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SML1091

Sigma-Aldrich

Homoharringtonine

≥98% (HPLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C29H39NO9
CAS Number:
26833-87-4
Molecular Weight:
545.62
MDL number:
MFCD03410264
UNSPSC Code:
12352200
PubChem Substance ID:
329825468
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

optical activity

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

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

2-8°C

SMILES string

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 key

HYFHYPWGAURHIV-JFIAXGOJSA-N

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Application

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.

Biochem/physiol Actions

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.

Features and Benefits

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.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300 + H310 + H330

Hazard Classifications

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

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Chemistry and Biology, 439-439 (1998)
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)
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)
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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