The Blue Bottle Experiment - Simple Demonstration of Self-Organization

Adamčíková, Ľubica; Ševčı́k, Peter

doi:10.1021/ed075p1580

Cited by 22 publications

(27 citation statements)

References 2 publications

(2 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The cycle can be repeated many times before the reactants run out or the solution turns brown due to side reactions [ 5 ]. For thin-layer reaction in a Petri dish, dot and line patterns of the oxidized indicator develop over a period of time [ 6 – 8 ]. Figure 1 shows the general reaction framework and figure 2 shows patterns and colours observed in different variations of the reaction.…”

Section: Introductionmentioning

confidence: 99%

“…In essence, there were attempts to test new reducing agents [ 7 , 11 , 16 ] and indicators [ 7 , 8 ], to elucidate the mechanism and kinetics of the reactions [ 5 , 11 ] and to model the pattern formation [ 6 , 19 – 23 , 26 ]. Pattern formation may be comparable to the Belousov–Zhabotinsky [ 27 ] and the Briggs–Rauscher [ 28 ] reactions.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

A DFT investigation of the blue bottle experiment:E^∘_half-cellanalysis of autoxidation catalysed by redox indicators

2017

View full text Add to dashboard Cite

The blue bottle experiment is a collective term for autoxidation reactions catalysed by redox indicators. The reactions are characterized by their repeatable cycle of colour changes when shaken/left to stand and intricate chemical pattern formation. The blue bottle experiment is studied based on calculated solution-phase half-cell reduction potential of related reactions. Our investigation confirms that the reaction in various versions of the blue bottle experiment published to date is mainly the oxidation of an acyloin to a 1,2-dicarbonyl structure. In the light of the calculations, we also propose new non-acyloin reducing agents for the experiment. These results can help guide future experimental studies on the blue bottle experiment.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

A DFT investigation of the blue bottle experiment:E^∘_half-cellanalysis of autoxidation catalysed by redox indicators

2017

View full text Add to dashboard Cite

show abstract

“…The addition of NADPH (final concentration, 50 M) led to bleaching again, and this cycle could be repeated. Thus, the enzymatic reduction of MB can be considered to be a quasiphysiological analogue of the chemical blue bottle experiment (1).…”

Section: Resultsmentioning

confidence: 99%

Interactions of Methylene Blue with Human Disulfide Reductases and Their Orthologues fromPlasmodium falciparum

Buchholz

Schirmer

Eubel

et al. 2008

Antimicrob Agents Chemother

150

122

View full text Add to dashboard Cite

Methylene blue (MB) has experienced a renaissance mainly as a component of drug combinations against Plasmodium falciparum malaria. Here, we report biochemically relevant pharmacological data on MB such as rate constants for the uncatalyzed reaction of MB at pH 7.4 with cellular reductants like NAD(P)H (k ‫؍‬ 4 M ؊1 s ؊1 ), thioredoxins (k ‫؍‬ 8.5 to 26 M ؊1 s ؊1 ), dihydrolipoamide (k ‫؍‬ 53 M ؊1 s ؊1 ), and slowly reacting glutathione. As the disulfide reductases are prominent targets of MB, optical tests for enzymes reducing MB at the expense of NAD(P)H under aerobic conditions were developed. The product leucomethylene blue (leucoMB) is auto-oxidized back to MB at pH 7 but can be stabilized by enzymes at pH 5.0, which makes this colorless compound an interesting drug candidate. MB was found to be an inhibitor and/or a redox-cycling substrate of mammalian and P. falciparum disulfide reductases, with the k cat values ranging from 0.03 s ؊1 to 10 s ؊1 at 25°C. Kinetic spectroscopy of mutagenized glutathione reductase indicates that MB reduction is conducted by enzyme-bound reduced flavin rather than by the active-site dithiol Cys 58 /Cys 63 . The enzyme-catalyzed reduction of MB and subsequent auto-oxidation of the product leucoMB mean that MB is a redox-cycling agent which produces H 2 O 2 at the expense of O 2 and of NAD(P)H in each cycle, turning the antioxidant disulfide reductases into pro-oxidant enzymes. This explains the terms subversive substrate or turncoat inhibitor for MB. The results are discussed in cellpathological and clinical contexts. Methylene blue (MB or MBϩ ) [also known as methylthionine hydrochloride or 3,7-bis(dimethylamino)phenothiazin-5-ium chloride] was the very first synthetic compound to be used as a drug. Paul Ehrlich, who introduced the concept of modern target-based chemotherapy using MB as an example, and Paul Guttmann described the compound as being an effective antimalarial agent (28). Despite its beneficial antimalarial activity, the drug disappeared from the scene because up-and-coming compounds such as chloroquine were more effective; in addition, soldiers resented taking MB because of inevitable but harmless side effects: green or blue urine and bluish sclerae (47, 55).After MB was revisited as an antimalarial agent (6, 53) and found to be an inhibitor of Plasmodium falciparum glutathione (GSH) reductase (GR) (23), it was studied as a partner drug in antimalarial drug combinations (2,39,48,51).Compared with other antiparasitic agents, MB is affordable and registered in most countries (as the treatment of choice for acute and chronic methemoglobinemia [16,17,36]), and it can be made internationally available in sufficient dosages (51). The price for treating a malaria episode in a child with an MB-containing drug combination would be less than €0.50 (40). Drug resistance has not been reported for MB and could not be provoked in rodent malaria models (52, 53).Because of its favorable properties, including the differential staining of cell biological structures and protein cr...

