From venoms to BBB shuttles: Synthesis and blood-brain barrier transport assessment of apamin and a nontoxic analog

Biopolymers

Volumn 100, Issue 6, 2013, Pages 675-686

  Oller Salvia, Benjamí ^a   Teixidó, Meritxell ^a   Giralt, Ernest ^b  

^a INSTITUTE FOR RESEARCH IN BIOMEDICINE   (Spain)

^b UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Apamin; Blood brain barrier; Blood brain barrier shuttles; Brain delivery; Peptide shuttles; Venoms

Indexed keywords

PEPTIDES;

ACTIVE TRANSPORT; APAMIN; BLOOD-BRAIN BARRIER; BRAIN DELIVERY; CELL-BASED; DRUG DISCOVERY; POTASSIUM CHANNELS; VENOMS;

BLOOD;

APAMIN; APOO PEPTIDE; BIOPOLYMER; CYSTEINE; DISULFIDE; PROPRANOLOL; PROTEINASE; SYNTHETIC PEPTIDE; THIOL DERIVATIVE; UNCLASSIFIED DRUG; PEPTIDE; VENOM;

ACTIVE TRANSPORT; AMINO ACID ANALYSIS; AQUEOUS SOLUTION; ARTICLE; BLOOD BRAIN BARRIER; CELL ADHESION; CELL MEMBRANE PERMEABILITY; CELL STRAIN CACO 2; CYCLIZATION; DEPROTECTION REACTION; DISULFIDE BOND; DRUG DELIVERY SYSTEM; HALF LIFE TIME; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; LIMIT OF DETECTION; MASS SPECTROMETRY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PEPTIDE SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; RNA TRANSLATION; SOLID PHASE SYNTHESIS; TRANSCYTOSIS; BRAIN; TRANSPORT AT THE CELLULAR LEVEL;

APAMIN; BIOLOGICAL TRANSPORT; BLOOD-BRAIN BARRIER; BRAIN; PEPTIDES; VENOMS;

EID: 84891672685     PISSN: 00063525     EISSN: 10970282     Source Type: Journal    
DOI: 10.1002/bip.22257     Document Type: Article

References (38)

