D1515

Doxorubicin hydrochloride

98.0-102.0% (HPLC)

• Synonim(y): Adriamycin, DOX, Hydroxydaunorubicin hydrochloride
• Empirical Formula (Hill Notation): C₂₇H₂₉NO₁₁ · HCl
• Numer CAS: 25316-40-9
• Masa cząsteczkowa: 579.98
• Beilstein: 4229251
• Numer EC: 246-818-3
• Numer MDL: MFCD00077757
• Identyfikator substancji w PubChem: 24893465
• NACRES: NA.76

Właściwości

• pochodzenie biologiczne: synthetic (organic)
• Poziom jakości: 200
• Próba: 98.0-102.0% (HPLC)
• forma: powder
• mp: 216 °C (dec.) (lit.)
• rozpuszczalność: water: 50.0-52.0 mg/mL, clear, orange to red
• spektrum działania antybiotyku: viruses
• Tryb działania: DNA synthesis | interferes
• temp. przechowywania: 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)

Opis

Opis ogólny

Chemical structure: tetracycline

Doxorubicin hydrochloride (DOX) is an anthracycline antibiotic isolated from Streptomyces peucetius var. caesius. The water soluble anti-cancer agent DOX is a hydroxy derivative of daunorubicin.

Zastosowanie

Doxorubicin hydrochloride has been used:

• in cell viability assays
• MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide) assay
• as a drug in polymeric PLGA-based microparticulate drug delivery
• to develop doxorubicin-resistant HepG2 cells (HepG2-DR) and K562 cells (K562-DR)

Działania biochem./fizjol.

Naturally fluorescent anthracycline antibiotic, anticancer drug. Doxorubicin is a substrate of MRP1 which was first cloned from a DOX-resistant lung cancer cell line. Fluorescent property has been exploited for the measurement of drug efflux pump activities as well as resolving the important question of intracellular localization of various multidrug resistance proteins and the role of subcellular organelles (Golgi and lysosome) in the sequestration of drugs and its implication in drug resistant phenotypes.

Substrate of MRP1; used for measurement of drug efflux pump activities. Doxorubicin hydrochloride (DOX) inhibits topoisomerase II by intercalating between base pairs and by inducing strand breaks, resulting in the inhibition of nucleic acid and protein synthesis. It also contributes to the formation of free radicals for the disruption of membrane lipids and DNA strands. DOX is used in the treatment of non-Hodgkin′s lymphoma and other cancers.

Uwaga dotycząca przygotowania

Soluble in water and in isotonic sodium chloride solution, slightly soluble in methanol. Practically insoluble in chloroform, ether, and in other organic solvents.

Inne uwagi

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

Informacja o środkach bezpieczeństwa

• piktogramy: GHS07,GHS08
• Hasło ostrzegawcze: Danger
• Zwroty wskazujące rodzaj zagrożenia: H302 - H340 - H350 - H360FD
• Zwroty wskazujące środki ostrożności: P202 - P264 - P270 - P280 - P301 + P312 - P308 + P313
• Klasyfikacja zagrożeń: Acute Tox. 4 Oral - Carc. 1B - Muta. 1B - Repr. 1B
• Kod klasy składowania: 6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Temperatura zapłonu °F: Not applicable
• Temperatura zapłonu °C: Not applicable
• Środki ochrony indywidualnej: Eyeshields, Gloves, type P3 (EN 143) respirator cartridges