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D1515

Doxorubicin -hydrochlorid

98.0-102.0% (HPLC)

Synonym(e):

Adriamycin, Adriamycin® -hydrochlorid, DOX, Hydroxydaunorubicin -hydrochlorid

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Ihnen/SKUVerfügbarkeitPreis
10 mg
Warenkorb auf Verfügbarkeit prüfen
€ 363,00

Über diesen Artikel

Empirische Formel (Hill-System):
C27H29NO11 · HCl
CAS-Nummer:
Molekulargewicht:
579.98
UNSPSC Code:
51281818
NACRES:
NA.76
PubChem Substance ID:
EC Number:
246-818-3
Beilstein/REAXYS Number:
4229251
MDL number:

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biological source

synthetic (organic)

Quality Segment

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)

General description

Doxorubicinhydrochlorid (DOX) ist ein Anthracyclin-Antibiotikum, das aus Streptomyces peucetius var. caesius isoliert wird. Der wasserlösliche Krebswirkstoff DOX ist ein Hydroxy-Derivat von Daunorubicin.

Doxorubicin führt außerdem zur Bildung von reaktiven Sauerstoffspezies (ROS), die DNA, Proteine und Membranen weiter schädigen. Es wirkt zytotoxisch, antitumoral, krebsbekämpfend und antineoplastisch und findet Anwendung in der Krebsforschung, Metabolomik, Zellbiologie und biochemischen Forschung.

Application

Doxorubicinhydrochlorid wurde verwendet:
  • in Zellviabilitätsassays
  • im MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazoliumbromid)-Assay
  • als Wirkstoff bei der polymeren PLGA-basierten Mikropartikel-Wirkstoffverabreichung
  • zur Entwicklung doxorubicinresistenter HepG2-Zellen (HepG2-DR) und K562-Zellen (K562-DR)

Biochem/physiol Actions

Natürlich fluoreszierendes Anthracyclin-Antibiotikum, Krebstherapeutikum. Doxorubicin ist ein Substrat von MRP1, das zuerst aus einer DOX-resistenten Lungenkrebs-Zelllinie kloniert wurde. Seine Fluoreszenzeigenschaften wurden genutzt, um die Wirkstoff-Effluxpumpenaktivität zu messen und die wichtigen Fragen der intrazellulären Lokalisation verschiedener multiresistenter Proteine sowie der Rolle subzellulärer Organellen (Golgi und Lysosom) bei der Sequestrierung von Wirkstoffen und deren Implikationen bei arzneimittelresistenten Phenotypen zu lösen.
Substrat von MRP1; zur Messung der Aktivität von Arzneimittel-Effluxpumpen. Doxorubicinhydrochlorid (DOX) hemmt Topoisomerase II, indem es sich zwischen Basenpaaren einlagert und Strangbrüche verursacht, wodurch die Nukleinsäure- und Proteinsynthese gehemmt wird. Es trägt außerdem zur Bildung freier Radikale bei, die Membranlipide und DNA-Stränge zerstören.

Features and Benefits

  • Für verschiedene Forschungsanwendungen geeignetes hochwertiges Antibiotikum
  • Ideal für die Zellbiologie, Metabolomik und biochemische Forschung.

Preparation Note

Fest verschlossen. Trocken. An einem gut belüfteten Ort aufbewahren. Unter Verschluss oder in einem zugänglichen Bereich aufbewahren
Löslich in Wasser und in isotonischer Kochsalzlösung, schwach löslich in Methanol. Praktisch unlöslich in Chloroform, Ether und anderen organischen Lösungsmitteln.

Other Notes

Behälter dicht verschlossen an einem trockenen und gut belüfteten Ort aufbewahren. Feuchtigkeitsempfindlich. Lichtempfindlich.
Füllen Sie bitte dieses Formular aus, um weitere Informationen zu unserem Sortiment an Biochemikalien zu erhalten.

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1 of 1

Dieser Artikel
44583D2975000BP990
mode of action

DNA synthesis | interferes

mode of action

DNA synthesis | interferes, enzyme | inhibits

mode of action

-

mode of action

-

antibiotic activity spectrum

viruses

antibiotic activity spectrum

neoplastics

antibiotic activity spectrum

-

antibiotic activity spectrum

-

Quality Level

200

Quality Level

200

Quality Level

-

Quality Level

-

form

powder

form

solid

form

-

form

solid

assay

98.0-102.0% (HPLC)

assay

98.0-102.0% (HPLC)

assay

-

assay

-

solubility

water: 50.0-52.0 mg/mL, clear, orange to red

solubility

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

solubility

-

solubility

-


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pictograms

Health hazardExclamation mark

signalword

Danger

Hazard Classifications

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

Lagerklasse

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

ppe

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



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Questions

1–10 of 12 Questions  
  1. 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/418/501/product-dating-information-06-25-mk.pdf

      Helpful?

  2. 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?

  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. How can I store a solution of Product D1515, Doxorubicin hydrochloride?

    1 answer
    1. 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.

      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 is the excitation and emission wavelength for Product D1515, Doxorubicin hydrochloride?

    1 answer
    1. Doxorubicin has excitation maximum at 470 nm and an emission maximum at 585 nm in ethanol.

      Helpful?

1–10 of 12 Questions  

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