Enhanced antitumour activity of 15-residue bovine lactoferricin derivatives containing bulky aromatic amino acids and lipophilic N-terminal modifications

Journal of Peptide Science

Volumn 9, Issue 8, 2003, Pages 510-517

  Eliassen, Liv Tone ^a   Haug, Bengt Erik ^a   Berge, Gerd ^a   Rekdal, Øystein ^a  

^a UNIVERSITY OF TROMSØ   (Norway)

Author keywords

Antitumoural peptides; Bovine lactoferricin; Bulky aromatic amino acids; Tryptophan

Indexed keywords

ALANINE; ALANINE DERIVATIVE; ANTINEOPLASTIC AGENT; AROMATIC AMINO ACID; CYSTEINE; GLUTAMINE; GLYCINE; LACTOFERRICIN; LONG CHAIN FATTY ACID; TRYPTOPHAN;

AMINO ACID SEQUENCE; AMINO ACID SUBSTITUTION; AMINO TERMINAL SEQUENCE; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG STRUCTURE; ENDOTHELIUM CELL; FIBROBLAST; HUMAN; HUMAN CELL; IN VITRO STUDY; LIPOPHILICITY; MOLECULAR SIZE; PRIORITY JOURNAL; PROTEIN MODIFICATION; STRUCTURE ACTIVITY RELATION; UMBILICAL VEIN;

AMINO ACIDS, AROMATIC; ANIMALS; ANTINEOPLASTIC AGENTS; CATTLE; CELL LINE; CELL LINE, TUMOR; CELL SURVIVAL; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; INHIBITORY CONCENTRATION 50; LACTOFERRIN; MOLECULAR STRUCTURE; OLIGOPEPTIDES; PEPTIDE FRAGMENTS;

BOVINAE;

EID: 0042978656     PISSN: 10752617     EISSN: None     Source Type: Journal    
DOI: 10.1002/psc.472     Document Type: Article

References (26)

