Art. -Nr.: HY-111224

GSK812397

GSK812397 is a CXCR4 antagonist with potential for the treatment of HIV infection. To evaluate the clinical potential of GSK812397, kilogram-scale agent candidates are needed. Here, an improved, scalable synthetic route for the CXCR4 antagonist GSK812397 is described. This new route has been scaled up in a 50-liter stationary facility to obtain 1.2 kg of agent substance in 20% overall yield and >99% chemical and enantiomeric purity in five steps. CXC chemokine receptor 4 (CXCR4) is a 7-transmembrane protein that functions in part as a host co-receptor for multiple strains of HIV-1. It is thought that targeting CXCR4 will help inhibit the replication of several late cytopathic viruses; therefore, CXCR4 antagonists are one of the most promising new classes of experimental anti-HIV agents. GSK812397 is a potent CXCR4 antagonist and is therefore a candidate for investigation for the treatment of HIV infection.

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CAS. Nr.: 878197-98-9
Formel: C₂₄H₃₂N₆O
Molecular Weight:420.55

Speicherung:

Please store the product under the recommended conditions in the Certificate of Analysis.

Data Sheet (272 KB)

GSK812397 Chemical Structure

CAS. Nr.: 878197-98-9

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Use of MCE Products

Strong Fluorescence Signal / Multi-Disciplinary Applications / High Fluorescence Specificity

Biologische Aktivität
- Beschreibung
- Cellular Effect
Chemical Information
Reinheit & Dokumentation
Verweise
Calculators
Help & FAQs
Classifications
Bioz

Biologische Aktivität

Beschreibung

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Alle CXCR Isoform-spezifische Produkte anzeigen :

