Synthesis and DNA-Binding Studies of a Dinuclear Gadolinium(iii)–Platinum(ii) Complex*
Jacob M. Fenton A B , Madleen Busse A B and Louis M. Rendina A C
+ Author Affiliations
- Author Affiliations
A School of Chemistry, The University of Sydney, Sydney, NSW 2006, Australia.
B These authors contributed equally to the project.
C Corresponding author. Email: lou.rendina@sydney.edu.au
Australian Journal of Chemistry 68(4) 576-580 https://doi.org/10.1071/CH14572
Submitted: 16 September 2014 Accepted: 9 October 2014 Published: 27 January 2015
Abstract
The synthesis and characterisation of a new dinuclear GdIII–PtII complex (1·PF6) containing a functionalised macrocyclic 1,4,7,10-tetraazacyclododecane-1,4,7-triacetic acid derivative linked to a PtII-terpy (terpy = 2,2′ : 6′,2″-terpyridine) unit by means of a short thiolato linker are reported. The complex was synthesised in six steps from cyclen by means of a modular synthetic strategy. A preliminary DNA-binding study with calf-thymus DNA (ct-DNA) was performed on 1·PF6 by means of linear dichroism (LD). The observed changes in the DNA LD signal in the presence of the metal complex are fully consistent with an intercalative binding mode. Furthermore, an induced negative LD signal in the ultraviolet absorption region of the complex provides strong evidence of a strong DNA-binding interaction. The in vitro cytotoxicity of 1·PF6 towards a human glioblastoma cell line (T98G) was also determined.
References
[1] P. Caravan, Chem. Soc. Rev. 2006, 35, 512.| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XkvFOitLo%3D&md5=3a03450d98ab4898ded481342102b24eCAS | 16729145PubMed |
[2] J. Reedijk, Curr. Opin. Chem. Biol. 1999, 3, 236.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXisVentL8%3D&md5=20a65929a4e5f475498c179987f1571aCAS | 10226048PubMed |
[3] Z. Zhang, S. A. Nair, T. J. McMurry, Curr. Med. Chem. 2005, 12, 751.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXivVCqtbo%3D&md5=00916995afb100c487246a2061673708CAS | 15853710PubMed |
[4] A. Forouzannia, G. M. Richards, D. Khuntia, M. P. Mehta, Expert Rev. Anticancer Ther. 2007, 7, 785.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXmtFOhtbk%3D&md5=7ac8eb347728d9abd955fc06432e5089CAS | 17555388PubMed |
[5] G. De Stasio, D. Rajesh, J. M. Ford, M. J. Daniels, R. J. Erhardt, B. H. Frazer, T. Tyliszczak, M. K. Gilles, R. L. Conhaim, S. P. Howard, J. F. Fowler, F. Esteve, M. P. Mehta, Clin. Cancer Res. 2006, 12, 206.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28Xht1Gluw%3D%3D&md5=67f749997dde5dc071ecf06c5410a6ddCAS | 16397044PubMed |
[6] M. P. Mehta, W. R. Shapiro, S. C. Phan, R. Gervais, C. Carrie, P. Chabot, R. A. Patchell, M. J. Glantz, L. Recht, C. Langer, R. K. Sur, W. H. Roa, M. A. Mahe, A. Fortin, C. Nieder, C. A. Meyers, J. A. Smith, R. A. Miller, M. F. Renschler, Int. J. Radiat. Oncol., Biol., Phys. 2009, 73, 1069.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXisVOgsb8%3D&md5=16900bb18b861dacb38236f3c9225143CAS |
[7] R. A. Miller, K. W. Woodburn, Q. Fan, I. Lee, D. Miles, G. Duran, B. Sikic, D. Magda, Clin. Cancer Res. 2001, 7, 3215.
| 1:CAS:528:DC%2BD3MXnvF2rs74%3D&md5=a25073fffe2bfe5f60d9ae583739e1f5CAS | 11595717PubMed |
[8] T. D. Mody, J. L. Sessler, J. Porphyrins Phthalocyanines 2001, 5, 134.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXht1Sgtb4%3D&md5=31bcd0eec4447b2511ee88b078ddc78cCAS |
[9] W. N. William, R. G. Zinner, D. D. Karp, Y. W. Oh, B. S. Glisson, S.-C. Phan, D. J. Stewart, J. Thorac. Oncol. 2007, 2, 745.
| Crossref | GoogleScholarGoogle Scholar | 17762342PubMed |
[10] E. L. Crossley, J. B. Aitken, S. Vogt, H. H. Harris, L. M. Rendina, Angew. Chem., Int. Ed. 2010, 49, 1231.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhslWluro%3D&md5=29bebb5b7ee22c2e34c9a83447e01bdbCAS |
[11] G. De Stasio, P. Casalbore, R. Pallini, B. Gilbert, F. Sanita, M. T. Ciotti, G. Rosi, A. Festinesi, L. M. Larocca, A. Rinelli, D. Perret, D. W. Mogk, P. Perfetti, M. P. Mehta, D. Mercanti, Cancer Res. 2001, 61, 4272.
| 1:CAS:528:DC%2BD3MXktVWqtb8%3D&md5=02c7640daef91eca4a2af4dbe922c5c8CAS | 11358855PubMed |
[12] E. L. Crossley, H. Y. V. Ching, J. A. Ioppolo, L. M. Rendina, in Bioinorganic Medicinal Chemistry (Ed. E. Alessio) 2011, pp. 285–305 (Wiley-VCH: Weinheim, Germany).
