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CycLuc1

Alias: CycLuc1 CycLuc 1CycLuc-1
CycLuc1,a synthetic luciferase substrate, is a brain penetrant luciferase substrate which displays NIR emission.
CycLuc1
CycLuc1 Chemical Structure CAS No.: 1247879-16-8
Product category: Reactive Oxygen Species
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
CycLuc1, a synthetic luciferase substrate, is a brain penetrant luciferase substrate which displays NIR emission. It improves bioluminescence imaging for intracranial glioblastoma xenografts.
CycLuc1 (CAS#: 1247879-16-8) is a synthetic cyclic alkylaminoluciferin substrate for firefly luciferase, specifically engineered to address the physicochemical and pharmacokinetic limitations of the natural substrate D-luciferin in bioluminescence imaging (BLI) applications. It is a small molecule with a molecular formula of C₁₃H₁₁N₃O₂S₂ and a molecular weight of approximately 305.38 g/mol. CycLuc1 is a brain-penetrant luciferase substrate that may be a superior BLI substrate compared to D-luciferin for monitoring tumor growth, particularly in intracranial models. It is supplied as a yellow to brown solid powder with a purity of ≥98%. For research use, it is typically stored at -20°C, protected from light.
Biological Activity I Assay Protocols (From Reference)
Targets
CycLuc1 is a substrate for firefly luciferase, an enzyme that catalyzes the oxidation of luciferin in the presence of ATP, magnesium, and oxygen, producing light (bioluminescence). Upon administration, CycLuc1 is taken up by cells and tissues, where it is metabolized by firefly luciferase to produce a bioluminescent signal. The compound has been engineered to have superior properties compared to D-luciferin, including enhanced brain penetration and red-shifted luminescence. Its primary "target" is the luciferase enzyme, which is used as a reporter in BLI applications. The signal produced by CycLuc1 can be detected by a sensitive camera, allowing for the non-invasive monitoring of biological processes in living animals.
ln Vitro
CycLuc1 demonstrates superior in vitro performance compared to D-luciferin. It has been shown to be a superior BLI substrate for monitoring tumor growth, with a signal that is up to 10 times brighter than D-luciferin. This enhanced signal intensity allows for more sensitive detection of small tumors and deeper tissues. The compound's red-shifted luminescence also improves tissue penetration. In vitro, the compound is used in luciferase assays to measure luciferase activity, where it produces a strong and stable luminescent signal. Its physicochemical properties include a molecular weight of 305.38 g/mol and solubility in DMSO at up to 40 mg/mL.
ln Vivo
In vivo, CycLuc1 has been shown to be a superior BLI substrate compared to D-luciferin for monitoring tumor growth, particularly in intracranial glioblastoma xenografts. Its brain-penetrant properties allow for the detection of luciferase-expressing tumors in the brain, which is not possible with D-luciferin due to its poor brain penetration. The compound produces a brighter and more sustained bioluminescent signal, enabling more accurate and sensitive monitoring of tumor growth and response to therapy. It is used in a variety of in vivo imaging applications, including the study of tumor progression, metastasis, and drug efficacy.
Enzyme Assay
In vitro luciferase assays for CycLuc1 are performed to measure its substrate activity. In a typical assay, firefly luciferase is incubated with CycLuc1, ATP, and Mg²⁺ in a suitable buffer (e.g., 25 mM Tris-glycine, pH 7.8, 15 mM MgSO₄, 5 mM ATP). The bioluminescence signal is measured using a luminometer. The signal intensity is compared to that of D-luciferin to assess the compound's relative activity. The assay can be used to optimize conditions for in vivo imaging and to study the kinetics of the luciferase reaction.
Cell Assay
In vitro cell-based assays for CycLuc1 are performed using cells that express firefly luciferase. Cells are cultured in a suitable medium and incubated with CycLuc1. The bioluminescence signal is measured using a plate reader equipped with a luminescence detection module. The signal intensity is a measure of luciferase activity and cell viability. The compound can be used to monitor luciferase expression in real-time and to study the effects of various treatments on luciferase activity.
Animal Protocol
In vivo animal studies for CycLuc1 are typically conducted in mouse models of cancer. Mice are implanted with luciferase-expressing tumor cells (e.g., glioblastoma cells), and the compound is administered via intravenous or intraperitoneal injection. Bioluminescence imaging is performed using an in vivo imaging system, and the signal is quantified. The compound's ability to detect tumors and monitor tumor growth over time is assessed. Its brain-penetrant properties are evaluated by comparing the signal in the brain to that obtained with D-luciferin.
ADME/Pharmacokinetics
CycLuc1 has a molecular weight of 305.38 g/mol and a molecular formula of C₁₃H₁₁N₃O₂S₂. It is soluble in DMSO at 40 mg/mL. For in vivo administration, it is typically dissolved in a suitable buffer (e.g., PBS) and administered via injection. The compound is light-sensitive and should be stored at -20°C, protected from light. Its pharmacokinetic properties are characterized by rapid distribution and clearance, typical of a small molecule.
Toxicity/Toxicokinetics
The toxicological profile of CycLuc1 is not extensively documented. As a research compound, its safety profile would be evaluated in preclinical studies. For laboratory handling, standard safety precautions for research chemicals should be observed, including the use of personal protective equipment (gloves, lab coat, safety goggles) and working in a well-ventilated area. The compound is intended for research use only and is not for human therapeutic or diagnostic use.
References

