Influence of the metal center and linker on the intracellular distribution and biological activity of organometal-peptide conjugates

Journal of Biological Inorganic Chemistry

Volumn 17, Issue 2, 2012, Pages 175-185

  Hu, Wanning ^a   Splith, Katrin ^b,c   Neundorf, Ines ^b,c   Merz, Klaus ^d   Schatzschneider, Ulrich ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b UNIVERSITY OF LEIPZIG   (Germany)

^c UNIVERSITY OF COLOGNE   (Germany)

^d RUHR UNIVERSITY BOCHUM   (Germany)

Author keywords

Anticancer activity; Bioorganometallic chemistry; Cell penetrating peptides; Cymantrene; Cytotoxicity

Indexed keywords

ANTINEOPLASTIC AGENT; CARBENE; CARBOXYFLUORESCEIN; CYCLOPENTADIEN 1 YL (3 CARBOXYLATO 1 OXOPROPYL)MANGANESE TRICARBONYL GLYCYLLEUCYLARGINYLLYSYL 5(6) CARBOXYFLUORESCEIN ARGINYLLEUCYLARGINYLLYSYLPHENYLALANYLARGINYLASPARAGINYLLYSYLISOLEUCYLLYSYLGLUTAMYLLYSINE AMIDE; CYCLOPENTADIEN 1 YL (3 CARBOXYLATO 1 OXOPROPYL)MANGANESE TRICARBONYL GLYCYLLEUCYLARGINYLLYSYLARGINYLLEUCYLARGINYLLYSYLPHENYLALANYLARGINYLASPARAGINYLLYSYLISOLEUCYLLYSYLGLUTAMYLLYSINE AMIDE; CYCLOPENTADIEN 1 YL (3 CARBOXYLATO 1 OXOPROPYL)RHENIUM TRICARBONYL GLYCYLLEUCYLARGINYLLYSYL 5(6) CARBOXYFLUORESCEIN ARGINYLLEUCYLARGINYLLYSYLPHENYLALANYLARGINYLASPARAGINYLLYSYLISOLEUCYLLYSYLGLUTAMYLLYSINE AMIDE; CYCLOPENTADIEN 1 YL (3 CARBOXYLATO 1 OXOPROPYL)RHENIUM TRICARBONYL GLYCYLLEUCYLARGINYLLYSYLARGINYLLEUCYLARGINYLLYSYLPHENYLALANYLARGINYLASPARAGINYLLYSYLISOLEUCYLLYSYLGLUTAMYLLYSINE AMIDE; CYMANTRENE CELL PENETRATING PEPTIDE CONJUGATE; MANGANESE; ORGANOMETALLIC COMPOUND; RHENIUM; UNCLASSIFIED DRUG; CELL PENETRATING PEPTIDE;

ARTICLE; BREAST CANCER; CELL NUCLEUS; CELL STRAIN MCF 7; CELL VIABILITY; CELLULAR DISTRIBUTION; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG PURIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG UPTAKE; ELECTROSPRAY MASS SPECTROMETRY; ELEMENTAL ANALYSIS; FLUORESCENCE MICROSCOPY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SOLID PHASE SYNTHESIS; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY; AMINO ACID SEQUENCE; BREAST TUMOR; CELL MEMBRANE PERMEABILITY; CHEMICAL STRUCTURE; CHEMISTRY; FEMALE; MOLECULAR GENETICS; TUMOR CELL LINE;

AMINO ACID SEQUENCE; ANTINEOPLASTIC AGENTS; BREAST NEOPLASMS; CELL LINE, TUMOR; CELL MEMBRANE PERMEABILITY; CELL-PENETRATING PEPTIDES; FEMALE; HUMANS; MANGANESE; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; ORGANOMETALLIC COMPOUNDS; RHENIUM; SOLID-PHASE SYNTHESIS TECHNIQUES;

EID: 84861207685     PISSN: 09498257     EISSN: 14321327     Source Type: Journal    
DOI: 10.1007/s00775-011-0840-5     Document Type: Article

References (31)

