Synthesis, X-ray structures, and cytotoxicity of rhenium(I) carbonyl 2-(dimethylamino)ethoxide complexes

Wang, Wenwu; Yan, Yaw Kai; Hor, T. S. Andy; Vittal, Jagadese J.; Wheaton, Jessica R.; Hall, Iris H.

doi:10.1016/s0277-5387(02)01045-8

Cited by 47 publications

(42 citation statements)

References 23 publications

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“…To the best of our knowledge, there has been limited investigation of the antiproliferative properties of Re I conjugates, and only limited reports of IC 50 values for Re I compounds 19. 20 We have conducted antiproliferative studies to determine the impact of the presence Re I in terms of cytotoxicity.…”

Section: Resultsmentioning

confidence: 99%

Preparation and characterization of nanofiltration composite membranes using polyacrylonitrile (PAN). II. Preparation and characterization of polyamide composite membranes

Oh¹,

Jegal²,

Lee³

2001

J of Applied Polymer Sci

114

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Polyamide (PA) composite membranes in which PA active layers were interconnected with support layers via the formation of ionic bonds were prepared by the interfacial polymerization of piperazine (PIP) with trimesoyl chloride (TMC) on the surfaces of microporous polyacrylonitrile (PAN) supports containing carboxylic acid groups. Formation of the ionic bonds through an acid-base reaction between ONH group of PIP and OCOOH of the support was studied using FTIR-ATR spectroscopy. Variation of the surface morphologies of the composite membranes that was induced by the presence of the ionic bonds was observed with a FESEM and an AFM. Permeation tests with various feed solutions such as PEG 600, Na 2 SO 4 , MgSO 4 , MgCl 2 , and NaCl solutions were carried out to see how the characteristics of the PAN supports affected on the flux and rejection of the corresponding PA composite membranes. Chemical stabilities of the composite membranes with the ionic bonds were studied and compared with that of a conventional PA composite membrane, using alcohol solutions.

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Section: Resultsmentioning

confidence: 99%

Preparation and characterization of nanofiltration composite membranes using polyacrylonitrile (PAN). II. Preparation and characterization of polyamide composite membranes

Oh¹,

Jegal²,

Lee³

2001

J of Applied Polymer Sci

114

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“…Ligand 24 was prepared by a procedure similar to that described for compound 15, except that compound 21 was used instead of compound 13. The crude product was further purified by basic alumina chromatography using a gradient of CHCl 3 2-(Bis((pyridin-2-yl)methyl)amino)acetic acid (27). Compound 27 was prepared according to published procedures with minor modifications.…”

Section: -((2r4s5r)-5-((8-aminooctyloxy)methyl)-4-hydroxytetrahydrmentioning

confidence: 99%

“…[27,28] We recently reported a rhenium(I)-folic acid conjugate that exhibited greater toxicity than cisplatin in a screen against a doxorubicin-and cisplatin-resistant human ovarian cancer cell line (A2780/AD) overexpressing the folate receptor. [29] Encouraged by the results of our previous investigation, we thought it would be intriguing to conjugate the [Re(CO) 3 ]…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Cytotoxicity, and Insight into the Mode of Action of Re(CO)₃ Thymidine Complexes

Bartholomä¹,

Vortherms²,

Hillier³

et al. 2010

ChemMedChem

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Nucleoside analogues are extensively used in the treatment of cancer and viral diseases. The antiproliferative properties of organorhenium(I) complexes, however, have been scarcely explored to date. Herein we present the syntheses, characterization, and in vitro evaluation of Re(I)(CO)(3) core complexes of thymidine and uridine. For the binding of the Re(I)(CO)(3) core, a tridentate dipicolylamine metal chelate was introduced at positions C5', C2', N3, and C5 with spacers of various lengths. The corresponding organometallic thymidine complexes were fully characterized by IR and NMR spectroscopy and mass spectrometry. Their cytotoxicity was assessed against the A549 lung carcinoma cell line. Toxicity is dependent on the site and mode of conjugation as well as on the nature and the length of the tether. Moderate toxicity was observed for conjugates carrying the rhenium moiety at position C5' or N3 (IC(50)=124-160 microM). No toxicity was observed for complexes modified at C2' or C5. Complex 53, with a dodecylene spacer at C5', exhibits remarkable toxicity and is more potent than cisplatin, with an IC(50) value of 6.0 microM. To the best of our knowledge, this is the first report of the antiproliferative properties of [M(CO)(3)](+1)-nucleoside conjugates. In competitive inhibition experiments with A549 cell lysates and purified recombinant human thymidine kinase 1 (hTK-1), enzyme inhibition was observed for complexes modified at either N3 or C5', but our results suggest that the toxicity cannot be attributed solely to interaction with hTK-1.

