| InChI=1S/C6H8O7.Bi/c7-3(8)1-6(13,5(11)12)2-4(9)10;/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12);/q;+3/p-3 |
| ANERHPOLUMFRDC-UHFFFAOYSA-K |
| [Bi+3].OC(CC([O-])=O)(CC([O-])=O)C([O-])=O |
|
|
bismuth(3+) 2-hydroxypropane-1,2,3-tricarboxylate
|
|
2-hydroxy-1,2,3-propanetricarboxylic acid bismuth salt
|
ChEBI
|
|
Bi-citrate
|
ChEBI
|
|
bismuth(III) citrate
|
ChEBI
|
|
citric acid bismuth(III) salt
|
ChEBI
|
|
813-93-4
|
CAS Registry Number
|
ChemIDplus
|
Silva KMMN, de Carvalho DÉL, Valente VMM, Campos Rubio JC, Faria PE, Silva-Caldeira PP (2019)
Concomitant and controlled release of furazolidone and bismuth(III) incorporated in a cross-linked sodium alginate-carboxymethyl cellulose hydrogel.
International journal of biological macromolecules 126, 359-366 [PubMed:30572056]
[show Abstract]
The combination of bismuth(III) citrate and the antibiotic furazolidone (FDZ) results in a synergetic effect on Helicobacter pylori eradication. However, the problems associated with their oral administration are challenges to overcome. Thus, in the present study, sodium alginate (SA)/carboxymethyl cellulose (CMC) blend hydrogels (SC) were developed for concomitant and controlled release of furazolidone and bismuth(III). The blank formulation (SCblank) and the three drug-loaded hydrogels (SCFDZ, SCBi, and SCFDZ-Bi) were prepared by casting method and characterized by infrared spectroscopy, scanning electron microscopy, differential scanning calorimetry, and X ray powder diffraction analyses. The swelling equilibrium and cumulative release amounts of FDZ and Bi3+ have indicated distinct behaviors of the hydrogels to different pH values. The bismuth-containing sample (SCFDZ-Bi) presents more resistance to degradation on a neutral solution and shows more suitable properties for controlled drug release than the sample without bismuth (SCFDZ). Microbiological studies, using Escherichia coli as a model, show bacteria viability reduction in presence of the drug-loaded samples. The developed system containing furazolidone and bismuth(III) appears to be promising for oral administration with concomitant and controlled release of these drugs aimed at the pharmacological treatment of gastrointestinal disorders. | Omouri Z, Hawari J, Fournier M, Robidoux PY (2018)
Bioavailability and chronic toxicity of bismuth citrate to earthworm Eisenia andrei exposed to natural sandy soil.
Ecotoxicology and environmental safety 147, 1-8 [PubMed:28822260]
[show Abstract]
The present study describes bioavailability and chronic effects of bismuth to earthworms Eisenia andrei using OECD reproduction test. Adult earthworms were exposed to natural sandy soil contaminated artificially by bismuth citrate. Average total concentrations of bismuth in soil recovered by HNO3 digestion ranged from 75 to 289mg/kg. Results indicate that bismuth decreased significantly all reproduction parameters of Eisenia andrei at concentrations ≥ 116mg/kg. However, number of hatched cocoons and number of juveniles seem to be more sensitive than total number of cocoons, as determined by IC50; i.e., 182, 123 and > 289mg/kg, respectively. Bismuth did not affect Eisenia andrei growth and survival, and had little effect on phagocytic efficiency of coelomocytes. The low immunotoxicity effect might be explained by the involvement of other mechanisms i.e. bismuth sequestered by metal-binding compounds. After 28 days of exposure bismuth concentrations in earthworms tissue increased with increasing bismuth concentrations in soil reaching a stationary state of 21.37mg/kg dry tissue for 243mg Bi/kg dry soil total content. Data indicate also that after 56 days of incubation the average fractions of bismuth available extracted by KNO3 aqueous solution in soil without earthworms varied from 0.0051 to 0.0229mg/kg, while in soil with earthworms bismuth concentration ranged between 0.310-1.347mg/kg dry soil. We presume that mucus and chelating agents produced by earthworms and by soil or/and earthworm gut microorganisms could explain this enhancement, as well as the role of dermal and ingestion routes of earthworms uptake to soil contaminant. | Erenburg SB, Trubina SV, Yukhin YM, Sharafutdinov MR (2017)
Structural characteristics of amorphous K-Bi citrate (De-Nol) and its aqueous solutions from EXAFS spectra.