1. Hartinger CG, Dyson PJ (2009) Chem Soc Rev 38:391-401
2. Melchart M, Sadler PJ (2006) In: Jaouen G (ed) Bioorganometallics. Wiley-VCH, Weinheim, pp 39-64
3. Strohfeldt K, Tacke M (2008) Chem Soc Rev 37:1174-1187
4. Todd RC, Lippard SJ (2009) Metallomics 1:280-291
5. Brooks H, Lebleu B, Vives E (2005) Adv Drug Deliv Rev 57:559-577
6. Fischer R, Fotin-Mleczek M, Hufnagel H, Brock R (2005) ChemBioChem 6:2126-2142
7. Turner JJ, Ivanova GD, Verbeure B, Williams D, Arzumanov AA, Abes S, Lebleu B, Gait MJ (2005) Nucleic Acids Res 33:6837-6849
8. Delehanty JB, Medintz IL, Pons T, Brunel FM, Dawson PE, Mattoussi H (2006) Bioconjug Chem 17:920-927
9. Lebleu B, Moulton HM, Abes R, Ivanova GD, Abes S, Stein DA, Iversen PL, Arzumanov AA, Gait MJ (2008) Adv Drug Deliv Rev 60:517-529
10. Schwarze SR, Ho A, Vocero-Akbani A, Dowdy SF (1999) Science 285:1569-1572
11. Langel Ü (2006) Handbook of cell-penetrating peptides. CRC Press, Boca Raton
12. Joliot A, Prochiantz A (2004) Nat Cell Biol 6:189-196
13. Mäe M, Langel Ü (2006) Curr Opin Pharmacol 6:509-514
14. Stewart KM, Horton KL, Kelley SO (2008) Org Biomol Chem 6:2242-2255
15. Neundorf I, Hoyer J, Splith K, Rennert R, Peindy N'Dongo HW, Schatzschneider U (2008) Chem Commun 5604-5606
16. Splith K, Neundorf I, Hu W, Peindy N'Dongo HW, Vasylyeva V, Merz K, Schatzschneider U (2010) Dalton Trans 39:2536-2545
17. Splith K, Hu W, Schatzschneider U, Gust R, Ott I, Onambele LA, Prokop A, Neundorf I (2010) Bioconjug Chem 21:1288-1296
18. Neundorf I, Rennert R, Hoyer J, Schramm F, Loebner K, Kitanovic I, Woelfl S (2009) Pharmaceuticals 2:49-65
19. Fulmer GR, Miller A J M, Sherden NH, Gottlieb HE, Nudelman A, Stoltz BM, Bercaw JE, Goldberg KI (2010) Organometallics 29:2176-2179
20. Peindy N'Dongo HW, Neundorf I, Merz K, Schatzschneider U (2008) J Inorg Biochem 102:2114-2119
21. Fischer R, Mader O, Jung G, Brock R (2003) Bioconjug Chem 14:653-660
22. Sheldrick GM (1996) SADABS. University of Göttingen
23. Sheldrick GM (1997) SHELXL-97. University of Göttingen
24. Peindy N'Dongo HW, Ott I, Gust R, Schatzschneider U (2009) J Organomet Chem 694:823-827
25. Rosita D, DeWit MA, Luyt LG (2009) J Med Chem 52:2196-2203
26. Bhattacharyya S (1998) J Org Chem 63:7101-7102
27. Peindy N'Dongo HW, Liu Y, Schmutz P, Spingler B, Alberto R (2009) J Organomet Chem 694:981-987
28. Fitzpatrick PJ, Le Page Y, Butler IS (1981) Acta Crystallogr Sect B 37:1052-1058
29. Schaffer P, Gleave JA, Lemon JA, Reid LC, Pacey LK, Farncombe TH, Boreham DR, Zubieta J, Babich JW, Doering LC, Valliant JF (2008) Nucl Med Biol 35:159-169
30. Policar C, Waern JB, Plamont MA, Clede S, Mayet C, Prazeres R, Ortega JM, Vessieres A, Dazzi A (2011) Angew Chem Int Ed 50:860-864
31. Uehara T, Koike M, Nakata H, Miyamoto S, Motoishi S, Hashimoto K, Oku N, Nakayama M, Arano Y (2003) Nucl Med Biol 30:327-334