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44583

Sigma-Aldrich

Doxorubicin hydrochloride

suitable for fluorescence, 98.0-102.0% (HPLC)

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Synonym(s):
DOX, Hydroxydaunorubicin hydrochloride
Empirical Formula (Hill Notation):
C27H29NO11 · HCl
CAS Number:
25316-40-9
Molecular Weight:
579.98
Beilstein:
4229251
EC Number:
246-818-3
MDL number:
MFCD00077757
PubChem Substance ID:
57650234

biological source

synthetic

Quality Level

200

Assay

98.0-102.0% (HPLC)

form

solid

color

orange to dark red

mp

216 °C (dec.) (lit.)

solubility

H2O: 50 mg/mL, clear, orange to red
DMSO: soluble
THF: soluble
ethanol: soluble
methanol: soluble

fluorescence

λem 580-590 nm

suitability

suitable for fluorescence

antibiotic activity spectrum

neoplastics

Mode of action

DNA synthesis | interferes
enzyme | inhibits

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)

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General description

Chemical structure: tetracycline

Application

Doxorubicin was used to induce apoptosis, and to induce cardiotoxicity in SK-N-MC cells . It is used to inhibit macromolecular biosynthesis.

Biochem/physiol Actions

Doxorubicin ia an antitumor antibiotic that intercalates DNA and inhibits macromolecular biosynthesis. DNA replication is haulted due to the inhibition of topoisomerase II. It is an inhibitor of reverse transcriptase and RNA polymerase and is an immunosuppressive agent .

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

Pictograms

Exclamation markHealth hazard
GHS07,GHS08

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 1B - Muta. 1B - Repr. 1B

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

监管及禁止进口产品

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

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    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  5. What is the function of Doxorubicin hydrochloride, Product 44583?

    In chemotherapy: "Doxorubicin HCl is the hydrochloride salt of doxorubicin, an anthracycline antibiotic with antineoplastic activity. Doxorubicin, isolated from the bacterium Streptomyces peucetius var. caesius, is the hydroxylated congener of daunorubicin."  -National Cancer Institute.

  6. At what concentration can Doxorubicin hydrochloride, Product 44583, be dissolved in water? At what concentration in DMSO?

    The solubility of Product No. 44583 tested in water (50 mg/mL), yielding a clear orange to red solution.  It is also soluble in DMSO (50 mg/mL), ethanol, methanol and tetrahydrofuran.

  7. How stable is a solution of Doxorubicin hydrochloride, Product 44583?

    According to the 11th edition of the chemicals encyclopedia published by the Royal Society of Chemistry, "aqueous solutions are unchanged after one month at 5 °C but unstable at higher temperatures or at either acid or alkaline pH.  Several studies cite that stability is related to pH, exposure to light and the medium used for storage. Doxorubicin hydrochloride is subject to light degradation at <0.5 mg/mL, with considerable loss of bioactivity. If stored at 25 °C in the dark in 5% glucose, pH 4.7 (or 3.3% glucose + 0.3% sodium chloride, pH 4.4), solutions were stable (5% or less change) for at least 4 weeks".

  8. How should I use Product D1515 - Doxorubicin hydrochloride to induce double strand breaks in the DNA of HeLa cells?

    We do not test Product D1515 - Doxorubicin hydrochloride for biological activity with HELA cells.  The following paper used 100 nM to 250 nM doxorubicin  Adam Hermawan, et al.,  Journal of Natural Remedies, Vol. 12/2 (2012) 108-114The following paper uses  0.01 to 1.0 mug/ml doxorubicin  SH Kim, et al., CANCER RESEARCH 32, 323-325, February 1972

  9. My question is not addressed here, how can I contact Technical Service for assistance?

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