show abstract

“…10 for other examples of chemical patterns driven by hydrodynamic instabilities.͒ The chemical reaction itself, sometimes called the blue bottle reaction, is well-documented. [11][12][13] As mentioned above, it consists of the alkaline oxidation of glucose by oxygen with methylene blue as a catalyst. The mixture is prepared and thoroughly mixed, thermostated for half an hour, further shaken and poured into an appropriate container ͑such as a Petri dish͒.…”

Section: Experimental Motivationmentioning

confidence: 99%

Chemoconvection: A chemically driven hydrodynamic instability

Bees

Pons

Sørensen

et al. 2001

The Journal of Chemical Physics

View full text Add to dashboard Cite

We describe theory and experiments concerning a chemical reaction, the alkaline oxidation of glucose with methylene blue as a catalyst, that is hypothesized to drive fluid motion via an overturning instability, as an example of a ''chemoconvective'' process. A theoretical model is developed to explain this phenomenon and linear analyses from steady and pseudosteady states are used to predict the basic length and time scales of the patterns which initially appear. These theoretical predictions, using kinetic parameters from recent independent experiments, are contrasted with results from pattern initiation experiments. Preliminary comparisons indicate good qualitative and quantitative agreement.

show abstract

The Blue Bottle Experiment - Simple Demonstration of Self-Organization

Cited by 22 publications

References 2 publications

A DFT investigation of the blue bottle experiment:E^∘_half-cellanalysis of autoxidation catalysed by redox indicators

A DFT investigation of the blue bottle experiment:E^∘_half-cellanalysis of autoxidation catalysed by redox indicators

Interactions of Methylene Blue with Human Disulfide Reductases and Their Orthologues fromPlasmodium falciparum

Chemoconvection: A chemically driven hydrodynamic instability

Contact Info

Product

Resources

About

The Blue Bottle Experiment - Simple Demonstration of Self-Organization

Cited by 22 publications

References 2 publications

A DFT investigation of the blue bottle experiment:E∘half-cellanalysis of autoxidation catalysed by redox indicators

A DFT investigation of the blue bottle experiment:E∘half-cellanalysis of autoxidation catalysed by redox indicators

Interactions of Methylene Blue with Human Disulfide Reductases and Their Orthologues fromPlasmodium falciparum

Chemoconvection: A chemically driven hydrodynamic instability

Contact Info

Product

Resources

About

A DFT investigation of the blue bottle experiment:E^∘_half-cellanalysis of autoxidation catalysed by redox indicators

A DFT investigation of the blue bottle experiment:E^∘_half-cellanalysis of autoxidation catalysed by redox indicators