Synthesis and Characterization of a Ruthenium(II)-Based Redox Conjugate for Reagentless Biosensing (original) (raw)
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Journal of Organometallic Chemistry, 2009
Isomers of dichlorobis(2-phenylazopyridine)ruthenium(II) [Ru(azpy) 2 Cl 2 ], especially the so-called a isomer, display remarkably high cytotoxicities against human tumor cell lines. Unfortunately, the parent [Ru(azpy) 2 Cl 2 ] compounds are poorly water-soluble. In this paper the synthesis and characterization of the new water-soluble ligand 2-phenylazopyridine-5-sulfonic acid (Hsazpy) is described. Use of this ligand in reaction with RuCl 3 gave two isomers, which were isolated as aand b-[NEt 4 ] 2 [Ru(sazpy) 2 Cl 2 ]. The compounds have been fully characterized by (2D) NMR spectroscopy. The molecular structure of the a isomer of [NEt 4 ] 2 [Ru(sazpy) 2 Cl 2 ]Á2H 2 O has been determined by single-crystal structure analysis. The packing in the crystal structure of a-[NEt 4 ] 2 [Ru(sazpy) 2 Cl 2 ]Á2H 2 O shows an interesting hydrogen-bonding pattern in which two water molecules are involved. One water molecule bridges between a Cl ligand and a SO 3 À group within one ruthenium moiety, the other water molecule forms a bridge between two SO 3 À groups from two different ruthenium centers, resulting in a chain-like structure. Preliminary evaluation of the cytotoxicity by means of the IC 50 value in A2780 cell line classifies a-[NEt 4 ] 2 [Ru(sazpy) 2 Cl 2 ] as non-toxic, but this does not rule out other anticancer activities.
Journal of Biological Inorganic Chemistry, 2004
The dichlorobis(2-phenylazopyridine)ruthenium(II) complexes, [Ru(azpy) 2 Cl 2 ], are under renewed investigation due to their potential anticancer activity. The three most common isomers a-, b-and c-[RuL 2 Cl 2 ] with L=o-tolylazopyridine (tazpy) and 4-methyl-2phenylazopyridine (mazpy) (a indicating the coordinating Cl, N(pyridine) and Nazo atoms in mutual cis, trans, cis positions, b indicating the coordinating Cl, N(pyridine) and Nazo atoms in mutual cis, cis, cis positions, and c indicating the coordinating Cl, N(pyridine) and Nazo atoms in mutual trans, cis, cis positions) are synthesized and characterized by NMR spectroscopy. The molecular structures of c-[Ru(tazpy) 2 Cl 2 ] and a-[Ru(mazpy) 2 Cl 2 ] are determined by X-ray diffraction analysis. The IC 50 values of the geometrically isomeric [Ru(tazpy) 2 Cl 2 ] and [Ru(mazpy) 2 Cl 2 ] complexes com-pared with those of the parent [Ru(azpy) 2 Cl 2 ] complexes are determined in a series of human tumour cell lines (MCF-7, EVSA-T, WIDR, IGROV, M19, A498 and H266). These data unambiguously show for all complexes the following trend: the a isomer shows a very high cytotoxicity, whereas the b isomer is a factor 10 less cytotoxic. The c isomers of [Ru(tazpy) 2 Cl 2 ] and [Ru(mazpy) 2 Cl 2 ] display a very high cytotoxicity comparable to that of the c isomer of the parent compound [Ru(azpy) 2 Cl 2 ] and to that of the a isomer. These biological data are of the utmost importance for a better understanding of the structure-activity relationships for the isomeric [RuL 2 Cl 2 ] complexes.
New Cytotoxic and Water-Soluble Bis(2-phenylazopyridine)ruthenium(II) Complexes
Journal of Medicinal Chemistry, 2003
New water-soluble bis(2-phenylazopyridine)ruthenium(II) complexes, all derivatives of the highly cytotoxic R-[Ru(azpy) 2 Cl 2 ] (R denoting the coordinating pairs Cl, N(py), and N(azo) as cis, trans, cis, respectively) have been developed. The compounds 1,1-cyclobutanedicarboxylatobis(2-phenylazopyridine)ruthenium(II), R-[Ru(azpy) 2 (cbdca-O,O′)] (1), oxalatobis(2-phenylazopyridine)ruthenium(II), R-[Ru(azpy) 2 (ox)] (2), and malonatobis(2-phenylazopyridine)ruthenium(II), R-[Ru(azpy) 2 (mal)] (3), have been synthesized and fully characterized. X-ray analyses of 1 and 2 are reported, and compound 1 is the first example in which the cbdca ligand is coordinated to a ruthenium center. The cytotoxicity of this series of water-soluble bis(2phenylazopyridine) complexes has been determined in A2780 human ovarian carcinoma and A2780cisR, the corresponding cisplatin-resistant cell line. For comparison reasons, the cytotoxicity of the complexes R-[Ru(azpy) 2 Cl 2 ], R-[Ru(azpy) 2 (NO 3) 2 ],-[Ru(azpy) 2 Cl 2 ] (indicating the coordinating pairs Cl, N(py), and N(azo) as cis, cis, cis, respectively), and-[Ru(azpy) 2-(NO 3) 2 ] have been determined in this cell line. All the bis(2-phenylazopyridine)ruthenium(II) compounds display a promising cytotoxicity in the A2780 cell line (IC 50) 0.9-10 µM), with an activity comparable to that of cisplatin and even higher than the activity of carboplatin. Interestingly, the IC 50 values of this series of ruthenium compounds (except the isomeric compounds) are similar in the cisplatin-resistant A2780cisR cell line compared to the normal cell line A2780, suggesting that the activity of these compounds might not be influenced by the multifactorial resistance mechanism that affect platinum anticancer agents.
