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Synthesis and cytotoxicity of dinuclear complexes containing ruthenium(II) bipyridyl units linked by a bis(pyridylimine) ligand

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McDonnell, Ursula, Kerchoffs, Jessica M. C. A., Castineiras, Rosa P. M., Hicks, Matthew R., Hotze, Anna C. G., Hannon, M. J. (Michael J.) and Rodger, Alison. (2008) Synthesis and cytotoxicity of dinuclear complexes containing ruthenium(II) bipyridyl units linked by a bis(pyridylimine) ligand. Dalton Transactions, Vol.37 (No.5). pp. 667-675. ISSN 1477-9226

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Official URL: http://dx.doi.org/10.1039/b711080d

Abstract

Enantiopure dinuclear ruthenium polypyridyl complexes of the form [Ru-2(LL)(4)L-1](PF6)(4) (LL = 2,2'-bipyridine (bpy) or 1,10-phenanthroline (phen); L-1 = C25H20N4 a bis(pyridylimine) ligand containing a diphenylmethane spacer) have been synthesized using the chiral building blocks cis-[Ru(bpy)(2)(py)(2)](2+) and cis-[Ru(phen)(2)(py)(2)](2+). These dinuclear ruthenium complexes have been characterised using NMR, mass spectrometry, UV-visible absorbance, circular dichroism and linear dichroism. The compounds exhibit good photo and thermal stability. The extinction coefficient for the bpy complex at 478 nm is epsilon(478) = 15 700 mol(-1) cm(-1) dm(3) and for the phen complex is epsilon(478) = 24900 mol(-1) cm(-1) dm(3). Both complexes have their longest wavelength (metal to ligand charge transfer) transition predominantly x/y (short axis)-polarised while the transitions at shorter wavelength are a mixture of x/y and z-polarisations, similar to both the copper helicate and iron triple helicate studied previously. Cytotoxicity studies reveal that the compounds are dramatically less active against cancer cell lines than the recently reported supramolecular cylinders prepared from the same bis(pyridylimine) ligand.

Item Type:

Journal Article

Subjects:

Q Science > QD Chemistry
Q Science > QP Physiology

Divisions:

Faculty of Science > Chemistry

Library of Congress Subject Headings (LCSH):

Transition metal complexes, Antineoplastic agents, Enantiomers, Electrochemistry, Ruthenium

Journal or Publication Title:

Dalton Transactions

Publisher:

Royal Society of Chemistry

ISSN:

1477-9226

Official Date:

7 February 2008

Dates:

Date	Event
7 February 2008	Published

Volume:

Vol.37

Number:

No.5

Number of Pages:

Page Range:

pp. 667-675

Identification Number:

10.1039/b711080d

Status:

Peer Reviewed

Publication Status:

Published

Access rights to Published version:

Restricted or Subscription Access

Funder:

Engineering and Physical Sciences Research Council (EPSRC), European Union (EU), Fundación Ramón Areces

Grant number:

MEIF-CT-2005-024818 (EU), HPRNCT- 2002-00175 (EU)

References:

