SML0911
TAK-779
≥98% (HPLC), HIV entry inhibitor, powder
Synonym(s):
N,N-Dimethyl-N-[4-[[[2-(4-methylphenyl)-6,7-dihydro-5H-benzohepten-8-yl]carbonyl]amino]benzyl]tetrahydro-2H-pyran-4-aminium chloride, TAK-799, Takeda 779
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About This Item
Empirical Formula (Hill Notation):
C33H39ClN2O2
CAS Number:
Molecular Weight:
531.13
UNSPSC Code:
51111800
NACRES:
NA.77
Product Name
TAK-779, ≥98% (HPLC)
SMILES string
Cl.[N+](C5CCOCC5)(Cc1ccc(cc1)\N=C(/[O-])\C2=Cc3c(ccc(c3)c4ccc(cc4)C)CCC2)(C)C
InChI
1S/C33H38N2O2.ClH/c1-24-7-11-27(12-8-24)28-14-13-26-5-4-6-29(22-30(26)21-28)33(36)34-31-15-9-25(10-16-31)23-35(2,3)32-17-19-37-20-18-32;/h7-16,21-22,32H,4-6,17-20,23H2,1-3H3;1H
InChI key
VDALIBWXVQVFGZ-UHFFFAOYSA-N
assay
≥98% (HPLC)
form
powder
color
white to beige
solubility
H2O: 3 mg/mL, clear (warmed)
storage temp.
2-8°C
Quality Level
Related Categories
Application
TAK-779 has been used to inhibit CC chemokine ligand 5 (CCL5)– C-C chemokine receptor type 5 (CCR5) interaction in vitro in natural killer (NK) cytotoxicity assay. It has also been used as a blocker of CCR5 to study its effects and to evaluate the opening of the Panx-1 channels on peripheral blood mononuclear cells (PBMCs) isolated from human immunodeficiency virus (HIV)-infected individuals.
Biochem/physiol Actions
TAK-779 inhibits human immunodeficiency virus (HIV) entrance by blocking the C-C chemokine receptor type 5 (CCR5). It also impairs the formation of atherosclerotic lesions by preventing T-helper 1 cells from entering the plaque. TAK-779 possesses anti-immunogenic properties. In an arthritis model, it could prevent the inflow of CCR5- and chemokine (C-X-C motif) receptor 3 (CXCR3)-positive T cells into inflamed joints. In mice, TTAK-779 protects the brain from focal cerebral ischemia.
TAK-779 is a potent, dual antagonist at chemokine receptors C-C chemokine receptor type 2 (CCR2) and C-C chemokine receptor type 5 (CCR5) with IC50 = 1.4 nM at CCR5 and 2.3 nM at CCR2. Antagonists of both CCR2 and CCR5 such as TAK-779 have been investigated for treatment of viruses, rheumatoid arthritis, multiple sclerosis, and cancer. CCR5 is particularly targeted for anti-HIV therapy, since HIV entry into cells requires chemokine coreceptors CCR5 and C-X-C motif chemokine receptor 4 (CXCR4).
TAK-779 is a potent, dual antagonist at chemokine receptors CCR2 and CCR5.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Mercedes Armand-Ugón et al.
The Journal of antimicrobial chemotherapy, 65(3), 417-424 (2010-01-14)
Identification of CCR5 as an antiretroviral target led to the development of several CCR5 antagonists in clinical trials and the approval of maraviroc. Evaluating the mechanism of drug resistance to CCR5 agents may have implications in the clinical development of
Sam Bastani et al.
Transplantation, 88(8), 995-1001 (2009-10-27)
BACKGROUND.: Recruitment of recipient mononuclear cells to the donor heart is a central event in the development of cardiac allograft vasculopathy (CAV). The role of individual chemokine receptors in this process is incompletely defined. TAK-779 (N,N-dimethyl-N-[4-[[[2-(4-methylphenyl)-6,7-dihydro-5H-benzocyclohepten-8-yl]carbonyl]amino]benzyl]tetra-hydro-2H-pyran-4-aminium chloride) is a synthetic
Fernando Arenzana-Seisdedos
Enfermedades infecciosas y microbiologia clinica, 26 Suppl 11, 5-11 (2009-03-14)
Viral entry is an early stage and specific of the infection in which different viral and cellular targets are accessible to therapeutic treatment. CXCR4 and CCR5 act in this process as coreceptor molecules of HIV for its entry into the
Theresa L Chang et al.
Journal of acquired immune deficiency syndromes (1999), 53(3), 292-302 (2010-01-13)
Macrophages are major HIV target cells. They support both productive and latent HIV-1 infection. Susceptibility of primary macrophages to HIV depends on the anatomical location and activation state of the cells. We demonstrate that peritoneal macrophages (PMs) are abundant in
Qinxue Hu et al.
The Journal of general virology, 91(Pt 12), 2965-2973 (2010-09-03)
The envelope glycoprotein (Env) of human immunodeficiency virus is key to viral entry of susceptible target cells and is therefore a major target for the design of vaccines and antiviral drugs. C-C chemokine receptor type 5 (CCR5)-using (R5) Env is
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