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SML0560

Sigma-Aldrich

BRACO19 hydrochloride

≥96% (HPLC), powder, telomerase inhibitor

Synonym(s):

N,N′-(9-(4-(Dimethylamino)phenylamino)acridine-3,6-diyl)bis(3-(pyrrolidin-1-yl)propanamide) hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C35H43N7O2 · xHCl
CAS Number:
1177798-88-7
Molecular Weight:
593.76 (free base basis)
MDL number:
MFCD23380200
UNSPSC Code:
12352200
PubChem Substance ID:
329825553
NACRES:
NA.77

product name

BRACO19 hydrochloride, ≥96% (HPLC)

Assay

≥96% (HPLC)

form

powder

storage condition

desiccated

color

yellow to brown

solubility

H2O: 5 mg/mL, clear

storage temp.

2-8°C

SMILES string

Cl.Cl.Cl.CN(C)c1ccc(Nc2c3ccc(NC(=O)CCN4CCCC4)cc3nc5cc(NC(=O)CCN6CCCC6)ccc25)cc1

InChI

1S/C35H43N7O2.3ClH/c1-40(2)28-11-7-25(8-12-28)38-35-29-13-9-26(36-33(43)15-21-41-17-3-4-18-41)23-31(29)39-32-24-27(10-14-30(32)35)37-34(44)16-22-42-19-5-6-20-42;;;/h7-14,23-24H,3-6,15-22H2,1-2H3,(H,36,43)(H,37,44)(H,38,39);3*1H

InChI key

MJAPNWJRLLDPAB-UHFFFAOYSA-N

Application

BRACO19 hydrochloride has been used to study the role of antiviral activity of G4-stabilizing agents in cells infected with latent human immunodeficiency virus -1 (HIV-1).

Biochem/physiol Actions

BRACO19 is a telomerase inhibitor that stabilizes G-quadruplexes, targeting telomeric G-quadruplexes, inducing DNA damage and cell-cycle arrest.
Telomerase is associated with tumor progression and is highly expressed in a number of tumors. BRACO19 is known to prevent the capping and catalytic action of telomerase and thus, might serve as an effective therapeutic approach for cancer treatment. BRACO19 establishes antiviral activity against HIV (human immunodeficiency virus).

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

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

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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Yu-Lun Chen et al.
The Chinese journal of physiology, 59(6), 331-347 (2016-11-07)
Lung resistance-related protein (LRP) is a human major vault protein (MVP) implicated in drug resistance of cancer cells in a cell-type dependent manner. The primary goal of the study was to understand the role(s) of LRP in doxorubicin (DOX) resistance
The G-quadruplex-interactive molecule BRACO-19 inhibits tumor growth, consistent with telomere targeting and interference with telomerase function.
Burger A M, et al.
Cancer Research, 65(4), 1489-1496 (2005)
Anti-HIV-1 activity of the G-quadruplex ligand BRACO-19.
Perrone R, et al.
The Journal of Antimicrobial Chemotherapy, 69(12), 3248-3258 (2014)
Shyam Sushama Jose et al.
Frontiers in genetics, 9, 345-345 (2018-09-14)
Telomeropathies are rare disorders associated with impaired telomere length control mechanisms that frequently result from genetic mutations in the telomerase complex. Dyskeratosis congenita is a congenital progressive telomeropathy in which mutation in the telomerase RNA component (TERC) impairs telomere maintenance
Deficiency in DNA damage response, a new characteristic of cells infected with latent HIV-1.
Piekna-Przybylska D, et al.
Cell Cycle, 16(10), 968-978 (2017)

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