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Principaux documents

44583

Sigma-Aldrich

Doxorubicine hydrochloride

suitable for fluorescence, 98.0-102.0% (HPLC)

Synonyme(s) :

DOX, Hydroxydaunorubicine hydrochloride

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About This Item

Formule empirique (notation de Hill):
C27H29NO11 · HCl
Numéro CAS:
Poids moléculaire :
579.98
Beilstein:
4229251
Numéro CE :
Numéro MDL:
Code UNSPSC :
51281818
ID de substance PubChem :
Nomenclature NACRES :
NA.76
Le tarif et la disponibilité ne sont pas disponibles actuellement.

Source biologique

synthetic

Niveau de qualité

Essai

98.0-102.0% (HPLC)

Forme

solid

Couleur

orange to dark red

Pf

216 °C (dec.) (lit.)

Solubilité

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

Fluorescence

λem 580-590 nm

Adéquation

suitable for fluorescence

Spectre d'activité de l'antibiotique

neoplastics

Mode d’action

DNA synthesis | interferes
enzyme | inhibits

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

MWWSFMDVAYGXBV-RUELKSSGSA-N

Informations sur le gène

human ... TOP2A(7153)

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Description générale

Chemical structure: tetracycline

Application

Doxorubicin was used to induce apoptosis, and to induce cardiotoxicity in SK-N-MC cells [1][2]. It is used to inhibit macromolecular biosynthesis.

Actions biochimiques/physiologiques

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 [3].

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Autres remarques

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

Pictogrammes

Health hazardExclamation mark

Mention d'avertissement

Danger

Mentions de danger

Classification des risques

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

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges


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Lot/Batch Number

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Consulter la Bibliothèque de documents

R L Momparler et al.
Cancer research, 36(8), 2891-2895 (1976-08-01)
The effect of adriamycin on DNA, RNA, and protein synthesis was investigated in cell-free systems and intact cells. In studies with purified mammalian cell enzymes, adriamycin produced a greater inhibition of DNA-dependent DNA polymerase than of RNA polymerase. The extent
Shujun Zhang et al.
Journal of natural products, 69(10), 1425-1428 (2006-10-28)
Two new guaianolides, named chinensiolides D (5) and E (6), were isolated from Ixeris chinensis Nakai, and their structures were determined to be 10alpha-hydroxy-3-oxoguaia-11(13)-eno-12,6alpha-lactone (5) and 10alpha-hydroxy-3beta-O-[2,6-di(p-hydroxyphenylacetyl)-beta-glucopylanosyl]guaia-4(15),11(13)-dieno-12,6alpha-lactone (6). The first isolation of (11S)-10alpha-hydroxy-3-oxoguaia-4-eno-12,6alpha-lactone (4) from natural sources and its characterization
Michael A Skinner et al.
Anticancer research, 28(4B), 2019-2025 (2008-08-30)
Medullary thyroid cancer (MTC) is generally resistant to chemotherapy and the frequent constitutive activation of RET (rearranged during transfection gene) in these tumors might inhibit drug-induced apoptosis. Each RET isoform was separately expressed in SK-N-MC cells (neural crest-derived tumor) and
Lisa Fujimura et al.
Cardiovascular research, 64(2), 315-321 (2004-10-16)
The Ndl gene, which encodes a novel kelch family protein, is expressed ubiquitously in mouse tissues. In vitro studies suggest that Ndl protein, which binds to actin filaments, functions as a cytoskeletal stabilizer. In order to elucidate a physiological function
Shuai Li et al.
Journal of biomedical nanotechnology, 10(8), 1480-1489 (2014-07-16)
Amphiphilic copolymers have been paid much attention for controlled drug release for many years due to their obvious advantages. In this study, an acid-triggered drug carrier system capable of rapid intracellular drug release is investigated for potential tumor therapy. The

Articles

Explore how antibiotics, particularly quinolones, inhibit nucleic acid synthesis by targeting topoisomerases, crucial for DNA replication processes.

Explore how antibiotics, particularly quinolones, inhibit nucleic acid synthesis by targeting topoisomerases, crucial for DNA replication processes.

Explore how antibiotics, particularly quinolones, inhibit nucleic acid synthesis by targeting topoisomerases, crucial for DNA replication processes.

Explore how antibiotics, particularly quinolones, inhibit nucleic acid synthesis by targeting topoisomerases, crucial for DNA replication processes.

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Questions

1–6 of 6 Questions  
  1. Doxorubicin (44583) can dissolve in PBS only or not?

    1 answer
    1. Yes, this product is soluble in water at 50 mg/mL. PBS and other aqueous buffers would also be an option.

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

    1 answer
    1. 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.

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

    1 answer
    1. 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.

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  4. What is the Department of Transportation shipping information for this product?

    1 answer
    1. 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.

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

    1 answer
    1. 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

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

    1 answer
    1. 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 °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".

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