; Dodd, J.; Attardo, G.; Labrecque, D.; Lamothe, S.; Gourdeau, H.; Tseng, B.; Drewe, J.; Cai, S.X. Discovery of 4-aryl-4H-chromenes as a new series of apoptosis inducers using a cell-and caspase-based high-throughput screening assay. 2. Structure- activity relationships of the 7- and 5-, 6-, 8-positions Bioorg. Med. Chem., 2005, 15, 4745-4751.
87. Kemnitzer, W.; Jiang, S.; Wang, Y.; Kasibhatla, S.; Grundy, C.; Bubenik, M.; Labrecque, D.; Denis, R.; Lamothe, S.; Attardo, G.; Gourdeau, H.; Tseng, B.; Drewe, J.; Cai, S.X. Discovery of 4-aryl-4H-chromenes as a new series of apoptosis inducers using a cell-and caspase-based HTS assay. Part 5: Modifications of the 2- and 3-positions. Bioorg. Med. Chem., 2008, 18, 603-607.
88. Kemnitzer, W., Drewe, J.; Jiang, S.; Zhang, H.; Grundy, C.; Labreque, D.; Bubenick, M.; Attardo, G.; Denis, R.; Lamothe, S.; Gourdeau, H.; Tseng, B.; Kasibhatla, S.; Cai, S.X. Discovery of 4-Aryl-4H-chromenes as a New Series of Apoptosis Inducers Using a Cell- and Caspase-Based High Throughput Screening Assay. 4. Structure-Activity Relationships of N-Alkyl Substituted Pyrrole Fused at the 7,8-Positions. J. Med. Chem., 2008, 51, 417-423.
89. Kemnitzer, W.; Jiang, S.; Zhang, H.; Kasibhatla, S.; Grundy, C.; Blais, C.; Attardo, G.; Denis, R.; Lamothe, S.; Gourdeau, H.; Tseng, B.; Drewe, J.; Cai, S.X. Discovery of 4-aryl-2-oxo-2H-chromenes as a new series of apoptosis inducers using a cell- and caspase-based high-throughput screening assay. Bioorg. Med. Chem. Lett., 2008, 18, 5571-5575.
90. Niles, R.M.; McFarland, M.; Weimer, M.B.; Redkar, A.; Fu, Y.M.; Meadows, G.G. Resveratrol is a potent inducer of apoptosis in human melanoma cells. Cancer Lett., 2003, 190, 157-163.
91. Li, H.; Wu, W.K.K.; Zheng, Z.; Che, C.T.; Yu, L.; Li, Z.J.; Wu, Y.C.; Cheng, K.W.; Yu, J.; Cho, C.H.; Wang, M. 2,3′,4,4′,5′-Pentamethoxy-trans-stilbene, a resveratrol derivative, is a potent inducer of apoptosis in colon cancer cells via targeting microtubules. J. Biochem. Pharmacol., 2009, 78, 1224-1232.
92. Kaap, S.; Quentin, I.; Tamiru, D.; Shaheen, M.; Eger, K.; Steinfelder, H. Structure activity analysis of the pro-apoptotic.; antitumor effect of nitrostyrene adducts and related compounds. J. Biochem. Pharmacol., 2003, 65, 603-610.
93. Reddy, M.A.; Jain, N.; Yada, D.; Kishore, C.; Reddy, V.J.; Reddy, P.S.; Addlagatta, A.; Kalivendi, S.V.; Sreedhar, B. Design and Synthesis of Resveratrol-Based Nitrovinylstilbenes as Antimitotic Agents. J. Med. Chem., 2011, 54 (19), 6751-6760.
94. Sanmartin, C.; Echeverria, M.; Mendivil, B.; Cordeu, L.; Cubedo, E.; Foncillas, J.G.; Font, M.; Palop, J.A. Synthesis and biological evaluation of new symmetrical derivatives as Cytotoxic agents and apoptosis inducers. Bioorg. Med. Chem., 2005; 13, 2031-2044.
95. Azuma, H.; Ijichi, S.; Kataoka, M.; Masuda, A.; Izumi, T.; Yoshimoto, T.; Tachibana, T. Short-chain 3-ketoceramides, strong apoptosis inducers against human leukemia HL-60 cells. Bioorg. Med. Chem., 2007, 15, 2860-2867.
96. Osanai, K.; Piwowar, K.R.L.; Dou, Q.P.; Chan, T.H. A para-amino substituent on the D-ring of green tea polyphenol epigallocatechin-3-gallate as a novel proteasome inhibitor and cancer cell apoptosis inducer. Bioorg. Med. Chem., 2007, 15, 5076-5082.