Cellular Effect

Cell Line	Type	Value	Description	References
HEK293	IC₅₀	0.56 nM Compound: GSK-812397	Inhibition of HIV1 HXB2 gp120-mediated viral infusion into HEK293 cells after 24 hrs by luciferase reporter gene assay Inhibition of HIV1 HXB2 gp120-mediated viral infusion into HEK293 cells after 24 hrs by luciferase reporter gene assay	[PMID: 19949058]
HEK293	IC₅₀	0.87 nM Compound: GSK-812397	Antagonist activity at human CXCR4 expressed in HEK293 cells assessed as inhibition of SDF1-induced response treated 30 mins before agonist challenge by FLIPR assay Antagonist activity at human CXCR4 expressed in HEK293 cells assessed as inhibition of SDF1-induced response treated 30 mins before agonist challenge by FLIPR assay	[PMID: 19949058]
HEK293	IC₅₀	1.07 nM Compound: GSK-812397	Antagonist activity at human CXCR4 expressed in HEK293 cells assessed as inhibition of SDF1-induced response treated before agonist challenge measured after 15 mins by FLIPR assay Antagonist activity at human CXCR4 expressed in HEK293 cells assessed as inhibition of SDF1-induced response treated before agonist challenge measured after 15 mins by FLIPR assay	[PMID: 19949058]
HEK293	IC₅₀	1.71 nM Compound: GSK-812397	Inhibition of HIV1 HXB2 gp120-mediated viral infusion into HEK293 cells after 24 hrs by luciferase reporter gene assay in presence of 45 mg/ml human serum albumin Inhibition of HIV1 HXB2 gp120-mediated viral infusion into HEK293 cells after 24 hrs by luciferase reporter gene assay in presence of 45 mg/ml human serum albumin	[PMID: 19949058]
HEK293	IC₅₀	1.97 nM Compound: GSK-812397	Inhibition of HIV1 HXB2 gp120-mediated viral infusion into HEK293 cells after 24 hrs by luciferase reporter gene assay in presence of alpha-acid glycoprotein and human serum albumin Inhibition of HIV1 HXB2 gp120-mediated viral infusion into HEK293 cells after 24 hrs by luciferase reporter gene assay in presence of alpha-acid glycoprotein and human serum albumin	[PMID: 19949058]
HEK293	IC₅₀	1.99 nM Compound: GSK-812397	Inhibition of HIV1 HXB2 gp120-mediated viral infusion into HEK293 cells after 24 hrs by luciferase reporter gene assay in presence of 1 mg/ml alpha-acid glycoprotein Inhibition of HIV1 HXB2 gp120-mediated viral infusion into HEK293 cells after 24 hrs by luciferase reporter gene assay in presence of 1 mg/ml alpha-acid glycoprotein	[PMID: 19949058]
HEK293	IC₅₀	2.41 nM Compound: GSK-812397	Antagonist activity at human CXCR4 expressed in HEK293 cells assessed as inhibition of SDF1-induced increase in intracellular calcium level treated 15 mins before agonist challenge measured after 1 hr by FLIPR assay Antagonist activity at human CXCR4 expressed in HEK293 cells assessed as inhibition of SDF1-induced increase in intracellular calcium level treated 15 mins before agonist challenge measured after 1 hr by FLIPR assay	[PMID: 19949058]
HEK293	IC₅₀	26.64 nM Compound: GSK-812397	Antagonist activity at human CXCR4 expressed in HEK293 cells assessed as inhibition of SDF1-induced response treated 30 mins before agonist challenge measured after 45 mins post compound washout by FLIPR assay Antagonist activity at human CXCR4 expressed in HEK293 cells assessed as inhibition of SDF1-induced response treated 30 mins before agonist challenge measured after 45 mins post compound washout by FLIPR assay	[PMID: 19949058]
HEK293	IC₅₀	3.36 nM Compound: GSK-812397	Antagonist activity at human CXCR4 expressed in HEK293 cells assessed as inhibition of SDF1-induced response treated before agonist challenge measured after 5 mins by FLIPR assay Antagonist activity at human CXCR4 expressed in HEK293 cells assessed as inhibition of SDF1-induced response treated before agonist challenge measured after 5 mins by FLIPR assay	[PMID: 19949058]
HEK293	IC₅₀	>1000 nM Compound: GSK-812397	Cytotoxicity against HEK293 cells after 24 hrs by MTS assay Cytotoxicity against HEK293 cells after 24 hrs by MTS assay	[PMID: 19949058]
HOS	IC₅₀	>1000 nM Compound: GSK-812397	Cytotoxicity against human HOS cells infected with HIV1 3B after 72 hrs by celltiter glow assay Cytotoxicity against human HOS cells infected with HIV1 3B after 72 hrs by celltiter glow assay	[PMID: 19949058]
HOS	IC₅₀	1.23 nM Compound: GSK-812397	Antiviral activity against HIV1 3B infected in human HOS cells after 72 hrs by luminescence assay Antiviral activity against HIV1 3B infected in human HOS cells after 72 hrs by luminescence assay	[PMID: 19949058]
HOS	IC₅₀	2.01 nM Compound: GSK-812397	Antiviral activity against HIV1 3B infected in human HOS cells after 72 hrs by luminescence assay in presence of 45 mg/ml human serum albumin Antiviral activity against HIV1 3B infected in human HOS cells after 72 hrs by luminescence assay in presence of 45 mg/ml human serum albumin	[PMID: 19949058]
HOS	IC₅₀	2.87 nM Compound: GSK-812397	Antiviral activity against HIV1 3B infected in human HOS cells after 72 hrs by luminescence assay in presence of 1 mg/ml alpha-acid glycoprotein Antiviral activity against HIV1 3B infected in human HOS cells after 72 hrs by luminescence assay in presence of 1 mg/ml alpha-acid glycoprotein	[PMID: 19949058]
HOS	IC₅₀	3.14 nM Compound: GSK-812397	Antiviral activity against HIV1 3B infected in human HOS cells after 72 hrs by luminescence assay in presence of alpha-acid glycoprotein and human serum albumin Antiviral activity against HIV1 3B infected in human HOS cells after 72 hrs by luminescence assay in presence of alpha-acid glycoprotein and human serum albumin	[PMID: 19949058]
HOS	IC₅₀	>1000 nM Compound: GSK-812397	Antiviral activity against HIV1 Bal infected in human HOS cells after 72 hrs by luminescence assay Antiviral activity against HIV1 Bal infected in human HOS cells after 72 hrs by luminescence assay	[PMID: 19949058]
PBMC	IC₅₀	>1000 nM Compound: GSK-812397	Cytotoxicity against human PBMC infected with HIV1 3B after 7 days by celltiter glow assay Cytotoxicity against human PBMC infected with HIV1 3B after 7 days by celltiter glow assay	[PMID: 19949058]
PBMC	CC₅₀	4.6 nM Compound: 28	Cytotoxicity against human PBMC cells Cytotoxicity against human PBMC cells	[PMID: 38879970]
U2OS	IC₅₀	2.1 nM Compound: GSK-812397	Antagonist activity at mouse CXCR4 expressed in human U2OS cells assessed as inhibition of SDF1-induced increase in intracellular calcium level by FLIPR assay Antagonist activity at mouse CXCR4 expressed in human U2OS cells assessed as inhibition of SDF1-induced increase in intracellular calcium level by FLIPR assay	[PMID: 19949058]
U2OS	IC₅₀	4.3 nM Compound: GSK-812397	Antagonist activity at rat CXCR4 expressed in human U2OS cells assessed as inhibition of SDF1-induced increase in intracellular calcium level by FLIPR assay Antagonist activity at rat CXCR4 expressed in human U2OS cells assessed as inhibition of SDF1-induced increase in intracellular calcium level by FLIPR assay	[PMID: 19949058]
U2OS	IC₅₀	6.6 nM Compound: GSK-812397	Antagonist activity at human CXCR4 expressed in human U2OS cells assessed as inhibition of SDF1-induced increase in intracellular calcium level by FLIPR assay Antagonist activity at human CXCR4 expressed in human U2OS cells assessed as inhibition of SDF1-induced increase in intracellular calcium level by FLIPR assay	[PMID: 19949058]
U2OS	IC₅₀	7.8 nM Compound: GSK-812397	Antagonist activity at monkey CXCR4 expressed in human U2OS cells assessed as inhibition of SDF1-induced increase in intracellular calcium level by FLIPR assay Antagonist activity at monkey CXCR4 expressed in human U2OS cells assessed as inhibition of SDF1-induced increase in intracellular calcium level by FLIPR assay	[PMID: 19949058]
U-937	IC₅₀	0.34 nM Compound: GSK-812397	Inhibition of CXCR4-mediated chemotaxis in SDF1-stimulated human U937 cells treated 15 mins before SDF1 challenge measured after 2 hrs by luminescence assay Inhibition of CXCR4-mediated chemotaxis in SDF1-stimulated human U937 cells treated 15 mins before SDF1 challenge measured after 2 hrs by luminescence assay	[PMID: 19949058]