[13] F. Issa, J. A. Ioppolo, L. M. Rendina, in Comprehensive Inorganic Chemistry II (Eds J. Reedijk, K. Poeppelmeier) 2013, Vol. 3, pp. 877–900 (Elsevier: Oxford, UK).
[14] C. Salt, A. J. Lennox, M. Takagaki, J. A. Maguire, N. S. Hosmane, Russ. Chem. Bull. 2004, 53, 1871.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXivFyktLw%3D&md5=410bfb81abc33f2891f081f7876639bcCAS |
[15] T. Goorley, H. Nikjoo, Radiat. Res. 2000, 154, 556.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXosVKhu78%3D&md5=94a51829fea88acd9e4777436b9786b1CAS | 11025652PubMed |
[16] D. E. Morrison, J. B. Aitkin, M. D. de Jonge, J. A. Ioppolo, H. H. Harris, L. M. Rendina, Chem. Commun. 2014, 50, 2252.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXitVensrw%3D&md5=c421f333d7243e576f0941d32a44333bCAS |
[17] D. A. Moore, L. Patterson, Org. Synth. 2008, 85, 10.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhsFWrsLs%3D&md5=07281d0d57ff62b3cdb5e612c6cb0e02CAS |
[18] E. M. Gale, A. K. Patra, T. C. Harrop, Inorg. Chem. 2009, 48, 5620.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXmvV2ktr8%3D&md5=e66e837779aa0b376d7ab545d1eec5b9CAS | 20507097PubMed |
[19] J. P. O’Neil, S. R. Wilson, J. A. Katzenellenbogen, Inorg. Chem. 1994, 33, 319.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXht1ensLg%3D&md5=4fcd909b9be4c0cc56b6d34519258b01CAS |
[20] C. Wängler, B. Wängler, M. Eisenhut, U. Haberkorn, W. Mier, Bioorg. Med. Chem. 2008, 16, 2606.
| Crossref | GoogleScholarGoogle Scholar | 18065226PubMed |
[21] N. Raghunand, G. P. Guntle, V. Gokhale, G. S. Nichol, E. A. Mash, B. Jagadish, J. Med. Chem. 2010, 53, 6747.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhtVCns7bF&md5=32edffc7968096f94197f512d1ecc9d7CAS | 20722424PubMed |
[22] D. A. Pearson, M. Blanchette, M. L. Baker, C. A. Guindon, Tetrahedron Lett. 1989, 30, 2739.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3cXhsFyrt74%3D&md5=319df5392964cb22960a5068ae92b21aCAS |
[23] S. J. Lippard, Acc. Chem. Res. 1978, 11, 211.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE1cXhs1ent7Y%3D&md5=73175aef045de45713b2bb6f37a29c14CAS |
[24] J. A. Todd, L. M. Rendina, Inorg. Chem. 2002, 41, 3331.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XktVaiu74%3D&md5=0f644807d1b0ad45653314cd8aea5d33CAS | 12079447PubMed |
[25] A. Rodger, B. Norden, Circular Dichroism & Linear Dichroism 1997 (Oxford University Press: Oxford).
[26] M. Eriksson, B. Nordén, in Methods in Enzymology (Eds J. B. Chaires, M. J. Waring) 2001, Vol. 340, pp. 68–98 (Academic Press: San Diego, CA).
[27] J. Rajendra, M. Baxendale, L. G. Dit Rap, A. Rodger, J. Am. Chem. Soc. 2004, 126, 11182.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXmslyqsLY%3D&md5=7f2bc0a2469e0360bf2dc52cad970c04CAS | 15355099PubMed |
[28] J. Rajendra, A. Rodger, Chem. –Eur. J. 2005, 11, 4841.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXoslGlsbg%3D&md5=51c44f67a389f3e62090698979013a5cCAS | 15954149PubMed |
[29] J. A. Bailey, M. G. Hill, R. E. Marsh, V. M. Miskowski, W. P. Schaefer, H. B. Gray, Inorg. Chem. 1995, 34, 4591.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXnsVKktLY%3D&md5=b18cb555e352b9dba50149ddf3e7dd06CAS |
[30] W. L. F. Armarego, C. Chai, Purification of Laboratory Chemicals, 5th Edition, 2003.
[31] G. Lowe,, T. Vilaivan, J. Chem. Res. 1996, 386.
| 1:CAS:528:DyaK28XltFCjtLw%3D&md5=2ad916331f3934ba15ff5183fc9e4d83CAS |
[32] M. D. Hall, S. Amjadi, M. Zhang, P. J. Beale, T. W. Hambley, J. Inorg. Biochem. 2004, 98, 1614.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXotF2mtbs%3D&md5=e2bc83159007143745535c1ba16d1a4dCAS | 15458824PubMed |
[33] T. Mosmann, J. Immunol. Methods 1983, 65, 55.
| Crossref | GoogleScholarGoogle Scholar | 1:STN:280:DyaL2c%2FovFSmtw%3D%3D&md5=96528a896d1bab0037f3d0792f9efa35CAS | 6606682PubMed |
