Synonym
Inflachromene; ICM;
IUPAC/Chemical Name
10-Hydroxy-7,7-dimethyl-2-phenyl-7,12b-dihydrochromeno[4,3-c][1,2,4]triazolo[1,2-a]pyridazine-1,3(2H,5H)-dione
InChi Key
VVOXDJYPDCSQMI-UHFFFAOYSA-N
InChi Code
InChI=1S/C21H19N3O4/c1-21(2)16-10-11-22-19(26)23(13-6-4-3-5-7-13)20(27)24(22)18(16)15-9-8-14(25)12-17(15)28-21/h3-10,12,18,25H,11H2,1-2H3
SMILES Code
O=C1N(C2=CC=CC=C2)C(N3CC=C(C(C)(C)OC4=C5C=CC(O)=C4)C5N31)=O
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
>2 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
Biological target:
Inflachromene, a microglial inhibitor, binds to HMGB1 and HMGB2 and exerts anti-inflammatory effects. Inflachromene effectively downregulates proinflammatory functions of HMGB and reduces neuronal damage. Inflachromene can be used for the research of neuroinflammatory disorders.
In vitro activity:
The total HMGB2 protein (Fig. 5A, left) was decreased by ICM (inflachromene) in CGR8 cells, which was in agreement with the report that ICM modified HMGB2 protein stability but not mRNA expression
Reference: Hepatol Commun. 2017 Oct;1(8):816-830. https://pubmed.ncbi.nlm.nih.gov/29218329/
In vivo activity:
ICM (inflachromene) treatment greatly reduced not only surface tumours (Fig. 7c and Extended Data Fig. 9b), but also microscopic lesions in DEN/Cre mice (Fig. 7d and Extended Data Fig. 9c). Indeed, ICM treatment significantly attenuated liver fibrosis in DEN/Cre livers, as supported by decreased fibrotic gene expression and collagen deposition (Fig. 7h and Extended Data Fig. 9l).
Reference: Nat Cell Biol. 2020 Jun;22(6):728-739. https://pubmed.ncbi.nlm.nih.gov/32367049/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
30.0 |
79.49 |
| DMSO |
30.0 |
79.49 |
| DMSO:PBS (pH 7.2) (1:4) |
0.2 |
0.53 |
| Ethanol |
2.5 |
6.62 |
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
377.40
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 |
Formulation protocol:
1. Zhao Y, Yang Z, Wu J, Wu R, Keshipeddy SK, Wright D, Wang L. High-mobility-group protein 2 regulated by microRNA-127 and small heterodimer partner modulates pluripotency of mouse embryonic stem cells and liver tumor initiating cells. Hepatol Commun. 2017 Oct;1(8):816-830. doi: 10.1002/hep4.1086. Epub 2017 Aug 28. Erratum in: Hepatol Commun. 2022 Nov;6(11):3285. PMID: 29218329; PMCID: PMC5678910.
2. Li F, Huangyang P, Burrows M, Guo K, Riscal R, Godfrey J, Lee KE, Lin N, Lee P, Blair IA, Keith B, Li B, Simon MC. FBP1 loss disrupts liver metabolism and promotes tumorigenesis through a hepatic stellate cell senescence secretome. Nat Cell Biol. 2020 Jun;22(6):728-739. doi: 10.1038/s41556-020-0511-2. Epub 2020 May 4. PMID: 32367049; PMCID: PMC7286794.
In vitro protocol:
1. Zhao Y, Yang Z, Wu J, Wu R, Keshipeddy SK, Wright D, Wang L. High-mobility-group protein 2 regulated by microRNA-127 and small heterodimer partner modulates pluripotency of mouse embryonic stem cells and liver tumor initiating cells. Hepatol Commun. 2017 Oct;1(8):816-830. doi: 10.1002/hep4.1086. Epub 2017 Aug 28. Erratum in: Hepatol Commun. 2022 Nov;6(11):3285. PMID: 29218329; PMCID: PMC5678910.
In vivo protocol:
1. Li F, Huangyang P, Burrows M, Guo K, Riscal R, Godfrey J, Lee KE, Lin N, Lee P, Blair IA, Keith B, Li B, Simon MC. FBP1 loss disrupts liver metabolism and promotes tumorigenesis through a hepatic stellate cell senescence secretome. Nat Cell Biol. 2020 Jun;22(6):728-739. doi: 10.1038/s41556-020-0511-2. Epub 2020 May 4. PMID: 32367049; PMCID: PMC7286794.
1: Kim YH, Kwak MS, Shin JM, Hayuningtyas RA, Choi JE, Shin JS. Inflachromene inhibits autophagy through modulation of Beclin 1 activity. J Cell Sci. 2018 Feb 20;131(4). pii: jcs211201. doi: 10.1242/jcs.211201. PubMed PMID: 29361549.
2: Zhao Y, Yang Z, Wu J, Wu R, Keshipeddy SK, Wright D, Wang L. High-mobility-group protein 2 regulated by microRNA-127 and small heterodimer partner modulates pluripotency of mouse embryonic stem cells and liver tumor initiating cells. Hepatol Commun. 2017 Oct;1(8):816-830. doi: 10.1002/hep4.1086. Epub 2017 Aug 28. PubMed PMID: 29218329; PubMed Central PMCID: PMC5678910.
3: Cho W, Koo JY, Park Y, Oh K, Lee S, Song JS, Bae MA, Lim D, Lee DS, Park SB. Treatment of Sepsis Pathogenesis with High Mobility Group Box Protein 1-Regulating Anti-inflammatory Agents. J Med Chem. 2017 Jan 12;60(1):170-179. doi: 10.1021/acs.jmedchem.6b00954. Epub 2016 Dec 21. PubMed PMID: 28001381.
4: Block ML. Neuroinflammation: modulating mighty microglia. Nat Chem Biol. 2014 Dec;10(12):988-9. doi: 10.1038/nchembio.1691. PubMed PMID: 25393492.
5: Lee S, Nam Y, Koo JY, Lim D, Park J, Ock J, Kim J, Suk K, Park SB. A small molecule binding HMGB1 and HMGB2 inhibits microglia-mediated neuroinflammation. Nat Chem Biol. 2014 Dec;10(12):1055-60. doi: 10.1038/nchembio.1669. Epub 2014 Oct 12. PubMed PMID: 25306442.
