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Merck

SML1091

高三尖杉酯碱

≥98% (HPLC), translation elongation inhibitor, powder

别名:

Ceflatonin, Cephalotaxine 4-methyl (2R)-2-hydroxy-2-(4-hydroxy-4-methylpentyl)butanedioate, Myelostat, NSC 141633, Omacetaxine mepesuccinate

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关于此项目

经验公式（希尔记法）:
C29H39NO9
化学文摘社编号:
26833-87-4
分子量:
545.62
MDL號碼:
MFCD03410264
分類程式碼代碼:
12352200
PubChem物質ID:
329825468
NACRES:
NA.77

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产品名称

高三尖杉酯碱, ≥98% (HPLC)

品質等級

100

化驗

≥98% (HPLC)

形狀

powder

光學活性

[α]/D -120 to -140°, c = 1 in chloroform-d

顏色

white to beige

溶解度

DMSO: 20 mg/mL, clear

儲存溫度

2-8°C

SMILES 字串

COC(=O)C[C@](O)(CCCC(C)(C)O)C(=O)O[C@H]1C2c3cc4OCOc4cc3CCN5CCC[C@]25C=C1OC

InChI

1S/C29H39NO9/c1-27(2,33)8-5-10-29(34,16-23(31)36-4)26(32)39-25-22(35-3)15-28-9-6-11-30(28)12-7-18-13-20-21(38-17-37-20)14-19(18)24(25)28/h13-15,24-25,33-34H,5-12,16-17H2,1-4H3/t24-,25-,28+,29-/m1/s1

InChI 密鑰

HYFHYPWGAURHIV-JFIAXGOJSA-N

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應用

Homoharringtonine has been used to check the cytotoxic activity against carfilzomib-resistant derivative of the LP-1 multiple myeloma (MM) cell line (LP-1/Cfz) and is used as a translation-inhibiting drug.

生化／生理作用

Homoharringtonine (Omacetaxine mepesuccinate) is a translation elongation inhibitor, a cytotoxic alkaloid originally isolated from the evergreen tree, Cephalotaxus hainanensis. Homoharringtonine binds to the 80S ribosome in eukaryotic cells and inhibits protein synthesis by interfering with chain elongation. Homoharringtonine blocks progression of leukemic cells from G1 phase into S phase and from G2 phase into M phase. Homoharringtonine (Omacetaxine mepesuccinate) was approved in October 2012 (Synribo) for the treatment of adult patients with Chronic Myelogenous Leukemia (CML) with resistance and/or intolerance to two or more tyrosine kinase inhibitors.
Homoharringtonine is a cephalotaxine ester that is also known as (HHT; 4-methyl (2R)-2-hydroxy-2-(4-hydroxy-4-methylpentyl)butanedioate). In gefitinib-resistant lung cancer cells, homoharringtonine promotes apoptosis and prevents signal transducer and activator of transcription 3 (STAT3) through IL-6 (interleukin-6) /JAK1 (janus kinase 1)/STAT3 signal pathway. It plays an important role in the treatment of malaria.
Homoharringtonine is a translation elongation inhibitor.

特點和優勢

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

象形圖

Skull and crossbones
GHS06

訊號詞

Danger

危險聲明

H300 + H310 + H330

危險分類

Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral

儲存類別代碼

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

水污染物質分類（WGK）

WGK 3

閃點（°F）

Not applicable

閃點（°C）

Not applicable

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
0000457329
0000457330
0000457330
0000433894
0000433894

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Chemistry and Biology, 439-439 (1998)
Rescue of a developmental arrest caused by a C. elegans heat-shock transcription-factor mutation by loss of ribosomal S6-kinase activity
Chisnell PJD, et al.
bioRxiv, 310086-310086 (2018)
Increased expression of the tight junction protein TJP1/ZO-1 is associated with upregulation of TAZ-TEAD activity and an adult tissue stem cell signature in carfilzomib-resistant multiple myeloma cells and high-risk multiple myeloma patients
Riz I and Hawley RG
Oncoscience, 4(7-8), 79-79 (2017)
Peter Chisnell et al.
Genetics, 210(3), 999-1009 (2018-09-20)
The widely conserved heat-shock response, regulated by heat-shock transcription factors, is not only essential for cellular stress resistance and adult longevity, but also for proper development. However, the genetic mechanisms by which heat-shock transcription factors regulate development are not well
Diego Rivera Gelsinger et al.
Nucleic acids research, 48(10), 5201-5216 (2020-05-10)
High-throughput methods, such as ribosome profiling, have revealed the complexity of translation regulation in Bacteria and Eukarya with large-scale effects on cellular functions. In contrast, the translational landscape in Archaea remains mostly unexplored. Here, we developed ribosome profiling in a
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