Sch 52901
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| Category | Bioactive by-products |
| Catalog number | BBF-02431 |
| CAS | |
| Molecular Weight | 710.9 |
| Molecular Formula | C31H30N6O6S4 |
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Description
Sch 52901 is an inhibitor of c-fos proto-oncogene induction, which is isolated from the fermentation of broth of the fungal culture (SCF-1168), Gliocladium sp.
Specification
| Synonyms | Sch-52901 |
| IUPAC Name | (1S,2S,3S,11R,14S)-3-[(1S,2S,3S,11R,14S)-14-ethyl-2-hydroxy-18-methyl-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]-2-hydroxy-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 | CCC12C(=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/C31H30N6O6S4/c1-5-27-23(41)37-21-29(15-11-7-9-13-17(15)33-21,19(39)31(37,47-45-27)25(43)35(27)4)28-14-10-6-8-12-16(14)32-20(28)36-22(40)26(2)34(3)24(42)30(36,18(28)38)46-44-26/h6-13,18-21,32-33,38-39H,5H2,1-4H3/t18-,19-,20+,21+,26-,27-,28+,29+,30-,31-/m0/s1 |
| InChI Key | BNGCIRYZSMUYSN-NRQMUMKPSA-N |
Properties
| Appearance | White Amorphous Powder |
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Melting Point | 199-200°C (dec.) |
Reference Reading
1. Inhibition of c-fos proto-oncogene induction by Sch 52900 and Sch 52901, novel diketopiperazine produced by Gliocladium sp
M Chu, I Truumees, M L Rothofsky, M G Patel, F Gentile, P R Das, M S Puar, S L Lin J Antibiot (Tokyo). 1995 Dec;48(12):1440-5. doi: 10.7164/antibiotics.48.1440.
Sch 52900 (1) and Sch 52901 (2), two new inhibitors of c-fos proto-oncogene induction, have been isolated from the fermentation of broth of the fungal culture (SCF-1168), Gliocladium sp. Along with compounds 1 and 2, a known compound verticillin A (3) was also obtained from the culture. Structure elucidation of 1 and 2, accomplished by analysis of spectral data in comparison with the data of 3, revealed both 1 and 2 were found to be closely related to the verticillin family of diketopiperazines. All three compounds prevented serum-stimulated transcription of the human c-fos promoter, using a fos/lac Z reporter gene assay, with IC50 values of 1.5, 18 and 0.5 microM of 1, 2 and 3, respectively. Northern analysis revealed the exposure of cells to compound 3 causes inhibition of both phorbol ester-induced c-fos induction of serum-induced JE induction in the absence of inhibiting RNA synthesis, as measured by [3H]uridine incorporation. There results suggest that this class of compounds exerts antitumor activity by blocking a signal transduction pathway that is common to and necessary for the induction of at least a subset of immediate early genes involved in cell proliferation.
2. Cytotoxic epipolythiodioxopiperazine alkaloids from filamentous fungi of the Bionectriaceae
Mario Figueroa, Tyler N Graf, Sloan Ayers, Audrey F Adcock, David J Kroll, Jilai Yang, Steven M Swanson, Ulyana Munoz-Acuna, Esperanza J Carcache de Blanco, Rajesh Agrawal, Mansukh C Wani, Blaise A Darveaux, Cedric J Pearce, Nicholas H Oberlies J Antibiot (Tokyo). 2012 Nov;65(11):559-64. doi: 10.1038/ja.2012.69. Epub 2012 Sep 12.
Bioactivity-directed fractionation of the organic extracts of two filamentous fungi of the Bionectriaceae, strains MSX 64546 and MSX 59553 from the Mycosynthetix library, led to the isolation of a new dimeric epipolythiodioxopiperazine alkaloid, verticillin H (1), along with six related analogs, Sch 52900 (2), verticillin A (3), gliocladicillin C (4), Sch 52901 (5), 11'-deoxyverticillin A (6) and gliocladicillin A (7). The structures of compounds 1-7 were determined by extensive NMR and HRMS analyses, as well as by comparisons to the literature. All compounds (1-7) were evaluated for cytotoxicity against a panel of human cancer cell lines, displaying IC(50) values ranging from 1.2 μM to 10 nM. Compounds 1-5 were examined for activity in the NF-κB assay, where compounds 2 and 3 revealed activity in the sub-micromolar range. Additionally, compounds 1, 3 and 4 were tested for EGFR inhibition using an enzymatic assay, while compound 3 was examined against an overexpressing EGFR(+ve) cancer cell line.
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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 ╳