Journal of inorganic biochemistry 166, 94-99 [PubMed:27838583]
[show Abstract]
EXAFS (Extended X-ray Absorption Fine Structure) spectra of an amorphous solid Bi complex with citrate (known as De-Nol) and its aqueous solutions in a wide concentration range are measured. For the solutions good agreement is revealed between their structural parameters and the averaged interatomic distances and coordination numbers of the crystalline polymeric bismuth citrate compound composed of 12-nuclear Bi clusters based on the structure Bi12O22. So, it is found that droplets of the colloidal solution have a core structure close to the solid Bi12O22 cluster structure. When the concentrated solution is diluted the cluster structure is somewhat modified, it remaining similar to the structure of the Bi12O22 cluster and even at a tenfold dilution and the nearest (oxygen) spheres of the Bi environment changing insignificantly. The appearance in this case of an additional oxygen atom at a large distance from the bismuth atom likely due to the presence of the oxygen atom from the hydroxyl group of the diluted aqueous solution. The appearance of such oxygen is in accordance with particles size increase for diluted solution obtained by small-angle X-ray diffraction measurements. It is established that the structure of the amorphous solid complex is multiphase and, as a whole, similar to the structure of the solid binuclear complexes. | Kokkinos C, Prodromidis M, Economou A, Petrou P, Kakabakos S (2015)
Disposable integrated bismuth citrate-modified screen-printed immunosensor for ultrasensitive quantum dot-based electrochemical assay of C-reactive protein in human serum.
Analytica chimica acta 886, 29-36 [PubMed:26320633]
[show Abstract]
A novel immunosensor based on graphite screen-printed electrodes (SPEs) modified with bismuth citrate was developed for the voltammetric determination of C-reactive protein (CRP) in human serum using quantum dots (QDs) labels. The sandwich-type immunoassay involved physisorption of CRP capture antibody on the surface of the sensor, sequential immunoreactions with CRP and biotinylated CRP reporter antibody and finally reaction with streptavidin-conjugated PbS QDs. The quantification of the target protein was performed with acidic dissolution of the PbS QDs and anodic stripping voltammetric detection of the Pb(II) released. Detection was performed at bismuth nanodomains formed on the sensor surface during the electrolytic preconcentration step, as bismuth citrate was reduced to metallic bismuth simultaneously with the deposition of Pb on the surface of the immunosensor. Under optimal conditions, the response was linear over the range 0.2-100 ng mL(-1) CRP and the limit of detection was 0.05 ng mL(-1) CRP. Since the modified SPE serves as both the biorecognition element and the QDs reader, the analytical procedure is simplified, the drawbacks of existing electroplated immunosensors are minimized while the proposed disposable sensing platform provides convenient, low-cost and ultrasensitive detection of proteins and wider scope for mass-production. | Dong F, Xiong T, Wang R, Sun Y, Jiang Y (2014)
Growth mechanism and photocatalytic activity of self-organized N-doped (BiO)₂CO₃ hierarchical nanosheet microspheres from bismuth citrate and urea.
