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安全信息

44583

Sigma-Aldrich

阿霉素 盐酸盐

suitable for fluorescence, 98.0-102.0% (HPLC)

别名:

DOX, 多柔比星® 盐酸盐, 羟基柔红霉素 盐酸盐

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About This Item

经验公式（希尔记法）:
C27H29NO11 · HCl
CAS号:
25316-40-9
分子量:
579.98
Beilstein:
4229251
EC 号:
246-818-3
MDL编号:
MFCD00077757
UNSPSC代码:
51281818
PubChem化学物质编号:
57650234
NACRES:
NA.76

生物来源

synthetic

质量水平

200

方案

98.0-102.0% (HPLC)

表单

solid

颜色

orange to dark red

mp

216 °C (dec.) (lit.)

溶解性

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

荧光

λem 580-590 nm

适用性

suitable for fluorescence

抗生素抗菌谱

neoplastics

作用机制

DNA synthesis | interferes
enzyme | inhibits

储存温度

2-8°C

SMILES字符串

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

基因信息

human ... TOP2A(7153)

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一般描述

化学结构：四环素

应用

阿霉素用于诱导细胞凋亡，并在 SK-N-MC 细胞中诱导心脏毒性。它用于抑制大分子的生物合成。

生化/生理作用

阿霉素是一种插入 DNA 并抑制大分子生物合成的抗肿瘤抗生素。由于拓扑异构酶 II 的抑制，DNA 复制被牵引。 它是逆转录酶和 RNA 聚合酶的抑制剂，是一种免疫抑制剂。

包装

无底玻璃瓶。内含物装在锥底内插管中。

其他说明

保存于密闭容器内，置于干燥通风处。

象形图

Health hazardExclamation mark
GHS08,GHS07

警示用语：

Danger

危险分类

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

储存分类代码

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

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

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

法规信息

监管及禁止进口产品

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
0000397923
0000397924
0000341638
0000298770
0000298770

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

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

    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. 

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

    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.

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

    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.

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

    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 <0.5 mg/mL, with considerable loss of bioactivity. If stored at 25 °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".

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

    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

  9. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

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
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.
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
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