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Key Documents

T7402

Sigma-Aldrich

Paclitaxel

from Taxus brevifolia, ≥95% (HPLC), powder

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About This Item

Fórmula empírica (Notação de Hill):
C47H51NO14
Número CAS:
Peso molecular:
853.91
Beilstein:
1420457
Número MDL:
Código UNSPSC:
12161501
ID de substância PubChem:
NACRES:
NA.77

fonte biológica

Taxus brevifolia

Ensaio

≥95% (HPLC)

forma

powder

cor

white

pf

213 °C (dec.) (lit.)

solubilidade

DMSO: 50 mg/mL (can be stored frozen for several months)
methanol: soluble 50 mg/mL, clear, colorless (undergoes transesterification)
ethanol: soluble

espectro de atividade do antibiótico

viruses

Modo de ação

DNA synthesis | interferes

originador

Bristol-Myers Squibb

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

[H][C@@]12C[C@H](O)[C@@]3(C)C(=O)[C@H](OC(C)=O)C4=C(C)[C@H](C[C@@](O)([C@@H](OC(=O)c5ccccc5)[C@]3([H])[C@@]1(CO2)OC(C)=O)C4(C)C)OC(=O)[C@H](O)[C@@H](NC(=O)c6ccccc6)c7ccccc7

InChI

1S/C47H51NO14/c1-25-31(60-43(56)36(52)35(28-16-10-7-11-17-28)48-41(54)29-18-12-8-13-19-29)23-47(57)40(61-42(55)30-20-14-9-15-21-30)38-45(6,32(51)22-33-46(38,24-58-33)62-27(3)50)39(53)37(59-26(2)49)34(25)44(47,4)5/h7-21,31-33,35-38,40,51-52,57H,22-24H2,1-6H3,(H,48,54)/t31-,32-,33+,35-,36+,37+,38-,40-,45+,46-,47+/m0/s1

chave InChI

RCINICONZNJXQF-MZXODVADSA-N

Procurando produtos similares? Visita Guia de comparação de produtos

Descrição geral

Chemical structure: taxoide

Aplicação

Paclitaxel has been used as a component of the dechorionation buffer for Gryllus bimaculatus eggs. Paclitaxel has also been used for studying its effect on the movement of all-trans retinoic acid (ATRA) differentiated NB4 cells.

Ações bioquímicas/fisiológicas

O Paclitaxel é um medicamento taxano antineoplásico e antimitótico potente, que se liga à terminação N da β-tubulina e estabiliza microtúbulos, interrompendo o ciclo celular na fase G2/M. O dano aos microtúbulos induz apoptose através de uma via dependente de JNK, seguida de uma via independente da JNK, possivelmente relacionada à ativação da proteína quinase A (PKA) ou da Raf-1 quinase, resultando na fosforilação de Bcl-2. Um metabólito importante da via do CYP2CB é o 6α-hidroxipaclitaxel (6α-OHP).

Características e benefícios

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by Bristol-Myers Squibb. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Embalagem

Bottomless glass bottle. Contents are inside inserted fused cone.

Atenção

O Paclitaxel é submetido a transesterificação em metanol e é hidrolisado em soluções aquosas.

Nota de preparo

Paclitaxel is soluble in methanol at 50 mg/ml and yields a clear, colorless solution. It is also soluble in DMSO (50 mg/ml) and ethanol.

Pictogramas

Health hazard

Palavra indicadora

Danger

Frases de perigo

Classificações de perigo

Muta. 2 - Repr. 1B - STOT RE 1 - STOT SE 2

Órgãos-alvo

Central nervous system,Bone marrow,Cardio-vascular system, Eyes,Central nervous system

Código de classe de armazenamento

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

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

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


Certificados de análise (COA)

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Isao Sarashina et al.
Development, growth & differentiation, 47(2), 99-108 (2005-03-18)
Early embryogenesis of the two-spotted cricket Gryllus bimaculatus was examined by scanning electron microscopy and several fluorescence staining methods, with special reference to these four issues: (i) the location of micropyles; (ii) the transfer of the female pronucleus following meiosis;
Joakim da Silva et al.
Biomaterials, 31(8), 2201-2208 (2009-12-18)
Whilst rigid, planar surfaces are often used to study cell migration, a physiological scenario requires three-dimensional (3D) scaffolds with tissue-like stiffness. This paper presents a method for fabricating periodic hydrogel scaffolds with a 3D honeycomb-like structure from colloidal crystal templates.
Karl-Heinz Altmann et al.
Natural product reports, 24(2), 327-357 (2007-03-29)
This review article provides an overview on the current state of research in the area of microtubule-stabilizing agents from natural sources, with a primary focus on the biochemistry, biology, and pharmacology associated with these compounds. A variety of natural products
Barbara T McGrogan et al.
Biochimica et biophysica acta, 1785(2), 96-132 (2007-12-11)
The taxanes, paclitaxel and docetaxel are microtubule-stabilizing agents that function primarily by interfering with spindle microtubule dynamics causing cell cycle arrest and apoptosis. However, the mechanisms underlying their action have yet to be fully elucidated. These agents have become widely
Zihao Wang et al.
Science signaling, 3(104), ra2-ra2 (2010-01-14)
Like phosphorylation, the addition of O-linked beta-N-acetylglucosamine (O-GlcNAcylation) is a ubiquitous, reversible process that modifies serine and threonine residues on nuclear and cytoplasmic proteins. Overexpression of the enzyme that adds O-GlcNAc to target proteins, O-GlcNAc transferase (OGT), perturbs cytokinesis and

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