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“…[19,20] We have conducted antiproliferative studies to determine the impact of the presence Re I in terms of cytotoxicity. Compounds g-1, 2, 3, and g-4 were tested against the FR-overexpressing A2780/AD and FR-free CHO cell lines for suitable comparison over a time period of 6 and 24 h (see Table 1).…”

Section: In Vitro Cell Cytotoxicitymentioning

confidence: 99%

Targeting the Folate Receptor (FR): Imaging and Cytotoxicity of Re^I Conjugates in FR‐Overexpressing Cancer Cells

et al. 2008

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The synthesis, characterization, in vitro imaging, and cytotoxic properties of a new folate conjugate of rhenium(I) are reported. The conjugate [FA-PEG-BQAV-Re(CO)3]+ (gamma-4) was screened against an adriamycin- and cisplatin-resistant human ovarian cancer cell line (A2780/AD) that overexpresses the folate receptor (FR). Compound gamma-4 was internalized by a folate-receptor-mediated endocytotic pathway, which results in internal accumulation of gamma-4. This was contrasted with a FR-negative Chinese hamster ovary cell line in which no internalization of gamma-4 was observed. gamma-4 was found to be cytotoxic with IC(50) values of 189 and 78 microM at 6 and 24 h, respectively, toward the FR-positive cell line. This is in contrast to the IC(50) value of 502 microM at 6 h and 84 microM at 24 h for cisplatin in the same cell line, with a significantly greater toxicity at the earlier time point. The cytotoxicity of gamma-4 as explained by interactions that occur between the rhenium(I) complex moiety and DNA is described.

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Synthesis, X-ray structures, and cytotoxicity of rhenium(I) carbonyl 2-(dimethylamino)ethoxide complexes

Cited by 47 publications

References 23 publications

Preparation and characterization of nanofiltration composite membranes using polyacrylonitrile (PAN). II. Preparation and characterization of polyamide composite membranes

Preparation and characterization of nanofiltration composite membranes using polyacrylonitrile (PAN). II. Preparation and characterization of polyamide composite membranes

Synthesis, Cytotoxicity, and Insight into the Mode of Action of Re(CO)₃ Thymidine Complexes

Targeting the Folate Receptor (FR): Imaging and Cytotoxicity of Re^I Conjugates in FR‐Overexpressing Cancer Cells

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Synthesis, X-ray structures, and cytotoxicity of rhenium(I) carbonyl 2-(dimethylamino)ethoxide complexes

Cited by 47 publications

References 23 publications

Preparation and characterization of nanofiltration composite membranes using polyacrylonitrile (PAN). II. Preparation and characterization of polyamide composite membranes

Preparation and characterization of nanofiltration composite membranes using polyacrylonitrile (PAN). II. Preparation and characterization of polyamide composite membranes

Synthesis, Cytotoxicity, and Insight into the Mode of Action of Re(CO)3 Thymidine Complexes

Targeting the Folate Receptor (FR): Imaging and Cytotoxicity of ReI Conjugates in FR‐Overexpressing Cancer Cells

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Synthesis, Cytotoxicity, and Insight into the Mode of Action of Re(CO)₃ Thymidine Complexes

Targeting the Folate Receptor (FR): Imaging and Cytotoxicity of Re^I Conjugates in FR‐Overexpressing Cancer Cells