Verticillin A
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| Category | Antibiotics |
| Catalog number | BBF-03443 |
| CAS | 889640-30-6 |
| Molecular Weight | 696.84 |
| Molecular Formula | C30H28N6O6S4 |
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Description
Verticillin A is originally isolated from Verticillium sp. Tm-759. It has the effect of anti-gram-positive bacteria, mycobacterium and protozoa, and has the inhibitory effect on the cancer of Ascites.
Specification
| Related CAS | 32164-16-2 (Deleted CAS) |
| Synonyms | [10b,10'b(11H,11'H)-Bi-3,11a-epidithio-11aH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole]-1,1',4,4'-tetrone, 2,2',3,3',5a,5'a,6,6'-octahydro-11,11'-dihydroxy-2,2',3,3'-tetramethyl-, (3S,3'S,5aR,5'aR,10bS,10'bS,11S,11'S,11aS,11'aS)-; [10b,10'b(11H,11'H)-Bi-3,11a-epidithio-11aH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole]-1,1',4,4'-tetrone, 2,2',3,3',5a,5'a,6,6'-octahydro-11,11'-dihydroxy-2,2',3,3'-tetramethyl-, [3S-[3α,5aβ,10bβ(3'R*,5'aS*,10'bR*,11'R*,11'aR*),11β,11aα]]-; Verticillin A, (+)-; (6S,6'S)-19,19'-Dideoxy-6,6'-dihydroxychetocin |
| IUPAC Name | (1S,2S,3S,11R,14S)-2-hydroxy-3-[(1S,2S,3S,11R,14S)-2-hydroxy-14,18-dimethyl-13,17-dioxo-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.01,12.03,11.04,9]octadeca-4,6,8-trien-3-yl]-14,18-dimethyl-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.01,12.03,11.04,9]octadeca-4,6,8-triene-13,17-dione |
| Canonical SMILES | CC12C(=O)N3C4C(C(C3(C(=O)N1C)SS2)O)(C5=CC=CC=C5N4)C67C(C89C(=O)N(C(C(=O)N8C6NC1=CC=CC=C71)(SS9)C)C)O |
| InChI | InChI=1S/C30H28N6O6S4/c1-25-21(39)35-19-27(13-9-5-7-11-15(13)31-19,17(37)29(35,45-43-25)23(41)33(25)3)28-14-10-6-8-12-16(14)32-20(28)36-22(40)26(2)34(4)24(42)30(36,18(28)38)46-44-26/h5-12,17-20,31-32,37-38H,1-4H3/t17-,18-,19+,20+,25-,26-,27+,28+,29-,30-/m0/s1 |
| InChI Key | IMGTYEJTVRXGLW-LRESJZTJSA-N |
Properties
| Appearance | Light Yellow Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; mycobacteria; neoplastics (Tumor) |
| Melting Point | 202-217°C |
| Density | 1.86±0.1 g/cm3 |
Reference Reading
1. Semisynthetic Derivatives of the Verticillin Class of Natural Products through Acylation of the C11 Hydroxy Group
Chiraz Soumia M Amrine, Andrew C Huntsman, Michael G Doyle, Joanna E Burdette, Cedric J Pearce, James R Fuchs, Nicholas H Oberlies ACS Med Chem Lett. 2021 Mar 19;12(4):625-630. doi: 10.1021/acsmedchemlett.1c00024. eCollection 2021 Apr 8.
The verticillins, a class of epipolythiodioxopiperazine alkaloids (ETPs) first described 50 years ago with the discovery of verticillin A (1), have gained attention due to their potent activity against cancer cells, noted both in vitro and in vivo. In this study, the complex scaffold afforded through optimized fermentation was used as a feedstock for semisynthetic efforts designed to explore the reactivity of the C11 and C11' hydroxy substituents. Functionality introduced at these positions would be expected to impact not only the potency but also the pharmacokinetic properties of the resulting compound. With this in mind, verticillin H (2) was used as a starting material to generate nine semisynthetic analogues (4-12) containing a variety of ester, carbonate, carbamate, and sulfonate moieties. Likewise, verticillin A succinate (13) was synthesized from 1 to demonstrate the successful application of this strategy to other ETPs. The synthesized compounds and their corresponding starting materials (i.e., 1 and 2) were screened for activity against a panel of melanoma, breast, and ovarian cancer cell lines: MDA-MB-435, MDA-MB-231, and OVCAR3. All analogues retained IC50 values in the nanomolar range, comparable to, and in some cases more potent than, the parent compounds.
2. Verticillin A increases the BIMEL/MCL-1 ratio to overcome ABT-737-resistance in human colon cancer cells by targeting the MEK/ERK pathway
Yuelin Guan, Kai Tu, Qiqian Huang, Feiyan Liu Biochem Biophys Res Commun. 2021 Aug 27;567:22-28. doi: 10.1016/j.bbrc.2021.05.103. Epub 2021 Jun 13.
ABT-737, a small molecule BH-3 mimetic, is less effective against human colon cancers due to its resistance. Verticillin A is a natural compound, which was previously purified from verticillium-infected mushrooms. Hence, we aimed at overcoming the ABT737 resistance observed in CRC tumors by combining Verticillin A with ABT-737 and figuring out the potential mechanism. In this study, we observed that Verticillin A could sensitize colon cancer to ABT-737-induced cell death through induction of mitochondrial-dependent apoptosis. Verticillin A could significantly increase the BIMEL/MCL-1 ratio to overcome ABT737 resistance through the suppression of the MEK/ERK pathway. In addition, up-regulation of BIM protein levels to activate BAX translocation results in apoptosis induction. Altogether, our work suggested the potential application of Verticillin A as a MEK inhibitor in BH3-mimetic-based therapy.
3. Erratum to: Verticillin A inhibits colon cancer cell migration and invasion by targeting c-Met
Qianqian Liu, Xueli Zeng, Yuelin Guan, Jingxin Lu, Kai Tu, Feiyan Liu J Zhejiang Univ Sci B. 2022 Apr 15;23(4):352. doi: 10.1631/jzus.B20e0190.
The online version of the original article can be found at https://doi.org/10.1631/jzus.B2000190 Erratum to: J Zhejiang Univ-Sci B (Biomed & Biotechnol) 2020 21(10):779-795 https://doi.org/10.1631/jzus.B2000190.
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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 ╳
