Synthesis, oxidation chemistry and cytotoxicity studies on ferrocene derivatives of diethylstilbestrol

AbstractClimacostol (5-(Z)-non-2-enyl-benzene-1,3-diol) is a natural toxin isolated from the freshwater ciliated protozoan Climacostomum virens and belongs to resorcinolic lipids, a group of compounds that show antimicrobial, antiparasitic, and anticancer activities. We investigated the cytotoxic activity of the chemically synthesized toxin and its alkyl and alkynyl derivatives on C. virens and nine other common species of free-living freshwater ciliates. Our results show that the cytotoxic potency of climacostol can be modulated by the substitution of the double bond present in the aliphatic chain of the toxin with a single or a triple one that was previously obtained during the synthesis of the unsaturated and saturated derivatives of the parent molecule. We demonstrated that the cytotoxicity level of the molecules considered in this study appears to be inversely correlated to the unsaturation level of their aliphatic chains, and that the potency of their action is also related to the target organism.

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Synthesis and Cytotoxicity Studies of Fluorinated Derivatives of Vanadocene Y

European Journal of Inorganic Chemistry ◽

10.1002/ejic.200900297 ◽

2009 ◽

Vol 2009 (19) ◽

pp. 2804-2810 ◽

Cited By ~ 24

Author(s):

Brendan Gleeson ◽

James Claffey ◽

Anthony Deally ◽

Megan Hogan ◽

Luis Miguel Menéndez Méndez ◽

...

Keyword(s):

Cytotoxicity Studies ◽

Fluorinated Derivatives ◽

Derivatives Of

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ChemInform Abstract: One-Pot Synthesis and Cytotoxicity Studies of New Mannich Base Derivatives of Polyether Antibiotic-Lasalocid Acid.

ChemInform ◽

10.1002/chin.201404208 ◽

2014 ◽

Vol 45 (4) ◽

pp. no-no

Author(s):

Adam Huczynski ◽

Jacek Rutkowski ◽

Izabela Borowicz ◽

Joanna Wietrzyk ◽

Ewa Maj ◽

...

Keyword(s):

Mannich Base ◽

One Pot ◽

One Pot Synthesis ◽

Cytotoxicity Studies ◽

Derivatives Of

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Synthesis and redox chemistry of 1,1′-bis(diphenylphosphino)ferrocene derivatives of R2C2Co2(CO)6 (R  MeO2C, CF3)

Journal of Organometallic Chemistry ◽

10.1016/s0022-328x(96)06590-4 ◽

1997 ◽

Vol 527 (1-2) ◽

pp. 179-190 ◽

Cited By ~ 14

Author(s):

C.John McAdam ◽

Noel W. Duffy ◽

Brian H. Robinson ◽

Jim Simpson

Keyword(s):

Redox Chemistry ◽

Ferrocene Derivatives ◽

Derivatives Of

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Electron-transfer biosensors

Philosophical Transactions of the Royal Society of London Series B Biological Sciences ◽

10.1098/rstb.1987.0020 ◽

1987 ◽

Vol 316 (1176) ◽

pp. 95-106 ◽

Cited By ~ 36

Keyword(s):

Electron Transfer ◽

Glucose Oxidase ◽

Organometallic Compound ◽

Electrode Reaction ◽

Transfer Reactions ◽

Ferrocene Derivatives ◽

Electron Transfer Reactions ◽

Redox Proteins ◽

Copper Protein ◽

Derivatives Of

The electrochemistry of redox proteins is now well established. Conditions exist which allow electron-transfer reactions of all simple proteins to proceed rapidly and reversibly at electrodes. Coupling of the electrode reaction to enzymes, for which the redox proteins act as cofactors, allows exploitation of this good electrochemistry. This is well illustrated by the enzyme-catalysed electrochemical oxidation of p -cresol to p -hydroxybenzaldehyde, which has been shown to proceed along with coupling to the electrode via the copper protein, azurin, or the organometallic compound ferroceneboronic acid. Ferrocene derivatives, in general, show a degree of versatility, coupling the electron-transfer reactions of many enzymes. Thus derivatives of the ferricinium ion act as excellent electron-transfer reagents from the enzyme glucose oxidase. The system is capable of detecting glucose in blood. Similar procedures, in conjunction with the appropriate enzyme, have yielded assays for, among others, H 2 O 2 and cholesterol.

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