SYNTHESIS, CHARACTERIZATION AND CYTOTOXIC ACTIVITY OF SOME Ru (II) COMPLEXES
Turkish Journal of Pharmaceutical Sciences, 2011
The synthesis and characterization of ruthenium complexes (Ru1–Ru8) of the type [Ru(S)2(K)], (where S = 1,10-phenanthroline/ 2,2’-bipyridine and K = iinh, inhba, na, mitsz) are described. These ligands form bidentate octahedral ruthenium complexes. The title compounds were subjected to in vitro cytostatic activity measurements against the human cancer T-lymphocyte cell lines Molt 4/C8 and CEM, and the murine tumor leukemia cell line L1210. In vitro evaluation of these ruthenium compounds revealed cytotoxic activity from 0.84 to 119 µg/mL against CEM, 3.7 to 158 µg/mL against Molt and 15 to ≥200 µg/mL against L1210 cell proliferation, depending the nature of the compound.
The synthesis and spectroscopic characterization of ruthenium complexes (R-1 to R-8) of the type [Ru(A) 2 (B)], (where A = 1,10-phenanthroline/2,2 0 -bipyridine and B = 3,4,5-tri-OCH 3 -DPC, 4-CH 3 -DPC, 4-N-(CH 3 ) 2 -DPC, 4-NO 2 -DPC are described. These ligands form bidentate octahedral ruthenium complexes. The title complexes were subjected to in vitro cytotoxic activity measurements against the human cancer T-lymphocyte cell lines MTT assay. In vitro evaluation of these ruthenium complexes revealed cytotoxic activity from 0.24 to 1.4 mg/mL against CEM, 0.44 to 1.9 mg/mL against Molt4/C8, 0.28 to 1.5 mg/mL against L1210, 0.24 to 0.98 mg/mL against HL60, and 0.25 to 1.2 mg/mL against BEL7402, depending the nature of the compound.
Synthesis, antineoplastic and cytotoxic activities of some mononuclear Ru (II) complexes
Journal of Enzyme Inhibition and Medicinal Chemistry, 2010
A series of mononuclear Ru(II) complexes of the type [Ru(S)(2)(K)](2+), where S = 1,10-phenanthroline/2,2'-bipyridine and K = 4-OH-btsz, 4-CH(3)-btsz, 3,4-di-OCH(3)-btsz, 4-OH-binh, 4-CH(3)-binh, 3,4-di-OCH(3)-binh, were prepared and characterized by elemental analysis, FTIR, (1)H-NMR, and mass spectroscopy. The complexes displayed metal-ligand charge transfer (MLCT) transitions in the visible region. These ligands formed bidentate octahedral ruthenium complexes. The title complexes were evaluated for their in vivo anticancer activity against a transplantable murine tumor cell line, Ehrlisch's ascites carcinoma (EAC), and in vitro cytotoxic activity against human cancer cell lines Molt 4/C(8) and CEM and murine tumor cell line L1210. The ruthenium complexes showed promising biological activity especially in decreasing tumor volume and viable ascites cell counts. Treatment with these complexes prolonged the life span of mice bearing EAC tumors by 10-52%. In vitro evaluation of these ruthenium complexes revealed cytotoxic activity from 0.21 to 24 muM against Molt 4/C(8), 0.16 to 19 microM against CEM, and 0.75 to 32 microM against L1210.
Synthesis and cytotoxic activity of some mononuclear Ru(II) Complexes
A series of mononuclear Ru(II) complexes of the type [Ru(T)2(S)]2+, where T=2,2'-bipyridine/1,10-phenanthroline and S= 4-N-(CH3)2-btsz, 4-OH-btsz, 4-N-(CH3)2-binh have been prepared and characterized by UV-Vis, IR, 1H-NMR, FAB-Mass spectroscopy, and elemental analysis. The title complexes were subjected to in vitro cytotoxic activity against human cancer cell line Molt 4/C8, CEM and murine tumor cell line L 1210. Invitro evaluation of these ruthenium complexes revealed cytotoxic activity from 1.30 to 50μM against Molt 4/C8, 0.30 to 24 μM aginst CEM, 0.87 to 41 μM against L1210 cell proliferation, depending on the nature of the compound
Medicinal Chemistry Research, 2016
The synthesis and characterization of ruthenium complexes (Ru-1–Ru-6) of the type [Ru(R)2(K)]2+ (where R = 1,10-phenanthroline/2,2′-bipyridyl and K = acetyl coumarin-inh, pyrazole-tch, acetyl coumarin-tsz, are described. These ligands form bidentate octahedral ruthenium complexes. The in vitro cytotoxic activities of the complexes measurement against the human cancer Tlymphocyte cell lines. In vitro evaluation of these title complexes revealed cytotoxicity from 0.34 to 1.4 µg/mL against CEM, 0.28 to 1.8 µg/mL against L1210, 0.44 to 2.5 µg/mL against Molt4/C8, 0.98 to 1.6 µg/mL against HL60, and 0.66 to 1.4 µg/mL against BEL7402. Ruthenium complexes Ru-5 & Ru-6 showed that quite significant anticancer activities over standard drugs.