Mithramycin A, Streptomyces plicatus

SKU
M-1072
  • CAS:18378-89-7
  • Formula:C52H76O24
  • MW:1085.0 Da
  • Appearance:Yellow Solid
  • Purity:98%

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Product Name Qty
Mithramycin A, Streptomyces plicatus
1 mg
$119.78
Mithramycin A, Streptomyces plicatus
5 mg
$252.89

Description

Antibiotic which also serves as a DNA binding fluorescent dye. Inhibits RNA synthesis.Mithramycin A Sensitizes TRAIL-Mediated Apoptosis in Various Malignant Cancer Cells. Mithramycin A sensitizes cancer cells to TRAIL-mediated apoptosis by down-regulation of XIAP gene promoter through Sp1 sites.Both subcutaneous and intraperitoneal MIT significantly suppressed the growth of carcinoid cells in nude mouse models. Mithramycin encapsulated in polymeric micelles by microfluidic technology a novel therapeutic protocol for beta-thalassemia.

More Information
Alternate Name/Synonyms
Plicamycin; Aureolic acid; Mitramycin; MA
SKU
M-1072
CAS #
18378-89-7
Chemical Name
(2S,3S)-2-[(2S,4R,5R,6R)-4-[(2S,4R,5S,6R)-4-[(2S,4S,5R,6R)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]oxy-3-[(1S,3S,4R)-3,4-dihydroxy-1-methoxy-2-oxopentyl]-6-[(2S,4R,5R,6R)-4-[(2S,4R,5S,6R)-4,5-dih
Chemical Formula
C52H76O24
Molecular Weight
1085.0 Da
Appearance
Yellow Solid
Purity
98%
Solubility
DMSO: clear yellow solution at 100 mg/mL
Melting Point
180-183°C
Preparation
N/A
Storage Temp
-20°C
THERAPEUTIC AREA
Oncological Disorders
USE
Mithramycin A is an antibiotic DNA/RNA polymerase and DNA binding transcriptional inhibitor observed to facilitate TNF-α and Fas-ligand induced apoptosis. As a DNA binding transcriptional inhibitor, mithramycin A binds to GC rich sequences located in the minor groove of DNA and is noted to be reversible and Mg2+ dependent. Additionally reported to a block transcriptional activation of the SV40 promoter via competitive binding against Sp1 transcription factor to GC rich areas in the early promoter. Mithramycin A is noted to supress TNF-α induced expression of fractalkine (CX3CL1) mRNA in a dose-dependent manner and to act as an effective differentiation agent of HL60 promyelocytic leukemia cells.
Merck Index
Merck Index: 12.7696.1996
MDL NUMBER
MFCD00135618
CHEMACX
X1009161-5
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/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
SMILES
Cc1c(cc2cc3c(c(c2c1O)O)C(=O)[C@H](C(C3)[C@@H](C(=O)[C@H]([C@@H](C)O)O)OC)O[C@H]4C[C@H]([C@@H]([C@H](O4)C)O)O[C@H]5C[C@H]([C@@H]([C@H](O5)C)O)O[C@H]6C[C@]([C@@H]([C@H](O6)C)O)(C)O)O[C@H]7C[C@H]([C@H]([C@H](O7)C)O)O[C@H]8C[C@H]([C@@H]([C@H](O8)C)O)O
Peptide sequence
Not Applicable
RTECS
PZ2800000
UN #'S
Not Applicable
PACKING GROUP
Not Applicable
HAZARD CLASS
Not Applicable
Handling
Avoid contact with skin and eyes. Do not breathe dust. Do not breathe vapors or spray mist. Use only in area provided with appropriate exhaust ventilation.
Citations
Thyroid transcription factor-1 (TTF-1) gene: identification of ZBP-89, Sp1, and TTF-1 sites in the promoter and regulation by TNF-α in lung epithelial cells Aparajita Das, Sunil Acharya, Koteswara Rao Gottipati, James B. McKnight, Hemakumar Chandru, Joseph L. Alcorn, and Vijay Boggaram Am J Physiol Lung Cell Mol Physiol, Oct 2011; 301: L427 - L440.
Citations_Hyperlink
http://ajplung.physiology.org/cgi/reprint/301/4/L427
Certificate of Analysis 1
Certificate of Analysis 2
Certificate of Analysis 3
GHS PICTOGRAMS
Handling Avoid contact with skin and eyes. Do not breathe dust. Do not breathe vapors or spray mist. Use only in area provided with appropriate exhaust ventilation.
UN #'S Not Applicable
Packing Group Not Applicable
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