Chemical Information

CAS. Nr. 878197-98-9
Molecular Weight 420.55
Formel C₂₄H₃₂N₆O
SMILES

OCC1=C(CN([C@@H]2C3=NC=CC=C3CCC2)C)N=C4C=CC=C(N5CCN(CC5)C)N14
Versand

Room temperature in continental US; may vary elsewhere.
Speicherung

Please store the product under the recommended conditions in the Certificate of Analysis.

Reinheit & Dokumentation

Select Batch:

Reinheit: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (272 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

Verweise

[1]. Kilogram-Scale Synthesis of the CXCR4 Antagonist GSK812397

Calculators

Molaritätsrechner

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass Mass

Konzentration Konzentration

Volumen Volumen

Molecular Weight Molecular Weight

Verdünnungsrechner

Konzentration _{(Stammlösung)} × Volumen _{(Stammlösung)} = Konzentration _{(Ziellösung)} × Volumen _{(Ziellösung)}

Konzentration _{(Stammlösung)} Konzentration _{(Stammlösung)}

Volumen _{(Stammlösung)} Volumen _{(Stammlösung)}

Konzentration _{(Ziellösung)} Konzentration _{(Ziellösung)}

Volumen _{(Ziellösung)} Volumen _{(Ziellösung)}

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

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GSK812397

Alle HIV Isoform-spezifische Produkte anzeigen

Alle CXCR Isoform-spezifische Produkte anzeigen

Biologische Aktivität

Beschreibung

Cellular Effect

Chemical Information

Reinheit & Dokumentation

Verweise

Calculators

Help & FAQs

Bioz

Keywords

Your Recently Viewed Products

GSK812397

Alle HIV Isoform-spezifische Produkte anzeigen

Alle CXCR Isoform-spezifische Produkte anzeigen

Biologische Aktivität

Beschreibung

Cellular Effect

Chemical Information

Reinheit & Dokumentation

Verweise

Calculators

Help & FAQs

GSK812397 Related Classifications

HY-111224 Related Classifications

Bioz

Keywords

Your Recently Viewed Products