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SML3237

Sigma-Aldrich

G-5555

≥98% (HPLC)

Synonym(s):

8-(((2r,5r)-5-Amino-1,3-dioxan-2-yl)methyl)-6-(2-chloro-4-(6-methylpyridin-2-yl)phenyl)-2-(methylamino)pyrido[2,3-d]pyrimidin-7(8H)-one, 8-[(trans -5-Amino-1,3-dioxan-2-yl)methyl]-6-[2-chloro-4-(6-methyl-2-pyridinyl)phenyl]-2-(methylamino)pyrido[2,3-d ]pyrimidin-7(8H )-one

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About This Item

Empirical Formula (Hill Notation):
C25H25ClN6O3
CAS Number:
1648863-90-4
Molecular Weight:
492.96
MDL number:
MFCD28506227
UNSPSC Code:
12352200
NACRES:
NA.77
Pricing and availability is not currently available.
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Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/L, clear

storage temp.

−20°C

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(1S, 2S)-1,2-Bis(4-nitrophenyl)ethylenediamine dihydrochloride 97%

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684120

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(1S,2S)-1,2-Bis(2,4,6-trimethylphenyl)ethylenediamine dihydrochloride 95%

684104

(1S,2S)-1,2-Bis(2,4,6-trimethylphenyl)ethylenediamine dihydrochloride

(1S, 2S)-1,2-di-1-Naphthyl-ethylenediamine dihydrochloride 97%

684147

(1S, 2S)-1,2-di-1-Naphthyl-ethylenediamine dihydrochloride

assay

97%

assay

96%

assay

95%

assay

97%

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

form

powder

form

powder

form

solid

form

powder

mp

202-207 °C

mp

235-239 °C

mp

>300 °C

mp

219-224 °C

optical activity

[α]22/D -84.0°, c = 1 in H2O

optical activity

[α]22/D +11°, c = 1 in H2O

optical activity

[α]20/D −129°, c = 1 in H2O

optical activity

[α]22/D +258.0°, c = 1 in H2O

functional group

amine

functional group

amine

functional group

amine

functional group

amine

General description

G-5555 is a selective p21-activated kinase (PAK1) inhibitor. In addition to this it also selectively inhibits eight kinases such as PAK2, PAK3, KHS1, lymphocyte-specific protein tyrosine kinase (LcK), Mammalian Ste20-like kinase 3 (MST3), Mammalian Ste20-like kinase 4 (MST4), salt-inducible kinase 2(SIK2), and Yeast Sps1/Ste20-related Kinase 1 (YSK1). G-5555 exhibits high stability and low human ether-à-go-go related gene (hERG) activity than other PAK inhibitors including FRAX1036.[1]

Biochem/physiol Actions

ATP site-targeting inhibitor against SIK1/2/3, MST3/4, PAK1/2, YANK1/3, MAP2K5 and MAP4K5. Reduces cellular MEK pS298 in cultures and in mice in vivo.
G-5555 is an ATP site-targeting inhibitor against salt-inducible kinases, MST3/4, p21-activated kinase 1/2, YANK1/3, MAP2K5, MAP4K5 (% inhibition at 100 nM = 98.6/93.5/99.8 (SIK1/2/3), 85/99.5 (MST3/4), 95.6/87 (PAK1/2), 94.7/96.5 (YANK1/3); 87/MAP2K5, 83/MAP4K5) with good selectivity over other kinases. G-5555 downregulates MEK pS298 in EBC1 cells in cultures (IC50 = 69 nM) and in H292 NSCLC tumors in mice in vivo (25 mg/kg p.o.) with good oral availability (mice F = 80%, monkeys F = 72%).
G-5555 is an ATP site-targeting inhibitor against salt-inducible kinases, MST3/4, p21-activated kinase 1/2, YANK1/3, MAP2K5, MAP4K5 (% inhibition at 100 nM = 98.6/93.5/99.8 (SIK1/2/3), 85/99.5 (MST3/4), 95.6/87 (PAK1/2), 94.7/96.5 (YANK1/3); 87/MAP2K5, 83/MAP4K5) with good selectivity over other kinases. G-5555 downregulates MEK pS298 in EBC1 cells in cultures (IC50 = 69 nM) and in H292 NSCLC tumors in mice in vivo (25 mg/kg p.o.) with good oral availability (mice F = 80%, monkeys F = 72%). PAK1 plays a crucial role in cancer progression, inhibiting this protein has the potential to reduce cancer development. Therefore, G-5555 may be a promising candidate for oncology research.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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    Clemens Simbrunner et al.
    ACS nano, 6(6), 4629-4638 (2012-05-19)
    We report on the epitaxial growth of periodic para-hexaphenyl (p-6P)/α-sexi-thiophene (6T) multilayer heterostructures on top of p-6P nanotemplates. By the chosen approach, 6T molecules are forced to align parallel to the p-6P template molecules, which yields highly polarized photoluminescence (PL)-emission
    Woon-Seok Kang et al.
    Korean journal of anesthesiology, 61(3), 210-215 (2011-10-26)
    Atrial fibrillation (AF) is the most common cardiac arrhythmia. Magnesium has been reported to be effective in reducing the incidence or prophylaxis of AF. Magnesium is also an essential constituent of many enzyme systems and plays a physiological role in
    Annealing effect in the sexithiophene:C70 small molecule bulk heterojunction organic photovoltaic cells
    Sakai, J.; et al.
    Solar Energy Mat. and Solar Cells, 93, 1149?1153-1149?1153 (2009)
    Clemens Simbrunner et al.
    Journal of the American Chemical Society, 133(9), 3056-3062 (2011-02-12)
    During the last years, self-assembled organic nanostructures have been recognized as a proper fundament for several electrical and optical applications. In particular, phenylenes deposited on muscovite mica have turned out to be an outstanding material combination. They tend to align
    Günther Schwabegger et al.
    Crystal growth & design, 13(2), 536-542 (2013-02-16)
    The morphology and structure of sexithiophene deposited on KCl (100) substrates was investigated by scanning force microscopy and specular X-ray diffraction measurements. Two different needle-like structures with {010} and {4̅11} contact planes have been observed as well as islands of
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