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D1515

Doxorubicin hydrochloride

Name: Doxorubicin hydrochloride
Brand: SIGMA

98.0-102.0% (HPLC)

Synonym(s):

Adriamycin, DOX, Hydroxydaunorubicin hydrochloride

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About This Item

Empirical Formula (Hill Notation):

C₂₇H₂₉NO₁₁ · HCl

CAS Number:

25316-40-9

Molecular Weight:

579.98

UNSPSC Code:

51281818

NACRES:

NA.76

PubChem Substance ID:

24893465

EC Number:

246-818-3

Beilstein/REAXYS Number:

4229251

MDL number:

MFCD00077757

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Properties

biological source

synthetic (organic)

Quality Level

200

assay

98.0-102.0% (HPLC)

form

powder

mp

216 °C (dec.) (lit.)

solubility

water: 50.0-52.0 mg/mL, clear, orange to red

antibiotic activity spectrum

viruses

mode of action

DNA synthesis | interferes

storage temp.

2-8°C

SMILES string

Cl[H].COc1cccc2C(=O)c3c(O)c4C[C@](O)(C[C@H](O[C@H]5C[C@H](N)[C@H](O)[C@H](C)O5)c4c(O)c3C(=O)c12)C(=O)CO

InChI

1S/C27H29NO11.ClH/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34;/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3;1H/t10-,13-,15-,17-,22+,27-;/m0./s1

InChI key

MWWSFMDVAYGXBV-RUELKSSGSA-N

Gene Information

human ... TOP2A(7153)

Description

General description

Doxorubicin hydrochloride (DOX) is an anthracycline antibiotic isolated from Streptomyces peucetius var. caesius. The water soluble anti-cancer agent DOX is a hydroxy derivative of daunorubicin.

Doxorubicin also leads to the generation of reactive oxygen species (ROS), which further damage DNA, proteins, and membranes. It exerts cytotoxic, antitumor, anticancer, and antineoplastic activity and finds application in cancer, metabolomics, cell biology, and biochemical research.

Application

Doxorubicin hydrochloride has been used:

in cell viability assays
MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide) assay
as a drug in polymeric PLGA-based microparticulate drug delivery
to develop doxorubicin-resistant HepG2 cells (HepG2-DR) and K562 cells (K562-DR)

Biochem/physiol Actions

Substrate of MRP1; used for measurement of drug efflux pump activities. Doxorubicin hydrochloride (DOX) inhibits topoisomerase II by intercalating between base pairs and by inducing strand breaks, resulting in the inhibition of nucleic acid and protein synthesis. It also contributes to the formation of free radicals for the disruption of membrane lipids and DNA strands.

Naturally fluorescent anthracycline antibiotic, anticancer drug. Doxorubicin is a substrate of MRP1 which was first cloned from a DOX-resistant lung cancer cell line. Fluorescent property has been exploited for the measurement of drug efflux pump activities as well as resolving the important question of intracellular localization of various multidrug resistance proteins and the role of subcellular organelles (Golgi and lysosome) in the sequestration of drugs and its implication in drug resistant phenotypes.

Features and Benefits

High-quality antibiotic suitable for multiple research applications
Ideal for Cell Biology, Metabolomics, and Biochemical research.

Preparation Note

Soluble in water and in isotonic sodium chloride solution, slightly soluble in methanol. Practically insoluble in chloroform, ether, and in other organic solvents.

Tightly closed. Dry. Keep in a well -ventilated place. Keep locked up or in an area accessible