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MedKoo Cat#: 555839 | Name: Diphenylterazine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Diphenylterazine is a bioluminescence agent. Diphenylterazine alone yields very little background, leading to excellent signal-to-background ratios

Chemical Structure

Diphenylterazine
Diphenylterazine
CAS#344940-63-2

Theoretical Analysis

MedKoo Cat#: 555839

Name: Diphenylterazine

CAS#: 344940-63-2

Chemical Formula: C25H19N3O

Exact Mass: 377.1528

Molecular Weight: 377.45

Elemental Analysis: C, 79.55; H, 5.07; N, 11.13; O, 4.24

Price and Availability

Size Price Availability Quantity
5mg USD 110.00 Ready to ship
10mg USD 185.00 Ready to ship
25mg USD 395.00 Ready to ship
50mg USD 675.00 Ready to ship
100mg USD 1,150.00 Ready to ship
200mg USD 1,950.00 Ready to ship
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Related CAS #
No Data
Synonym
Diphenylterazine; DTZ;
IUPAC/Chemical Name
2-benzyl-6,8-diphenylimidazo[1,2-a]pyrazin-3(7H)-one
InChi Key
HYQVAZNNCBIZSK-UHFFFAOYSA-N
InChi Code
InChI=1S/C25H19N3O/c29-25-21(16-18-10-4-1-5-11-18)27-24-23(20-14-8-3-9-15-20)26-22(17-28(24)25)19-12-6-2-7-13-19/h1-15,17,26H,16H2
SMILES Code
O=C1C(CC2=CC=CC=C2)=NC3=C(C4=CC=CC=C4)NC(C5=CC=CC=C5)=CN31
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Coelenterazine (CTZ)-utilizing marine luciferases and their derivatives have attracted significant attention because of their ATP-independency, fast enzymatic turnover, and high bioluminescence brightness. However, marine luciferases typically emit blue photons and their substrates, including CTZ and the recently developed diphenylterazine (DTZ), have poor water solubility, hindering their in vivo applications
Biological target:
Diphenylterazine (DTZ) is a bioluminescence agent.
In vitro activity:
The bioluminescence of the new reporters was further evaluated using transiently transfected Human Embryonic Kidney (HEK) 293T cells. Under all conditions, the brightness of DTZ with teLuc or Antares2 was two to three orders of magnitude higher than that of FLuc/d-luciferin. Moreover, DTZ alone yielded very little background, leading to excellent signal-to-background ratios. Furthermore, DTZ elicited minimal cell toxicity at millimolar concentrations. Reference: Nat Methods. 2017 Oct;14(10):971-974. https://pubmed.ncbi.nlm.nih.gov/28869756/
In vivo activity:
To further evaluate the reporters for imaging deep-tissue targets, hydrodynamic transfection was utilized to express luciferase genes within the internal organs of mice. After intraperitoneal injections of 0.3 µmol individual luciferin substrates, teLuc/DTZ generated ~52-fold higher emission than FLuc/d-luciferin. With 3.3 µmol of each substrate (a dose recommended for AkaLumine-HCl9), teLuc/DTZ was ~32-fold brighter than FLuc/d-luciferin and ~15-fold brighter than FLuc/AkaLumine-HCl. Moreover, teLuc with 3.3 µmol DTZ was still ~12-fold brighter than FLuc with 10 µmol d-luciferin (equivalent to the standard ~150 mg/kg FLuc imaging condition). DTZ injections into untransfected BALB/c mice did not yield any background emission. Furthermore, the bioluminescence resulting from intraperitoneally injected DTZ displayed extended kinetics, suggesting that both teLuc and Antares2 are suitable for time-lapse BLI. Reference: Nat Methods. 2017 Oct;14(10):971-974. https://pubmed.ncbi.nlm.nih.gov/28869756/
Solvent mg/mL mM
Solubility
DMSO 75.0 198.71
DMF 11.1 29.44
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 377.45 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Yeh HW, Karmach O, Ji A, Carter D, Martins-Green MM, Ai HW. Red-shifted luciferase-luciferin pairs for enhanced bioluminescence imaging. Nat Methods. 2017 Oct;14(10):971-974. doi: 10.1038/nmeth.4400. Epub 2017 Sep 4. PMID: 28869756; PMCID: PMC5678970. 2. O'Sullivan JJ, Medici V, Heffern MC. A caged imidazopyrazinone for selective bioluminescence detection of labile extracellular copper(ii). Chem Sci. 2022 Mar 23;13(15):4352-4363. doi: 10.1039/d1sc07177g. PMID: 35509459; PMCID: PMC9006956. 3. Yeh HW, Xiong Y, Wu T, Chen M, Ji A, Li X, Ai HW. ATP-Independent Bioluminescent Reporter Variants To Improve in Vivo Imaging. ACS Chem Biol. 2019 May 17;14(5):959-965. doi: 10.1021/acschembio.9b00150. Epub 2019 Apr 17. PMID: 30969754; PMCID: PMC6528180.
In vitro protocol:
1. Yeh HW, Karmach O, Ji A, Carter D, Martins-Green MM, Ai HW. Red-shifted luciferase-luciferin pairs for enhanced bioluminescence imaging. Nat Methods. 2017 Oct;14(10):971-974. doi: 10.1038/nmeth.4400. Epub 2017 Sep 4. PMID: 28869756; PMCID: PMC5678970. 2. O'Sullivan JJ, Medici V, Heffern MC. A caged imidazopyrazinone for selective bioluminescence detection of labile extracellular copper(ii). Chem Sci. 2022 Mar 23;13(15):4352-4363. doi: 10.1039/d1sc07177g. PMID: 35509459; PMCID: PMC9006956.
In vivo protocol:
1. Yeh HW, Karmach O, Ji A, Carter D, Martins-Green MM, Ai HW. Red-shifted luciferase-luciferin pairs for enhanced bioluminescence imaging. Nat Methods. 2017 Oct;14(10):971-974. doi: 10.1038/nmeth.4400. Epub 2017 Sep 4. PMID: 28869756; PMCID: PMC5678970. 2. Yeh HW, Xiong Y, Wu T, Chen M, Ji A, Li X, Ai HW. ATP-Independent Bioluminescent Reporter Variants To Improve in Vivo Imaging. ACS Chem Biol. 2019 May 17;14(5):959-965. doi: 10.1021/acschembio.9b00150. Epub 2019 Apr 17. PMID: 30969754; PMCID: PMC6528180.
Yeh HW, Xiong Y, Wu T, et al. ATP-Independent Bioluminescent Reporter Variants To Improve in Vivo Imaging. ACS Chem Biol. 2019;14(5):959-965. doi:10.1021/acschembio.9b00150