Highly cytotoxic trithiophenolatodiruthenium complexes of the type [(η6-p-MeC6H4Pr i ) 2Ru2(SC6H4-p-X)3] +: Synthesis, molecular structure, electrochemistry, cytotoxicity, and glutathione oxidation potential

Journal of Biological Inorganic Chemistry

Volumn 17, Issue 6, 2012, Pages 951-960

  Giannini, Federico ^a   Furrer, Julien ^a   Ibao, Anne Flore ^b   Süss Fink, Georg ^b   Therrien, Bruno ^b   Zava, Olivier ^c   Baquie, Mathurin ^c   Dyson, Paul J ^c   Štěpnička, Petr ^d  

^a UNIVERSITY OF BERN   (Switzerland)

^b UNIVERSITÉ DE NEUCHÂTEL   (Switzerland)

^c EPFL   (Switzerland)

^d CHARLES UNIVERSITY   (Czech Republic)

Author keywords

Cancer; Cytotoxicity; Glutathione oxidation; Lipophilicity; Ruthenium

Indexed keywords

ANTINEOPLASTIC METAL COMPLEX; CISPLATIN; RUTHENIUM COMPLEX;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG MECHANISM; DRUG SYNTHESIS; ELECTROCHEMICAL ANALYSIS; FEMALE; GLUTATHIONE METABOLISM; HUMAN; HUMAN CELL; OXIDATION REDUCTION POTENTIAL; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; X RAY DIFFRACTION;

ANTINEOPLASTIC AGENTS; CELL PROLIFERATION; CRYSTALLOGRAPHY, X-RAY; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; ELECTROCHEMISTRY; GLUTATHIONE; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; RUTHENIUM; STRUCTURE-ACTIVITY RELATIONSHIP; SULFHYDRYL COMPOUNDS; TUMOR CELLS, CULTURED;

EID: 84865646301     PISSN: 09498257     EISSN: 14321327     Source Type: Journal    
DOI: 10.1007/s00775-012-0911-2     Document Type: Article

References (41)

