SML1091

Sigma-Aldrich

Homoharringtonine

≥98% (HPLC)

Sinônimo(s):
Ceflatonin, NSC 141633, Cephalotaxine 4-methyl (2R)-2-hydroxy-2-(4-hydroxy-4-methylpentyl)butanedioate, Omacetaxine mepesuccinate, Myelostat
Empirical Formula (Hill Notation):
C29H39NO9
Número CAS:
Peso molecular:
545.62
Número MDL:
ID de substância PubChem:

Nível de qualidade

100

teor

≥98% (HPLC)

forma

powder

atividade óptica

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

cor

white to beige

solubilidade

DMSO: 20 mg/mL, clear

temperatura de armazenamento

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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Aplicação

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.

Embalagem

10, 50 mg in glass bottle

Ações bioquímicas/fisiológicas

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 (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.

Pictogramas

Skull and crossbones

Palavra indicadora

Danger

Frases de perigo

RIDADR

UN 1544PSN1 6.1 / PGII

WGK Alemanha

WGK 3

Ponto de fulgor (ºF)

Not applicable

Ponto de fulgor (ºC)

Not applicable

Certificado de análise
Certificado de origem
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...
Bernhard Hampoelz et al.
Cell, 179(3), 671-686 (2019-10-19)
The molecular events that direct nuclear pore complex (NPC) assembly toward nuclear envelopes have been conceptualized in two pathways that occur during mitosis or interphase, respectively. In gametes and embryonic cells, NPCs also occur within stacked cytoplasmic membrane sheets, termed...
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