1. Bezault J, Bhimani R, Wiprovnick J, Furmanski P. Human lactoferrin inhibits growth of solid tumors and development of experimental metastases in mice. Cancer Res. 1994; 54: 2310-2312.
2. Sekine K, Watanabe E, Nakamura J, Takasuka N, Kim DJ, Asamoto M, Krutovskikh V, Baba-Toriyama H, Ota T, Moore MA, Masuda M, Sugimoto H, Nishino H, Kakizoe T, Tsuda H. Inhibition of azoxymethane-initiated colon tumor by bovine lactoferrin administration in F344 rats. Jpn J. Cancer Res. 1997; 88: 523-526.
3. Yoo YC, Watanabe S, Watanabe R, Hata K, Shimazaki K, Azuma I. Bovine lactoferrin and lactoferricin inhibit tumor metastasis in mice. Adv. Exp. Med. Biol. 1998; 443: 285-291.
4. Iigo M, Kuhara T, Ushida Y, Sekine K, Moore MA, Tsuda H. Inhibitory effects of bovine lactoferrin on colon carcinoma 26 lung metastasis in mice. Clin. Exp. Metastasis 1999; 17: 35-40.
5. Eliassen LT, Berge G, Sveinbjørnsson B, Svendsen JS, Vorland LH, Rekdal Ø. Evidence for a direct antitumor mechanism of action of bovine lactoferricin. Anticancer Res. 2002; 22: 2703-2710.
6. Moore SA, Anderson BF, Groom CR, Haridas M, Baker EN. Three-dimensional structure of diferric bovine lactoferrin at 2.8 angstrom resolution. J. Mol. Biol. 1997; 274: 222-236.
7. Tomita M, Bellamy W, Takase M, Yamauchi K, Wakabayashi H, Kawase K. Potent antibacterial peptides generated by pepsin digestion of bovine lactoferrin. J. Dairy Sci. 1991; 74: 4137-4142.
8. Bellamy W, Takase M, Yamauchi K, Wakabayashi H, Kawase K, Tomita M. Identification of the bactericidal domain of lactoferrin. Biochim. Biophys. Acta 1992; 1121: 130-136.
9. Rekdal Ø, Andersen J, Vorland LH, Svendsen JS. Construction and synthesis of lactoferricin derivatives with enhanced antibacterial activity. J. Peptide Sci. 1999; 5: 32-45.
10. Yang N, Stensen W, Svendsen JS, Rekdal Ø. Enhanced antitumor activity and selectivity of lactoferrin-derived peptides. J. Peptide Res. 2002; 60: 187-197.
11. Yang N, Lejon T, Rekdal Ø. Antitumor activity and specificity as a function of substitutions in the lipophilic sector of helical lactoferrin-derived peptides. J. Peptide Sci. in press.
12. Lawyer C, Pai S, Watabe M, Borgia P, Mashimo T, Eagleton L, Watabe K. Antimicrobial activity of a 13 amino acid tryptophan-rich peptide derived from a putative porcine precursor protein of a novel family of antibacterial peptides. FEBS Lett. 1996; 390: 95-98.
13. Nagpal S, Gupta V, Kaur KJ, Salunke DM. Structure-function analysis of tritrypticin, an antibacterial peptide of innate immune origin. J. Biol. Chem. 1999; 274: 23296-23304.
14. Strøm MB, Rekdal Ø, Svendsen JS. Antibacterial activity of 15-residue lactoferricin derivatives. J. Pept. Res. 2000; 56: 265-274.
15. Haug BH, Svendsen JS. The role of tryptophan in the antibacterial activity of a 15-residue bovine lactoferricin peptide. J. Peptide Sci. 2001; 7: 190-196.
16. Haug BE, Skar ML, Svendsen JS. Bulky aromatic amino acids increase the antibacterial activity of 15-residue bovine lactoferricin derivatives. J. Peptide Sci. 2001; 7: 425-432.
17. Chou PY, Fasman GD. Empirical predictions of protein conformation. Annu. Rev. Biochem. 1978; 42: 251-276.
18. Lôw M, Kisfaludy L, Jaeger E, Thamm P, Knof S, Wonsch E. [Direct tert-butylation of tryptophan: preparation of 2,5,7-tri-tert-butyltryptophan (author's transl)]. Hoppe Seyler's Z. Physiol. Chem. 1978; 359: 1637-1642.
19. Haug BE, Andersen J, Rekdal Ø, Svendsen JS. Synthesis of a 2-arylsulfonylated tryptophan; the antibacterial activity of bovine lactoferricin peptides containing Trp(2-Pmc). J. Peptide Sci. 2002; 8: 307-313.
20. Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods 1983; 65: 55-63.
21. Nikaido H, Vaara M. Molecular basis of bacterial outer membrane permeability. Microbiol. Rev. 1985; 49: 1-32.
22. Benedetti E, Bavoso A, Di Blasio B, Pavone V, Pedone C, Toniolo C. Peptaibol antibiotics. A study on the helical structure of the 2-9 sequence of emerimicins III and IV. Proc. Natl Acad. Sci. USA 1982; 79: 7951-7954.
23. Brückner H, Graf H. Paracelsin, a peptide antibiotic containing α-aminoisobutyric acid, isolated from Trichoderma reesi Simmons. Part A. Experientia 1983; 39: 528-530.
24. Auvin-Guette C, Rebuffat S, Prigent Y, Bodo B. Trichogin A IV, an 11 residue lipopeptaibol from Trichoderma longibrachiatum. J. Am. Chem. Soc. 1992; 114: 2170-2174.
25. α-acyl chain length on the membrane-modifying properties of synthetic analogs of the lipopeptaibol Trichogin GA IV. J. Am. Chem. Soc. 1996; 118: 4952-4958.
26. Johnstone SA, Gelmon K, Mayer LD, Hancock RE, Bally MB. In vitro characterization of the anticancer activity of membrane-active cationic peptides. I. Peptide-mediated cytotoxicity and peptide-enhanced cytotoxic activity of doxorubicin against wild-type and p-glycoprotein over-expressing tumor cell lines. Anticancer Drug Des. 2000; 15: 151-160.