Synthesis, Characterization, and Assessment of Cytotoxic Properties of a Series of Titanocene Dichloride Derivatives

Causey, Patrick; Baird, Michael C.; Cole, Susan P.C.

doi:10.1021/om049679w

Cited by 97 publications

(51 citation statements)

References 31 publications

(34 reference statements)

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“…The synthetic part of this study describes the pathway toward functionalized molybdenum compounds together with detailed analytical and spectroscopic characterization. Structures of one key intermediate (12) and two final products (18 and 21) were elucidated by single crystal X-ray diffraction analysis. The functionalization of the outer coordination sphere of molybdenum(II) compounds with ammonium functions has strong impact on cytotoxicity.…”

Section: Discussionmentioning

confidence: 99%

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Highly Water‐Soluble Cyclopentadienyl and Indenyl Molybdenum(II) Complexes – Second Generation of Molybdenum‐Based Cytotoxic Agents

et al. 2016

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(2016). Highly water-soluble cyclopentadienyl and indenyl molybdenum(II) complexes -second generation of molybdenum-based cytotoxic agents. European Journal of Inorganic Chemistry, 2016Chemistry, (4), 519-529. doi:10.1002 This article may be used for non-commercial purposes in accordance With Wiley-VCH Terms and Conditions for self-archiving". Ondřej Mrózek, [a] Lucie Šebestová, [b] Jaromír Vinklárek,* [a] Martina Řezáčová, [c] Aleš Eisner, [b] Zdeňka Růžičková, [a] and Jan Honzíček [d] Abstract [BF4]2 were determined by the X-ray crystallography. All synthesized compounds exhibit increased activity against human leukemia cell lines MOLT-4 and HL-60. They are about one order of magnitude more active than cisplatin. This study has proven that modification of the outer coordination sphere of molybdenum complexes has a strong impact on their activity and may be successfully used for a design of novel highly cytotoxic active species.

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Section: Discussionmentioning

confidence: 99%

“…Analytical and spectroscopic data are in line with those published elsewhere. [12] Synthesis of C5H5CH2CH2N(CH2)5 (7). The reaction was carried out as was described for compound 7, but with NaCp (1; 4.4 g; 50 mmol), ClCH2CH2N(CH2)5 (4; 6.8 g, 46 mmol).…”

Section: Synthesis Of Clch2ch2nme2 (3)mentioning

confidence: 99%

Highly Water‐Soluble Cyclopentadienyl and Indenyl Molybdenum(II) Complexes – Second Generation of Molybdenum‐Based Cytotoxic Agents

et al. 2016

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“…In addition, the mechanism of action of these titanocene compounds is not clear. Very recently, more synthetic effort has been employed to increase the cytotoxicity of titanocene dichloride derivatives [10][11][12][13]. Additional novel synthetic approaches have allowed us to synthesise [1,2-di(cyclopentadienyl)-1,2-di-(4-N,Ndimethylaminophenyl)-ethanediyl] titanium dichloride, which has an IC 50 value of 2.7 · 10 −4 M when tested for cytotoxic effects on the LLC-PK cell line [14].…”

Section: Introductionmentioning

confidence: 99%

Novel titanocene anti-cancer drugs and their effect on apoptosis and the apoptotic pathway in prostate cancer cells

et al. 2006

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Advanced prostate cancer is not curable by current treatment strategies indicating a significant need for new chemotherapeutic options. Highly substituted ansa-titanocene compounds have shown promising cytotoxic activity in a range of cancers. The objectives of this study are to examine the effects of these titanocene compounds on prostate cancer cells. Prostate cell lines were treated with three novel titanocene compounds and compared to titanocene dichloride and cisplatin. Percent apoptosis, viability and cell cycle were assessed using propidium iodide DNA incorporation with flow cytometry. Cytochrome C was assessed by western blotting of mitochondrial and cytoplasmic fractions. Apoptosis Inducing Factor was assessed by confocal microscopy. These novel compounds induced more apoptosis compared to cisplatin in a dose dependent manner. Compound Y had the most significant effect on cell cycle and apoptosis. Despite the release of cytochrome C from the mitochondrial fraction there was no inhibition of apoptosis with the pan caspase inhibitor, ZVAD-FMK. AIF was shown to translocate from the cytosol to the nucleus mediating a caspase independent cell death. Bcl-2 over expressing PC-3 cells, which were resistant to cisplatin induced apoptosis, underwent apoptosis following treatment with all the titanocene compounds. This study demonstrates possible mechanisms by which these novel titanocene compounds can mediate their apoptotic effect in vitro. The fact that they can induce more apoptosis than cisplatin in advanced cancer cell lines would confer an advantage over cisplatin. They represent exciting new agents with future potential for the treatment of advanced prostate cancer.

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“…Analytical and spectroscopic data are in line with those published elsewhere. [33] Synthesis of 3-(C5H4NCH2)C9H7 (4). The reaction was carried out as described for compound 3 but with NaInd (2; 6.91 g, 50 mmol).…”

Section: Synthesis Of C5h4nch2clmentioning

confidence: 99%

Indenyl Compounds with Constrained Hapticity: The Effect of Strong Intramolecular Coordination

Mrózek¹,

Vinklárek²,

Růžičková³

et al. 2016

Eur J Inorg Chem

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A series of cyclopentadienyl and indenyl molybdenum(II) compounds with intramolecularly coordinated pyridine arm, including scorpionate-like species bearing two irreversibly coordinated arms on indenyl core, was synthesized and characterized. All presented structural types were confirmed by X-ray diffraction analysis. Due to π-basicity of pyridine, the intramolecular interaction is considerably stronger than in case of analogous species bearing tertiary amines in the side chain. Although the starting compounds for syntheses are isostructural, the reaction outcomes differ considerably. The cyclopentadienyl precursor gives a pentacoordinated η 5 :κN-compound while the indenyl analogue produces a hexacoordinated species with unprecedented η 3 :κN-coordination mode of the indenyl ligand representing an unusual example of so-called indenyl effect. The unusually high stability of η 3 :κN-coordination compounds toward η 3 to η 5 haptotropic rearrangement was clarified by theoretical calculations. As the strong intramolecular interaction prevents rotation of indenyl, it cannot reach a conformation suitable for η 3 to η 5 rearrangement. As a result, the low hapticity is effectively locked.

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Synthesis, Characterization, and Assessment of Cytotoxic Properties of a Series of Titanocene Dichloride Derivatives

Cited by 97 publications

References 31 publications

Highly Water‐Soluble Cyclopentadienyl and Indenyl Molybdenum(II) Complexes – Second Generation of Molybdenum‐Based Cytotoxic Agents

Highly Water‐Soluble Cyclopentadienyl and Indenyl Molybdenum(II) Complexes – Second Generation of Molybdenum‐Based Cytotoxic Agents

Novel titanocene anti-cancer drugs and their effect on apoptosis and the apoptotic pathway in prostate cancer cells

Indenyl Compounds with Constrained Hapticity: The Effect of Strong Intramolecular Coordination

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