Antifungal nickel(II) complexes derived from amino sugars against pathogenic yeast, Candida albicans

Yano, Shigenobu; Inoue, Shintaro; Nouchi, Reiko; Mogami, Kaoru; Shinohara, Yoshie; Yasuda, Yukiko; Kato, Masako; Tanase, Tomoaki; Kakuchi, Toyoji; Mikata, Yuji; Suzuki, Takahito; Yamamoto, Yasuhiro

doi:10.1016/s0162-0134(97)10004-6

Cited by 26 publications

(9 citation statements)

References 19 publications

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“…A potential benefit of utilizing this approach is that the carbohydrate can remain pendant, thereby being freely available to interact with carbohydrate transport and metabolic pathways in the body. Examples of this approach in medicinal inorganic chemistry include carbohydrate‐appended cisplatin analogues as potent antitumour agents,13, 15 antifungal Ni II complexes derived from amino sugars,16 as well as carbohydrate‐appended metal complexes of the radioisotopes 99m Tc and 186 Re for potential use in nuclear imaging and therapy 8. 11, 14 In many cases however the resultant metal complexes exhibit binding of the carbohydrate moiety to the metal center which limits the targeting potential of these compounds.…”

Section: Introductionmentioning

confidence: 99%

Novel Carbohydrate‐Appended Metal Complexes for Potential Use in Molecular Imaging

Storr

Obata

Fisher

et al. 2004

Chemistry A European J

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Seven discrete sugar-pendant diamines were complexed to the {M(CO)(3)}(+) ((99m)Tc/Re) core: 1,3-diamino-2-propyl beta-D-glucopyranoside (L(1)), 1,3-diamino-2-propyl beta-D-xylopyranoside (L(2)), 1,3-diamino-2-propyl alpha-D-mannopyranoside (L(3)), 1,3-diamino-2-propyl alpha-D-galactopyranoside (L(4)), 1,3-diamino-2-propyl beta-D-galactopyranoside (L(5)), 1,3-diamino-2-propyl beta-(alpha-D-glucopyranosyl-(1,4)-D-glucopyranoside) (L(6)), and bis(aminomethyl)bis[(beta-D-glucopyranosyloxy)methyl]methane (L(7)). The Re complexes [Re(L(1)-L(7))(Br)(CO)(3)] were characterized by (1)H and (13)C 1D/2D NMR spectroscopy which confirmed the pendant nature of the carbohydrate moieties in solution. Additional characterization was provided by IR spectroscopy, elemental analysis, and mass spectrometry. Two analogues, [Re(L(2))(CO)(3)Br] and [Re(L(3))(CO)(3)Br], were characterized in the solid state by X-ray crystallography and represent the first reported structures of Re organometallic carbohydrate compounds. Conductivity measurements in H(2)O established that the complexes exist as [Re(L(1)-L(7))(H(2)O)(CO)(3)]Br in aqueous conditions. Radiolabelling of L(1)-L(7) with [(99m)Tc(H(2)O)(3)(CO)(3)](+) afforded in high yield compounds of identical character to the Re analogues. The radiolabelled compounds were determined to exhibit high in vitro stability towards ligand exchange in the presence of an excess of either cysteine or histidine over a 24 h period.

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Section: Introductionmentioning

confidence: 99%

Novel Carbohydrate‐Appended Metal Complexes for Potential Use in Molecular Imaging

Storr

Obata

Fisher

et al. 2004

Chemistry A European J

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“…28 Antifungal activity of NiCl 2 •6H 2 O and nickel(II) complexes derived from amino sugars against C. albicans was reported by Yano et al with MIC values in the 200-250 µM range, which is 2.5-5-fold higher in comparison to the MIC values of 1-3. 29 Furthermore, the complexes from the present study showed better anti-Candida activities in comparison to nickel(II) complexes with pyrazoline-based ligand, which had MIC values ranging from 100 -1000 µg mL -1 . 30 It was shown that certain selectivity against Candida strains by nickel(II) compounds was due to the competitive inhibition of fungal chitinase (chitin-degradation enzyme).…”

