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S5826

Sigma-Aldrich

SYUIQ-5

≥98% (HPLC)

Synonym(s):

N′-(10H-Indolo [3,2-b]quinolin-11-yl)-N, N-dimethyl-propane-1,3-diamine

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About This Item

Empirical Formula (Hill Notation):
C20H22N4
CAS Number:
188630-47-9
Molecular Weight:
318.42
MDL number:
MFCD17215940
UNSPSC Code:
12352200
PubChem Substance ID:
329824555
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

yellow

solubility

DMSO: ≥20 mg/mL

storage temp.

2-8°C

SMILES string

CN(C)CCCNc1c2ccccc2nc3c4ccccc4[nH]c13

InChI

1S/C20H22N4/c1-24(2)13-7-12-21-18-14-8-3-5-10-16(14)22-19-15-9-4-6-11-17(15)23-20(18)19/h3-6,8-11,23H,7,12-13H2,1-2H3,(H,21,22)

InChI key

CTDCVGDSVHUYMA-UHFFFAOYSA-N

Application

SYUIQ-5 may be used in autophagy and DNA damage-inducing cell signaling studies.

Biochem/physiol Actions

SYUIQ-5 is a Cryptolepine derivative, which induces and stabilizes G-quadruplexes. In CNE2 and HeLa cancer cells SYUIQ-5 triggers rapid and potent telomere DNA damage through TRF2 delocalization from telomeres and induces cell death by autophagy. In low concentration the compound caused senescence and telomere shortening. It is a potent cytotoxic agent.

Pictograms

Environment
GHS09

Signal Word

Warning

Hazard Statements

H400

Precautionary Statements

P273 - P391 - P501

Hazard Classifications

Aquatic Acute 1

Storage Class Code

11 - Combustible Solids

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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Andrea Funke et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 22(9), 3170-3181 (2016-01-26)
The interaction of phenyl-substituted indolo[3,2-b]quinolines with DNA G-quadruplexes of different topology were studied by using a combination of spectroscopic and calorimetric methodologies. N5-Methylated indoloquinoline derivatives ((Me) PIQ) with an aminoalkyl side chain exhibit high affinities for the parallel-stranded MYC quadruplex
Cindy K Miranti et al.
Oncotarget, 11(19), 1758-1776 (2020-06-02)
The androgen receptor (AR) is a major driver of prostate cancer development and progression. Men who develop advanced prostate cancer often have long-term cancer control when treated with androgen-deprivation therapies (ADT). Still, their disease inevitably becomes resistant to ADT and
Mary E Gagou et al.
Oncotarget, 5(22), 11381-11398 (2014-11-02)
Unwinding duplex DNA is a critical processing step during replication, repair and transcription. Pif1 are highly conserved non-processive 5'->3' DNA helicases with well-established roles in maintenance of yeast genome stability. However, the function of the sole member of Pif1 family

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