1. King, G. F., Expert Opin Biol Ther 2011, 11, 1469-1484.
2. Utkin, Y. N.; Osipov, A. V., Cent Nerv Syst Agents Med Chem 2007, 7, 97-107.
3. de Boer, A. G.; Gaillard, P. J., Annu Rev Pharmacol Toxicol 2007, 47, 323-355.
4. Malakoutikhah, M.; Teixido, M.; Giralt, E., Angew Chem Int Ed Engl 2011, 50, 7998-8014.
5. Vincent, J. P.; Schweitz, H.; Lazdunski, M., Biochemistry 1975, 14, 2521-2525.
6. Haberman, E., Science 1972, 177, 314-322.
7. Wulff, H.; Kolski-Andreaco, A.; Sankaranarayanan, A.; Sabatier, J. M.; Shakkottai, V., Curr Med Chem 2007, 14, 1437-1457.
8. Habermann, E., Pharmacol Ther 1984, 25, 255-270.
9. Cosand, W. L.; Merrifield, R. B., Proc Natl Acad Sci USA 1977, 74, 2771-2775.
10. Labbé-Jullié, C.; Granier, C.; Albericio, F.; Defendini, M. L.; Ceard, B.; Rochat, H.; van Rietschoten, J., Eur J Biochem 1991, 196, 639-645.
11. Li, C.; Pazgier, M.; Liu, M.; Lu, W. Y.; Lu, W., Angew Chem Int Ed Engl 2009, 48, 8712-8715.
12. Chau, M. H.; Nelson, J. W., Biochemistry 1992, 31, 4445-4450.
13. Huyghues-Despointes, B. M.; Nelson, J. W., Biochemistry 1992, 31, 1476-1483.
14. Ramalingam, K.; Snyder, G. H., Biochemistry 1993, 32, 11155-11161.
15. Dempsey, C. E.; Sessions, R. B.; Lamble, N. V.; Campbell, S. J., Biochemistry 2000, 39, 15944-15952.
16. Fiori, S.; Pegoraro, S.; Rudolph-Bohner, S.; Cramer, J.; Moroder, L., Biopolymers 2000, 53, 550-564.
17. Schroll, A. L.; Hondal, R. J.; Flemer, S., Jr., J Pept Sci 2012, 18, 1-9.
18. Wemmer, D.; Kallenbach, N. R., Biochemistry 1983, 22, 1901-1906.
19. Pease, J. H.; Wemmer, D. E., Biochemistry 1988, 27, 8491-8498.
20. Glushka, J.; Lee, M.; Coffin, S.; Cowburn, D., J Am Chem Soc 1989, 111, 7716-7722.
21. Giralt, E.; Albericio, F.; Pedroso, E.; Granier, C.; van Rietschoten, J., Tetrahedron 1982, 38, 1193-1201.
22. Albericio, F.; Granier, C.; Labbé-Jullié, C.; Seagar, M.; Couraud, F.; van Rietschoten, J., Tetrahedron 1984, 40, 4313-4326.
23. Brazil, B. T.; Cleland, J. L.; McDowell, R. S.; Skelton, N. J.; Paris, K.; Horowitz, P. M., J Biol Chem 1997, 272, 5105-5111.
24. Weston, C. J.; Cureton, C. H.; Calvert, M. J.; Smart, O. S.; Allemann, R. K., ChemBioChem 2004, 5, 1075-1080.
25. Kaiser, E.; Colescott, R. L.; Bossinger, C. D.; Cook, P. I., Anal Biochem 1970, 34, 595-598.
26. Christensen, T., Acta Chem Scand B 1979, 33, 763-766.
27. Malakoutikhah, M.; Teixido, M.; Giralt, E., J Med Chem 2008, 51, 4881-4889.
28. Garberg, P. B. M.; Borg, N.; Cecchelli, R.; Fenart, L.; Hurst, R. D.; Lindmark, T.; Mabondzo, A.; Nilsson, J. E.; Raub, T. J.; Stanimirovic, D.; Teraski, T.; Öberg, J.-O.; Österberg, T., Toxicol Vitro 2005, 19, 299-334.
29. Yang, Y.; Sweeney, W. V.; Schneider, K.; Chait, B. T.; Tam, J. P., Protein Sci 1994, 3, 1267-1275.
30. Malakoutikhah, M.; Prades, R.; Teixido, M.; Giralt, E., J Med Chem 2010, 53, 2354-2363.
31. Teixido, M.; Zurita, E.; Malakoutikhah, M.; Tarrago, T.; Giralt, E., J Am Chem Soc 2007, 129, 11802-11813.
32. Culot, M.; Lundquist, S.; Vanuxeem, D.; Nion, S.; Landry, C.; Delplace, Y.; Dehouck, M. P.; Berezowski, V.; Fenart, L.; Cecchelli, R., Toxicol Vitro 2008, 22, 799-811.
33. Prades, R.; Guerrero, S.; Araya, E.; Molina, C.; Salas, E.; Zurita, E.; Selva, J.; Egea, G.; Lopez-Iglesias, C.; Teixido, M.; Kogan, M. J.; Giralt, E., Biomaterials 2012, 33, 7194-7205.
34. Béliveau, R.; Demeule, M., WO2004060403A2, 2004.
35. Strong, N. E. H., Eur J Biochem 1987, 163, 267-273.
36. Wiranowska, M.; Colina, L. O.; Johnson, J. O., Cancer Cell Int 2011, 11, 27.
37. Akan, M.; Ata, B.; Olsen, T., Oper Res 2012, 60, 1505-1519.
38. Garcia, A. E.; Tai, K. P.; Puttamadappa, S. S.; Shekhtman, A.; Ouellette, A. J.; Camarero, J. A., Biochemistry 2011, 50, 10508-10519.