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M6891

Sigma-Aldrich

Mithramycin A from Streptomyces plicatus

≥90% (HPLC)

Synonym(s):

Aureolic acid, Plicamycin

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About This Item

Empirical Formula (Hill Notation):
C52H76O24
CAS Number:
18378-89-7
Molecular Weight:
1085.15
Beilstein/REAXYS Number:
5236667
MDL number:
MFCD00135618
UNSPSC Code:
12161501
PubChem Substance ID:
24897127
NACRES:
NA.77

Quality Level

200

assay

≥90% (HPLC)

antibiotic activity spectrum

neoplastics

mode of action

DNA synthesis | interferes

storage temp.

2-8°C

SMILES string

[H][C@]1(Cc2cc3cc(O[C@H]4C[C@@H](O[C@H]5C[C@@H](O)[C@H](O)[C@@H](C)O5)[C@@H](O)[C@@H](C)O4)c(C)c(O)c3c(O)c2C(=O)[C@H]1O[C@H]6C[C@@H](O[C@H]7C[C@@H](O[C@H]8C[C@](C)(O)[C@H](O)[C@@H](C)O8)[C@H](O)[C@@H](C)O7)[C@H](O)[C@@H](C)O6)[C@H](OC)C(=O)[C@@H](O)[C@@H](C)O

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/t19-,20-,21-,22-,23-,24-,27+,28-,30-,31-,32-,33+,34+,35+,36+,37+,41+,42-,43+,44-,45-,49+,50+,51-,52+/m1/s1

InChI key

CFCUWKMKBJTWLW-BGLFSJPPSA-N

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General description

Chemical structure: aureolic acid

Biochem/physiol Actions

Anticancer antibiotic. Inhibits transcription and protein synthesis. Binds to DNA in native chromatin. Substrate of Pgp in MDR phenotypes.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Waise Quarni et al.
Scientific reports, 9(1), 15202-15202 (2019-10-28)
The pivotal role of cancer initiating stem cells (CSCs) in tumor initiation, growth, metastasis and drug resistance has led to the postulation of a 'total cancer therapy' paradigm, which involves targeting both cancer cells and CSCs for effective therapy. However
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Cancers, 11(12) (2019-12-01)
Resistance to chemotherapy is a major clinical challenge in the treatment of pancreatic ductal adenocarcinoma (PDAC). Here, we provide evidence that Rho associated coiled-coil containing protein kinase 2 (ROCK2) maintains gemcitabine resistance in gemcitabine resistant pancreatic cancer cells (GR cells).
Xiaoqin Yan et al.
Investigative ophthalmology & visual science, 61(6), 45-45 (2020-06-24)
A previous study reported that vasoactive intestinal peptide (VIP) can regulate the cytoskeleton of Schlemm's canal (SC) endothelium and expand the SC lumen in a rat glaucoma model. In this study, we aimed to investigate the molecular mechanism of VIP
Marina Isshiki et al.
Biological & pharmaceutical bulletin, 36(2), 299-304 (2013-02-02)
Recent epidemiological studies have shown that moderate coffee consumption is associated with a lower risk of certain types of cancers, particularly colon cancer in postmenopausal women. To elucidate the molecular basis for the preventive action of coffee, we investigated the
Chun-Wei Hsu et al.
Biometals : an international journal on the role of metal ions in biology, biochemistry, and medicine, 26(1), 1-12 (2012-10-26)
Mithramycin (Mith) forms a drug-metal complex with a 2:1 stoichiometry by chelation with a Ni(II) ion, which was determined using circular dichroism spectroscopy. Mith exhibits an increased affinity (~55 fold) for Ni(II) in the presence of DNA compared to the
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