Enantiomer-specific bioactivities of peptidomimetic analogues of mastoparan and mitoparan: Characterization of inverso mastoparan as a highly efficient cell penetrating peptide

Bioconjugate Chemistry

Volumn 23, Issue 1, 2012, Pages 47-56

  Jones, Sarah ^a   Howl, John ^a  

^a UNIVERSITY OF WOLVERHAMPTON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CELL MEMBRANES; CYTOLOGY; ENANTIOMERS; PEPTIDES;

CELL-PENETRATING PEPTIDE; COMPREHENSIVE COMPARISONS; D-AMINO ACIDS; L-ENANTIOMERS; PEPTIDE ANALOGS; PEPTIDOMIMETICS; RETRO-INVERSO TRANSFORMATION; STABLE PEPTIDES; STRUCTURE-ACTIVITY RELATIONSHIPS; SYNTHESISED;

BIOACTIVITY;

MASTOPARAN; MITOPARAN; PEPTIDOMIMETIC AGENT; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG CYTOTOXICITY; DRUG STRUCTURE; ENANTIOMER; HUMAN; HUMAN CELL; MAST CELL DEGRANULATION; STRUCTURE ANALYSIS;

EID: 84855951575     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc2002924     Document Type: Article

References (43)

1. Hirai, Y., Yasuhara, T., Yoshida, H., Nakajima, T., Fujino, M., and Kitada, C. (1979) A new mast cell degranulating peptide "mastoparan" in the venom of Vespula lewisii Chem. Pharm. Bull. (Tokyo) 27, 1942-1944 (Pubitemid 10223843)
2. Soomets, U., Hällbrink, M., Zorko, M., and Langel, Ü. (1997) From galanin and mastoparan to galparan and transportan Curr. Top. Pept. Prot. Res. 2, 83-113
3. Jones, S. and Howl, J. (2006) Biological applications of the receptor mimetic peptide mastoparan Curr. Protein Pept. Sci. 7, 501-508 (Pubitemid 44883927)
4. Jones, S. and Howl, J. (2009) Mastoparans. Bioactive Peptides (Howl, J. and Jones, S., Eds.) pp 429-445, Chapter 18, CRC Press, Boca Raton.
5. Farquhar, M., Soomets, U., Bates, R.,L., Martin, A., Langel, Ü., and Howl, J. (2002) Novel mastoparan analogs induce differential secretion from mast cells Chem. Biol. 9, 63-70 (Pubitemid 34155865)
6. Pooga, M., Hällbrink, M., Zorko, M., and Langel, Ü. (1998) Cell penetration by transportan FASEB J. 12, 67-77 (Pubitemid 28060272)
7. +-ATPase and reverses its inhibition by oubain Regul. Pept. 62, 47-52
8. Longland, C. L., Mezna, M., Langel, Ü., Hällbrink, M., Soomets, U., Wheatley, M., Michelangeli, M., and Howl, J. (1988) Biochemical mechanisms of calcium mobilisation induced by mastoparan and chimeric hormone-mastoparan analogues Cell Calcium 24, 27-34
9. Chahdi, A., Choi, W. S., Kim, Y. M., and Beaven, M. A. (2003) Mastoparan selectively activates phospholipase D2 in cell membranes J. Biol. Chem. 278, 12039-12045 (Pubitemid 36800180)
10. o by mastoparan, related amphiphilic peptides and hydrophobic amines J. Biol. Chem. 265, 14176-14186
11. oα by peptides representing sequence permutations of mastoparan Proc. Natl. Acad. Sci. U.S.A. 89, 8268-8277
12. Sukumar, M. and Higashijima, T. (1992) G protein-bound conformation of mastopran-X, a receptor mimetic peptide J. Biol. Chem. 267, 21421-21424
13. 10]MP Regul. Pept. 121, 121-128 (Pubitemid 38901070)
14. Karle, I. L. (2006) Helix-promoters, non-natural residues, retro-peptides and non-peptidic inserts. In Peptides: Chemistry, Structure and Biology (Kaumaya, P. T. P. and Hodges, R. S., Eds.) pp 543-545, Chapter 224, Mayflower Scientific Ltd, Kingswinford.
15. Liu, S., Wang, F., Tang, L., Gui, W., Cao, P., Liu, X., Poon, A. W., Shaw, P. C., and Jiang, T. (2007) Crystal structure of mastoparan from Polistes jadwagae at 1.2 Å resolution J. Struct. Biol. 160, 28-34 (Pubitemid 47405232)
16. Jones, S., Martel, C., Belzacq-Casagrande, A. S., Brenner, C., and Howl, J. (2008) Mitoparan and target-selective chimeric analogues: Membrane translocation and intracellular redistribution induces mitochondrial apoptosis Biochim. Biophys. Acta 1783, 849-863
17. Pooga, M., Hällbrink, M., Zorko, M., and Langel, Ü. (1998) Cell penetration by transportan FASEB J. 12, 67-77 (Pubitemid 28060272)
18. Soomets, U., Lindgren, M., Gallet, X., Hällbrink, M., Elmquist, A., Balaspiri, L., Zorko, M., Pooga, M., Brasseur, R., and Langel, Ü. (2000) Deletion analogues of transportan Biochim. Biophys. Acta 1467, 165-176 (Pubitemid 30621595)
19. Chorev, M. and Goodman, M. (1993) A dozen years of retro-inverso peptidomimetics Acc. Chem. Res. 26, 266-273
20. Chorev, M. and Goodman, M. (1996) Recent developments in in retro peptides and proteins-an ongoing topochemical explanation Trends Biotechnol. 13, 438-445
21. Passante, E. and Frankish, N. (2009) The RBL-2H3 cell line: its provenance and suitability as a model for the mast cell Inflamm. Res. 58, 737-745
