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Merck

D1515

Sigma-Aldrich

Doxorrubicina hydrochloride

98.0-102.0% (HPLC)

Sinónimos:

Adriamicina, DOX, Hidroxidaunorrubicina hydrochloride

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10 MG
US$ 341,00

US$ 341,00


Fecha estimada de envío01 de abril de 2025


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10 MG
US$ 341,00

About This Item

Fórmula empírica (notación de Hill):
C27H29NO11 · HCl
Número de CAS:
Peso molecular:
579.98
Beilstein/REAXYS Number:
4229251
EC Number:
MDL number:
UNSPSC Code:
51281818
PubChem Substance ID:
NACRES:
NA.76

US$ 341,00


Fecha estimada de envío01 de abril de 2025


Solicitar un pedido a granel

biological source

synthetic (organic)

Quality Level

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)

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General description

El clorhidrato de doxorrubicina (DOX) es un antibiótico antraciclínico aislado de Streptomyces peucetius var. caesius.[1][2] El antineoplásico hidrosoluble DOX[3] es un derivado hidroxi de la daunorrubicina.[4]

La doxorrubicina también induce la generación de especies reactivas del oxígeno (ROS), que dañan aún más el ADN, las proteínas y las membranas. Ejerce actividad citotóxica, antitumoral, anticancerígena y antineoplásica y encuentra aplicación en la investigación sobre el cáncer, la metabolómica, la biología celular y la bioquímica.[4]

Application

El clorhidrato de doxorrubicina se ha utilizado:
  • en ensayos de viabilidad celular[5]
  • en el ensayo del MTT (bromuro de 3-(4,5-dimetiltiazol-2-il)-2,5-difeniltetrazolio)[6]
  • como medicamento en la administración de fármacos en micropartículas compuestas de PLGA[7]
  • para desarrollar células HepG2 resistentes a la doxorrubicina (HepG2-DR) y células K562 (K562-DR)[8]

Biochem/physiol Actions

Antibiótico antraciclina naturalmente fluorescente, antineoplásico. La doxorrubicina es un sustrato de la MRP1, que se clonó por primera vez de una línea de células de cáncer de pulmón resistentes a la DOX. Su propiedad fluorescente se ha explotado para medir las actividades de la bomba de expulsión activa de medicamentos, así como para resolver la importante cuestión de la localización intracelular de varias proteínas de resistencia a múltiples fármacos y el papel de los orgánulos subcelulares (aparato de Golgi y lisosomas) en el secuestro de medicamentos y su implicación en los fenotipos resistentes a fármacos.
Sustrato de la MRP1; utilizado para medir la actividad de las bombas de expulsión activa de medicamentos. El clorhidrato de doxorrubicina (DOX) inhibe a la topoisomerasa II intercalándose entre los pares de bases e induciendo la rotura de las cadenas, lo que produce la inhibición de la síntesis de ácidos nucleicos y proteínas.[1] También contribuye a la formación de radicales libres para la alteración de los lípidos de la membrana y las hebras de ADN.[1]

Features and Benefits

  • Antibiótico de gran calidad adecuado para múltiples aplicaciones experimentales
  • Ideal para investigación en biología celular, metabolómica y bioquímica.

Preparation Note

Soluble en agua y en disolución de cloruro sódico isotónica, ligeramente soluble en metanol. Prácticamente insoluble en cloroformo, éter y otros disolventes orgánicos.

Storage and Stability

Bien cerrado. Seco. Consérvese en un lugar bien ventilado. Manténgalo bajo llave o en un área accesible

Other Notes

Mantenga el recipiente herméticamente cerrado y en un lugar bien ventilado. Sensible a la humedad. Sensible a la luz.
Si desea más información sobre nuestra gama de productos bioquímicos, cumplimente este formulario.

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pictograms

Health hazardExclamation mark

signalword

Danger

Hazard Classifications

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

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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


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Questions

1–10 of 12 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

      Helpful?

  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. How to store after reconstitution and for how long is it stable?

    1 answer
    1. Aliquots are stable for up to 3 months at -20°C or for up to 6 months at -70°C. Avoid repeated freeze/thaw cycles.

      Helpful?

  4. What is the difference between Doxorubicin hydrochloride Products D1515 and 44583?

    1 answer
    1. The D1515 and 44583 Doxorubicin HCl products are physically identical. Each has a minimum purity specification of 98%. However, the 44583 product option is tested for suitability in fluorescence applications while the D1515 is assigned basic tests for general research use.

      The following links taken from the peer reviewed papers may be of interest:
      https://www.sigmaaldrich.com/search/d1515?focus=papers&page=1&perpage=30&sort=relevance&term=d1515&type=citation_search

      https://www.sigmaaldrich.com/search/44583?focus=papers&page=1&perpage=30&sort=relevance&term=44583&type=citation_search

      Helpful?

  5. Si può prolungare la stabilità del prodotto D1515 sciolto in soluzione acquosa e successivamente conservato a -20°C?

    1 answer
    1. Solution stability studies have not been performed on this product, however, the available literature suggests that solutions are most stable refrigerated. It is recommended to add 3 - 5% glucose or lactose as a stabilizer for long-term storage. Commercially available solutions were found to be stable for at least 1 month at -20°C and up to 1 year at 4°C.

      This product, in solution, will degrade in alkaline pH conditions or when exposed to light for extended periods.

      Helpful?

  6. Whta is the pka and logP of Doxorubicin hydrochloride ID D1515

    1 answer
    1. See the link below to DrugBank Online for these data:
      https://go.drugbank.com/salts/DBSALT000060

      Helpful?

  7. Is this product suitable for in vivo applications?

    1 answer
    1. This product has not been tested for in vitro or in vivo use. However, the listed Peer-Reviewed Papers suggest that customers have been successful in these applications. Note that the product is not tested for endotoxin and the solution would require filter sterilization prior to use.

      Please view the peer-reviewed papers here: https://www.sigmaaldrich.com/search/d1515?focus=papers&page=1&perpage=30&sort=relevance&term=d1515&type=citation_search.

      Helpful?

  8. 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?

  9. What is the difference between Doxorubicin hydrochloride Products D1515 and D1317?

    1 answer
    1. Product No. D1317, Doxorubicin hydrochloride solution has been discontinued and is no longer available.  We now offer Product No. D1515 which is a powder.

      Helpful?

  10. What can be used to make a solution of Product D1515, Doxorubicin hydrochloride?

    1 answer
    1. The solubility of doxorubicin is tested in water (50 mg/mL), yielding a clear orange to red solution.

      Helpful?

1–10 of 12 Questions  

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