IUPAC/Chemical Name
(2Z)-2-[(3,4-dihydroxyphenyl)methylene]-5-methyl-3(2H)-furanone
InChi Key
NLZQGBCUKNUDED-SDQBBNPISA-N
InChi Code
InChI=1S/C12H10O4/c1-7-4-11(15)12(16-7)6-8-2-3-9(13)10(14)5-8/h2-6,13-14H,1H3/b12-6-
SMILES Code
OC1=CC=C(/C=C2OC(C)=CC\2=O)C=C1O
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
Biological target:
Inotilone is a cyclooxygenase (COX) inhibitor that inhibits COX-2 over COX-1.
In vitro activity:
Inotilone at 50 μM notably inhibited the activity of MMP-2 in A549 cells and the activity of MMP-9 in LLC cells (Fig. 4A). These results suggest that the anti-metastatic effect of inotilone is related to inhibition of the enzymatic degradative processes of cancer cell metastasis.
Reference: Sci Rep. 2019 Feb 20;9(1):2344. https://pubmed.ncbi.nlm.nih.gov/30787353/
In vivo activity:
As shown in Fig. 5d, PRIM1 protein expression in the inotilone-treated BT-474 tumor-bearing mice was significantly suppressed compared with the control mice. These findings suggest that the suppression of PRIM1 in tumor tissues was involved in the inotilone-treated BT-474 xenografted tumor growth in mice.
Reference: Int J Cancer. 2019 Feb 1;144(3):615-630. https://pubmed.ncbi.nlm.nih.gov/30097999/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
218.21
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. Chao W, Deng JS, Li PY, Kuo YH, Huang GJ. Inotilone from Inonotus linteus suppresses lung cancer metastasis in vitro and in vivo through ROS-mediated PI3K/AKT/MAPK signaling pathways. Sci Rep. 2019 Feb 20;9(1):2344. doi: 10.1038/s41598-019-38959-z. PMID: 30787353; PMCID: PMC6382761.
2. Huang GJ, Huang SS, Deng JS. Anti-inflammatory activities of inotilone from Phellinus linteus through the inhibition of MMP-9, NF-κB, and MAPK activation in vitro and in vivo. PLoS One. 2012;7(5):e35922. doi: 10.1371/journal.pone.0035922. Epub 2012 May 8. PMID: 22590514; PMCID: PMC3348146.
3. Lee WH, Chen LC, Lee CJ, Huang CC, Ho YS, Yang PS, Ho CT, Chang HL, Lin IH, Chang HW, Liu YR, Wu CH, Tu SH. DNA primase polypeptide 1 (PRIM1) involves in estrogen-induced breast cancer formation through activation of the G2/M cell cycle checkpoint. Int J Cancer. 2019 Feb 1;144(3):615-630. doi: 10.1002/ijc.31788. Epub 2018 Nov 21. PMID: 30097999.
In vitro protocol:
1. Chao W, Deng JS, Li PY, Kuo YH, Huang GJ. Inotilone from Inonotus linteus suppresses lung cancer metastasis in vitro and in vivo through ROS-mediated PI3K/AKT/MAPK signaling pathways. Sci Rep. 2019 Feb 20;9(1):2344. doi: 10.1038/s41598-019-38959-z. PMID: 30787353; PMCID: PMC6382761.
2. Huang GJ, Huang SS, Deng JS. Anti-inflammatory activities of inotilone from Phellinus linteus through the inhibition of MMP-9, NF-κB, and MAPK activation in vitro and in vivo. PLoS One. 2012;7(5):e35922. doi: 10.1371/journal.pone.0035922. Epub 2012 May 8. PMID: 22590514; PMCID: PMC3348146.
In vivo protocol:
1. Lee WH, Chen LC, Lee CJ, Huang CC, Ho YS, Yang PS, Ho CT, Chang HL, Lin IH, Chang HW, Liu YR, Wu CH, Tu SH. DNA primase polypeptide 1 (PRIM1) involves in estrogen-induced breast cancer formation through activation of the G2/M cell cycle checkpoint. Int J Cancer. 2019 Feb 1;144(3):615-630. doi: 10.1002/ijc.31788. Epub 2018 Nov 21. PMID: 30097999.
2. Huang GJ, Huang SS, Deng JS. Anti-inflammatory activities of inotilone from Phellinus linteus through the inhibition of MMP-9, NF-κB, and MAPK activation in vitro and in vivo. PLoS One. 2012;7(5):e35922. doi: 10.1371/journal.pone.0035922. Epub 2012 May 8. PMID: 22590514; PMCID: PMC3348146.
1. Wangun, H.V.K., Härtl, A., Kiet, T.T., et al. Inotilone and related phenylpropanoid polyketides from Inonotus sp. and their identification as potent COX and XO inhibitors. Organic & Biomolecular Chemistry 4, 2545-2548 (2006).
2. Shamshina, J.L., and Snowden, T.S. Convergent synthesis of potent COX-2 inhibitor inotilone. Tetrahedron Letters 48, 3767-3769 (2007).
3. Huang, G.-J., Huang, S.-S., and Deng, J.-S. Anti-inflammatory activities of inotilone from Phellinus linteus through the inhibition of MMP-9, NF-kB, and MAPK activation in vitro and in vivo. PLoS One 7(5), e35922 (2012).
4. Hwang, B.S., Lee, M.-S., Lee, S.W., et al. Neuraminidase inhibitors from the fermentation broth of Phellinus linteus. Mycobiology 42(2), 189-192 (2014).
5. Lee, M.-S., Hwang, B.S., Lee, I.-K., et al. Chemical constituents of the culture broth of Phellinus linteus and their antioxidant activity. Mycobiology 43(1), 43-48 (2015).
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