10,11-Dehydrocurvularin
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04230 |
| CAS | 1095588-70-7 |
| Molecular Weight | 290.31 |
| Molecular Formula | C16H18O5 |
| Purity | >98% by HPLC |
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Description
It is a 12-membered macrocyclic lactone incorporating a resorcinyl moiety, produced by a number of fungal species including curvularia, penicillium and alternaria. It inhibits cell division by disrupting mitotic spindle formation and acts as a developmental regulator by inhibiting self-sporulation in alternaria alternata.
Specification
| Related CAS | 21178-57-4 (S-isomer) |
| Synonyms | (4R,8E)-4,5,6,7-Tetrahydro-11,13-dihydroxy-4-methyl-2H-3-benzoxacyclododecin-2,10(1H)-dione; (+)-(10E,15R)-10,11-Dehydrocurvularin; ent-Dehydrocurvularin; (R)-10,11-Dehydrocurvularin; 4,5-[[(7R)-1-Oxo-2-octene-1,7-diyl]oxy(1-oxoethane-1,2-diyl)]benzene-1,3-diol |
| Storage | Store at -20°C |
| IUPAC Name | (5R,9E)-13,15-dihydroxy-5-methyl-4-oxabicyclo[10.4.0]hexadeca-1(12),9,13,15-tetraene-3,11-dione |
| Canonical SMILES | CC1CCCC=CC(=O)C2=C(CC(=O)O1)C=C(C=C2O)O |
| InChI | InChI=1S/C16H18O5/c1-10-5-3-2-4-6-13(18)16-11(8-15(20)21-10)7-12(17)9-14(16)19/h4,6-7,9-10,17,19H,2-3,5,8H2,1H3/b6-4+/t10-/m1/s1 |
| InChI Key | AVIRMQMUBGNCKS-DFVUYQKZSA-N |
| Source | Curvularia sp. |
Properties
| Appearance | Off-white to Pale Beige Solid |
| Boiling Point | 576.3±50.0°C at 760 mmHg |
| Melting Point | >213°C (dec.) |
| Density | 1.349 g/cm3 |
| Solubility | Slightly soluble in DMSO, Ethanol, Methanol |
Reference Reading
1. Inhibition of human glioblastoma multiforme cells by 10,11-dehydrocurvularin through the MMP-2 and PI3K/AKT signaling pathways
Hao Yan, Yu Gu, Jin Cao, Pingxin Lin, Zhenhao Fu, Ye Li Eur J Pharmacol . 2022 Dec 5;936:175348. doi: 10.1016/j.ejphar.2022.175348.
Glioblastoma, formerly known as glioblastoma multiforme (GBM), is a malignant nervous system tumor with high morbidity, recurrence rate, and mortality. Treating glioblastoma is difficult due to complicating factors, and novel therapeutic strategies are required to overcome resistance. In this study, we investigate the glioblastoma inhibitory activity of 10,11-dehydrocurvularin (DCV), a polyketide compound with broad biological activities, despite the fact that its anti-glioma properties and related mechanisms have yet to be studied. We look at how DCV affects glioblastoma cell lines U251 and U87 versus HEB cells. We discover that DCV inhibits glioblastoma cell proliferation, colony formation, migration, and invasion, as well as causing cell apoptosis. DCV treatment inhibits AKT phosphorylation and decreases the level of the PI3K/AKT pathway downstream protein MMP2. Our findings suggest that DCV could be a candidate for developing more potent glioblastoma chemotherapeutic drugs.
2. Review of 10,11-Dehydrocurvularin: Synthesis, Structural Diversity, Bioactivities and Mechanisms
ZhiYong Guo, FuGui Zhou, Yiqing Zhou, Zhangshuang Deng, XianJun Yu Mini Rev Med Chem . 2022;22(6):836-847. doi: 10.2174/1389557521666210428132256.
10,11-Dehydrocurvularin is a natural benzenediol lactone (BDL) with a 12-membered macrolide fused to a resorcinol ring produced as a secondary metabolite by many fungi. In this review, we summarized the pieces of literature regarding biosynthesis, chemical synthesis, biological activities, and assumed work mechanisms of 10,11-dehydrocurvularin, which presented a potential for agricultural and pharmaceutical uses.
3. Dehydrocurvularin is a potent antineoplastic agent irreversibly blocking ATP-citrate lyase: evidence from chemoproteomics
Nai-Kei Wong, Yiqing Zhou, Zhangshuang Deng, Youli Xiao, Zhiyong Guo, Kun Zou Chem Commun (Camb) . 2019 Apr 4;55(29):4194-4197. doi: 10.1039/c9cc00256a.
Natural-product macrolide 10,11-dehydrocurvularin (DCV) was revealed to be a potent irreversible inhibitor of ATP-citrate lyase (ACLY) via classical chemoproteomic profiling, which mechanistically illuminates the anti-cancer mode of action of DCV and its analogues.
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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 ╳