Section: Biological Activity Of the Nickel(ii) Complexes 1-3mentioning

confidence: 63%

“…30 It was shown that certain selectivity against Candida strains by nickel(II) compounds was due to the competitive inhibition of fungal chitinase (chitin-degradation enzyme). 29 In parallel, to determine the applicability of complexes 1-3 as potential antifungals, their in vitro cytotoxicity against healthy human lung fibroblasts was examined (Table II, Fig. 2).…”

Section: Biological Activity Of the Nickel(ii) Complexes 1-3mentioning

confidence: 99%

In vitro antimicrobial activity and cytotoxicity of nickel(II) complexes with different diamine ligands

Drašković¹,

Glišić

Vojnović

et al. 2017

JSCS

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Three diamines, 1,3-propanediamine (1,3-pd), 2,2-dimethyl-1,3-propanediamine (2,2-diMe-1,3-pd) and (±)-1,3-pentanediamine (1,3-pnd), were used for the synthesis of nickel(II) complexes 1-3, respectively, of the general formula [Ni(L) 2 (H 2 O) 2 ]Cl 2. The stoichiometries of the complexes were confirmed by elemental microanalysis, and their structures were elucidated by spectroscopic (UV-Vis and IR) and molar conductivity measurements. The complexes 1-3, along with NiCl 2 •6H 2 O and the diamine ligands, were evaluated against a panel of microbial strains that are associated with skin, wound, urinary tract and nosocomial infections. The obtained results revealed no significant activity of 1-3 against the investigated bacterial strains. On the other hand, they showed good antifungal activity against pathogenic Candida strains, with minimum inhibitory concentration (MIC) values in the range from 15.6 to 62.5 µg mL-1. The best anti-Candida activity was observed for complex 2 against C. parapsilosis, while the least susceptible to the effect of the complexes was C. krusei. The antiproliferative effect on normal human lung fibroblast cell line MRC-5 was also evaluated in order to determine the therapeutic potential of nickel(II) complexes 1-3. These complexes showed lower negative effects on the viability of the MRC-5 cell line than the clinically used nystatin and comparable selectivity indexes to that of this antifungal drug.

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“…Their activity has frequently been thought to be due to their ability to chelate trace metals (Chandra and Gupta, 2005). Moreover, Nickel (II) complex derived from aminosugars showed effective antifungal activity against pathogenic Yeast, Candida albicans with MIC, this complex act as inhibitor for chitinase (chitin-degradation enzyme) enzyme of C. albicans (Yano et al, 1998). In addition, Nickel (II) complex of 5-methyl 2-furfural thiosemicarbazonehave carried out in vitro for antifungal activity on human pathogenic fungi, Aspergillus fumigatus and Candida albicans , and in vivo for toxicity on mice (Jouad et al, 2001).…”

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confidence: 99%

Biological Screening of a Novel Nickel (II) Tyrosine Complex

Islam

Noman

et al. 2007

Mycobiology

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A newly synthesized Nickel (II) tyrosine complex was screened as potential antimicrobial agent against a number of medically important bacteria (Bacillus subtilis, Streptococcus β-haemolytica, Escherichia coli, Shigella dysenterae) and fungi (Aspergillus fumigatus, Candida albicans, Aspergillus niger, Aspergillus flavus, Penicillium sp.) strains. were used for antifungal activity. The antimicrobial activity was evaluated using the Agar Disc method. Moreover, the minimum inhibitory concentration of the complexes was determined against the same pathogenic bacteria and the values were found between 4~64 µg ml-1. Brine shrimp bioassay was carried out for cytotoxicity measurements of the complexes. The LC50 values were calculated after probit transformation of the resulting mortality data and found to be 6 µg ml-1.

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Antifungal nickel(II) complexes derived from amino sugars against pathogenic yeast, Candida albicans

Cited by 26 publications

References 19 publications

Novel Carbohydrate‐Appended Metal Complexes for Potential Use in Molecular Imaging

Novel Carbohydrate‐Appended Metal Complexes for Potential Use in Molecular Imaging

In vitro antimicrobial activity and cytotoxicity of nickel(II) complexes with different diamine ligands

Biological Screening of a Novel Nickel (II) Tyrosine Complex

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