1 B. Lippert, Cisplatin, Chemistry and Biochemistry of A Leading
Anti-Cancer Drug, Wiley-VCH, Weinheim, 1999; J. Reedijk, Chem.
Commun., 1996, 801–806; Z. J. Guo and P. J. Sadler, Adv. Inorg. Chem.,
2000, 49, 183–306; J. D. Roberts, J. Peroutka and N. Farrell, J. Inorg.
Biochem., 1999, 77, 51–57; S. J. Lippard and J. M. Berg, Principles
of Bioinorganic Chemistry, University Science Books, Mill Valley, CA,
1994.
2 W.H. Ang andP. J.Dyson, Eur. J. Inorg. Chem., 2006, 4003–18; A.C.G.
Hotze, S. E. Caspers,D. de Vos, H.Kooijman,A. L. Spek, A. Flamigni,
M. Bacac, G. Sava, J. G. Haasnoot and J. Reedijk, JBIC, J. Biol.
Inorg. Chem., 2004, 9, 354; R. E. Morris, P. J. Sadler, H. Chen and
D. Jodrell, US Patent, US 6,750251 B2, 2004; Y. K. Yan, M. Melchart,
A. Habtemariam and P. J. Sadler, Chem. Commun., 2005, 4764–4776;
M. J. Clarke, Coord. Chem. Rev., 2003, 236, 209–233.
3 E. Alessio, G. Mestroni, A. Bergamo and G. Sava, Curr. Top. Med.
Chem., 2004, 4, 1525–1535; E. Alessio, G. Mestroni, A. Bergamo and
G. Sava, Met. Ions Biol. Syst., 2004, 42, 323–351.
4 C. G. Hartinger, S. Zorbas-Selfried, M. A. Jakupee, B. Kynast, H.
Zorbas and B. K. Keppler, J. Inorg. Biochem., 2006, 100, 891–904.
5 A. Juris, V. Balzani, F. Barigelletti, S. Campagna, P. Belser and
A. Von Zelewsky, Coord. Chem. Rev., 1988, 84, 8; V. Balzani
and F. Scandola, Supramolecular Photochemistry, Ellis Horwood,
Chichester, 1991; V. Balzani, S. Campagna, G. Denti, A. Juris,
S. Serroni and M. Venturi, Acc. Chem. Res., 1998, 31, 26; V.
Balzani, A. Juris, M. Venturi, S. Campagna and S. Serroni, Chem.
Rev., 1996, 96, 759; L. DeCola, Chimia, 1996, 50, 214; E. C.
Constable, Chem. Commun., 1997, 1073; S. Bernard, C. Blum, A.
Beyeler, L. DeCola and V. Balzani, Coord. Chem. Rev., 1999, 192,
155; A. Von, Zelewsky and P. Belser, Chimia, 1998, 52, 620; J.-P.
Sauvage, J.-P. Collin, J.-C. Chambron, S. Guillerez and C. Coudret,
Chem. Rev., 1994, 94, 993; M. Hissler, A. El-ghayoury, A. Harriman
and R. Ziessel, Angew. Chem., Int. Ed., 1998, 37, 1717; M. D. Ward,
Chem. Soc. Rev., 1995, 24, 121;N.W. Alcock, P. R. Barker, J.M. Haider,
M. J. Hannon, C. L. Painting, Z. Pikramenou, E. A. Plummer, K.
Rissanen and P. Saarenketo, J. Chem. Soc., Dalton Trans., 2000, 4702;
H. Krass, E. A. Plummer, J. M. Haider, P. R. Barker, N. W. Alcock,
Z. Pikramenou, M. J. Hannon and D. G. Kurth, Angew. Chem., Int.
Ed., 2001, 40, 3862; J. M. Haider and Z. Pikramenou, Chem. Soc. Rev.,
2005, 34, 120; M. Zukalova, A. Zukal, L. Kavan, M. K. Nazeeruddin,
P. Liska and M. Gratzel, Nano Lett., 2005, 5, 1789; O. Bossart,
L. De Cola, S. Welter and G. Calzaferri, Chem.–Eur. J., 2004, 10,
5771.
6 M. J. Hannon, Chem. Soc. Rev., 2007, 36, 280–295; A. D. Richards and
A. Rodger, Chem. Soc. Rev., 2007, 36, 471; K. K. Patel, E. A. Plummer,
M. Darwish, A. Rodger and M. J. Hannon, J. Inorg. Biochem., 2002,
91, 220; B. Onfelt, P. Lincoln and B. Norden, J. Am. Chem. Soc., 2001,
123, 3630; B. T. Farrer and H. H. Thorp, Inorg. Chem., 2000, 39, 44;
J. G. Collins, A. D. Sleeman, J. R. Aldrich-Wright, I. Greguric and
T. W. Hambley, Inorg. Chem., 1998, 37, 3133; P. Lincoln, E. Tuite and
B. Norden, J. Am. Chem. Soc., 1997, 119, 1454; S. D. Choi,M. S. Kim,
S. K. Kim, P. Lincoln, E. Tuite and B. Nord´en, Biochemistry, 1997, 36,
214; J. K. Barton, Pure Appl. Chem., 1989, 61, 563; S. Satyanarayana,
J. C. Dabrowiak and J. B. Chaires, Biochemistry, 1993, 32, 2573; F.
Pierard and A. Kirsch-De Mesmaeker, Inorg. Chem. Commun., 2006,
9, 111.
7 B. Onfelt, P. Lincoln and B. Nord´en, J. Am. Chem. Soc., 2001, 123,
