CRM646-A
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| Category | Bioactive by-products |
| Catalog number | BBF-02795 |
| CAS | |
| Molecular Weight | 690.77 |
| Molecular Formula | C36H50O13 |
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Description
It is originally isolated from Acremonium sp. MT70646. CRM646-A had a strong inhibitory effect on the movement of B16-H10 melanoma cells with IC50 of 15 μmol/L.
Specification
| Synonyms | CRM-646-A; CHEMBL3347523 |
| IUPAC Name | (2S,3S,4S,5R,6S)-6-[4-(4-carboxy-3-hydroxy-5-methylphenoxy)carbonyl-3-hydroxy-5-pentadecylphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid |
| Canonical SMILES | CCCCCCCCCCCCCCCC1=C(C(=CC(=C1)OC2C(C(C(C(O2)C(=O)O)O)O)O)O)C(=O)OC3=CC(=C(C(=C3)C)C(=O)O)O |
| InChI | InChI=1S/C36H50O13/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-22-18-24(48-36-31(41)29(39)30(40)32(49-36)34(44)45)20-26(38)28(22)35(46)47-23-17-21(2)27(33(42)43)25(37)19-23/h17-20,29-32,36-41H,3-16H2,1-2H3,(H,42,43)(H,44,45)/t29-,30-,31+,32-,36+/m0/s1 |
| InChI Key | PNRVAHOSWLWYPO-QJUVDKAYSA-N |
Properties
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Boiling Point | 865.8±65.0°C at 760 mmHg |
| Density | 1.3±0.1 g/cm3 |
Reference Reading
1. The development of inhibitors of heparanase, a key enzyme involved in tumour metastasis, angiogenesis and inflammation
Vito Ferro, Edward Hammond, Jon K Fairweather Mini Rev Med Chem. 2004 Aug;4(6):693-702. doi: 10.2174/1389557043403729.
Heparanase is an endo-beta-glucuronidase that degrades the glycosaminoglycan heparan sulfate, a major component of the extracellular matrix and basement membranes, and has been implicated in such processes as inflammation, angiogenesis and metastasis. The identification of inhibitors of heparanase is an attractive approach towards developing new therapeutics for metastatic tumours and chronic inflammatory diseases. This review focuses on heparanase inhibitors that have been isolated or synthesised to date. More recent developments in the understanding of heparanase structure and function that may ultimately aid in the future design of inhibitors with improved potency and specificity, are also discussed.
2. CRM646-A, a Fungal Metabolite, Induces Nucleus Condensation by Increasing Ca2+ Levels in Rat 3Y1 Fibroblast Cells
Yukihiro Asami, Sun-Ok Kim, Jun-Pil Jang, Sung-Kyun Ko, Bo Yeon Kim, Hiroyuki Osada, Jae-Hyuk Jang, Jong Seog Ahn J Microbiol Biotechnol. 2020 Jan 28;30(1):31-37. doi: 10.4014/jmb.1908.08043.
We previously identified a new heparinase inhibitor fungal metabolite, named CRM646-A, which showed inhibition of heparinase and telomerase activities in an in vitro enzyme assay and antimetastatic activity in a cell-based assay. In this study, we elucidated the mechanism by which CRM646-A rapidly induced nucleus condensation, plasma membrane disruption and morphological changes by increasing intracellular Ca2+ levels. Furthermore, PD98059, a mitogen-activated protein kinase (MEK) inhibitor, inhibited CRM646-A-induced nucleus condensation through ERK1/2 activation in rat 3Y1 fibroblast cells. We identified CRM646-A as a Ca2+ ionophore-like agent with a distinctly different chemical structure from that of previously reported Ca2+ ionophores. These results indicate that CRM646-A has the potential to be used as a new and effective antimetastatic drug.
3. Total synthesis of CRM646-A and -B, two fungal glucuronides with potent heparinase inhibition activities
Ping Wang, Zhaojun Zhang, Biao Yu J Org Chem. 2005 Oct 28;70(22):8884-9. doi: 10.1021/jo051384k.
[reaction: see text] CRM646-A (1) and -B (2), two fungal glucuronides with a dimeric 2,4-dihydroxy-6-alkylbenzoic acid (orcinol p-depside) aglycone showing significant heparinase and telomerase inhibition activities, were synthesized for the first time. The successful approach involved construction of the phenol glucuronidic linkage, via coupling of the orsellinate derivative 27 with glucuronate bromide 7, before assembly of the phenolic ester linkage in the depside aglycone. Attempts via direct glycosylation of the depside aglycone derivatives were not successful.
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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 ╳
