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SML2620

Sigma-Aldrich

Bromonoscapine

≥98% (HPLC)

Synonym(s):

(S)-3-((R)-9-bromo-4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-6,7-dimethoxyisobenzofuran-1(3H)-one, 9-Bromonoscapine, EM 011

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About This Item

Empirical Formula (Hill Notation):
C22H22BrNO7
CAS Number:
488721-01-3
Molecular Weight:
492.32
MDL number:
MFCD28969854
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -100 to -120°, c = 1 in dichloromethane

color

faint yellow to dark orange

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

Brc1c2c(c(c3c1CCN([C@H]3[C@H]4OC(=O)c5c4ccc(c5OC)OC)C)OC)OCO2

InChI

1S/C22H22BrNO7/c1-24-8-7-10-13(19(28-4)21-20(15(10)23)29-9-30-21)16(24)17-11-5-6-12(26-2)18(27-3)14(11)22(25)31-17/h5-6,16-17H,7-9H2,1-4H3/t16-,17+/m1/s1

InChI key

PLMUFLAOTAHIIZ-SJORKVTESA-N

Biochem/physiol Actions

Bromonoscapine is a microtubular disrupting agent that exhibits potent cytotoxic activity against breast, lung and other cancers.
microtubular disrupting agent

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Akhilesh Kumar Verma et al.
Bioorganic & medicinal chemistry, 14(19), 6733-6736 (2006-06-21)
Three haloderivatives of noscapine 2-4 were synthesized chemoselectively and their in vitro cytotoxicity was assessed by MTT assay on U-87 human glioblastoma cell lines. At 50 microM concentration after 72 h, 9-chloronoscapine 2, 9-bromonoscapine 3 (EM011), and 9-iodonoscapine 4 killed
Jun Zhou et al.
Molecular pharmacology, 63(4), 799-807 (2003-03-20)
Noscapine, a microtubule-interfering agent, has been shown to arrest mitosis, to induce apoptosis, and to have potent antitumor activity. We report herein that two brominated derivatives of noscapine, 5-bromonoscapine (5-Br-nosc) and reduced 5-bromonoscapine (Rd 5-Br-nosc), have higher tubulin binding activity
Maged Henary et al.
Biochemical pharmacology, 92(2), 192-205 (2014-08-16)
Noscapine, an opium-derived 'kinder-gentler' microtubule-modulating drug is in Phase I/II clinical trials for cancer chemotherapy. However, its limited water solubility encumbers its development into an oral anticancer drug with clinical promise. Here we report the synthesis of 9 third-generation, water-soluble

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