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D-Desthiobiotin

Cat No.:V30254 Purity: ≥98%
D-Desthiobiotin is a biotin analogue used in affinity chromatography and protein chromatography.
D-Desthiobiotin
D-Desthiobiotin Chemical Structure CAS No.: 533-48-2
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
D-Desthiobiotin is a biotin analogue used in affinity chromatography and protein chromatography. D-Desthiobiotin can also be used for labeling, detection and isolation of proteins and cells.
D-Desthiobiotin (CAS#: 533-48-2) is a biotin derivative used in affinity chromatography and protein chromatography, as well as for protein and cell labeling, detection, and isolation. It is a modified form of biotin that binds less tightly to avidin and streptavidin than biotin while still providing excellent specificity in affinity purification methods. D-Desthiobiotin exhibits a variety of bioactivities across several targets and shows potency of 1000.0 against NCOR2. It is a protein cross-linking agent and a precursor in the synthesis of biotin. Its molecular formula is C10H18N2O3 with a molecular weight of 214.26 g/mol.
Biological Activity I Assay Protocols (From Reference)
Targets
D-Desthiobiotin targets avidin, streptavidin, and other biotin-binding proteins. Its strong affinity for avidin or streptavidin makes it useful in biotin-streptavidin-based assays. The compound binds to avidin and streptavidin with lower affinity compared to biotin, making it suitable for applications requiring temporary and reversible binding. D-Desthiobiotin also targets NCOR2 with a potency of 1000.0. As an endogenous metabolite, it participates in biotin-related metabolic pathways.
ln Vitro
In vitro, D-Desthiobiotin is used in affinity chromatography and protein chromatography for protein purification and isolation. Its applications extend to in vitro and in vivo protein labeling, detection, and cellular separation techniques within biochemical research. The compound's reversible binding to streptavidin and avidin makes it valuable for applications requiring temporary and reversible binding. D-Desthiobiotin is a versatile biotin analog employed in protein and cell labeling, detection, and isolation. It is a precursor in the synthesis of biotin.
ln Vivo
In vivo, D-Desthiobiotin is used for protein labeling, detection, and cellular separation techniques. Its applications extend to in vivo protein labeling and detection within biochemical research. The compound's reversible binding to streptavidin and avidin makes it suitable for in vivo applications where temporary binding is desired. D-Desthiobiotin is a biotin derivative used in various research applications. Further in vivo studies have evaluated its utility in protein labeling and detection systems.
Enzyme Assay
D-Desthiobiotin binding assays involve measuring affinity for avidin, streptavidin, and other biotin-binding proteins. Binding affinity is assessed using surface plasmon resonance, isothermal titration calorimetry, or fluorescence-based binding assays. The compound's lower affinity compared to biotin enables reversible binding studies. For NCOR2 binding, affinity assays are performed using appropriate detection methods. Assays are performed in appropriate buffer systems with positive controls such as biotin. Competitive binding assays may be used to determine relative binding affinities.
Cell Assay
D-Desthiobiotin cell-based assays are conducted in various cell types for protein labeling, detection, and cellular separation. Cells are cultured in appropriate media and treated with D-Desthiobiotin-conjugated probes. Labeling efficiency is assessed by fluorescence microscopy or flow cytometry. For affinity chromatography applications, cell lysates are passed through D-Desthiobiotin-conjugated affinity columns and bound proteins are eluted. Cell viability is assessed by standard assays. Experiments are performed with appropriate positive and negative controls.
Animal Protocol
D-Desthiobiotin in vivo studies are conducted in animal models for protein labeling and detection. Animals are administered D-Desthiobiotin-conjugated probes via injection. Tissue distribution and protein labeling are assessed by imaging or biochemical analysis. The compound's reversible binding properties enable studies where temporary labeling is desired. For cellular separation studies, cells are labeled with D-Desthiobiotin and isolated using affinity methods. Animals are monitored for clinical signs. Tissues are collected for histopathological and biochemical analysis at study endpoints. Studies are conducted in accordance with institutional animal care guidelines.
ADME/Pharmacokinetics
D-Desthiobiotin (MW 214.26 g/mol, C10H18N2O3) is a biotin derivative and protein cross-linking agent. It is a modified form of biotin lacking the thiophene ring. The compound is soluble in water and other appropriate solvents. It is stable under recommended storage conditions. D-Desthiobiotin is a precursor in the synthesis of biotin. Pharmacokinetic properties such as half-life, bioavailability, and tissue distribution would be determined in species-specific studies. The compound is typically used as a labeling reagent in research applications.
Toxicity/Toxicokinetics
D-Desthiobiotin is generally well-tolerated as a research reagent. The compound is a biotin derivative with established safety profiles for in vitro and in vivo applications. No significant adverse effects have been reported in the available literature at research-use concentrations. The compound is intended for research use only. Standard laboratory safety practices should be employed when handling this compound. Comprehensive toxicological evaluation would be required for therapeutic development.
References

