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sBADA

Cat No.:V85035 Purity: ≥98%
sBADA
sBADA Chemical Structure CAS No.: 2376838-11-6
Product category: Fluorescent Dye
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
Other Sizes
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Product Description
sBADA is an effective green fluorescent dye. sBADA is a sulfonated BODIPY-FL 3-amino-D-alanine. sBADA is used for in situ labeling of peptidoglycan in bacterial cell walls. (λex=490 nm, λem=510 nm).
sBADA (CAS#: 2376838-11-6) is a green sulfonated BODIPY-FL 3-amino-D-alanine (sBADA), also known as a fluorescent D-amino acid (FFDA). It has the molecular formula C17H21BF2N4O6S and a molecular weight of 458.24. sBADA is used as a fluorescent probe for labeling peptidoglycans in live bacterial cell walls in situ. The compound exhibits excitation/emission wavelengths of approximately 490/510 nm and has an extinction coefficient of 49,000 M-1cm-1. It is a sulfonated form of BADA with increased hydrophilicity and thermostability. sBADA is soluble in DMSO to 10 mM and should be stored at -20°C. The compound is widely used in microbiology research for studying bacterial cell wall synthesis, peptidoglycan dynamics, and bacterial morphology.
Biological Activity I Assay Protocols (From Reference)
Targets
sBADA targets bacterial peptidoglycan, the major structural component of the bacterial cell wall. Peptidoglycan is a mesh-like polymer composed of alternating N-acetylglucosamine (NAG) and N-acetylmuramic acid (NAM) residues cross-linked by short peptide chains. It provides structural integrity and shape to bacterial cells and is a critical target for antibiotics such as penicillin and vancomycin. sBADA is a fluorescent D-amino acid that is incorporated into the peptidoglycan of live bacteria through the action of transpeptidases and other enzymes involved in cell wall synthesis. By labeling peptidoglycan, sBADA enables visualization of bacterial cell wall synthesis and dynamics in real time. The sulfonated modification enhances the compound's hydrophilicity and thermostability compared to the parent compound BADA, improving its performance in aqueous biological environments.
ln Vitro
sBADA is used as a fluorescent probe for in situ labeling of peptidoglycans in live bacteria. It is a green fluorescent dye with excitation/emission wavelengths of approximately 490/510 nm. The compound's fluorescence allows for visualization of bacterial cell walls using fluorescence microscopy, enabling researchers to study peptidoglycan synthesis, dynamics, and bacterial morphology in real time. sBADA is particularly useful for studying bacterial cell division, as incorporation of the fluorescent D-amino acid into nascent peptidoglycan can be used to label sites of active cell wall synthesis. The sulfonated form of BADA has increased hydrophilicity and thermostability, which improves its performance in aqueous biological environments. The extinction coefficient of 49,000 M-1cm-1 indicates strong fluorescence, enabling sensitive detection.
ln Vivo
In vivo activity of sBADA is not applicable in the context of therapeutic or pharmacological activity, as the compound is a fluorescent probe rather than a drug. Its "in vivo" application refers to its use in live bacteria for labeling peptidoglycans. sBADA can be applied to live bacterial cultures, where it is incorporated into the peptidoglycan of growing bacteria, enabling real-time imaging of cell wall dynamics. It has been used to label peptidoglycans in various bacterial species, including both Gram-positive and Gram-negative bacteria. The sulfonated form offers improved hydrophilicity and thermostability, making it suitable for use in complex biological environments. The compound's green fluorescence allows for easy detection using standard fluorescence microscopy equipment. However, sBADA has no pharmacological activity in animal models and is not used as a therapeutic agent.
Enzyme Assay
In vitro enzyme or receptor binding assay protocols are not directly applicable to sBADA, as it is a fluorescent probe rather than an enzyme inhibitor or receptor ligand. However, protocols for its use involve labeling of peptidoglycans in bacterial cells. A typical protocol involves preparing a bacterial culture in exponential growth phase, adding sBADA to the culture at concentrations typically ranging from 10 to 500 μM, and incubating for a defined period (e.g., 5-60 minutes) at the appropriate growth temperature. After labeling, bacteria are washed to remove excess probe, and samples are prepared for fluorescence microscopy or flow cytometry. For microscopy, bacteria are fixed or mounted directly on slides and imaged using a fluorescence microscope with appropriate filter sets (excitation ~490 nm, emission ~510 nm). The probe can also be used for pulse-chase experiments to study peptidoglycan turnover and dynamics. Appropriate controls include unlabeled bacteria and bacteria labeled with the parent compound BADA for comparison.
Cell Assay
In vitro cell-based assay protocols for sBADA involve labeling live bacteria with the fluorescent probe to study peptidoglycan dynamics. A standard protocol would involve growing bacteria (e.g., Escherichia coli, Bacillus subtilis, or other species) in liquid culture to mid-log phase (OD600 ~0.4-0.6). sBADA is added to the culture at concentrations ranging from 10 to 500 μM, and the culture is incubated at 37°C (or appropriate growth temperature) for 5-60 minutes. After labeling, bacteria are harvested by centrifugation, washed with PBS or growth medium to remove excess probe, and resuspended in an appropriate buffer. For microscopy, a small aliquot of labeled bacteria is placed on a glass slide, covered with a coverslip, and imaged using a fluorescence microscope with a 490 nm excitation filter and a 510 nm emission filter. For flow cytometry, labeled bacteria are analyzed using a flow cytometer equipped with a 488 nm laser and appropriate emission filters. The probe can also be used in pulse-chase experiments, where labeled bacteria are washed and incubated in probe-free medium to follow peptidoglycan turnover.
Animal Protocol
In vivo animal experimental protocols are not applicable to sBADA, as the compound is used as a fluorescent probe for labeling bacteria rather than as a drug for animal studies. However, sBADA could potentially be used in ex vivo or in situ labeling of bacteria in infected tissues or in animal models of infection. A hypothetical protocol for such applications would involve administering sBADA locally (e.g., by injection into infected tissues) or applying it to tissue samples ex vivo, followed by fluorescence microscopy to visualize bacteria. The sulfonated modification of sBADA enhances its hydrophilicity, which may improve its performance in complex biological environments such as tissues. However, specific protocols for in vivo or ex vivo applications in animal models have not been extensively reported. The compound is not intended for therapeutic use and should not be administered systemically to animals for pharmacological purposes.
ADME/Pharmacokinetics
Pharmacokinetic properties are not applicable to sBADA in the context of drug development, as the compound is a fluorescent probe used for labeling bacteria rather than a therapeutic agent. However, the compound's physicochemical properties are relevant to its use as a probe. sBADA is a sulfonated BODIPY-FL derivative with improved hydrophilicity and thermostability compared to the parent compound BADA. It is soluble in DMSO to 10 mM and exhibits strong green fluorescence with excitation/emission at ~490/510 nm. The compound should be stored at -20°C for long-term stability. The sulfonated modification increases water solubility, which is advantageous for applications in aqueous biological environments. However, specific PK parameters such as half-life, volume of distribution, clearance, and bioavailability are not relevant to its use as a research probe.
Toxicity/Toxicokinetics
Toxicological data for sBADA are limited, as the compound is intended for research use only and has not undergone systematic toxicity testing. No acute toxicity (LD50), subchronic toxicity, genotoxicity, or reproductive toxicity studies have been reported specifically for this compound. As with all fluorescent dyes, potential hazards may include skin and eye irritation, and appropriate safety precautions should be taken when handling the compound. The compound is not intended for human use and should be handled with standard laboratory safety practices, including wearing appropriate personal protective equipment, working in a fume hood, and avoiding inhalation, ingestion, or skin contact. Researchers should consult the material safety data sheet (MSDS) for specific safety information and handling recommendations. The compound should be stored at -20°C as recommended.
References

