Vermiculine
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-02746 |
| CAS | 37244-00-1 |
| Molecular Weight | 392.40 |
| Molecular Formula | C20H24O8 |
Online Inquiry
Description
Vermiculine is produced by the strain of Pen. vermiculatum CCM-F-2. It has anti-protozoal and anti-tumor effects, and it also has a less potent effect against gram-positive bacteria.
Specification
| Synonyms | Vermiculin; NSC657321; (-)-Vermiculine; 1,11-diene-2,5,10,13-tetrone,8,16-bis(2-oxopropyl)-, (3E,8S,11E,16S)- |
| IUPAC Name | (3E,11E)-8,16-bis(2-oxopropyl)-1,9-dioxacyclohexadeca-3,11-diene-2,5,10,13-tetrone |
| Canonical SMILES | CC(=O)CC1CCC(=O)C=CC(=O)OC(CCC(=O)C=CC(=O)O1)CC(=O)C |
| InChI | InChI=1S/C20H24O8/c1-13(21)11-17-7-3-15(23)6-10-20(26)28-18(12-14(2)22)8-4-16(24)5-9-19(25)27-17/h5-6,9-10,17-18H,3-4,7-8,11-12H2,1-2H3/b9-5+,10-6+ |
| InChI Key | CFDVIOQSLRJWSU-NXZHAISVSA-N |
Properties
| Appearance | Colorless Acicular Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; neoplastics (Tumor) |
| Boiling Point | 437.13°C at 760 mmHg |
| Melting Point | 175-177°C |
| Density | 1.2464 g/cm3 |
Reference Reading
1. Immunosuppressive effects of vermiculine in vitro and in allotransplantation system in vivo
A Zajícová, M Múcková, M Krulová, Z Rychnavská, V Holán Int Immunopharmacol. 2001 Oct;1(11):1939-45. doi: 10.1016/s1567-5769(01)00119-9.
Vermiculine, a macrocyclic aglycosidic dilactone isolated from Penicillium vermiculatum, has been shown to have immunomodulatory properties. Here, we tested the effects of vermiculine on selected parameters of cell-mediated immunity in vitro and on skin allograft survival in vivo. Vermiculine inhibited in a dose-dependent manner the proliferation of mouse spleen cells stimulated with Concanavalin A ((Con A), i.e. T-cell mitogen), bacterial lipopolysaccharide ((LPS), B-cell mitogen) or with irradiated allogeneic cells. In addition, vermiculine dose-dependently inhibited the production of Thl (IL-2, IFN-gamma) and Th2 (IL-4, IL-10) cytokines and suppressed the production of nitric oxide (NO) by activated macrophages. When compared with cyclosporine (CsA), vermiculine was less inhibitory for IL-2 gene expression and IL-2 synthesis, comparably suppressive on IL-10 production and even more inhibitory for NO synthesis. These observations suggest that vermiculine and CsA inhibit immune reactions by different mechanisms. Treatment of graft recipients with vermiculine or CsA prolonged survival of skin allografts in a mouse model. The combination of both drugs enhanced the survival of allografts significantly more than either drug alone. The results thus suggest that vermiculine is a potential immunosuppressive drug acting by a mechanism distinct from that of CsA, and thus it may be used alone or in combination with other drugs for immunoregulatory purposes.
2. Concise Total Synthesis of (-)-Vermiculine through a Rhodium-Catalyzed C2 -Symmetric Dimerization Strategy
Philip Steib, Bernhard Breit Chemistry. 2019 Mar 7;25(14):3532-3535. doi: 10.1002/chem.201900216. Epub 2019 Feb 12.
A short and efficient synthesis of the C2 -symmetric antibiotic (-)-vermiculine by utilizing an enantioselective catalytic one-step dimerization methodology as key-step to construct the core structure is reported. The late-stage modifications feature a double metathesis homologation followed by a double Wacker-type oxidation. These key-steps allowed the synthesis of vermiculine in only seven steps, starting from commercially available building blocks.
3. Macrodiolide Diversification Reveals Broad Immunosuppressive Activity That Impairs the cGAS-STING Pathway
Han Liu, Rasmus N Ottosen, Kira M Jennet, Esben B Svenningsen, Tobias F Kristensen, Mette Biltoft, Martin R Jakobsen, Thomas B Poulsen Angew Chem Int Ed Engl. 2021 Aug 16;60(34):18734-18741. doi: 10.1002/anie.202105793. Epub 2021 Jul 16.
The development of new immunomodulatory agents can impact various areas of medicine. In particular, compounds with the ability to modulate innate immunological pathways hold significant unexplored potential. Herein, we report a modular synthetic approach to the macrodiolide natural product (-)-vermiculine, an agent previously shown to possess diverse biological effects, including cytotoxic and immunosuppressive activity. The synthesis allows for a high degree of flexibility in modifying the macrocyclic framework, including the formation of all possible stereoisomers. In total, 18 analogues were prepared. Two analogues with minor structural modifications showed clearly enhanced cancer cell line selectivity and reduced toxicity. Moreover, these compounds possessed broad inhibitory activity against innate immunological pathways in human PBMCs, including the DNA-sensing cGAS-STING pathway. Initial mechanistic characterization suggests a surprising impairment of the STING-TBK1 interaction.
Recommended Products
| BBF-03753 | Baicalin | Inquiry |
| BBF-01693 | Doxorubicin EP Impurity A (Daunorubicin) | Inquiry |
| BBF-03754 | CASTANOSPERMINE | Inquiry |
| BBF-05862 | Epirubicin | Inquiry |
| BBF-01825 | Loganin | Inquiry |
| BBF-02642 | Lactonamycin | Inquiry |
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 ╳
