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CybLuc

Alias: Cyb-Luc; Cyb Luc; 1649470-26-7; N-Cyclobutylaminoluciferin; (4S)-2-[6-(Cyclobutylamino)benzo[d]thiazol-2-yl]-4,5-dihydrothiazole-4-carboxylic acid; orb1697634; SCHEMBL29360346; CybLuc
Cat No.:V18930 Purity: ≥98%
CybLuc is an aminoluciferin analogue
CybLuc
CybLuc Chemical Structure CAS No.: 1649470-26-7
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price
500mg
1g
Other Sizes
Official Supplier of:
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Product Description

CybLuc is an aminoluciferin derivative for deep bioluminescence imaging.

The effectiveness of in vivo bioluminescence imaging (BLI) is hampered by the significant absorption and scattering of shorter wavelength light (<600 nm) by blood and tissues, which weakens the signal from conventional D-luciferin. CybLuc addresses these shortcomings by offering a red-shifted emission spectrum (max. 600 nm) for improved tissue penetration. Coupled with its greater lipophilicity and metabolic stability, these properties make CybLuc an ideal agent for in vivo studies.
Biological Activity I Assay Protocols (From Reference)
Targets
Bioluminescence imaging agent; Firefly luciferase (enzyme substrate). Acts as a superior substrate for bioluminescence imaging compared to D-luciferin.
ln Vitro
In Vitro: CybLuc is an effective aminoluciferin derivative designed for deep bioluminescence imaging. It exhibits properties superior to D-luciferin.
ln Vivo
In Vivo: CybLuc demonstrates effectiveness in deep bioluminescence imaging applications in mouse models. It provides a rapid (4-5 minutes), long-lasting, and steady signal peak following intravenous (i.v.) injection in mice. It is shown to readily cross the blood-brain barrier and provides much improved noninvasive bioluminescence imaging (BLI) of the brain at a lower dose compared to D-luciferin. It yields about a 10-fold higher bioluminescent signal than D-luciferin in certain implanted cancer cell models (e.g., Luc2 luciferase-expressing 4T1 breast cancer cells implanted into the mammary fat pads of BABL/c mice).
Animal Protocol
Animal Protocol: In mouse studies, CybLuc is administered via intravenous (i.v.) injection. A rapid (4-5 min), long-lasting, and steady signal peak is observed following the injection.
References
[1]. cybLuc: An Effective Aminoluciferin Derivative for Deep Bioluminescence Imaging. Anal Chem. 2017 May 2;89(9):4808-4816.
Additional Infomation
CybLuc (CAS: 1649470-26-7) is a synthetic aminoluciferin derivative. It exhibits a higher affinity for luciferase and a luminescence intensity approximately 5.7 times that of aminoluciferin and 3.2 times that of D-luciferin. Its excellent light output is maintained over a wide concentration range (1-100 µM). It has been used in research related to glioma imaging and therapeutic development. To improve the efficiency of firefly luciferase/luciferin bioluminescence imaging, researchers developed a series of N-cycloalkyl aminoluciferins (cyaLuc) by introducing lipophilic N-cycloalkyl substituents. Experimental results show that these cyaLuc are effective substrates for natural firefly luciferase (Fluc), capable of generating enhanced bioluminescent signals in vitro, intracellularly, and in vivo. Notably, in animal experiments, the bioluminescence intensity of N-cyclobutylaminofluorescein (cybLuc) at a concentration of 10 μM (0.1 mL)—only 0.01% of the standard dose of d-luciferin (dLuc) commonly used in mouse imaging—was 20 times that of the same concentration of d-luciferin (dLuc) or aminoluciferin (aLuc). Longer in vivo emission imaging using cybLuc suggests that it can be used for long-term observation. Regarding the mechanism of action of cybLuc, the co-crystal structure data of firefly luciferase and oxidized cybLuc obtained by us indicate that oxidized cybLuc binds to oxidized luciferin in the same pocket. Most importantly, our results suggest that the high sensitivity of cybLuc in brain tumor imaging makes it a promising candidate for wider application in deep tissues. [1]
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C15H15N3O2S2
Molecular Weight
333.4
Exact Mass
333.0606
Elemental Analysis
C, 54.03; H, 4.53; N, 12.60; O, 9.60; S, 19.23
CAS #
1649470-26-7
PubChem CID
139593819
Appearance
Typically exists as solid at room temperature
LogP
3.5
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
7
Rotatable Bond Count
4
Heavy Atom Count
22
Complexity
483
Defined Atom Stereocenter Count
1
SMILES
C1CC(C1)NC2=CC3=C(C=C2)N=C(S3)C4=N[C@H](CS4)C(=O)O
InChi Key
DRLXXHYUKOJAOR-LLVKDONJSA-N
InChi Code
InChI=1S/C15H15N3O2S2/c19-15(20)11-7-21-13(18-11)14-17-10-5-4-9(6-12(10)22-14)16-8-2-1-3-8/h4-6,8,11,16H,1-3,7H2,(H,19,20)/t11-/m1/s1
Chemical Name
(4S)-2-[6-(cyclobutylamino)-1,3-benzothiazol-2-yl]-4,5-dihydro-1,3-thiazole-4-carboxylic acid
Synonyms
Cyb-Luc; Cyb Luc; 1649470-26-7; N-Cyclobutylaminoluciferin; (4S)-2-[6-(Cyclobutylamino)benzo[d]thiazol-2-yl]-4,5-dihydrothiazole-4-carboxylic acid; orb1697634; SCHEMBL29360346; CybLuc
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)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.9994 mL 14.9970 mL 29.9940 mL
5 mM 0.5999 mL 2.9994 mL 5.9988 mL
10 mM 0.2999 mL 1.4997 mL 2.9994 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.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
An example of molarity calculation using the molarity calculator is shown below:
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?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

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:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • 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:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
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)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
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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