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44583

Sigma-Aldrich

Doxorrubicina hydrochloride

suitable for fluorescence, 98.0-102.0% (HPLC)

Sinónimos:

DOX, Hidroxidaunorrubicina hydrochloride

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About This Item

Fórmula empírica (notación de Hill):
C27H29NO11 · HCl
Número de CAS:
25316-40-9
Peso molecular:
579.98
Beilstein:
4229251
Número CE:
246-818-3
Número MDL:
MFCD00077757
Código UNSPSC:
51281818
ID de la sustancia en PubChem:
57650234
NACRES:
NA.76
En este momento no podemos mostrarle ni los precios ni la disponibilidad

origen biológico

synthetic

Nivel de calidad

200

Ensayo

98.0-102.0% (HPLC)

Formulario

solid

color

orange to dark red

mp

216 °C (dec.) (lit.)

solubilidad

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

fluorescencia

λem 580-590 nm

idoneidad

suitable for fluorescence

espectro de actividad antibiótica

neoplastics

Modo de acción

DNA synthesis | interferes
enzyme | inhibits

temp. de almacenamiento

2-8°C

cadena 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

Clave InChI

MWWSFMDVAYGXBV-RUELKSSGSA-N

Información sobre el gen

human ... TOP2A(7153)

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Descripción general

Chemical structure: tetracycline

Aplicación

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

Acciones bioquímicas o fisiológicas

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].

Envase

Bottomless glass bottle. Contents are inside inserted fused cone.

Otras notas

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

Pictogramas

Health hazardExclamation mark
GHS08,GHS07

Palabra de señalización

Danger

Frases de peligro

H302,H340,H350,H360FD

Clasificaciones de peligro

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

Código de clase de almacenamiento

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

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

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

Elija entre una de las versiones más recientes:

Certificados de análisis (COA)

Lot/Batch Number
0000397923
0000397924
0000298770
0000397923
0000341638

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Daunorubicin hydrochloride European Pharmacopoeia (EP) Reference Standard

D0125000

Daunorubicin hydrochloride

Paclitaxel from semisynthetic, ≥98%

Sigma-Aldrich

T7191

Paclitaxel

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
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
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
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
C Main et al.
Health technology assessment (Winchester, England), 10(9), 1-132 (2006-03-21)
To examine the clinical effectiveness and cost-effectiveness of intravenous formulations of topotecan monotherapy, pegylated liposomal doxorubicin hydorocholoride (PLDH) monotherapy and paclitaxel used alone or in combination with a platinum-based compound for the second-line or subsequent treatment of advanced ovarian cancer.
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Questions

1–8 of 8 Questions  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

      Helpful?

  3. 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.

      Helpful?

  4. 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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  5. 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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  6. 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.

      Helpful?

  7. 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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  8. 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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