Dalton transactions (Cambridge, England : 2003) 43, 6631-6642 [PubMed:24509694]
[show Abstract]
Synthesis of nano-/microstructured functional materials with 3D hierarchical microspheres structure has provided new opportunities for optimizing their physical and chemical properties. This work revealed a new growth mechanism of self-organized N-doped (BiO)2CO3 hierarchical microspheres which were fabricated by hydrothermal treatment of bismuth citrate and urea without an additive. Based on time-dependent observation, several evolution processes were believed to account for the formation of the self-organized N-doped (BiO)2CO3 hierarchical microspheres. Initially, crystallized (BiO)4CO3(OH)2 particles were formed during the nucleation and crystallization processes. Subsequently, the intermediate (BiO)4CO3(OH)2 reacted with CO3(2-) to generate (BiO)2CO3 growth nuclei on the surface of the CO2 bubbles which can act as heterogeneous nucleation centers. Next, the (BiO)2CO3 growth nuclei aggregated together after the consumption of CO2 bubbles with the increased concentration of OH(-) and further grew to be nanosheets. The microspheres constructed by small nanosheets further grew with the consumption of small particles. Finally, all (BiO)4CO3(OH)2 transformed to the (BiO)2CO3 phase, accompanied by the doping of N element into the lattice of (BiO)2CO3, and thereby, the well-defined N-doped (BiO)2CO3 hierarchical microspheres were shaped. Depending on the distance between neighboring CO2 bubbles, the resulting microspheres can be linked or dispersed. Besides, the gradual release of CO2 bubbles and CO3(2-) played a crucial role in controlling the nucleation and growth process, resulting in different sizes of microspheres. The fabricated N-doped (BiO)2CO3 hierarchical microspheres displayed admirably efficient and durable photocatalytic activity under both UV and visible light towards removal of NO, which is mainly attributed to the introduction of N element and the special hierarchical structure. This work provides new insights into the controlled synthesis of photocatalytic nano/microstructures for potential environmental and energetic applications. | Li Q, Liu H, Dong F, Fu M (2013)
Hydrothermal formation of N-doped (BiO)2CO3 honeycomb-like microspheres photocatalysts with bismuth citrate and dicyandiamide as precursors.
Journal of colloid and interface science 408, 33-42 [PubMed:23948459]
[show Abstract]
In order to develop efficient visible light driven photocatalysts for environmental application, novel N-doped (BiO)2CO3 honeycomb-like hierarchical microspheres were fabricated by an one-pot and template-free hydrothermal method, firstly using bismuth citrate and dicyandiamide as precursors. The as-prepared samples were characterized by XRD, SEM, FT-IR, PL, XPS, and UV-vis DRS in detail. The results indicated that the crystal structure and morphology of the samples can be tuned by hydrothermal reaction temperature. The source of nitrogen doping was from dicyandiamide, which also played a key role in hydrolyzing bismuth citrate to produce bismuth ions and citrate ions. The ammonium ions from the decomposition of dicyandiamide reacted with bismuth ions and carbonate ions from decomposition of citrate ions, producing in situ N-doped (BiO)2CO3 microspheres. The doped nitrogen substituted for oxygen in (BiO)2CO3 and was responsible for the band gap reduction of N-doped (BiO)2CO3. The as-prepared N-doped (BiO)2CO3 microspheres were applied for removal of NO in air and exhibited excellent visible light activity, exceeding that of N-doped TiO2 and C-doped TiO2. Time-dependent evolutions of crystal structure, morphology, chemical composition, and optical property were investigated systematically to reveal the growth mechanism of the honeycomb-like (BiO)2CO3 microspheres. The growth process involved multiple steps, including reaction, nucleation, crystallization, aggregation, and recrystallization. The proposed growth mechanism could provide new insights into the design and fabrication of hierarchical materials with advanced properties. | Yang N, An Y, Cai J, Hu L, Zeng Y, Mao Z, Chen G, Sun H (2010)
Polymeric architectures of bismuth citrate based on dimeric building blocks.
