TMC-264
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02549 |
| CAS | |
| Molecular Weight | 352.72 |
| Molecular Formula | C16H13ClO7 |
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Description
TMC-264 is a STAT6 activation inhibitor produced by Phoma sp. TC 1674. It suppressed expression of IL-4 driven luciferase and germline Cepsilon mRNA with IC50 values of 0.3 and 0.4 μmol/L, respectively, and inhibited tyrosine phosphorylation of STAT6 with an IC50 value of 1.6 μmol/L.
Specification
| Synonyms | TMC 264 |
| IUPAC Name | 2-chloro-1,7-dihydroxy-3,9-dimethoxy-1-methylbenzo[c]chromene-4,6-dione |
| Canonical SMILES | CC1(C2=C(C(=O)C(=C1Cl)OC)OC(=O)C3=C2C=C(C=C3O)OC)O |
| InChI | InChI=1S/C16H13ClO7/c1-16(21)10-7-4-6(22-2)5-8(18)9(7)15(20)24-12(10)11(19)13(23-3)14(16)17/h4-5,18,21H,1-3H3 |
| InChI Key | UMKWAHOXPWRVRW-UHFFFAOYSA-N |
Reference Reading
1. Bioactive Dibenzo-α-pyrone Derivatives from the Endophytic Fungus Rhizopycnis vagum Nitaf22
Daowan Lai, Ali Wang, Yuheng Cao, Kaiyi Zhou, Ziling Mao, Xuejiao Dong, Jin Tian, Dan Xu, Jungui Dai, Yu Peng, Ligang Zhou, Yang Liu J Nat Prod. 2016 Aug 26;79(8):2022-31. doi: 10.1021/acs.jnatprod.6b00327. Epub 2016 Jul 21.
Six new dibenzo-α-pyrones, rhizopycnolides A (1) and B (2) and rhizopycnins A-D (3-6), together with eight known congeners (7-14), were isolated from the endophytic fungus Rhizopycnis vagum Nitaf22 obtained from Nicotiana tabacum. The structures of the new compounds were unambiguously elucidated using NMR, HRESIMS, TDDFT ECD calculation, and X-ray crystallography data. Rhizopycnolides A (1) and B (2) feature an uncommon γ-butyrolactone-fused dibenzo-α-pyrone tetracyclic skeleton (6/6/6/5), while rhizopycnin B (4) was the first amino group containing dibenzo-α-pyrone. Rhizopycnolides A (1) and B (2) are proposed to be biosynthesized from polyketide and tricarboxylic acid cycle pathways. The isolated compounds were tested for their antibacterial, antifungal, and cytotoxic activities. Among them, rhizopycnolide A (1), rhizopycnins C (5) and D (6), TMC-264 (8), penicilliumolide D (11), and alternariol (12) were active against the tested pathogenic bacteria Agrobacterium tumefaciens, Bacillus subtilis, Pseudomonas lachrymans, Ralstonia solanacearum, Staphylococcus hemolyticus, and Xanthomonas vesicatoria with MIC values in the range 25-100 μg/mL. Rhizopycnin D (6) and TMC-264 (8) strongly inhibited the spore germination of Magnaporthe oryzae with IC50 values of 9.9 and 12.0 μg/mL, respectively. TMC-264 (8) showed potent cytotoxicity against five human cancer cell lines (HCT-116, HepG2, BGC-823, NCI-H1650, and A2780) with IC50 values of 3.2-7.8 μM.
2. Separation and purification of bioactive botrallin and TMC-264 by a combination of HSCCC and semi-preparative HPLC from endophytic fungus Hyalodendriella sp. Ponipodef12
Ziling Mao, Ruiya Luo, Haiyu Luo, Jin Tian, Hongwei Liu, Yang Yue, Mingan Wang, Youliang Peng, Ligang Zhou World J Microbiol Biotechnol. 2014 Sep;30(9):2533-42. doi: 10.1007/s11274-014-1678-0. Epub 2014 Jun 5.
Two dibenzo-α-pyrones, botrallin (1) and TMC-264 (2) were preparatively separated from crude ethyl acetate extract of the endophytic fungus Hyalodendriella sp. Ponipodef12, which was isolated from the hybrid 'Neva' of Populus deltoides Marsh × P. nigra L. using a combination of high-speed counter-current chromatography (HSCCC) and semi-preparative HPLC. Botrallin (1) with 74.73% of purity and TMC-264 (2) with 82.29% of purity were obtained through HSCCC by employing a solvent system containing n-hexane-ethyl acetate-methanol-water at a volume ratio of 1.2:1.0:0.9:1.0. It was the first time for TMC-264 (2) to be isolated from this fungus. TMC-264 (2) showed strong antimicrobial and antinematodal activity, and botrallin (1) exhibited moderate inhibitory activity on acetylcholinesterase.
3. Enhanced production of botrallin and TMC-264 with in situ macroporous resin adsorption in mycelial liquid culture of the endophytic fungus Hyalodendriella sp. Ponipodef12
Haiyu Luo, Hongwei Liu, Yuheng Cao, Dan Xu, Ziling Mao, Yan Mou, Jiajia Meng, Daowan Lai, Yang Liu, Ligang Zhou Molecules. 2014 Sep 10;19(9):14221-34. doi: 10.3390/molecules190914221.
Hyalodendriella sp. Ponipodef12, an endophytic fungus from the hybrid "Neva" of Populus deltoides × P. nigra, is a high producer of the bioactive dibenzo-α-pyrones botrallin and TMC-264. However, both the botrallin and TMC-264 produced by Hyalodendriella sp. Ponipodef12 were retained as both intracellular and extracellular products. The aim of this study was to evaluate an in situ macroporous resin adsorption for enhancement of botrallin and TMC-264 production in mycelial liquid culture of Hyalodendriella sp. Ponipodef12. Production of botrallin and TMC-264 was most effectively enhanced by macroporous resin DM-301 among the thirteen nonionic macroporous resins tested. The highest botrallin yield (51.47 mg/L, which was 2.29-fold higher than the control at 22.49 mg/L) was obtained by adding resin DM-301 at 4.38% (g/mL) to the culture broth on day 24 and allowing a period of 4 days for adsorption. The highest TMC-264 yield reached 47.74 mg/L, which was 11.76-fold higher than that of the control (4.06 mg/L), and was achieved by adding DM-301 resin at 4.38% (w/v) in the culture broth on day 24 and allowing a period of 6 days for adsorption. The results show that in situ resin adsorption is an effective strategy for enhancing production of botrallin and TMC-264, and also for facilitating their recovery from mycelial liquid culture of Hyalodendriella sp. Ponipodef12.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
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