Dicyanocobinamide

Manufactured by Merck Group

Dicyanocobinamide is a laboratory chemical compound used in various analytical and research applications. It is a form of cobalamin, a class of organometallic compounds containing a cobalt ion. Dicyanocobinamide serves as a precursor or intermediate in the synthesis of other cobalamin-related compounds. Its core function is to provide a source of the cobalt ion for further chemical transformations or analyses, without making claims about its specific intended uses.

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Lab products found in correlation

Cyanocobalamin, by Merck Group (2 mentions) Cobalamin, by Greiner (2 mentions) Uv star 675801, by Agilent Technologies (2 mentions) Synergy 2, by Tecan (2 mentions) Methylcobalamin, by Merck Group (2 mentions) Adenosylcobalamin, by Merck Group (2 mentions) Hydroxocobalamin, by Merck Group (2 mentions) Infinite m1000 pro, by Tecan (2 mentions) Optima lc ms grade, by Thermo Fisher Scientific (1 mentions) Ginsenoside rb1, by Merck Group (1 mentions) Cn 2cbi, by Merck Group (1 mentions) Hcook, by Merck Group (1 mentions) Sodium borohydride, by Merck Group (1 mentions) Hydroxocobalamin hydrochloride, by Merck Group (1 mentions) Potassium formate, by Merck Group (1 mentions)

Spelling variants of this product

Dicyanocobinamide (Cbi, (2 citations)

6 protocols using dicyanocobinamide

Quantification of Dicyanocobinamide and Dinitrocobinamide in Pig Plasma

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Dicyanocobinamide (100%) was purchased from Sigma-Aldrich (St. Louis, MO). Dinitrocobinamide (91.0%) was obtained from SRI International (Menlo Park, CA). Ginsenoside Rb1 (93.28%), purchased from Sigma-Aldrich, was used as the internal standard (IS) during the extraction and analysis. Stock solutions of Dicyanocobinamide and dinitrocobinamide were each prepared at a concentration of 2,000 µg/mL in water. Subsequent working stock solutions of Dicyanocobinamide and dinitrocobinamide were prepared in water from the stock solutions for use in preparation of calibration standards and QC samples. Stock solutions of Ginsenoside Rb1 were prepared at a concentration of 1,000 µg/mL in methanol. Working stock solutions of Ginsenoside Rb1 were prepared in methanol from the stock solutions at 120 µg/mL. All water, methanol, and acetonitrile used for extractions and for the preparation of standards and mobile phases were Optima™ LC/MS-grade (Fisher Scientific, Hampton, NH).
Seven different sources of Yorkshire pig plasma was obtained from Bioreclamation, LLC (Westbury, NY) containing tri-potassium EDTA and was stored at ≤ −20°C. The plasma was thawed unassisted at room temperature and was spiked appropriately with the working stock solutions to prepare the different calibration standard levels and QC samples described below.

McCracken B.A, & Brittain M.K. (2015). High Performance Liquid Chromatography Tandem Mass Spectrometry Assay for the Determination of Cobinamide in Pig Plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 1006, 104-111.

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Efficient Synthesis of (H2O)OHCbi

Cited 1 time

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Ten milligrams of (CN)₂Cbi or dicyanocobinamide (Sigma-Aldrich), whose UV–visible spectrum was identical to the reported spectrum,^{35 (link),36 (link)} was dissolved in 3 mL of anaerobic 0.1 M NaOH, and small aliquots of sodium borohydride pellets were added every 5 min, until a molar excess of about 10-fold of borohydride over (CN)₂Cbi was reached. The reaction proceeded for about 1.5 h until the mixture was tranferred into a beaker and quenched by the addition of acidified water. The final pH was adjusted to 3, and the mixture was purified over a 1 g Sep Pak C₁₈ reverse phase column (Waters). The column was preconditioned prior to sample loading by washing once with 100% methanol and five times thereafter with 0.1% (v/v) TFA (trifluoroacetic acid). After the sample had passed through the column, salts were removed by washing with 0.1% TFA for five column volumes. This was followed by elution with 100% methanol, and the collected orange fractions were evaporated overnight at room temperature. The collected product (6 mg) was identified as (H₂O)OHCbi by its UV–visible absorption spectrum, which was identical to the spectrum reported in the literature.^{35 (link),36 (link)}

Parthasarathy A., Stich T.A., Lohner S.T., Lesnefsky A., Britt R.D, & Spormann A.M. (2015). Biochemical and EPR-Spectroscopic Investigation into Heterologously Expressed Vinyl Chloride Reductive Dehalogenase (VcrA) from Dehalococcoides mccartyi Strain VS. Journal of the American Chemical Society, 137(10), 3525-3532.

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Synthesis and Characterization of Cobalamin Derivatives

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The chloride salt of aquacobalamin
([H₂OCbl]Cl), dicyanocobinamide [(CN)₂Cbi],
and potassium formate (HCOOK) were purchased from Sigma and used as
obtained. Diaquacobinamide {[(H₂O)₂Cbi]²⁺} was prepared by adding NaBH₄ to an aqueous solution
of (CN)₂Cbi, loading the reaction mixture on a C18 SepPack
column, washing it with doubly distilled H₂O, and eluting
the product with methanol, as described in previous reports.^{24 (link),30 (link)} Co(II)Cbl and Co(II)Cbi⁺ were prepared by adding a small
volume of saturated HCOOK to degassed solutions of H₂OCbl⁺ and (H₂O)₂Cbi²⁺, respectively,
and the progress of the reduction was monitored spectrophotometrically.

