Sch 52900
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| Category | Bioactive by-products |
| Catalog number | BBF-02430 |
| CAS | |
| Molecular Weight | 726.9 |
| Molecular Formula | C31H30N6O7S4 |
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Description
Sch 52900 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-52900 |
| IUPAC Name | (1S,2S,3S,11R,14S)-2-hydroxy-3-[(1S,2S,3S,11R,14S)-2-hydroxy-14-(1-hydroxyethyl)-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]-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 | CC(C12C(=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)O |
| InChI | InChI=1S/C31H30N6O7S4/c1-13(38)29-25(44)37-21-28(15-10-6-8-12-17(15)33-21,19(40)31(37,48-46-29)24(43)35(29)4)27-14-9-5-7-11-16(14)32-20(27)36-22(41)26(2)34(3)23(42)30(36,18(27)39)47-45-26/h5-13,18-21,32-33,38-40H,1-4H3/t13?,18-,19-,20+,21+,26-,27+,28+,29-,30-,31-/m0/s1 |
| InChI Key | PRYIVLXRWBBBJH-AUZUSQCWSA-N |
Properties
| Appearance | White Amorphous Powder |
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Melting Point | 202-205°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. Induction of differentiation in acute promyelocytic leukemia cells (HL-60) by the verticillin derivative Sch 52900
Gerhard Erkel, Alexandra Gehrt, Timm Anke, Olov Sterner Z Naturforsch C J Biosci. 2002 Jul-Aug;57(7-8):759-67. doi: 10.1515/znc-2002-7-834.
The HL-60 cell line, derived from a patient with acute promyelocytic leukemia, is a widely used model system to study the cellular and molecular events involved in differentiation of leukemic cells. In a screening for inducers of differentiation of HL-60 cells, cultures of Gliocladium strain 4-93 were found to produce Sch 52900, a previously isolated diketopiperazine (Chu et al,. J Antibiotics 48, 1440-1445). Sch 52900 induced the differentation of 50-69% of HL-60 cells at concentrations of 6.8-13.6 nM as measured by nitro-blue tetrazolium chloride (NBT) reduction which was followed by apoptosis as shown by DNA fragmentation. Our results demonstrate that growth arrest and the induction of differentiation by Sch 52900 is due to the induction of the cell cycle inhibitor p21WAF and an inhibition of the extracellular signal-regulated kinase (ERK) signaling pathway which leads to the activation of the transcription factor AP-1.
3. 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 ╳