97. Chen, H.L.; Chang, C.Y.; Lee, H.T.; Lin, H.H.; Lu, P.J.; Yang, C.N.; Shiau, C.W.; Shaw, A.Y. Synthesis and pharmacological exploitation of clioquinol-derived copper-binding apoptosis inducers triggering reactive oxygen species generation and MAPK pathway activation. Bioorg. Med. Chem., 2009, 17, 7239-7247.
98. Tai, V.W.F.; Sperandio, D.; Shelton, E.J.; Litvak, J.; Pararajasingham, K.; Cebon, B.; Lohman, J.; Eksterowicz, J.; Kantak, S.; Sabbatini, P.; Brown, C.; Zeitz, J.; Reed, C.; Maske, B.; Graupe, D.; Estevez, A.; Oeh, J.; Wong, D.; Ni, Y.; Sprengeler, P.; Yee, R.; Magill, C.; Neri, A.; Cai, S.X.; Drewe, J.; Qiu, L.; Herich, J.; Tseng, B.; Kasibhatla, S.; Spencer, J.R. Discovery and structure-activity relationship of 2-phenyl-oxazole-4-carboxamide derivatives as potent apoptosis inducers. Bioorg. Med. Chem. Lett., 2006, 16, 4554-4558.
99. Romagnoli, R.; Baraldi, P.G.; Carrion, M.D.; Cruz, O.L.; Preti, D.; Tabrizi, M.A.; Fruttarolo, F.; Heilmann, J.; Bermejo, J.; Estevez, F. Hybrid molecules containing benzo[4,5]imidazo-[1,2-d]thiadiazole and α-bromoacryloyl moieties as potent apoptosis inducers on human myeloid leukemia cells. Bioorg. Med. Chem. Lett., 2007, 17, 2844-2848.
100. Wang, Z.; Shi, X.H.; Wang, J.; Zhou, T.; Xu, Y.Z.; Huang, T.T.; Li, Y.F.; Zhao, Y.L.; Yang, L.; Yang, S.Y.; Yu, L.T.; Wei, Y.Q. Synthesis, structure-activity relationships and preliminary antitumor evaluation of benzothiazole-2-thiol derivatives as novel apoptosis inducers. Bioorg. Med. Chem., 2011, 20, 1097-1101.
101. Pan, M.H.; Lai, Y.S.; Lai, C.S.; Wang, Y.J.; Li, S.; Lo, C.Y.; Dushenkov, S.; Ho, C.T. 5-Hydroxy-3,6,7,8,3′,4′-hexamethoxy-flavone induces apoptosis through reactive oxygen species production, growth arrest and DNA damage-inducible gene 153 expression, and caspase activation in human leukemia cells. J. Agric. Food. Chem., 2007, 55, 5081-5091.
102. Cincinelli, R.; Dallavalle, S.; Merlini, L.; Penco, S.; Pisano, C.; Carminati, P.; Giannini, G.; Vesci, L.; Gaetano, C.; Illy, B.; Zuco, V.; Supino, R.; Zunino, F. A novel atypical retinoid endowed with proapoptotic and antitumor Activity. J. Med. Chem., 2003, 46, 909-912.
103. Azuma, H.; Takao, R.; Shikata, K.; Niiro, H.; Tachibana, T.; Ogino, K. Synthesis and Potent Antileukemic activities of N-Lactylsphingosine and N-Lactyldihydrosphingosine. J. Med. Chem., 2003, 46, 3445-3447.
104. Leon, F.; Quintana, J.; Rivera, A.; Estevez, F.; Bermejo, J. Lanostanoid Triterpenes from Laetiporus sulphureus and Apoptosis Induction on HL-60 Human Myeloid Leukemia Cells. J. Nat. Prod., 2004; 67, 2008-2011.
105. Banerjee, R.; Roy, S.; Reddy, B.S.; Sudhakar, G.; Kumar, M.J. 17β-Estradiol-Linked Nitro-L-arginine as Simultaneous Inducer of Apoptosis in Melanoma and Tumor-Angiogenic Vascular Endothelial. Cells. Mol. Pharmaceutics, 2011, 8, 350-359.
106. Xia, Z.; Farhana, L.; Correa, R.G.; Das, J.K.; Castro, D.J.; Yu, J.; Oshima, R.G.; Reed, J.C.; Fontana, J.A.; Dawson, M.I. Heteroatom-Substituted Analogues of Orphan Nuclear Receptor Small Heterodimer Partner Ligand and Apoptosis Inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic Acid. J. Med. Chem., 2011, 54, 3793-3816.