Pallares I.G., Moore T.C., Escalante-Semerena J.C, & Brunold T.C. (2014). Spectroscopic Studies of the Salmonella enterica Adenosyltransferase Enzyme SeCobA: Molecular-Level Insight into the Mechanism of Substrate Cob(II)alamin Activation. Biochemistry, 53(50), 7969-7982.

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Synthesis and Purification of Diaquacobinamide

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Dicyanocobinamide [(CN)₂Cbi], hydroxocobalamin hydrochloride [HOCbl·HCl], sodium borohydride (NaBH₄), and potassium formate (HCOOK) were purchased from Sigma Aldrich and used without further purification. Diaquacobinamide (H₂O)₂Cbi²⁺ was prepared from (CN)₂Cbi according to the following procedure. About 3–5 mg of (CN)₂Cbi were dissolved in 5 mL MilliQ water and sparged for 60 min with N₂. The red/purple solution was then transferred via cannula to a sealed vial containing ~27 mg NaBH₄ and left stirring overnight under a slow stream of N₂. The resulting brown/purple solution was re-oxidized in air over several hours. Once fully oxidized, the solution was loaded onto a C18 Sep Pak column, washed with (i) ultrapure water (30 mL), (ii) a 20% methanol solution until the orange-colored band moved towards the eluting end of the column, and (iii) again with ultrapure water (10 mL), and finally eluted with 100% methanol. Purified (H₂O)₂Cbi²⁺ was collected under vacuum. Co(II)Cbl and Co(II)Cbi⁺ were generated anaerobically by reduction of aqueous solutions of HOCbl and (H₂O)₂Cbi²⁺ with ~40–60 μL of a saturated solution of HCOOK. The progress of the reduction was monitored spectrophotometrically.

Stracey N.G., Costa F.G., Escalante-Semerena J.C, & Brunold T.C. (2018). Spectroscopic Study of the EutT Adenosyltransferase from Listeria monocytogenes: Evidence for the Formation of a Four-Coordinate Cob(II)alamin Intermediate.. Biochemistry, 57(34), 5088-5095.

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Corrinoid Spectroscopic Characterization

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Cyano cobalamin, adenosyl cobalamin, methyl cobalamin, hydroxo cobalamin, and dicyanocobinamide were purchased from MilliporeSigma. All other corrinoids used in this study were produced in bacterial cultures and purified in cyanated form as previously described (Mok and Taga, 2013; Sokolovskaya et al., 2019; Sokolovskaya et al., 2020; Yi et al., 2012) . For the experiments in Figures 4 andS7, corrinoids other than cobalamin were chemically adenosylated to obtain the coenzyme (5'-deoxyadenosylated) form as previously described (Sokolovskaya et al., 2019; Sokolovskaya et al., 2020) .
UV/Vis spectra were collected from corrinoid samples in UV/Vis-transparent 96-well microtiter plates (greiner bio-one UV-STAR® 675801) using a BioTek Synergy 2 or Tecan Infinite M1000 Pro plate reader. To measure concentrations of corrinoid stock solutions, corrinoid samples were diluted 10-fold in 10 mM sodium cyanide to obtain the dicyanated base-off form of the corrinoid. The concentration of the dicyanated corrinoid was calculated using the extinction coefficient ε580 = 10.1 mM -1 cm -1 (Mok et al., 2020; Stupperich et al., 1988) . For adenosylated corrinoids used in Figures 4 andS7, base-on/off constitution at neutral pH was measured as the ratio of spectral absorbance at 525 nm and 458 nm in phosphate buffered saline solution pH 7.3 at 37°C (Fieber et al., 2002; Hoffmann et al., 2000) .

Kennedy K.J., Widner F.J., Sokolovskaya O.M., Innocent L.V., Procknow R.R., Mok K.C., & Taga M.E. (2022). Cobalamin riboswitches are broadly sensitive to corrinoid cofactors to enable an efficient gene regulatory strategy.

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Quantification and Characterization of Corrinoids

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Cyano cobalamin, adenosyl cobalamin, methyl cobalamin, hydroxo cobalamin, and dicyanocobinamide were purchased from MilliporeSigma. All other corrinoids used in this study were produced in bacterial cultures and purified in cyanated form as previously described (82 (link), 95 (link), 117 , 118 (link)). For the experiments in Fig. 4 and Fig. S5, corrinoids other than cobalamin were chemically adenosylated to obtain the coenzyme (5′-deoxyadenosylated) form as previously described (82 (link), 117 ).
UV/Vis spectra were collected from corrinoid samples in UV/Vis-transparent 96-well microtiter plates (greiner bio-one UV-STAR 675801) using a BioTek Synergy 2 or Tecan Infinite M1000 Pro plate reader. To measure concentrations of corrinoid stock solutions, corrinoid samples were diluted 10-fold in 10 mM sodium cyanide to obtain the dicyanated base-off form of the corrinoid. The concentration of the dicyanated corrinoid was calculated using the extinction coefficient ε580 = 10.1 mM⁻¹ cm⁻¹ (52 (link), 119 (link)). For adenosylated corrinoids used in Fig. 4 and Fig. S5, base-on tendency at neutral pH was measured as the ratio of spectral absorbance at 525 nm and 458 nm in phosphate-buffered saline solution pH 7.3 at 37°C (47 (link), 59 (link)).

Kennedy K.J., Widner F.J., Sokolovskaya O.M., Innocent L.V., Procknow R.R., Mok K.C, & Taga M.E. (2022). Cobalamin Riboswitches Are Broadly Sensitive to Corrinoid Cofactors to Enable an Efficient Gene Regulatory Strategy. mBio, 13(5), e01121-22.

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