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DNA binding by Ru(II)–bis(bipyridine)–pteridinyl complexes

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Abstract

The interactions of five bis(bipyridyl) Ru(II) complexes of pteridinyl-phenanthroline ligands with calf thymus DNA have been studied. The pteridinyl extensions were selected to provide hydrogen-bonding patterns complementary to the purine and pyrimidine bases of DNA and RNA. The study includes three new complexes [Ru(bpy)2(L-pterin)]2+, [Ru(bpy)2(L-amino)]2+, and [Ru(bpy)2(L-diamino)]2+ (bpy is 2,2′-bipyridine and L-pterin, L-amino, and L-diamino are phenanthroline fused to pterin, 4-aminopteridine, and 2,4-diaminopteridine), two previously reported complexes [Ru(bpy)2(L-allox)]2+ and [Ru(bpy)2(L-Me2allox)]2+ (L-allox and L-Me2allox are phenanthroline fused to alloxazine and 1,3-dimethyalloxazine), the well-known DNA intercalator [Ru(bpy)2(dppz)]2+ (dppz is dipyridophenazine), and the negative control [Ru(bpy)3]2+. Reported are the syntheses of the three new Ru–pteridinyl complexes and the results of calf thymus DNA binding experiments as probed by absorption and fluorescence spectroscopy, viscometry, and thermal denaturation titrations. All Ru–pteridine complexes bind to DNA via an intercalative mode of comparable strength. Two of these four complexes—[Ru(bpy)2(L-pterin)]2+ and [Ru(bpy)2(L-allox)]2+—exhibit biphasic DNA melting curves interpreted as reflecting exceptionally stable surface binding. Three new complexes—[Ru(bpy)2(L-diamino)]2+, [Ru(bpy)2(L-amino)]2 and [Ru(bpy)2(L-pterin)]2+—behave as DNA molecular “light switches.”

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Notes

  1. Software programs used for X-ray data processing, structure solution and ORTEP drawing are CrystalClear, Rigaku Corporation (1999); CrystalStructure, Crystal Structure Analysis Package, Rigaku/MSC (2002); REQAB4, R.A. Jacobsen (1994), private communication; SIR97 [28]. SHELXL-97: Program for the Refinement of Crystal Structures, G.M. Sheldrick (1997), University of Göttingen, Germany; and ORTEP-II: A Fortran Thermal Ellipsoid Plot Program for Crystal Structure Illustrations, C.K. Johnson (1976) ORNL-5138. Refinement produced residuals evaluated as R 1 = ∑ ||F o| − |F c||/∑ |F o|, wR 2 = {∑ w(F 2o  – F 2c )2/∑ w(F 2o )2}1/2, and goodness of fit equal to [∑ w(F 2o  – F 2c )2/(n − p)]1/2, where n is the number of reflections and p is the number of parameters refined.

Abbreviations

bpy:

2,2′-Bipyridine

CT:

Calf thymus

DMSO-d 6 :

Dimethyl sulfoxide-d 6

dppz:

Dipyridophenazine

ESI-MS:

Electrospray ionization mass spectrometry

FT:

Fourier transform

L-allox:

2,4-Diketopteridino[6,7-f]phenanthroline

L-amino:

4-Aminopteridino[6,7-f]phenanthroline

L-diamino:

2,4-Diaminopteridino[6,7-f]phenanthroline

L-Me2allox:

1,3-Dimethyl-2,4-diketopteridino[6,7-f]phenanthroline

L-pteridine:

Pteridinyl-phenanthroline

L-pterin:

2-Diamino-4(3H)-oxopteridino[6,7-f]phenanthroline

Tris:

Tris(hydroxymethyl)aminomethane

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Acknowledgements

We wish to thank Pat Carroll and the Facility for X-ray Crystallography in the Chemistry Department of the University of Pennsylvania and Alanna Albano and Lindsay Alaishuski for their contributions to early development of this project.

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Authors and Affiliations

  1. Department of Chemistry, Bryn Mawr College, Bryn Mawr, PA, 19010, USA

    Shannon R. Dalton, Belinda Leung, Sanda Win, Courtney Megatulski & Sharon J. Nieter Burgmayer

  2. Department of Chemistry, St. Lawrence University, Canton, NY, 13617, USA

    Samantha Glazier

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  1. Shannon R. Dalton
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Correspondence to Sharon J. Nieter Burgmayer.

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Dalton, S.R., Glazier, S., Leung, B. et al. DNA binding by Ru(II)–bis(bipyridine)–pteridinyl complexes. J Biol Inorg Chem 13, 1133–1148 (2008). https://doi.org/10.1007/s00775-008-0399-y

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