[1]. Abstract 4112: Synthetic luciferin, CycLuc1, improves bioluminescence imaging for intracranial glioblastoma xenografts. 10.1158/1538-7445.AM2018-4112.

[2]. A synthetic luciferin improves bioluminescence imaging in live mice. Nat Methods. 2014 Apr;11(4):393-5. doi: 10.1038/nmeth.2839. Epub 2014 Feb 9. Erratum in: Nat Methods. 2014 Apr;11(4):395.

Additional Infomation
CycLuc1 is a synthetic cyclic alkylaminoluciferin substrate for firefly luciferase. It has a molecular formula of C₁₃H₁₁N₃O₂S₂ and a molecular weight of approximately 305.38 g/mol. The compound is a brain-penetrant luciferase substrate that produces a signal up to 10 times brighter than D-luciferin. It is used for in vivo bioluminescence imaging, particularly for monitoring tumor growth in intracranial models. CycLuc1 is supplied as a yellow to brown solid powder with a purity of ≥98%. It is for research use only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C₁₃H₁₁N₃O₂S₂
Molecular Weight
305.375339746475
Exact Mass
305.029
CAS #
1247879-16-8
PubChem CID
91885395
Appearance
Yellow to brown solid powder
Density
1.8±0.1 g/cm3
Boiling Point
606.8±65.0 °C at 760 mmHg
Flash Point
320.8±34.3 °C
Vapour Pressure
0.0±1.8 mmHg at 25°C
Index of Refraction
1.929
LogP
1.01
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
7
Rotatable Bond Count
2
Heavy Atom Count
20
Complexity
459
Defined Atom Stereocenter Count
1
SMILES
C1CNC2=CC3=C(C=C21)N=C(S3)C4=N[C@H](CS4)C(=O)O
InChi Key
HBZBAMXERPYTFS-SECBINFHSA-N
InChi Code
InChI=1S/C13H11N3O2S2/c17-13(18)9-5-19-11(16-9)12-15-8-3-6-1-2-14-7(6)4-10(8)20-12/h3-4,9,14H,1-2,5H2,(H,17,18)/t9-/m1/s1
Chemical Name
(4S)-2-(6,7-Dihydro-5H-pyrrolo[3,2-f]benzothiazol-2-yl)-4,5-dihydro-4-thiazolecarboxylic acid
Synonyms
CycLuc1 CycLuc 1CycLuc-1
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: This product requires protection from light (avoid light exposure) during transportation and storage.
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 : ≥ 83.33 mg/mL (~272.87 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (6.81 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 (6.81 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.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.2746 mL 16.3730 mL 32.7461 mL
5 mM 0.6549 mL 3.2746 mL 6.5492 mL
10 mM 0.3275 mL 1.6373 mL 3.2746 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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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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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)
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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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