Conjugation of a novel Apaf-1 inhibitor to peptide-based cell-membrane transporters:. Effective methods to improve inhibition of mitochondria-mediated apoptosis

Peptides

Volumn 28, Issue 5, 2007, Pages 958-968

  Orzáez, Mar ^a   Mondragón, Laura ^a   Marzo, Isabel ^b   Sanclimens, Glòria ^c   Messeguer, Àngel ^c   Pérez Payá, Enrique ^a,d   Vicent, María J ^a  

^a CENTRO DE INVESTIGACIÓN PRÍNCIPE FELIPE   (Spain)

^b UNIVERSITY OF ZARAGOZA   (Spain)

^c DEPARTMENT OF ENVIRONMENTAL CHEMISTRY   (Spain)

^d INSTITUTO DE BIOMEDICINA DE VALENCIA   (Spain)

Author keywords

Apoptosis; Apoptosome inhibitors; Cell penetrating peptides; Conformational analysis; Drug delivery systems; Membrane mimetics

Indexed keywords

APOPTOTIC PROTEASE ACTIVATING FACTOR 1; CELL PENETRATING PEPTIDE; PENETRATIN; PEPTOID; TRANSACTIVATOR PROTEIN;

APOPTOSIS; ARTICLE; CELL MEMBRANE PERMEABILITY; CELL VIABILITY; CONTROLLED STUDY; DRUG DELIVERY SYSTEM; DRUG MECHANISM; DRUG STRUCTURE; ENZYME ACTIVATION; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; PRIORITY JOURNAL;

AMINO ACID SEQUENCE; APOPTOSIS; APOPTOSOMES; APOPTOTIC PROTEASE-ACTIVATING FACTOR 1; CARRIER PROTEINS; CELL LINE; CELL LINE, TUMOR; CELL SURVIVAL; CIRCULAR DICHROISM; FLOW CYTOMETRY; GENE PRODUCTS, TAT; HUMANS; MICROSCOPY, CONFOCAL; MITOCHONDRIA; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; PEPTIDES; PEPTOIDS; PROTEIN CONFORMATION;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 34247505132     PISSN: 01969781     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.peptides.2007.02.014     Document Type: Article

References (39)