22. Pontén, J. and Macintyre, E. H. (1968) Long term culture of normal and neoplastic human glia Acta Pathol. Microbiol. Scand. A 74, 465-486
23. Carmichael, J., DeGraff, W. G., Gazdar, A. F., Minna, J. D., and Mitchell, J. B. (1987) Evaluation of tetrazolium-based semiautomated colorimetric assay. Assessment of chemosensitivity testing Cancer Res. 47, 936-942 (Pubitemid 17027905)
24. Holm, T., Johansson, H., Lundberg, P., Pooga, M., Lindgren, M., and Langel, Ü. (2006) Studying the uptake of cell-penetrating peptides Nat. Protoc. 1, 1001-1005
25. Seo, P. R., Teksin, Z. S., Kao, J. P. Y, and Polli, J. E. (2006) Lipid composition effect on permeability across PAMPA Eur. J. Pharm. Sci. 29, 259-268 (Pubitemid 44602405)
26. Howl, J., Prochazka, Z., Wheatley, M., and Slaninova, J. (1999) Novel strategies for the design of receptor-selective vasopressin analogues: Aib-substitution and retro-inverso transformation Br. J. Pharmacol. 128, 647-652 (Pubitemid 29504755)
27. Pfeiffer, D. R., Gudz, T. I., Novgorodov, S. A., and Erdahl, W. L. (1995) The peptide mastoparan is a potent facilitator of the mitochondrial permeability transition J. Biol. Chem. 270, 4923-4932
28. Isersky, C., Metzger, H., and Buell, D. N. (1975) Cell cycle-associated changes in receptors for IgE during growth and differentiation of a rat basophilic leukemia cell line J. Exp. Med. 141, 1147-1162
29. Jones, S., Holm, T., Mager, I., Langel, U., and Howl, J. (2010) Characterization of bioactive cell penetrating peptides from human cytochrome c: Protein mimicry and development of a novel apoptogenic agent Chem. Biol. 17, 735-744
30. Raagel, H., Saalik, P., Hansen, M., Langel, U., and Pooga, M. (2009) CPP-protein constructs induce a population of non-acidic vesicles during trafficking through endo-lysosomal pathway J. Controlled Release 139, 108-117
31. Saalik, P., Padari, K., Niinep, A., Lorents, A., Hansen, M., Jokitalo, E., Langel, U., and Pooga, M. (2009) Protein delivery with transportans is mediated by calveolae rather than flotillin-dependent pathways Bioconjugate Chem. 20, 877-887
32. Pelkmans, L. and Helenius, A. (2002) Endocytosis via Caveolae Traffic 3, 311-320 (Pubitemid 34461041)
33. Pelkmans, L., Burli, T., Zerial, M., and Helenius, A. (2004) Caveolin-stabilized membrane domains as multifunctional transport and sorting devices in endocytic membrane traffic Cell 118, 767-780 (Pubitemid 39221735)
34. Rejman, J., Bragonzi, A., and Conese, M. (2005) Role of clathrin- and caveolae-mediated endocytosis in gene transfer mediated by lipo- and polyplexes Mol. Ther. 12, 468-474 (Pubitemid 41150132)
35. Mäe, M., El Andaloussi, S., Lundin, P., Oskolkov, N., Johansson, H. J., Guterstam, P., and Langel, U. (2009) A stearylated CPP for the delivery of splice correcting oligonucleotides using a non-covalent co-incubation strategy J. Controlled Release 134, 221-227
36. Lehto, T., Simonson, O. E., Mäger, I., Ezzat, K., Sork, H., Copolovici, D. M., Viola, J. R., Zaghloul, E. M., Lundin, P., Moreno, P. M., Mäe, M., Oskolkov, N., Suhorutšenko, J., Smith, C. E., and El Andaloussi, S. (2011) A peptide-based vector for efficient gene transfer in vitro and in vivo Mol. Ther. 19, 1457-1467
37. Lundin, P., Johansson, H., Guterstam, P., Holm, T., Hansen, M., Langel, U., and El Andaloussi, S. (2008) Distinct uptake routes of cell-penetrating peptide conjugates Bioconjugate Chem. 19, 2535-2542
38. Higashijima, T., Wakamatsu, K., Takemitsu, M., Fujino, M., Nakajima, T., and Miyazawa, T. (1983) Conformational change of mastoparan from wasp venom on binding with phospholipid membrane FEBS Lett. 152, 227-230 (Pubitemid 13129700)
39. 15N-NMR spectroscopy in oriented lipid bilayers Eur. J.Biochem. 268, 302-309 (Pubitemid 32862660)
40. Snyder, E. L., Meade, B. R., Saenz, C. C., and Dowdy, S. F. (2004) Treatment of terminal peritoneal carcinomatosis by transducible p53-activating peptide PLoS Biol. 2, 186-193
41. Baker, R. D., Howl, J., and Nicholl, I. D. (2007) A sychnologic cell penetrating peptide mimic of P21(WAF1/CIP1) is pro-apoptogenic Peptides 28, 731-740 (Pubitemid 46349324)
42. Howl, J., Jones, S., and Farquhar, M. (2003) Intracellular delivery of bioactive peptides to RBL-2H3 cells induces beta-hexosaminidase secretion and phospholipase D activation ChemBioChem 4, 1312-1316 (Pubitemid 38036412)
43. i3α induces the dual phosphorylation of p42/p44 MAP kinases Biochim. Biophys. Acta 1745, 207-214 (Pubitemid 41207893)