Fluorescent analogs of Trypsin inhibitor SFTI-1 isolated from sunflower seeds - Synthesis and applications

Biopolymers - Peptide Science Section

Volumn 102, Issue 1, 2014, Pages 124-135

  Lesner, Adam ^a   Karna, Natalia ^a   Psurski, Mateusz ^b,c   Łe¸gowska, Anna ^a   Wysocka, Magdalena ^a   Guzow, Katarzyna ^a   Sieradzan, Adam ^a   Sieńczyk, Marcin ^b   Trzonkowski, Piotr ^d   Pikuła, Michał ^d   Zieliński, Maciej ^d   Kosikowska, Paulina ^a   Łukajtis, Rałał ^a   Łe¸gowska, Monika ^a   De¸bowski, Dawid ^a   Wiczk, Wiesław ^a   Rolka, Krzysztof ^a  

^a UNIVERSITY OF GDA SK   (Poland)

^b WROCLAW UNIVERSITY OF TECHNOLOGY   (Poland)

^c INSTITUTE OF IMMUNOLOGY AND EXPERIMENTAL THERAPY   (Poland)

^d MEDICAL UNIVERSITY OF GDANSK   (Poland)

Author keywords

Fluorescence; Proteinase inhibitors; SFTI 1

Indexed keywords

AMINO ACIDS; CELL CULTURE; CYTOTOXICITY; ENZYME INHIBITION; ENZYMES;

ENZYME-INHIBITOR COMPLEX; FLUORESCENT PEPTIDES; FLUORESCENT TECHNIQUE; INHIBITION CONSTANTS; INHIBITORY ACTIVITY; ORDERS OF MAGNITUDE; PROTEINASE INHIBITORS; SFTI-1;

FLUORESCENCE;

3 [2 (2',4',5', TRIMETHOXYPHENYL)BENZOXAZOL 5 YL] L ALANINE [2,4,5 (OME)3PH]BOX ALA); BENZOXAZOLE (3 [2 (4 DIPHENYLAMINOPHENYL)BENZOXAZOL 5 YL] L ALANINE [94NPH2)PH]BOX ALA; BENZOXAZOLE DERIVATIVE; CHYMOTRYPSIN INHIBITOR; FLUORESCENT DYE; PEPTIDE; SUNFLOWER TRYPSIN INHIBITOR 1; TRYPSIN INHIBITOR; UNCLASSIFIED DRUG; CYCLOPEPTIDE; SFTI-1 PEPTIDE, SUNFLOWER; CHYMOTRYPSIN; FLUORESCENT PEPTIDE; PEPTIDE DERIVATIVE; TRYPSIN; TRYPSIN INHIBITOR SFTI 1;

ACUTE LYMPHOBLASTIC LEUKEMIA; AMINO ACID SEQUENCE; ARTICLE; CELL MEMBRANE PERMEABILITY; CONJUGATE; CONTROLLED STUDY; ENZYME INHIBITION; ENZYME INHIBITOR COMPLEX; FIBROBLAST; GEL PERMEATION CHROMATOGRAPHY; HUMAN; HUMAN CELL; INHIBITION CONSTANT; MCF 7 CELL LINE; PEPTIDE SYNTHESIS; PLANT SEED; SUNFLOWER; ANIMAL; BOVINE; CELL LINE; CHEMISTRY; FLOW CYTOMETRY; FLUORESCENCE; FLUORESCENCE MICROSCOPY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOLATION AND PURIFICATION; MOLECULAR GENETICS; SIZE EXCLUSION CHROMATOGRAPHY; SYNTHESIS; TIME FACTOR; CANCER CELL; CYTOTOXICITY; DRUG SYNTHESIS; PROTEIN DEGRADATION;

AMINO ACID SEQUENCE; ANIMALS; BENZOXAZOLES; CATTLE; CELL LINE; CELL MEMBRANE PERMEABILITY; CHROMATOGRAPHY, GEL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FLOW CYTOMETRY; FLUORESCENCE; HELIANTHUS; HUMANS; MICROSCOPY, FLUORESCENCE; MOLECULAR SEQUENCE DATA; PEPTIDES, CYCLIC; SEEDS; TIME FACTORS; TRYPSIN INHIBITORS;

BOVINAE; HELIANTHUS;

