New peptide conjugates with 9-aminoacridine: Synthesis and binding to DNA

Journal of Peptide Science

Volumn 12, Issue 7, 2006, Pages 472-480

  šebestík, Jaroslav ^a   Stibor, Ivan ^b   Hlváček, Jan ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^b INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

Author keywords

Mild intercalators into DNA; Peptide 9 aminoacridine conjugates; Polymer supported synthesis tuners of DNA interaction with strong binders; Solution synthesis

Indexed keywords

9 FLUORENYLMETHYLOXYCARBONYLISOLEUCYLOCTYLCHLOROTRITYL RESIN; 9 FLUORENYLMETHYLOXYCARBONYLPHENYLGLUTAMYLTRITYLGLYCYLISOLEUCYLAMINOACRIDINE; 9 FLUORENYLMETHYLOXYCARBONYLPHENYLGLUTAMYLTRITYLGLYCYLISOLEUCYLHYDROXIDE; AMINOACRIDINE DERIVATIVE; AMINOCAPROIC ACID; BENZYLOXYCARBONYLPHENYLGLUTAMYLHYDROXIDE; HISTIDYLPHENYLGLUTAMYLGLYCYLISOLEUCYLAMINOACRIDINE; INTERCALATING AGENT; N (BENZYLOXYCARBONYL) N' (ACRIDIN 9 YL)ETHANE 1,2 DIAMINE; N (BENZYLOXYCARBONYL)ETHANE 1,2 DIAMINE; PEPTIDE DERIVATIVE; SYNTHETIC PEPTIDE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; BINDING COMPETITION; BINDING SITE; CALIBRATION; DRUG CONJUGATION; DRUG DNA BINDING; DRUG SYNTHESIS; ELECTROPHORESIS; FLUORESCENCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE;

AMINACRINE; AMINO ACID SEQUENCE; ANIMALS; BASE SEQUENCE; CATTLE; DNA; KINETICS; MOLECULAR STRUCTURE; OLIGODEOXYRIBONUCLEOTIDES; OLIGOPEPTIDES; PROTEIN BINDING;

EID: 33745942106     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.752     Document Type: Article

References (31)

