Glucose ferrocenyl-oxazolines: Coordination behavior toward [Pd(η3-allyl)Cl]2 studied by ESI-MS

Hartinger, Christian G.; Nazarov, Alexey A.; Galanski, Markus; Reithofer, Michael R.; Keppler, Bernhard K.

doi:10.1016/j.jorganchem.2005.03.062

Cited by 18 publications

(9 citation statements)

References 32 publications

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“…The cytotoxicity and antimicrobial activity of these conjugates were investigated on different cancer cell lines and microbes, respectively. [16][17][18][19][20][21] Cyclopentadienyl rings of ferrocene have been linked through side chains containing carboxylate, [22] amide, [23] ether and triazole moieties [24,25] to the carbohydrates. The compounds show antibacterial activity against both Gram-positive and Gram-negative pathogens.…”

Section: Introductionmentioning

confidence: 99%

“…However, the introduction of carbohydrates through esters and amide linkages to the ferrocene can impart hydrophilic character to these conjugates 16–21. Cyclopentadienyl rings of ferrocene have been linked through side chains containing carboxylate,22 amide,23 ether and triazole moieties24,25 to the carbohydrates. Although heterocyclic ring systems play a crucial role in numerous biologically active compounds,26–29 there are very few reports on the bioactivity of such systems attached to ferrocene–carbohydrate scaffolds 30.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Crystal Structure, Electronic Spectroscopy, Electrochemistry and Biological Studies of Ferrocene–Carbohydrate Conjugates

et al. 2012

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A series of six new ferrocene-carbohydrate conjugates was prepared from pentose and hexose sugar derivatives. These include the ferrocenecarbaldehyde acetal 2, four ferrocenyltriazoles 4a-d derived from furanose sugar and the ferrocenyltriazole 4e derived from a pyranose sugar. The compounds were characterised by spectroscopic means and the structures of the new conjugates 2 and 4a were determined by means of X-ray crystallography. A UV/Vis study of these compounds performed in aqueous solutions under physiological conditions confirmed their stability. The CD spectral analysis shows the effect of the nature of substituents of the carbohydrate moieties. The electrochemical studies conducted in a buffer solution display one-electron reversible oxidation processes for these compounds. These results indicate that the compounds are suitable for conducting bio-[a]

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis, Crystal Structure, Electronic Spectroscopy, Electrochemistry and Biological Studies of Ferrocene–Carbohydrate Conjugates

et al. 2012

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“…59 Moreover, the pyranose rings in 1,2-O-ethylidene-or 1,2:3,4-di-O-isopropylidene-a-D D-galactopyranose derivatives have been generally found to feature conformations between screw-boat O S 5 and twist-boat O T 2 , even if not coordinated to any metal ion. [60][61][62][63][64][65][66] The distortion from the chair conformation found for these compounds is generally attributed for the rigid acetal or ketal protecting groups.…”

Section: Pyranose Ring Conformationmentioning

confidence: 99%

Nickel(II) complexes with Schiff-base ligands derived from epimeric pyranose backbones as 2,3-chelators: modeling the coordination chemistry of chitosan

Burkhardt

Görls

Plass

2008

Carbohydrate Research

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“…[40][41][42][43][44] In addition to these advantages, the hydrophilicity of ferrocenecarbohydrate conjugates can be tuned by protecting and deprotecting the hydroxyl group on the carbohydrate skeleton. Ferrocene-carbohydrate complexes have been at the forefront of scientific research for their use as electrochemical probes [45][46][47][48] and biological activity. [49][50][51][52][53][54][55][56][57][58][59] Most of the biologically active ferrocene-carbohydrate conjugates have been prepared from glucose and glucosamine sugars and they have shown significant anti-malarial activities.…”

Section: Introductionmentioning

confidence: 99%

Effect of amide-triazole linkers on the electrochemical and biological properties of ferrocene-carbohydrate conjugates

et al. 2013

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Amide-triazole linker incorporated ferrocene-carbohydrate conjugates were prepared by adopting a regiospecific copper(II)-catalysed 1,3-cycloaddition of ferrocenoyl propargylamide and isopropylidene/acetyl protected carbohydrate azides. Hydrophilic ferrocene glycoside with an amide-triazole linker was synthesised by deacetylation of the hydroxyl groups. All the new compounds were characterised by UV-visible and electrochemical studies and they were found to be stable in organic solvents as well as in the buffer system under physiological conditions (pH = 7.0). The diffusion coefficient (D(f)) of the conjugates was also calculated by means of cyclic voltammetric studies. It was observed that while the molecular weight of the compounds had no significant effect on the diffusion coefficient, the hydrophobic/hydrophilic nature of the carbohydrate scaffold displayed varied diffusion coefficient values. Stabilization of the compounds in buffer solution under physiological pH led to almost identical diffusion coefficient values. The compounds derived from xylose and ribose exhibited cytotoxicity on hormone-dependent and hormone-independent breast cancer cell lines, whereas the conjugates derived from glucose and galactose were found to be non-toxic in nature. The compounds did not show any antimicrobial activity against Gram-positive and Gram-negative pathogens.

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Glucose ferrocenyl-oxazolines: Coordination behavior toward [Pd(η3-allyl)Cl]2 studied by ESI-MS

Cited by 18 publications

References 32 publications

Synthesis, Crystal Structure, Electronic Spectroscopy, Electrochemistry and Biological Studies of Ferrocene–Carbohydrate Conjugates

Synthesis, Crystal Structure, Electronic Spectroscopy, Electrochemistry and Biological Studies of Ferrocene–Carbohydrate Conjugates

Nickel(II) complexes with Schiff-base ligands derived from epimeric pyranose backbones as 2,3-chelators: modeling the coordination chemistry of chitosan

Effect of amide-triazole linkers on the electrochemical and biological properties of ferrocene-carbohydrate conjugates

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