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S4526

Sigma-Aldrich

Salinomycin

from Streptomyces albus, ≥98% (HPLC), powder, MDRP-1 inhibitor

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About This Item

Empirical Formula (Hill Notation):
C42H70O11
CAS Number:
53003-10-4
Molecular Weight:
751.00
EC Number:
258-290-1
UNSPSC Code:
12352200
PubChem Substance ID:
329824546
NACRES:
NA.77

product name

Salinomycin, from Streptomyces albus, ≥98% (HPLC)

biological source

Streptomyces albus

Quality Level

200

Assay

≥98% (HPLC)

mp

112.5-113.5 °C (lit.)

antibiotic activity spectrum

neoplastics

Mode of action

cell membrane | interferes

storage temp.

2-8°C

SMILES string

CC[C@H]([C@H]1CC[C@H](C)[C@@H](O1)[C@@H](C)[C@H](O)[C@H](C)C(=O)[C@H](CC)[C@H]2O[C@@]3(O[C@@]4(CC[C@](C)(O4)[C@H]5CC[C@](O)(CC)[C@H](C)O5)[C@H](O)C=C3)[C@H](C)C[C@@H]2C)C(O)=O

InChI

1S/C42H70O11/c1-11-29(38(46)47)31-15-14-23(4)36(50-31)27(8)34(44)26(7)35(45)30(12-2)37-24(5)22-25(6)41(51-37)19-16-32(43)42(53-41)21-20-39(10,52-42)33-17-18-40(48,13-3)28(9)49-33/h16,19,23-34,36-37,43-44,48H,11-15,17-18,20-22H2,1-10H3,(H,46,47)/t23-,24-,25+,26-,27-,28-,29+,30-,31+,32+,33+,34+,36+,37-,39-,40+,41-,42-/m0/s1

InChI key

KQXDHUJYNAXLNZ-XQSDOZFQSA-N

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General description

Chemical structure: polyether

Application

Salinomycin was used as a standard in the development of LC-MS/MS method for detection of residual coccidiostats in egg and muscle samples. It was used to screen out CD44+CD24- mesenchymal-like subpopulation within breast carcinomas.

Biochem/physiol Actions

Salinomycin produced by Streptomyces albus is a carboxylic polyether ionophore with antibiotic and anti-cancer properties. It induces cell death in some types of cancer cells such as breast, lung, gastric cancer, leukemia and osteosarcoma. Salinomycin inhibits multidrug resistance protein 1 and induces apoptosis by the generation of reactive oxygen species that cause DNA damage and inactivation of Stat3. Use of salinomycin as antibiotic results in lowered spermatozoa count and motility and decreased steroidogenesis in mice.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300

Hazard Classifications

Acute Tox. 2 Oral

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

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’.

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Soshi Kusunoki et al.
Gynecologic oncology, 129(3), 598-605 (2013-03-19)
We previously demonstrated that side-population (SP) cells in human endometrial cancer cells (Hec1 cells) and in rat endometrial cells expressing oncogenic human K-Ras protein (RK12V cells) have features of cancer stem cells (CSCs). Hec1-SP cells showed enhanced migration and the
Jan Czerwiński et al.
Archives of animal nutrition, 66(2), 102-116 (2012-05-31)
The effect of dietary sodium butyrate (SB) or salinomycin (SAL) or both additives on performance, small intestinal morphology and microbial ecology of broiler chickens was studied. A growth trial was conducted with 96 Ross 308 female broilers from 1 to
J S van der Linde-Sipman et al.
Veterinary pathology, 36(2), 152-156 (1999-03-31)
In April 1996, an outbreak of toxic polyneuropathy in cats occurred in the Netherlands. All cats had been fed one of two brands of dry cat food from one manufacturer. Chemical analyses of these foods, stomach contents, and liver and
K H Koo et al.
Cell death & disease, 4, e693-e693 (2013-06-29)
Salinomycin has been shown to control breast cancer stem cells, although the mechanisms underlying its anticancer effects are not clear. Deregulation of cell cycle regulators play critical roles in tumorigenesis, and they have been considered as anticancer targets. In this
Katia Sampieri et al.
Seminars in cancer biology, 22(3), 187-193 (2012-07-10)
Cancer stem cells (CSCs) represent a subpopulation of tumour cells endowed with self-renewal and multi-lineage differentiation capacity but also with an innate resistance to cytotoxic agents, a feature likely to pose major clinical challenges towards the complete eradication of minimal
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