3630–3637; F. Westerlund, L. M. Wilhelmsson, B. Nord´en and P.
Lincoln, J. Phys. Chem. B, 2005, 109, 21140–21144 and references
therein.
8 P. Lincoln and B. Nord´en, PCT/SE98/01655, 1998; B. Onfelt, L.
Gostring, P. Lincoln, B. Nord´en and A. Onfelt, Mutagenesis, 2002,
17, 317–20.
9 A. C. G. Hotze, E. P. L. van der Geer, H. Kooijman, A. L. Spek, J. G.
Haasnoot and J. Reedijk, Eur. J. Inorg. Chem., 2005, 2648–2657.
10 M. J. Hannon, V. Moreno, M. J. Prieto, E. Molderheim, E. Sletten, I.
Meistermann, C. J. Isaac, K. J. Sanders and A. Rodger, Angew. Chem.,
Int. Ed., 2001, 40, 880–4; I. Meistermann, V. Moreno, M. J. Prieto, E.
Molderheim, E. Sletten, S. Khalid, P.M. Rodger, J. Peberdy, C. J. Isaac,
A. Rodger andM. J. Hannon, Proc. Natl. Acad. Sci. U. S. A., 2002, 99,
5069–74.
11 C. Uerpmann, J. Malina, M. Pascu, G. J. Clarkson, V. Moreno, A.
Rodger, A. Grandas and M. J. Hannon, Chem.–Eur. J., 2005, 11, 1750–
6; L. J. Childs, J. Malina, B. E. Rolfsnes, M. Pascu, M. J. Prieto, M. J.
Broome, P. M. Rodger, E. Sletten, V. Moreno, A. Rodger and M. J.
Hannon, Chem.–Eur. J., 2006, 12, 4919–4927.
12 A. Oleksi, A. G. Blanco, R. Boer, I. Us ´on, J. Aymami, A. Rodger,M. J.
Hannon and M. Coll, Angew. Chem., Int. Ed., 2006, 45, 1227–1231; J.
Malina, M. J. Hannon and V. Brabec, Chem.–Eur. J., 2007, 14, 3871–
3877; L. Cerasino, M. J. Hannon and E. Sletten, Inorg. Chem., 2007,
46, 6245–6251.
13 M. J. Hannon,C. L. Painting, J.Hamblin,A. Jackson andW.Errington,
Chem. Commun., 1997, 1807–1808; J. M. C. A. Kerckhoffs, J. C.
Peberdy, I. Meistermann, L. J. Childs, C. J. Isaac, C. R. Pearmund,
V. Reudegger, S. Khalid, N. W. Alcock, M. J. Hannon and A.
Rodger, Dalton Trans., 2007, 734–742; M. J. Hannon, I. Meistermann,
C. J. Isaac, C. Blomme, J. R. Aldrich-Wright and A. Rodger, Chem.
Commun., 2001, 1078–1079.
14 A. C. G. Hotze, B. M. Kariuki and M. J. Hannon, Angew. Chem., Int.
Ed., 2006, 45, 4839–4842; G. I. Pascu, A. C. G. Hotze, C. Sanchez
Cano, B. M. Kariuki and M. J. Hannon, Angew. Chem., Int. Ed.,
2007, 46, 4374–4378; M. J. Hannon, A. Rodger and N. H. Mann,
PCT/GB2004/004227, 2004.
15 A. C. G. Hotze, J. A. Faiz, N. Mourtzis, G. I. Pascu, P. R. A. Webber,
G. J. Clarkson, K. Yannakopoulou, Z. Pikramenou andM. J. Hannon,
Dalton Trans., 2006, 3025–3034.
16 P. Cai, M. X. Li, C. Y. Duan, F. Lu, D. Guo and Q. J. Meng,
New J. Chem., 2005, 29, 1011–1016.
17 S. Chakraborty, P. Munshi and G. K. Lahiri, Polyhedron, 1999, 18,
1437–1444.
18 H. Xua and A. Von Zelewsky, Inorg. Chem., 1995, 34, 1591.
19 M. A. Ismail, K. J. Sanders, G. C. Fennel, H. C. Latham, P. Wormell
and A. Rodger, Biopolymers, 1998, 46, 127–143.
20 A. Rodger, B. Nord´en, Circular dichroism and linear dichroism, Oxford
University Press, Oxford, 1997.
21 J. H. Eggers and E. W. Thulstrup, Eighth European congress on
molecular spectroscopy, Copenhagen, 1965.
22 B. P. Sullivan, D. J. Salmon and T. J. Meyer, Inorg. Chem., 1978, 17,
3334.
23 O.Morgan, S.Wang,S.-A. Bae,R. J.Morgan,A.D. Baker, T. C. Strekas
and R. Engel, J. Chem. Soc., Dalton Trans., 1997, 3773–3776.
24 J. E. Collins, J. J. S. Lamba, J. C. Love, J. E. McAlvin, C. Ng, B. P.
Peters, X. Wu and C. L. Fraser, Inorg. Chem., 1999, 38, 2020–2024.
25 B. Bosnich and F. P. Dwyer, Aust. J. Chem., 1966, 19, 2229–2233.
26 C. Hiort, P. Lincoln and B. Nord´en, J. Am. Chem. Soc., 1993, 115,
3448–3454.
27 S. Khalid, P. M. Rodger and A. Rodger, J. Liq. Chromatogr., 2005, 28,
2995–3003.
28 C. Hiort, B. Nord´en and A. Rodger, J. Am. Chem. Soc., 1990, 112,
1971–1982.