Cob(I)alamin reacts with sucralose to afford an alkylcobalamin: Relevance to in vivo cobalamin and sucralose interaction

Motwani, Hitesh V.; Qiu, Shiran; Golding, Bernard T.; Kylin, Henrik; Törnqvist, Margareta

doi:10.1016/j.fct.2010.11.037

Cited by 20 publications

(5 citation statements)

References 44 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Some compounds may also react directly with compounds that are key for cell function. For example, as halogens are leaving groups, halogenated aliphatics my react with endogenous or exogenous nucleophiles, including DNA and proteins (Motwani et al 2011), affecting the efficiency of biological processes.…”

Section: Biomassmentioning

confidence: 99%

Chlorine cycling and the fate of Cl in terrestrial environments

Svensson

Kylin

Montelius

et al. 2021

Environ Sci Pollut Res

Self Cite

View full text Add to dashboard Cite

Chlorine (Cl) in the terrestrial environment is of interest from multiple perspectives, including the use of chloride as a tracer for water flow and contaminant transport, organochlorine pollutants, Cl cycling, radioactive waste (radioecology; 36Cl is of large concern) and plant science (Cl as essential element for living plants). During the past decades, there has been a rapid development towards improved understanding of the terrestrial Cl cycle. There is a ubiquitous and extensive natural chlorination of organic matter in terrestrial ecosystems where naturally formed chlorinated organic compounds (Clorg) in soil frequently exceed the abundance of chloride. Chloride dominates import and export from terrestrial ecosystems while soil Clorg and biomass Cl can dominate the standing stock Cl. This has important implications for Cl transport, as chloride will enter the Cl pools resulting in prolonged residence times. Clearly, these pools must be considered separately in future monitoring programs addressing Cl cycling. Moreover, there are indications that (1) large amounts of Cl can accumulate in biomass, in some cases representing the main Cl pool; (2) emissions of volatile organic chlorines could be a significant export pathway of Cl and (3) that there is a production of Clorg in tissues of, e.g. plants and animals and that Cl can accumulate as, e.g. chlorinated fatty acids in organisms. Yet, data focusing on ecosystem perspectives and combined spatiotemporal variability regarding various Cl pools are still scarce, and the processes and ecological roles of the extensive biological Cl cycling are still poorly understood.

show abstract

Section: Biomassmentioning

confidence: 99%

Chlorine cycling and the fate of Cl in terrestrial environments

Svensson

Kylin

Montelius

et al. 2021

Environ Sci Pollut Res

Self Cite

View full text Add to dashboard Cite

show abstract

“…In an in vitro study using human liver cells, sucralose was found to react with cob(I)alamin, a reduced form of vitamin B 12 , forming alkylcobalamin (Suc-Cbl), and it was suggested that such reactions, may affect the cobalamin levels, analogous to exposure to epoxides and nitrous oxide [11]. Moreover, sucralose has raised concerns as a possible human health hazard, mostly in public media, because of its chlorinated structure [12], [13].…”

Section: Introductionmentioning

confidence: 99%

Sucralose Induces Biochemical Responses in Daphnia magna

et al. 2014

View full text Add to dashboard Cite

The intense artificial sweetener sucralose has no bioconcentration properties, and no adverse acute toxic effects have been observed in standard ecotoxicity tests, suggesting negligible environmental risk. However, significant feeding and behavioural alterations have been reported in non-standard tests using aquatic crustaceans, indicating possible sublethal effects. We hypothesized that these effects are related to alterations in acetylcholinesterase (AChE) and oxidative status in the exposed animals and investigated changes in AChE and oxidative biomarkers (oxygen radical absorbing capacity, ORAC, and lipid peroxidation, TBARS) in the crustacean Daphnia magna exposed to sucralose (0.0001–5 mg L−1). The sucralose concentration was a significant positive predictor for ORAC, TBARS and AChE in the daphnids. Moreover, the AChE response was linked to both oxidative biomarkers, with positive and negative relationships for TBARS and ORAC, respectively. These joint responses support our hypothesis and suggest that exposure to sucralose may induce neurological and oxidative mechanisms with potentially important consequences for animal behaviour and physiology.

show abstract

“…The most representative of these is methionine synthase (MetH), ,, which is responsible for the regeneration of methionine from homocysteine. Other examples involve methanol-dependent cobalamin or corrinoid/Fe–S protein. , Another key function played by cob(I)alamin is the biosynthesis of adenosylcobalamin (AdoCbl), in a process guided by ATP:corrinoid adenosyltransferases (ACAs). − The pivotal role of cob(I)alamin is also revealed in reductive dehalogenation of halogenated compounds, a process involved in dehalorespiration in several anaerobic bacteria. − Finally, the reactions with N 2 O, NO, NO 2 – , NO 3 – , sucralose, epoxides, and SO 2 – have also been explored, adding to the diversity of processes that rely on the super-reduced form of vitamin B 12 . − …”

Section: Introductionmentioning

confidence: 99%

Cob(I)alamin: Insight Into the Nature of Electronically Excited States Elucidated via Quantum Chemical Computations and Analysis of Absorption, CD and MCD Data

2013

View full text Add to dashboard Cite

The nature of electronically excited states of the super-reduced form of vitamin B(12) (i.e., cob(I)alamin or B(12s)), a ubiquitous B(12) intermediate, was investigated by performing quantum-chemical calculations within the time-dependent density functional theory (TD-DFT) framework and by establishing their correspondence to experimental data. Using response theory, the electronic absorption (Abs), circular dichroism (CD) and magnetic CD (MCD) spectra of cob(I)alamin were simulated and directly compared with experiment. Several issues have been taken into considerations while performing the TD-DFT calculations, such as strong dependence on the applied exchange-correlation (XC) functional or structural simplification imposed on the cob(I)alamin. In addition, the low-lying transitions were also validated by performing CASSCF/MC-XQDPT2 calculations. By comparing computational results with existing experimental data a new level of understanding of electronic excitations has been established at the molecular level. The present study extends and confirms conclusions reached for other cobalamins. In particular, the better performance of the BP86 functional, rather than hybrid-type, was observed in terms of the excitations associated with both Co d and corrin π localized transitions. In addition, the lowest energy band was associated with multiple metal-to-ligand charge transfer excitations as opposed to the commonly assumed view of a single π → π* transition followed by vibrational progression. Finally, the use of the full cob(I)alamin structure, instead of simplified molecular models, shed new light on the spectral analyses of cobalamin systems and revealed new challenges of this approach related to long-range charge transfer excitations involving side chains.

show abstract

Cob(I)alamin reacts with sucralose to afford an alkylcobalamin: Relevance to in vivo cobalamin and sucralose interaction

Cited by 20 publications

References 44 publications

Chlorine cycling and the fate of Cl in terrestrial environments

Chlorine cycling and the fate of Cl in terrestrial environments

Sucralose Induces Biochemical Responses in Daphnia magna

Cob(I)alamin: Insight Into the Nature of Electronically Excited States Elucidated via Quantum Chemical Computations and Analysis of Absorption, CD and MCD Data

Contact Info

Product

Resources

About