1. Denny WA, Atwell GJ, Baguley BC. 'Minimal' DNA-intercalating agents as anti-tumor drugs: 2-styrylquinoline analogues of amsacrine. Anticancer Drug Des. 1987; 2: 263-270.
2. Denny WA. DNA intercalating ligands as anti-cancer drugs: prospects for future design. Anticancer Drug Des. 1989; 4: 241-263.
3. Denny WA. Acridine-4-carboxamides and the concept of minimal DNA intercalators. In Small Molecule DNA and RNA Binders, Demeunynck M, Bailly C, Wilson WD (eds). Wiley: New York, 2003; 482-502.
4. Carlson CB, Beal PA. Solid-phase synthesis of acridine-based threading intercalator peptides. Bioorg. Med. Chem. Lett. 2000; 10: 1979-1982.
5. Carlson CB, Beal PA. Solid-phase synthesis of acridine-peptide conjugates and their analysis by tandem mass spectrometry. Org. Lett. 2000; 2: 1465-1468.
6. Carlson CB, Beal PA. Point of attachment and sequence of immobilized peptide-acridine conjugates control affinity for nucleic acids. J. Am. Chem. Soc. 2002; 124: 8510-8511.
7. Takenaka S, Iwamasa K, Takagi M, Nishino N, Mihara H, Fujimoto TJ. Synthesis of a 9-acridinyl nonapeptide containing the DNA recognizing region of 434 phage repressor protein. J. Heterocycl. Chem. 1996; 33: 2043-2046.
8. Tabor AB. Synthesis of a peptide-intercalator hybrid based on the bZIP motif from GCN4. Tetrahedron 1996; 52: 2229-2234.
9. Record MT Jr, Ha J-H, Fisher M. Use of equilibrium and kinetic measurements to determine the thermodynamic origins of stability and specificity and mechanism of formation of site specific complexes between proteins and helical DNA. Methods Enzymol. 1991; 208: 291-343.
10. Horton N, Lewis M. Calculation of the free energy of association for protein complexes. Protein Sci. 1992; 1: 169-181.
11. Manning GS. The molecular theory of polyelectrolyte solutions with applications to the electrostatic properties of polynucleotides. Q. Rev. Biophys. 1978; 11: 179-246.
12. Record MT Jr, Anderson CF, Lohman TM. Thermodynamic analysis of ion effects on the binding and conformational equilibria of proteins and nucleic acids: the roles of ion association or release, screening, and ion effects on water activity. Q. Rev. Biophys. 1978; 11: 103-178.
13. Graves DE, Velea LM. Intercalative binding of small molecules to nucleic acids. Curr. Org. Chem. 2000; 4: 915-929.
14. Medhi C, Mitchell JBO, Price SL, Tabor AB. Electrostatic factors in DNA intercalation. Biopolymers (Nucleic Acid Sciences) 1999; 52: 84-93.
15. Alam MR, Maeda M, Sasaki S. DNA-binding peptides searched from the solid-phase combinatorial library with the use of the magnetic beads attaching the target duplex DNA. Bioorg. Med. Chem. 2000; 8: 465-473.
16. Kaiser E, Colescott PL, Bossinger CD, Cook PI. Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides. Anal. Biochem. 1970; 34: 595-598.
17. Krchák V, Vágner J, Šafáo P, Lebl M. Noninvasive continuous monitoring of solid-phase peptide synthesis by acid-base indicator. Collect. Czech. Chem. Commun. 1988; 53: 2542-2548.
18. Eeoovský V. Synthesis of pressinoic acid by enzymatically catalyzed formation of peptide bonds. Collect. Czech. Chem. Commun. 1986; 51: 1352-1360.
19. Boyd SA, Fung AKL, Baker WR, Mantei RA, Stein HH, Cohen J, Barlow JL, Klinghofer V, Wessale JL, Verburg KM, Polakowski JS, Adler AL, Calzadilla SV, Kovar P, Yao Z, Hutchins CW, Denissen JF, Grabowski BA, Cepa S, Hoffman DJ, Garren KW, Kleinert HD. Nonpeptide renin inhibitors with good intraduodenal bioavailability and efficacy in dog. J. Med. Chem. 1994; 37: 2991-3007.
20. Atwell GJ, Denny WA. Monoprotection of a, ω-akanediamines with the N-benzyloxycarbonyl group. Synthesis 1984; 1032-1033.
21. Albert A, Ritchie B. 9-Aminoacridine. Org. Synth. 3: 53-55.
22. Karagianis G, Reiss JA. Preparation and characterization of porphyrin-acridine conjugates as bifunctional antitumor agents. Aust. J. Chem. 1995; 48: 1693-1706.
23. Abiko T, Kumikawa M, Dazai S, Sekino H, Higuchi H. The effect of STF and its analogs on T cells with cellular immunodeficiency. Chem. Pharm. Bull. 1979; 27: 2207-2211.
24. Kim H-K, Cho T-S, Kim SK. Ionic strength dependent binding mode of 9-aminoacridine to DNA. Bull. Korean Chem. Soc. 1996; 17: 358-362.
25. Martinez J, Bali JP, Rodriguez M, Castro B, Magous R, Laur J, Lignon MF. Synthesis and biological activities of some pseudopeptide analogs of tetragastrin: the importance of the peptide backbone. J. Med. Chem. 1985: 28: 1874-1879.
26. Coste J, Le-Nguyen D, Castro B. PyBOP®: A new peptide coupling reagent devoid of toxic by-product. Tetrahedron Lett. 1990; 31: 205-208.
27. Albertsson P-A. Partition of Cell Particles and Macromolecules. John Wiley & Sons, Almqvist & Wiksell: New York, Stockholm, 1960.
28. Karup G, Meldal M, Nielsen PE, Buchardt O. 9-Acridinylpeptides and 9-acridinyl-4-nitrophenylsulfonylpeptides. Int. J. Pept. Protein Res. 1988; 32: 331-343.
29. Norden B, Tjerneld F. Structure of methylene blue-DNA complexes studies by linear and circular dichroism spectroscopy. Biopolymers 1982; 21: 1713-1734.
30. Kodicek M, Karpenko V. Biofyzikalni Chemie (2nd edn). Academia: Prague, 2000.
31. Carrasco C, Facompre M, Chisholm JD, Van Vranken DL, Wilson WD, Bailly C. DNA sequence recognition by the indolocarbazole antitumor antibiotic AT2433-B1 and its diastereoisomer. Nucleic Acids Res. 2002; 30: 1774-1781.