1. Acehan D., Jiang X.J., Morgan D.G., Heuser J.E., Wang X.D., and Akey C.W. Three-dimensional structure of the apoptosome: implications for assembly, procaspase-9 binding, and activation. Mol Cell 9 (2002) 423-432
2. Astriab-Fisher A., Sergueev D., Fisher M., Shaw B.R., and Juliano R.L. Conjugates of antisense oligonucleotides with the Tat and antennapedia cell-penetrating peptides: effects on cellular uptake, binding to target sequences, and biologic actions. Pharm Res 19 (2002) 744-754
3. Berlose J.P., Convert O., Derossi D., Brunissen A., and Chassaing G. Conformational and associative behaviors of the third helix of antennapedia homeodomain in membrane-mimetic environments. Eur J Biochem 242 (1996) 372-386
4. Brooks H., Lebleu B., and Vives E. Tat peptide-mediated cellular delivery: back to basics. Adv Drug Deliv Rev 57 (2005) 559-577
5. Chen Y.N., Sharma S.K., Ramsey T.M., Jiang L., Martin M.S., Baker K., et al. Selective killing of transformed cells by cyclin/cyclin-dependent kinase 2 antagonists. Proc Natl Acad Sci USA 96 (1999) 4325-4329
6. Christiaens B., Symoens S., Vanderheyden S., Engelborghs Y., Joliot A., Prochiantz A., et al. Tryptophan fluorescence study of the interaction of penetratin peptides with model membranes. Eur J Biochem 269 (2002) 2918-2926
7. Dietz G.P.H., and Bähr M. Delivery of bioactive molecules into the cell: the Trojan horse approach. Mol Cell Neurosci 27 (2004) 85-131
8. Dostmann W.R., Taylor M.S., Nickl C.K., Brayden J.E., Frank R., and Tegge W.J. Highly specific, membrane-permeant peptide blockers of cGMP-dependent protein kinase I alpha inhibit NO-induced cerebral dilation. Proc Natl Acad Sci USA 97 (2000) 14772-14777
9. Fillon Y.A., Anderson J.P., and Chmielewski J. Cell penetrating agents based on a polyproline helix scaffold. J Am Chem Soc 127 (2005) 11798-11803
10. Garcia-Calvo M., Peterson E.P., Leiting B., Ruel R., Nicholson D.W., and Thornberry N.A. Inhibition of human caspases by peptide-based and macromolecular inhibitors. J Biol Chem 273 (1998) 32608-32613
11. Gratton J.P., Yu J., Griffith J.W., Babbitt R.W., Scotland R.S., Hickey R., et al. Cell-permeable peptides improve cellular uptake and therapeutic gene delivery of replication-deficient viruses in cells and in vivo. Nat Med 9 (2003) 357-362
12. Green D.R., and Kroemer G. Pharmacological manipulation of cell death: clinical applications in sight?. J Clin Invest 115 (2005) 2610-2617
13. Gregoire C.J., and Loret E.P. Conformational heterogeneity in two regions of TAT results in structural variations of this protein as a function of HIV-1 isolates. J Biol Chem 271 (1996) 22641-22646
14. Jayaraman G., Kumar T.K.S., Arunkumar A.I., and Yu C. 2,2,2-Trifluoroethanol induces helical conformation in an all β-sheet protein. Biochem Biophys Res Commun 222 (1996) 33-37
15. Jiang X.J., and Wang X.D. Cytochrome c promotes caspase-9 activation by inducing nucleotide binding to Apaf-1. J Biol Chem 275 (2000) 31199-31203
16. Jiang X.J., and Wang X.D. Cytochrome C-mediated apoptosis. Ann Rev Biochem 73 (2004) 87-106
17. Kalivendi S.V., Konorev E.A., Cunningham S., Vanamala S.K., Kaji E.H., Joseph J., et al. Doxorubicin activates nuclear factor of activated T-lymphocytes and Fas ligand transcription: role of mitochondrial reactive oxygen species and calcium. Biochem J 389 (2005) 527-539
18. Lademann U., Cain K., Gyrd-Hansen M., Brown D., Peters D., and Jaattela M. Diarylurea compounds inhibit caspase activation by preventing the formation of the active 700-kilodalton apoptosome complex. Mol Cell Biol 23 (2003) 7829-7837
19. Liou J.S., Chen J.S., and Faller D.V. Characterization of p21(Ras)-mediated apoptosis induced by protein kinase C inhibition and application to human tumor cell lines. J Cell Physiol 198 (2004) 277-294
20. Lopez-Garcia B., Marcos J.F., Abad C., and Perez-Paya E. Stabilisation of mixed peptide/lipid complexes in selective antifungal hexapeptides. Biochim Biophys Acta 1660 (2004) 131-137
21. Malet G., Martín A.G., Orzáez M., Vicent M.J., Masip I., Sanclimens G., et al. Small molecule inhibitors of Apaf-1-related caspase-3/-9 activation that control mitochondrial-dependent apoptosis. Cell Death Differ 13 (2006) 1523-1532
22. Martin A.G., and Fearnhead H.O. Apocytochrome c blocks caspase-9 activation and Bax-induced apoptosis. J Biol Chem 277 (2002) 50834-50841
23. Nguyen J.T., and Wells J.A. Direct activation of the apoptosis machinery as a mechanism to target cancer cells. Proc Natl Acad Sci USA 100 (2003) 7533-7538
24. Pastor M.T., Lopez de la Paz M., Lacroix E., Serrano L., and Perez-Paya E. Combinatorial approaches: a new tool to search for highly structured beta-hairpin peptides. Proc Natl Acad Sci USA 99 (2002) 614-619
25. Persson D., Thoren P.E.G., Lincoln P., and Norden B. Vesicle membrane interactions of penetratin analogues. Biochemistry 43 (2004) 11045-11055
26. Rabanal F., Ludevid M.D., Pons M., and Giralt E. CD of proline-rich polypeptides: application to the study of the repetitive domain of maize glutelin-2. Biopolymers 33 (1993) 1019-1028
27. Rebbaa A., Chou P.M., Emran M., and Mirkin B.L. Doxorubicin-induced apoptosis in caspase-8-deficient neuroblastoma cells is mediated through direct action on mitochondria. Cancer Chem Pharmacol 48 (2001) 423-428
28. Reed J.C. Mechanisms of apoptosis regulation. Cytometry 11 (2002) 26-27
29. Ruzza P., Calderan A., Guiotto A., Osler A., and Borin G. Tat cell-penetrating peptide has the characteristics of a poly(proline) II helix in aqueous solution and in SDS micelles. J Pept Sci 10 (2004) 423-426
30. Ryoo H.D., Gorenc T., and Steller H. Apoptotic cells can induce compensatory cell proliferation through the JNK and the wingless signaling pathways. Dev Cell 7 (2004) 491-501
31. Schwarze S.R., Hruska K.A., and Dowdy S.F. Protein transduction: unrestricted delivery into all cells?. Trends Cell Biol 10 (2000) 290-295
32. Scott C.W., Sobotka-Briner C., Wilkins D.E., Jacobs R.T., Folmer J.J., Frazee W.J., et al. Novel small molecule inhibitors of caspase-3 block cellular and biochemical features of apoptosis. J Pharmacol Exp Ther 304 (2003) 433-440
33. Spierings D., McStay G., Saleh M., Bender C., Chipuk J., Maurer U., et al. Connected to death: the (unexpurgated) mitochondrial pathway of apoptosis. Science 310 (2005) 66-67
34. Thoren P.E.G., Persson D., Esbjorner E.K., Goksor M., Lincoln P., and Norden B. Membrane binding and translocation of cell-penetrating peptides. Biochemistry 43 (2004) 3471-3489
35. Thoren P.E.G., Persson D., Karlsson M., and Norden B. The antennapedia peptide penetratin translocates across lipid bilayers-the first direct observation. FEBS Lett 482 (2000) 265-268
36. Wang X., Zhu S., Drozda M., Zhang W.H., Stavrovskaya I.G., Cattaneo E., et al. Minocycline inhibits caspase-independent and-dependent mitochondrial cell death pathways in models of Huntington's disease. Proc Natl Acad Sci USA 100 (2003) 10483-10487
37. Wu S., Ko Y.S., Teng M.S., Ko Y.L., Hsu L.A., Hsueh C., et al. Adriamycin-induced cardiomyocyte and endothelial cell apoptosis: In vitro and in vivo studies. J Mol Cell Cardiol 34 (2002) 1595-1607
38. Zheng T.S., Hunot S., Kuida K., Momoi T., Srinivasan A., Nicholson D.W., et al. Deficiency in caspase-9 or caspase-3 induces compensatory caspase activation. Nat Med 6 (2000) 1241-1247
39. Zhu S., Stavrovskaya I.G., Drozda M., Kim B.Y.S., Ona V., Li M.W., et al. Minocycline inhibits cytochrome c release and delays progression of amyotrophic lateral sclerosis in mice. Nature 417 (2002) 74-78