Skip to Content
Merck
All Photos(2)

Documents

M6891

Sigma-Aldrich

Mithramycin A from Streptomyces plicatus

≥90% (HPLC)

Synonym(s):

Aureolic acid, Plicamycin

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C52H76O24
CAS Number:
Molecular Weight:
1085.15
Beilstein:
5236667
MDL number:
UNSPSC Code:
12161501
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

Looking for similar products? Visit Product Comparison Guide

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

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, 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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
Yang Zhou et al.
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).
S Min et al.
Genes and immunity, 13(8), 621-631 (2012-10-05)
The alterations induced in dendritic cells (DCs) in the cancer microenvironment have not been extensively explored. We found that the tumor-associated factor TGF-β may selectively upregulate the expression of miR-27a via the SP1 transcription factor. Importantly, miR-27a altered the activity
Fouad S El-Mayet et al.
Journal of virology, 98(1), e0143623-e0143623 (2023-12-12)
Bovine alphaherpesvirus 1 (BoHV-1) infections cause respiratory tract disorders and suppress immune responses, which can culminate in bacterial pneumonia. Following acute infection, BoHV-1 establishes lifelong latency in sensory neurons present in trigeminal ganglia (TG) and unknown cells in pharyngeal tonsil.
Ushasree Mrudulakumari Vasudevan et al.
Biotechnology advances, 41, 107550-107550 (2020-05-04)
Flavonoids, terpenoids, and polyketides are structurally diverse secondary metabolites used widely as pharmaceuticals and nutraceuticals. Most of these molecules exist in nature as glycosides, in which sugar residues act as a decisive factor in their architectural complexity and bioactivity. Engineering

Articles

Discover Bioactive Small Molecules for ADME/Tox

Discover Bioactive Small Molecules for ADME/Tox

Discover Bioactive Small Molecules for ADME/Tox

Discover Bioactive Small Molecules for ADME/Tox

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service