Science China. Chemistry 53, 2152-2158 [PubMed:32214995]
[show Abstract]
Four bismuth complexes, (H2En)[Bi2(cit)2(H2O)4/3]·(H2O) x (1), (H2En)3[Bi2(cit)2Cl4]·(H2O) x (2), (HPy)2[Bi2(cit)2(H2O)8/5]·(H2O) x (3) and (H2En)[Bi2(cit)2](H2O) x (4) [cit = citrate4-; En = ethylenediamine; Py = pyridine] have been synthesized and crystallized. The crystal structures reveal that the basic building blocks in all of these complexes are bismuth citrate dimeric units which combine to form polymeric architectures. The embedded protonated ethylenediamine and pyridine moieties in the polymeric frameworks have been identified by X-ray crystallography and solid-state cross polarization/magic angle spinning (CP/MAS) 13C NMR. Based on the framework of complex 1, a structural model of a clinically used antiulcer drug, ranitidine bismuth citrate (RBC) was generated. The behavior of the protonated amine-bismuth citrate complexes in acidic aqueous solution has been studied by electrospray ionization-mass spectrometry (ESI-MS).Electronic supplementary materialSupplementary material is available for this article at 10.1007/s11426-010-4113-x and is accessible for authorized users. | Stringfellow K, McReynolds J, Lee J, Byrd J, Nisbet D, Farnell M (2009)
Effect of bismuth citrate, lactose, and organic acid on necrotic enteritis in broilers.
Poultry science 88, 2280-2284 [PubMed:19834076]
[show Abstract]
Clostridium perfringens-associated necrotic enteritis causes significant economic losses. The objective of this study was to evaluate the effect of bismuth citrate, lactose, and organic acid on the development of necrotic enteritis in broilers. The first study was a dose response that evaluated bismuth citrate at 50, 100, or 200 ppm on bacterial intestinal colonization and lesion development associated with our C. perfringens challenge model. The second study evaluated bismuth citrate, lactose, and citric acid on intestinal pH and lesion development. For the third study, we determined if lactose would enhance the efficacy of bismuth citrate against intestinal colonization and lesion development associated with C. perfringens. In study 1, intestinal lesion scores at the 50, 100, and 200 ppm bismuth citrate treatment level were reduced (P < or = 0.05) when compared with the birds fed 0 ppm bismuth citrate. Intestinal C. perfringens colonization of the 100 and 200 ppm bismuth citrate treatment group was significantly reduced when compared with birds fed 0 ppm bismuth citrate. In study 2, we found no significant differences in lesion development, after C. perfringens challenge, between birds fed 100 ppm bismuth citrate or fed a combination of 100 ppm bismuth citrate with dietary lactose or citric acid relative to the controls. The intestinal pH of birds fed 100 ppm bismuth citrate or fed a combination of 100 ppm bismuth citrate with dietary lactose or citric acid was not significantly reduced when compared with the controls. However, a significant reduction in pH was observed in birds fed a combination of 100 ppm bismuth citrate and lactose relative to the negative controls. In study 3, a decrease (P < or = 0.05) in intestinal lesion scores occurred in birds fed lactose with 100 ppm bismuth citrate, compared with the positive controls. There were no significant differences in intestinal bacterial colonization. These preliminary data suggest that bismuth citrate may reduce intestinal lesion development and C. perfringens colonization in broilers infected with necrotic enteritis. | von Recklinghausen U, Hartmann LM, Rabieh S, Hippler J, Hirner AV, Rettenmeier AW, Dopp E (2008)
Methylated bismuth, but not bismuth citrate or bismuth glutathione, induces cyto- and genotoxic effects in human cells in vitro.
