Doxorubicin hydrochloride - CAS 25316-40-9 Catalog number: BADC-00038

Description

Doxorubicin is an anthracycline antibiotic with antineoplastic activity produced by the bacterium Streptomyces peucetius var. Doxorubicin is an antibiotic agent that inhibits DNA topoisomerase II and induces DNA damage and apoptosis.

Synonyms

Doxorubicin HCl

IUPAC Name

(7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride

Canonical SMILES

CC1C(C(CC(O1)OC2CC(CC3=C(C4=C(C(=C23)O)C(=O)C5=C(C4=O)C=CC=C5OC)O)(C(=O)CO)O)N)O.Cl

InChI

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

InChIKey

MWWSFMDVAYGXBV-RUELKSSGSA-N

Solubility

Soluble ethanol, methanol, DMF, DMSO

Melting Point

>168°C

Flash Point

443.8°C

LogP

1.50360

PSA

206.07000

Vapor Pressure

9.64E-28mmHg at 25°C

In Vitro

MTT assay in MCF7 cells showed significantly higher (p<0.0001) cytotoxicity for doxorubicin hydrochloride in SPIONs than doxorubicin hydrochloride solution (IC50 values 6.294±0.4169 and 11.316±0.1102μgmL(-1), respectively).

In Vivo

When CVA21 was combined with doxorubicin hydrochloride, synergistically enhanced cell death was observed when CVA21 was administered both simultaneously or 24 h prior to doxorubicin hydrochloride exposure. Doxorubicin hydrochloride had no effect on CVA21 replication. Through the use of an orthotopic (MDA-MB-231-luc) xenograft SCID mouse model of human breast cancer we showed that a single intravenous injection of CVA21 in combination with an intraperitoneal injection of doxorubicin hydrochloride resulted in significantly greater tumor reduction compared to either agent alone.

Clinical Trial Information

Source

Streptomyces peucetius

Appearance

Orange Crystal Powder

Purity

>98%

Quantity

Milligrams-Grams

Quality Standard

USP

Shelf Life

≥360 days if stored properly

Shipping

-20°C (International: -20°C)

Storage

Store at -20°C

Pictograms

Irritant; Health Hazard

Signal Word

Danger

Boiling Point

810.3°C at 760 mmHg

Assay

160 μL of Hela cells suspension (3×104 cell/mL) is dispensed into three 96-well U-bottom microplates and incubated for 24 h at 37°C in a fully humidified atmosphere of 5% CO2. In plate 1, serial dilutions of Doxorubicin (20 μL; final concentration, 0.1-2 μM) and Simvastatin (20 μL; final concentration, 0.25-2 μM) are added to a final volume of 200 μL and incubated for another 72 h. In plates 2 and 3 serial dilutions of each drug (Simvastatin or Doxorubicin, 40 μL) are added. After an incubation period of 24 h, the medium is aspirated and the cells are washed in PBS. Then, serial dilutions of other drug (40 μL) are added and supplemented with culture medium to a final volume of 200 μL, and incubated for 48 h. Doxorubicin and Simvastatin are used individually as positive controls (40 μL in each well), and the cells treated only with solvent are considered as negative controls. To evaluate cell survival, 20 μL of MTT solution (5 mg/mL in PBS) is added to each well and incubated for 3 h. Then the media is replaced with 150 μL of DMSO, and complete solubilization of formazan crystals is achieved by repeated pipetting of the solution. Absorbance is then determined at 540 nm by an ELISA plate reader. Each drug concentration is assayed in 4 or 8 wells and repeated 3 times. The cytotoxic/cytostatic effect of Doxorubicin is expressed as the relative viability (% control) and calculated. Percentage of cell survival in the negative control is assumed as 100.