1. SJ Dougan PJ Sadler 2007 Chimia 61 704 715 10.2533/chimia.2007.704 1:CAS:528:DC%2BD2sXhsVyhtr7O
2. AM Pizarro A Habtemariam PJ Sadler 2010 Top Organomet Chem 32 21 56 10.1007/978-3-642-13185-1-2 1:CAS:528:DC%2BC3cXhtl2iurzJ
3. PJ Dyson 2007 Chimia 61 698 703 10.2533/chimia.2007.698 1:CAS:528:DC%2BD2sXhsVyhsbnM
4. A Casini CG Hartinger AA Nazarov PJ Dyson 2010 Top Organomet Chem 32 57 80 10.1007/978-3-642-13185-1-3 1:CAS:528:DC%2BC3cXhtl2iurzK
5. RE Morris RE Aird PdS Murdoch H Chen J Cummings ND Hughes S Pearsons A Parkin G Boyd DI Jodrell PJ Sadler 2001 J Med Chem 44 3616 3621 11606126 10.1021/jm010051m 1:CAS:528:DC%2BD3MXntF2hsrw%3D
6. Allardyce CS, Dyson PJ, Ellis DJ, Heath SL (2001) Chem Commun 1396-1397
7. G Süss-Fink 2010 Dalton Trans 39 1673 1688 20449402 10.1039/b916860p
8. Melchart M, Sadler PJ (2006) In: Jaouen G (ed) Bioorganometallics, Wiley-VCH, Weinheim, pp 39-64
9. M Bacac ACG Hotze K van der Schilden JG Haasnoot S Pacor E Alessio G Sava J Reedijk 2004 J Inorg Biochem 98 402 412 14729322 10.1016/j.jinorgbio.2003.12. 003 1:CAS:528:DC%2BD2cXjsVyksQ%3D%3D
10. Schluga P, Hartinger CG, Egger A, Reisner E, Galanski M, Jakupec MA, Keppler BK (2006) Dalton Trans 1796-1802
11. H Chen JA Parkinson RE Morris PJ Sadler 2003 J Am Chem Soc 125 173 186 12515520 10.1021/ja027719m 1:CAS:528:DC%2BD38XovFCnsLg%3D
12. F Wang H Chen S Parsons IDH Oswald JE Davidson PJ Sadler 2003 Chem Eur J 9 5810 5820 14673852 10.1002/chem.200304724 1:CAS:528:DC%2BD2cXhvVGk
13. Yan YK, Melchart M, Habtemariam A, Sadler PJ (2005) Chem Commun 4764-4776
14. A Egger VB Arion E Reisner B Cebrian-Losantos S Shova G Trettenhahn BK Keppler 2005 Inorg Chem 44 122 132 15627368 10.1021/ic048967h 1:CAS:528:DC%2BD2cXhtVCrsbvF
15. H Chen JA Parkinson O Novakova J Bella F Wang A Dawson R Gould S Parsons V Brabec PJ Sadler 2003 Proc Natl Acad Sci USA 100 14623 14628 14657383 10.1073/pnas.2434016100 1:CAS:528:DC%2BD3sXpvFaru7k%3D
16. F Wang J Xu A Habtemariam J Bella PJ Sadler 2005 J Am Chem Soc 127 17734 17743 16351102 10.1021/ja053387k 1:CAS:528:DC%2BD2MXht1Gjt7nL
17. B Wu SM Ong M Groessl Z Adhireksan CG Hartinger PJ Dyson CA Davey 2011 Chem Eur J 17 3562 3566 21344528 10.1002/chem.201100298 1:CAS:528: DC%2BC3MXjtFWnsLk%3D
18. SJ Dougan A Habtemariam SE McHale S Pearsons PJ Sadler 2008 Proc Natl Acad Sci USA 105 11628 11633 18687892 10.1073/pnas.0800076105 1:CAS:528:DC%2BD1cXhtVCnur%2FL
19. M Gras B Therrien G Süss-Fink O Zava PJ Dyson 2010 Dalton Trans 39 10305 10313 20890536 10.1039/c0dt00887g 1:CAS:528:DC%2BC3cXhtlSmsrnN
20. F Chérioux CM Thomas T Monnier G Süss-Fink 2003 Polyhedron 22 543 548 10.1016/S0277-5387(02)01376-1
21. F Giannini G Süss-Fink J Furrer 2011 Inorg Chem 50 10552 10554 21981265 10.1021/ic201941j 1:CAS:528:DC%2BC3MXht1OrsbnE
22. MA Bennett TN Huang TW Matheson AK Smith 1982 Inorg Synth 21 74 78 10.1002/9780470132524.ch16 1:CAS:528:DyaL3sXlsVWmtQ%3D%3D
23. Mashima K, Mikami A, Nakamura A (1992) Chem Lett 1795-1798
24. Chérioux F, Therrien B, Süss-Fink G (2003) Eur J Inorg Chem 1043-1047
25. GM Sheldrick 2008 Acta Crystallogr A 64 112 122 18156677 10.1107/S0108767307043930
26. LJ Farrugia 1997 J Appl Crystallogr 30 565 10.1107/S0021889897003117 1:CAS:528:DyaK2sXnt1KgsLg%3D
27. C Hansch A Leo RW Taft 1991 Chem Rev 91 165 195 10.1021/cr00002a004 1:CAS:528:DyaK3MXhs1ehsLo%3D
28. MG Mendoza-Ferri CG Hartinger RE Eichinger N Stolyarova K Severin MA Jakupec AA Nazarov BK Keppler 2008 Organometallics 27 2405 2407 10.1021/om800207t 1:CAS:528:DC%2BD1cXlsFynsrg%3D
29. MG Mendoza-Ferri CG Hartinger AA Nazarov W Kandioller K Severin BK Keppler 2008 Appl Organomet Chem 22 326 332 10.1002/aoc.1394 1:CAS:528:DC%2BD1cXntlWiurY%3D
30. MG Mendoza-Ferri CG Hartinger MA Mendoza M Groessl A Egger RE Eichinger JB Mangrum NP Farrell M Maruszak PJ Bednarski F Klein A Jakupec AA Nazarov K Severin BK Keppler 2009 J Med Chem 52 916 925 19170599 10.1021/jm8013234 1:CAS:528:DC%2BD1MXht1Oitr0%3D
31. MG Mendoza-Ferri CG Hartinger AA Nazarov RE Eichinger MA Jakupec AA Nazarov K Severin BK Keppler 2009 Organometallics 28 6260 6265 10.1021/om900715j 1:CAS:528:DC%2BD1MXht1KntrjE
32. SM Meier M Hanif W Kandioller BK Keppler CG Hartinger 2012 J Inorg Biochem 108 91 95 22420927 10.1016/j.jinorgbio.2011.08.011 1:CAS:528: DC%2BC38Xkt1emtbo%3D
33. N Satoh 2010 Biochem Genet 48 816 821 20628807 10.1007/s10528-010-9362-z 1:CAS:528:DC%2BC3cXhtFWqtLvK
34. A Pastore A Lo Russo M Greco G Rizzoni G Federici 2001 Clin Chem 47 1467 1469 11468240 1:CAS:528:DC%2BD3MXls1Squ70%3D
35. Advanced Chemistry Development (2012) ACD/ChemSketch, version 12.0. Advanced Chemistry Development, Toronto
36. J Achrem-Achremowicza E Kȩpczyńskab M Zylewskib Z Janeczkoc 2010 Biomed Chromatogr 24 261 267
37. Scolaro C, Chaplin AB, Hartinger CG, Bergamo A, Cocchietto M, Keppler BK, Sava G, Dyson PJ (2007) Dalton Trans 5065-5072
38. AK Renfrew L Juillerat-Jeanneret PJ Dyson 2011 J Organomet Chem 696 772 779 10.1016/j.jorganchem.2010.09.067 1:CAS:528:DC%2BC3MXmslCqsQ%3D%3D
39. L Fetzer B Boff M Ali XJ Meng JP Collin C Sirlin C Gaiddon M Pfeffer 2011 Dalton Trans 40 8869 8878 21837342 10.1039/c1dt10322a 1:CAS:528: DC%2BC3MXhtVKhtLbK
40. Gianferrara T, Brastos I, Alessio E (2009) Dalton Trans 7588-7598
41. A Bergamo C Gaiddon JHM Schellen JH Beijnen G Sava 2012 J Inorg Biochem 106 90 99 22112845 10.1016/j.jinorgbio.2011.09.030 1:CAS:528:DC%2BC3MXhsFOgtbfN