Self-assembly of Cationic, Hetero- or Homo-nuclear Ru(II) Macrocyclic Rectangles and Their Photophysical, Electrochemical and Biological Studies

Overview

Journal Organometallics

Publisher American Chemical Society

Date 2011 Dec 20

PMID 22180698

Citations 12

Authors

Vaishali Vajpayee

Young Ho Song

Yoon Jung Yang

Se Chan Kang

Timothy R Cook

Dong Wook Kim

Myoung Soo Lah

In Su Kim

Ming Wang

Peter J Stang

Ki-Whan Chi

Affiliations

Soon will be listed here.

Abstract

A series of supramolecular rectangles, including two mixed-metal Ru/Pt complexes, have been formed by the coordination-driven self-assembly of a range of arene-Ru "molecular clip" acceptors (1a-1d) with rigid dipyridyl-based ligands (2a-2d) over the course of 10 hours in solution. The isolated products were characterized by multinuclear NMR ((1)H and (13)C or (31)P), HR-ESI-MS and an X-ray diffraction study to support the ascribed two-component rectangular structures. The rectangles were further characterized by UV-Vis and fluorescence studies. The redox behaviors of rectangles 3ca and 3da were also determined using cyclic voltammetry. Additionally, the antitumor activities of the suite of rectangles were determined against various human cancer cell lines and significant activity was shown by complexes 3ca, 3da, 3cb, 3cc and 3cd, with IC(50) values as low as 2.65 μM.

Citing Articles

Construction of emissive ruthenium(II) metallacycle over 1000 nm wavelength for in vivo biomedical applications.

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Metal-Coordinated Supramolecular Self-Assemblies for Cancer Theranostics.

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Biomedical Applications of Metal Organic Polygons and Polyhedra (MOPs).

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Investigation of the Anticancer Activity of Coordination-Driven Self-AssembledTwo-Dimensional Ruthenium Metalla-Rectangle.

Vardhan H, Nafady A, Al-Enizi A, Khandker K, El-Sagher H, Verma G Molecules. 2019; 24(12).

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References

Bar A, Chakrabarty R, Mostafa G, Mukherjee P . Self-assembly of a nanoscopic Pt12Fe12 heterometallic open molecular box containing six porphyrin walls. Angew Chem Int Ed Engl. 2008; 47(44):8455-9. DOI: 10.1002/anie.200803543. View

Lehn J . Supramolecular chemistry: receptors, catalysts, and carriers. Science. 1985; 227(4689):849-56. DOI: 10.1126/science.227.4689.849. View

Zhang W, Han Y, Lin Y, Jin G . Synthesis and characterization of molecular rectangles of half-sandwich p-cymene ruthenium complexes bearing oxamidato ligands. Dalton Trans. 2009; (39):8426-31. DOI: 10.1039/b909357e. View

Yu S, Huang H, Li S, Jiao Q, Li Y, Wu B . Solution self-assembly, spontaneous deprotonation, and crystal structures of bipyrazolate-bridged metallomacrocycles with dimetal centers. Inorg Chem. 2005; 44(25):9471-88. DOI: 10.1021/ic0509332. View

Vajpayee V, Song Y, Lee M, Kim H, Wang M, Stang P . Self-assembled arene-ruthenium-based rectangles for the selective sensing of multi-carboxylate anions. Chemistry. 2011; 17(28):7837-44. PMC: 3358929. DOI: 10.1002/chem.201100242. View

Yan Y, Melchart M, Habtemariam A, Sadler P . Organometallic chemistry, biology and medicine: ruthenium arene anticancer complexes. Chem Commun (Camb). 2005; (38):4764-76. DOI: 10.1039/b508531b. View

Dyson P, Sava G . Metal-based antitumour drugs in the post genomic era. Dalton Trans. 2006; (16):1929-33. DOI: 10.1039/b601840h. View

Kawamichi T, Kodama T, Kawano M, Fujita M . Single-crystalline molecular flasks: chemical transformation with bulky reagents in the pores of porous coordination networks. Angew Chem Int Ed Engl. 2008; 47(42):8030-2. DOI: 10.1002/anie.200802545. View

Barry N, Zava O, Furrer J, Dyson P, Therrien B . Anticancer activity of opened arene ruthenium metalla-assemblies. Dalton Trans. 2010; 39(22):5272-7. DOI: 10.1039/c001521k. View

10.

Han Y, Lin Y, Jia W, Wang G, Jin G . Template-controlled topochemical photodimerization based on "organometallic macrocycles" through single-crystal to single-crystal transformation. Chem Commun (Camb). 2008; (15):1807-9. DOI: 10.1039/b717554j. View

11.

Leininger S, Olenyuk B, Stang P . Self-assembly of discrete cyclic nanostructures mediated by transition metals. Chem Rev. 2001; 100(3):853-908. DOI: 10.1021/cr9601324. View

12.

Vajpayee V, Song Y, Yang Y, Kang S, Kim H, Kim I . Coordination Driven Self-Assembly and Anticancer Activity of Molecular Rectangles Containing Octahedral Ruthenium Metal Centers. Organometallics. 2011; 30(12):3242-3245. PMC: 3138154. DOI: 10.1021/om200294x. View

13.

Therrien B, Suss-Fink G, Govindaswamy P, Renfrew A, Dyson P . The "complex-in-a-complex" cations [(acac)2M subset Ru6(p-iPrC6H4Me)6(tpt)2(dhbq)3]6+: A trojan horse for cancer cells. Angew Chem Int Ed Engl. 2008; 47(20):3773-6. DOI: 10.1002/anie.200800186. View

14.

Jude H, Disteldorf H, Fischer S, Wedge T, Hawkridge A, Arif A . Coordination-driven self-assemblies with a carborane backbone. J Am Chem Soc. 2005; 127(34):12131-9. DOI: 10.1021/ja053050i. View

15.

Bondy C, Gale P, Loeb S . Metal-organic anion receptors: arranging urea hydrogen-bond donors to encapsulate sulfate ions. J Am Chem Soc. 2004; 126(16):5030-1. DOI: 10.1021/ja039712q. View

16.

Badjic J, Nelson A, Cantrill S, Turnbull W, Stoddart J . Multivalency and cooperativity in supramolecular chemistry. Acc Chem Res. 2005; 38(9):723-32. DOI: 10.1021/ar040223k. View

17.

Magennis S, Habtemariam A, Novakova O, Henry J, Meier S, Parsons S . Dual triggering of DNA binding and fluorescence via photoactivation of a dinuclear ruthenium(II) arene complex. Inorg Chem. 2007; 46(12):5059-68. DOI: 10.1021/ic062111q. View

18.

Peinador C, Pia E, Blanco V, Garcia M, Quintela J . Complexation of pyrene in aqueous solution with a self-assembled palladium metallocycle. Org Lett. 2010; 12(7):1380-3. DOI: 10.1021/ol1004577. View

19.

Schweiger M, Seidel S, Arif A, Stang P . Solution and solid state studies of a triangle-square equilibrium: anion-induced selective crystallization in supramolecular self-assembly. Inorg Chem. 2002; 41(9):2556-9. DOI: 10.1021/ic0112692. View

20.

Das N, Ghosh A, Singh O, Stang P . Facile synthesis of enantiopure chiral molecular rectangles exhibiting induced circular dichroism. Org Lett. 2006; 8(8):1701-4. DOI: 10.1021/ol060365+. View