Synonym
TG53; TG-53; TG 53
IUPAC/Chemical Name
5-Chloro-N-[4-[[4-(dimethylamino)-6-methyl-2-pyrimidinyl]amino]phenyl]-2-methoxy-benzamide
InChi Key
JHHHSGYKBKIUBG-UHFFFAOYSA-N
InChi Code
InChI=1S/C21H22ClN5O2/c1-13-11-19(27(2)3)26-21(23-13)25-16-8-6-15(7-9-16)24-20(28)17-12-14(22)5-10-18(17)29-4/h5-12H,1-4H3,(H,24,28)(H,23,25,26)
SMILES Code
O=C(NC1=CC=C(NC2=NC(C)=CC(N(C)C)=N2)C=C1)C3=CC(Cl)=CC=C3OC
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
2934.99.03.00
More Info
Tissue transglutaminase (TG2) mediates protein crosslinking through generation of ε-(γ-glutamyl) lysine isopeptide bonds and promotes cell adhesion through interaction with fibronectin (FN) and integrins. Cell adhesion to the peritoneal matrix regulated by TG2 facilitates ovarian cancer dissemination. Therefore, disruption of the TG2-FN complex by small molecules may inhibit cell adhesion and metastasis
Biological target:
Km: 2.06 μM (recombinant Fluc protein)
In vitro activity:
The bioluminescence produced by AkaLumine-HCl in reactions with native firefly luciferase is in the near-infrared wavelength ranges (λmax=677 nm), and yields significantly increased target-detection sensitivity from deep tissues with maximal signals attained at very low concentrations, as compared with D-luciferin and emerging synthetic luciferin CycLuc1. These characteristics offer a more sensitive and accurate method for non-invasive bioluminescence imaging with native firefly luciferase in various animal models.
Reference:
Kuchimaru T, Iwano S, Kiyama M, Mitsumata S, Kadonosono T, Niwa H, Maki S, Kizaka-Kondoh S. A luciferin analogue generating near-infrared bioluminescence achieves highly sensitive deep-tissue imaging. Nat Commun. 2016 Jun 14;7:11856. doi: 10.1038/ncomms11856. PMID: 27297211; PMCID: PMC4911627.
In vivo activity:
HIF-active cells can be visualized using AkaBLI, an ultra-sensitive in vivo bioluminescence imaging technology that produces an intense near-infrared light upon reaction of Akaluc with the D-luciferin analog AkaLumine-HCl. By orthotopic transplantation of E0771, a mouse triple negative breast cancer cell line without a reporter gene, into HVA-Tg, we succeeded in noninvasively monitoring bioluminescence signals from HIF-active stromal cells as early as 8 days after transplantation.
Reference:
Miyabara H, Hirano R, Watanabe S, Soriano JCC, Watanabe H, Kuchimaru T, Kitada N, Kadonosono T, Maki SA, Kondoh G, Kizaka-Kondoh S. In vivo optical imaging of tumor stromal cells with hypoxia-inducible factor activity. Cancer Sci. 2023 Oct;114(10):3935-3945. doi: 10.1111/cas.15907. Epub 2023 Jul 22. PMID: 37482942; PMCID: PMC10551579.
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
100.0 |
295.12 |
| H2O |
50.0 |
147.56 |
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
411.89
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.
| 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 |
In vitro protocol:
Kuchimaru T, Iwano S, Kiyama M, Mitsumata S, Kadonosono T, Niwa H, Maki S, Kizaka-Kondoh S. A luciferin analogue generating near-infrared bioluminescence achieves highly sensitive deep-tissue imaging. Nat Commun. 2016 Jun 14;7:11856. doi: 10.1038/ncomms11856. PMID: 27297211; PMCID: PMC4911627.
Zambito G, Gaspar N, Ridwan Y, Hall MP, Shi C, Kirkland TA, Encell LP, Löwik C, Mezzanotte L. Evaluating Brightness and Spectral Properties of Click Beetle and Firefly Luciferases Using Luciferin Analogues: Identification of Preferred Pairings of Luciferase and Substrate for In Vivo Bioluminescence Imaging. Mol Imaging Biol. 2020 Dec;22(6):1523-1531. doi: 10.1007/s11307-020-01523-7. Epub 2020 Sep 14. PMID: 32926287; PMCID: PMC7666294.
In vivo protocol:
Miyabara H, Hirano R, Watanabe S, Soriano JCC, Watanabe H, Kuchimaru T, Kitada N, Kadonosono T, Maki SA, Kondoh G, Kizaka-Kondoh S. In vivo optical imaging of tumor stromal cells with hypoxia-inducible factor activity. Cancer Sci. 2023 Oct;114(10):3935-3945. doi: 10.1111/cas.15907. Epub 2023 Jul 22. PMID: 37482942; PMCID: PMC10551579.
Hendrickx S, Bulté D, Mabille D, Mols R, Claes M, Ilbeigi K, Ahmad R, Dirkx L, Van Acker SI, Caljon G. Comparison of Bioluminescent Substrates in Natural Infection Models of Neglected Parasitic Diseases. Int J Mol Sci. 2022 Dec 16;23(24):16074. doi: 10.3390/ijms232416074. PMID: 36555716; PMCID: PMC9781651.
1: Yakubov B, Chen L, Belkin AM, Zhang S, Chelladurai B, Zhang ZY, Matei D. Small molecule inhibitors target the tissue transglutaminase and fibronectin interaction. PLoS One. 2014 Feb 20;9(2):e89285. doi: 10.1371/journal.pone.0089285. eCollection 2014. PubMed PMID: 24586660; PubMed Central PMCID: PMC3930694.
2: Herrera VL, Ponce LR, Ruiz-Opazo N. Genome-wide scan for interacting loci affecting human cholesteryl ester transfer protein-induced hypercholesterolemia in transgenic human cholesteryl ester transfer protein F2-intercross rats. J Hypertens. 2007 Aug;25(8):1608-12. PubMed PMID: 17620956.
3: Herrera VL, Shen L, Lopez LV, Didishvili T, Zhang YX, Ruiz-Opazo N. Chlamydia pneumoniae accelerates coronary artery disease progression in transgenic hyperlipidemia-genetic hypertension rat model. Mol Med. 2003 May-Aug;9(5-8):135-42. PubMed PMID: 14571321; PubMed Central PMCID: PMC1430827.
4: Herrera VM, Didishvili T, Lopez LV, Zander K, Traverse S, Gantz D, Herscovitz H, Ruiz-Opazo N. Hypertension exacerbates coronary artery disease in transgenic hyperlipidemic Dahl salt-sensitive hypertensive rats. Mol Med. 2001 Dec;7(12):831-44. PubMed PMID: 11844871; PubMed Central PMCID: PMC1950013.