[1]. Toward a Hybrid Biosensor System for Analysis of Organic and Volatile Fatty Acids in Fermentation Processes. Front Chem. 2018 Jul 17;6:284.

[2]. Secondary anchor targeted cell release. Biotechnol Bioeng

[3]. Expression and biochemical characterization of the human enzyme N-terminal asparagine amidohydrolase. Biochemistry. 2011 Apr 12;50(14):3025-33.

[4]. Biotin Enhances Testosterone Production in Mice and Their Testis-Derived Cells. Nutrients. 2022 Nov 10;14(22):4761.

Additional Infomation
(4R,5S)-Dethiobiotin is the (4R,5S)-isomer of dethiobiotin. It is the conjugate acid of (4R,5S)-dethiobiotin(1-). It is the enantiomer of (4S,5R)-dethiobiotin. Dethiobiotin is a metabolite found or produced in Escherichia coli (K12 strain, MG1655 strain). Dethiobiotin has been reported to be detected in Scaphyglottis livida, and relevant data are available. Dethiobiotin is a metabolite found or produced in Saccharomyces cerevisiae. See also: dl-dethiobiotin (note moved to).
D-Desthiobiotin is a biotin derivative used in affinity chromatography and protein chromatography for protein purification and isolation. It binds to avidin and streptavidin with lower affinity than biotin, enabling reversible binding applications. The compound is used for protein and cell labeling, detection, and separation. D-Desthiobiotin targets NCOR2 with a potency of 1000.0. All applications are limited to non-human research use.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C10H17N2O3-
Molecular Weight
213.25358
Exact Mass
214.131
CAS #
533-48-2
Related CAS #
D-Desthiobiotin; 533-48-2
PubChem CID
445027
Appearance
White to off-white solid powder
Density
1.1±0.1 g/cm3
Boiling Point
476.4±18.0 °C at 760 mmHg
Melting Point
156-158 °C
Flash Point
241.9±21.2 °C
Vapour Pressure
0.0±2.6 mmHg at 25°C
Index of Refraction
1.473
Source
Endogenously produced metabolite: Human Gut Microbiota Metabolites
Originated from microorganisms: Synechococcus elongatus
LogP
0.31
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
6
Heavy Atom Count
15
Complexity
243
Defined Atom Stereocenter Count
2
SMILES
C[C@H]1[C@H](NC(N1)=O)CCCCCC(O)=O
InChi Key
AUTOLBMXDDTRRT-JGVFFNPUSA-N
InChi Code
InChI=1S/C10H18N2O3/c1-7-8(12-10(15)11-7)5-3-2-4-6-9(13)14/h7-8H,2-6H2,1H3,(H,13,14)(H2,11,12,15)/t7-,8+/m0/s1
Chemical Name
6-[(4R,5S)-5-methyl-2-oxoimidazolidin-4-yl]hexanoic acid
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~62.5 mg/mL (~291.70 mM)
H2O : ~1 mg/mL (~4.67 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (9.71 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (9.71 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (9.71 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


Solubility in Formulation 4: 3.7 mg/mL (17.27 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication (<60°C).

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.6893 mL 23.4467 mL 46.8933 mL
5 mM 0.9379 mL 4.6893 mL 9.3787 mL
10 mM 0.4689 mL 2.3447 mL 4.6893 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration: mg/mL;

Method for preparing DMSO stock solution: mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation::Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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