Chemical research in toxicology 21, 1219-1228 [PubMed:18826176]
[show Abstract]
Bismuth compounds are widely used in industrial processes and products. In medicine, bismuth salts have been applied in combination with antibiotics for the treatment of Helicobacter pylori infections, for the prevention of diarrhea, and in radioimmunotherapy. In the environment, bismuth ions can be biotransformed to the volatile bismuth compound trimethylbismuth (Me3Bi) by methanobacteria. Preliminary in-house studies have indicated that bismuth ions are methylated in the human colon by intestinal microflora following ingestion of bismuth-containing salts. Information concerning cyto- and genotoxicity of these biomethylated products is limited. In the present study, we investigated the cellular uptake of an organic bismuth compound [monomethylbismuth(III), MeBi(III)] and two other bismuth compounds [bismuth citrate (Bi-Cit) and bismuth glutathione (Bi-GS)] in human hepatocytes, lymphocytes, and erythrocytes using ICP-MS. We also analyzed the cyto- and genotoxic effects of these compounds to investigate their toxic potential. Our results show that the methylbismuth compound was better taken up by the cells than Bi-Cit and Bi-GS. All intracellularly detected bismuth compounds were located in the cytosol of the cells. MeBi(III) was best taken up by erythrocytes (36%), followed by lymphocytes (17%) and hepatocytes (0.04%). Erythrocytes and hepatocytes were more susceptible to MeBi(III) exposure than lymphocytes. Cytotoxic effects of MeBi(III) were detectable in erythrocytes at concentrations >4 microM, in hepatocytes at >130 microM, and in lymphocytes at >430 microM after 24 h of exposure. Cytotoxic effects for Bi-Cit and Bi-GS were much lower or not detectable in the used cell lines up to a tested concentration of 500 microM. Exposure of lymphocytes to MeBi(III) (250 microM for 1 h and 25 microM/50 microM for 24 h) resulted in significantly increased frequencies of chromosomal aberrations (CA) and sister chromatid exchanges (SCE), whereas Bi-Cit and Bi-GS induced neither CA nor SCE. Our study also showed an intracellular production of free radicals caused by MeBi(III) in hepatocytes but not in lymphocytes. These data suggest that biomethylation of bismuth ions by the intestinal microflora of the human colon leads to an increase in the toxicity of the primary bismuth salt. | Hutson JC (2005)
Effects of bismuth citrate on the viability and function of Leydig cells and testicular macrophages.
Journal of applied toxicology : JAT 25, 234-238 [PubMed:15856528]
[show Abstract]
Bismuth is present in several popular over-the-counter drugs for nausea and diarrhea and is occasionally abused by patients with chronic gastrointestinal disorders. The most common consequence of bismuth overdose is neurological dysfunction. In experimental animals, bismuth overdose results in lowered serum testosterone levels, suggesting that reproductive dysfunction may be an additional component of bismuth toxicity. Although the precise mechanisms responsible for the lowered testosterone levels are unknown, it has been shown that bismuth accumulates within testicular macrophages. This may be important because these cells, which are commonly found in direct contact with Leydig cells, are known to exert paracrine influences on the Leydig cells for local control of testosterone production. However, bismuth may also exert direct effects on Leydig cells because it passes by these cells on its way to the phagocytic macrophages. The purpose of the present studies was to isolate both testicular macrophages and Leydig cells from rat testis and study the direct effects of bismuth on these cells with regard to their viability and function. We found that when Leydig cells were treated for 24 h with bismuth (1-100 microM) no change in viability or secretion of testosterone was observed. However, when testicular macrophages were similarly treated with bismuth a significant effect on viability was observed with as little as 6.25 microM bismuth, with near-complete cell death at 50 microM after 24 h. However, bismuth had no effect on the viability on testicular macrophages at 50 microM up to 8 h, therefore, we studied the secretion of tumor necrosis factor alpha (TNF-alpha) after 4 h of exposure to 50 microM bismuth and found no influence on the production of TNF-alpha. Taken together, it seems likely that bismuth has no direct effects on Leydig cells but, rather, lowers testosterone levels by killing testicular macrophages, thereby interrupting their local paracrine influence on Leydig cells through factors other than TNF-alpha. |
|