[1].Hsu YP, et, al. Full color palette of fluorescent d-amino acids for in situ labeling of bacterial cell walls. Chem Sci. 2017 Sep 1;8(9):6313-6321.

Additional Infomation
sBADA is a research-grade fluorescent probe used for labeling peptidoglycans in live bacterial cell walls. It is a green sulfonated BODIPY-FL 3-amino-D-alanine (sBADA) or fluorescent D-amino acid (FFDA). The compound exhibits excitation/emission wavelengths of approximately 490/510 nm and has an extinction coefficient of 49,000 M-1cm-1. The sulfonated modification provides increased hydrophilicity and thermostability compared to the parent compound BADA. sBADA is used in microbiology research to study bacterial cell wall synthesis, peptidoglycan dynamics, and bacterial morphology. It has not entered clinical trials and is not approved for any therapeutic indication. Its mechanism of action involves incorporation into bacterial peptidoglycan through the action of transpeptidases and other cell wall synthesis enzymes, enabling visualization of active cell wall synthesis. The compound is available exclusively for research purposes and is not intended for diagnostic, therapeutic, or human applications.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Exact Mass
458.124
CAS #
2376838-11-6
PubChem CID
138991774
Appearance
Solid powder
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
10
Rotatable Bond Count
7
Heavy Atom Count
31
Complexity
1010
Defined Atom Stereocenter Count
1
SMILES
[B-]1(N2C(=CC(=C2C=C3[N+]1=C(C(=C3)S(=O)(=O)O)CCC(=O)NC[C@H](C(=O)O)N)C)C)(F)F
InChi Key
OLMGTLBVHKBMSH-GFCCVEGCSA-N
InChi Code
InChI=1S/C17H21BF2N4O6S/c1-9-5-10(2)23-14(9)6-11-7-15(31(28,29)30)13(24(11)18(23,19)20)3-4-16(25)22-8-12(21)17(26)27/h5-7,12H,3-4,8,21H2,1-2H3,(H,22,25)(H,26,27)(H,28,29,30)/t12-/m1/s1
Chemical Name
(2R)-2-amino-3-[3-(2,2-difluoro-10,12-dimethyl-5-sulfo-1-aza-3-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-3,5,7,9,11-pentaen-4-yl)propanoylamino]propanoic 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

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light.
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)
Typically soluble in DMSO (e.g. 10 mM)
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Calculator

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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
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
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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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