Mithramycin A
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| Category | Antineoplastic |
| Catalog number | BBF-02556 |
| CAS | 18378-89-7 |
| Molecular Weight | 1085.14 |
| Molecular Formula | C52H76O24 |
| Purity | >98% |
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Description
Mimosamycin is a glycoside antibiotic produced by Str. argillaceus, Str. plicatus and Str. tanashiensis. It has anti-Gram-positive bacteria and mycobacterial activity. It can inhibit HeLa cells.
Specification
| Synonyms | plicamycin; Mitramycin |
| Shelf Life | Hygroscopic, Decomp Slowly In Light, & Decomp In Heat |
| Storage | -20°C |
| IUPAC Name | 2-[4-[4-(4,5-dihydroxy-4,6-dimethyloxan-2-yl)oxy-5-hydroxy-6-methyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]oxy-3-(3,4-dihydroxy-1-methoxy-2-oxopentyl)-6-[4-(4,5-dihydroxy-6-methyloxan-2-yl)oxy-5-hydroxy-6-methyloxan-2-yl]oxy-8,9-dihydroxy-7-methyl-3,4-dihydro-2H-anthracen-1-one |
| Canonical SMILES | CC1C(C(CC(O1)OC2CC(OC(C2O)C)OC3=CC4=CC5=C(C(=O)C(C(C5)C(C(=O)C(C(C)O)O)OC)OC6CC(C(C(O6)C)O)OC7CC(C(C(O7)C)O)OC8CC(C(C(O8)C)O)(C)O)C(=C4C(=C3C)O)O)O)O |
| InChI | InChI=1S/C52H76O24/c1-18-29(72-34-14-30(43(58)21(4)68-34)73-33-13-28(54)42(57)20(3)67-33)12-26-10-25-11-27(49(66-9)48(63)41(56)19(2)53)50(47(62)39(25)46(61)38(26)40(18)55)76-36-16-31(44(59)23(6)70-36)74-35-15-32(45(60)22(5)69-35)75-37-17-52(8,65)51(64)24(7)71-37/h10,12,19-24,27-28,30-37,41-45,49-51,53-61,64-65H,11,13-17H2,1-9H3 |
| InChI Key | CFCUWKMKBJTWLW-UHFFFAOYSA-N |
| Source | Streptomyces argillaceus |
Properties
| Appearance | Yellow Crystal |
| Application | antibiotics, Antineoplastic, Fluorescent dyes, Nucleic acid synthesis inhibitors, Protein synthesis inhibitors |
| Antibiotic Activity Spectrum | Gram-positive bacteria; mycobacteria |
| Boiling Point | 1169.8°C at 760 mmHg |
| Melting Point | 184-187°C |
| Density | 1.48 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO limited water solubility |
| LogP | -0.25 at pH 7.4 |
Reference Reading
1.Glucocorticoids regulate MiR-29c levels in vascular smooth muscle cells through transcriptional and epigenetic mechanisms.
Chuang TD;Khorram O Life Sci. 2017 Oct 1;186:87-91. doi: 10.1016/j.lfs.2017.08.007. Epub 2017 Aug 8.
AIMS: ;The objective of this study was to determine the underlying mechanism by which glucocorticoids (GCs) induce of miR-29c expression in vascular smooth muscle cells.;MAIN METHODS: ;QRT-PCR was used for miR-29c detection. Protein levels were determined by western blotting. Knockdown of SP1, DNMT1 and DNMT3A was achieved through transfection with their specific respective siRNAs. The effect of GCs on SP1 activity was determined by luciferase reporter assay and the methylation status in miR-29c promoter was detected by methylation specific PCR. CHIP assay was used to determine the binding ability of SP1 and glucocorticoid receptor (GR) in miR-29c promoter.;KEY FINDINGS: ;Treatment of RASMC with SP1 siRNA or SP1 inhibitor, mithramycin A, as well as DNMT1 and DNMT3A siRNAs and an inhibitor of DNMTs, Decitabine, resulted in increased expression of miR-29c (P<0.05). Treatment RASMC with dexamethasone (DEX, 0.1μM) for 24h reduced the expression of SP1 and phosphorylated SP1 at threonine 453 protein levels, repressed SP1 activity, and inhibited the expression of DNMT1 and DNMT3A proteins (P<0.05). Treatment with mifepristone, a GR antagonist, blocked the inhibitory effect of DEX on DNMT1 and DNMT3A protein expression.
2.Induction of HO-1 by carbon monoxide releasing molecule-2 attenuates thrombin-induced COX-2 expression and hypertrophy in primary human cardiomyocytes.
Chien PT;Lin CC;Hsiao LD;Yang CM Toxicol Appl Pharmacol. 2015 Dec 1;289(2):349-59. doi: 10.1016/j.taap.2015.09.009. Epub 2015 Sep 15.
Carbon monoxide (CO) is one of the cytoprotective byproducts of heme oxygenase (HO)-1 and exerts anti-inflammatory action in various models. However, the detailed mechanisms underlying CO-induced HO-1 expression in primary human cardiomyocytes remain largely unidentified. We used primary left ventricle myocytes as a model and applied CO releasing molecule (CORM)-2 to investigate the relationship of CO and HO-1 expression. We herein used Western blot, real-time PCR, promoter activity and EIA to investigate the role of HO-1 expression protecting against thrombin-mediated responses. We found that thrombin-induced COX-2 expression, PGE2 release and cardiomyocyte hypertrophy markers (increase in ANF/BNP, α-actin expression and cell surface area) was attenuated by pretreatment with CORM-2 which was partially reversed by hemoglobin (Hb) or ZnPP (an inhibitor of HO-1 activity), suggesting that HO-1/CO system may be of clinical importance to ameliorate heart failure through inhibition of inflammatory responses. CORM-2-induced HO-1 protein expression, mRNA and promoter was attenuated by pretreatment with the inhibitors of Pyk2 (PF431396), PDGFR (AG1296), PI3K (LY294002), Akt (SH-5), p38 (SB202530), JNK1/2 (SP600125), FoxO1 (AS1842856) and Sp1 (mithramycin A).
3.p53 cooperates with Sp1 to regulate breed-dependent expression of glucocorticoid receptor in the liver of preweaning piglets.
Zou H;Jiang Z;Li R;Jia Y;Yang X;Ni Y;Zhao R PLoS One. 2013 Aug 7;8(8):e70494. doi: 10.1371/journal.pone.0070494. eCollection 2013.
Previous studies indicate that Chinese indigenous pig breeds demonstrate distinct pattern of glucocorticoid receptor (GR) expression, which is associated with their unique growth and metabolic phenotypes. Here we sought to unravel the transcriptional mechanisms underlying the breed-specific hepatic GR expression in preweaning Chinese Erhualian (EHL) and Western Large White (LW) piglets. Total GR mRNA and the predominant GR mRNA variant 1-9/10 were expressed significantly higher in EHL compared with LW piglets (P<0.01), which was associated with more enriched histone H3 acetylation on 1-9/10 promoter (P<0.05). Nuclear content of transcription factor specificity protein 1 (Sp1) was significantly lower in EHL piglets, yet its binding to GR 1-9/10 promoter was significantly higher in EHL piglets, as revealed by chromatin immunoprecipitation assays. Although p53 binding to GR promoter 1-9/10 did not differ between breeds, expression of p53 mRNA and protein, as well as its binding to Sp1, were significantly higher in EHL piglets. Moreover, p53 activator doxorubicin significantly enhanced GR 1-9/10 promoter activity in HepG2 cells at 100 nM, which was associated with significantly higher protein content of p53 and GR.
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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 ╳