EID: 84900484892     PISSN: 00063525     EISSN: 10970282     Source Type: Journal    
DOI: 10.1002/bip.22442     Document Type: Article

References (24)

1. Luckett, S.; Santiago Garcia, R.; Barker, J. J.; Konarev, A. V.; Shewry, P. R.; Clarke, A. R.; Brady, R. L. J Mol Biol 1999, 290, 525-533.
2. Zabłotna, E.; Kaźmierczak, K.; Jaśkiewicz, A.; Stawikowski, M.; Kupryszewski, G.; Rolka K. Biochem Biophys Res Commun 2002, 292, 855-859.
3. Lesner, A.; Łe¸gowska, A.; Wysocka, M.; Rolka, K. Curr Pharm Design 2011, 17, 4308-4317.
4. Derossi, D.; Joliot, A. H.; Chassaing, G.; Prochiantz, A. J Biol Chem 1994, 269, 10444-10450.
5. Koren, E.; Torchilin, V. P. Trends Mol Med 2012, 18, 385-393.
6. Craik, D. J. Toxins 2012, 4, 139-156.
7. Gould, A.; Ji, Y.; Aboye, T. L.; Camarero, J. A. Curr Pharm Des 2011, 17, 4294-4307.
8. Greenwood, K. P.; Daly, N. L.; Brown, D. L.; Stow, J. L.; Craik, D. J. Int J Biochem Cell Biol 2007, 39, 2252-2264.
9. Contreras, J.; Elnagar, A. Y. O.; Hamm-Alvarez, S. F.; Camarero, J. A. J Control Release 2011, 155, 134-143.
10. Cascales, L.; Henriques, S. T.; Kerr, M. C.; Huang, Y.-H.; Sweet, M. J.; Daly, N. L.; Craik, D. J. J Biol Chem 2011, 286, 36932-36943.
11. Guzow, K.; Milewska, M.; Wiczk, W. Spectrochim. Acta A 2005, 61, 1133-1140.
12. Guzow, K.; Zielińska, J.; Mazurkiewicz, K.; Karolczak, J.; Wiczk, W. J Photochem Photobiol A: Chem 2005, 175, 57-68.
13. Boy, R. G.; Mier, W.; Nothelfer, E. M.; Altmann, A.; Eisenhut, M.; Kolmar, H.; Tomaszowski, M.; Krämer, S.; Haberkorn, U. Mol Imaging Biol 2010, 12, 377-385.
14. Guzow, K.; Szmigiel, D.; Wróblewski, D.; Milewska, M.; Karolczak, J.; Wiczk, W. J Photochem Photobiol A: Chem 2007, 187, 87-96.
15. Wünsch, E. Synthese von Peptiden, 15; Houben-Weyl, E. Müller, Eds.; Georg Thieme Verlag: Stuttgart, 1974; p 317.
16. nd ed.; Pierce Chemical Company: Rockford, IL, 1984; p 63.
17. Wysocka, M.; Kwiatkowska, B.; Rzadkiewicz, M.; Lesner, A.; Rolka, K. Comb Chem High Throughput Screen 2007, 10, 171-180.
18. Yang, Y.; Sweeney, W. V.; Schneider, K.; Chait, B. T.; Tam, J. P. Protein Sci 1994, 3 1267-1275.
19. Park, S. J. Effect of Amino Acid Replacement in Ovomucoid Third Domains upon Their Association with Serine Proteinase. PhD Thesis, Purdue University, IN, 1985.
20. Empie, M. W.; Laskowski, M., Jr. Biochemistry 1982, 21, 2274-2284.
21. Leatherbarrow, R. J. GraFit Version 5. Erithacus Software, Horley, 2001.
22. Łukajtis, R.; Ł¸gowska, A.; Wysocka, M.; De¸bowski, D.; Lesner A.; Rolka, K. J Pept Sci 2011, 17, 281-287.
23. Łegowska, A.; Bulak, E.;, Wysocka, M.; Jákiewicz, A.; Lesner, A.; Debowski, D.; Rolka, K. Bioorg Med Chem 2008, 16, 5644-5652.
24. Pereira, H. J.; Salgado, M. C.; Oliveira, E. B. J Chromatogr B Analyt Technol Biomed Life Sci 2009, 877, 2039-2044.