SML2916
AAL-R
≥98% (HPLC)
别名:
(R)-2-Amino-2-methyl-4-[4-(heptyloxy)phenyl]butan-1-ol, (R)-2-Amino-4-(4-(heptyloxy)phenyl)-2-methylbutan-1-ol, (R)-2-Amino-4-(4-heptyloxyphenyl)-2-methylbutanol, AAL(R)
产品名称
AAL-R, ≥98% (HPLC)
InChI
1S/C18H31NO2/c1-3-4-5-6-7-14-21-17-10-8-16(9-11-17)12-13-18(2,19)15-20/h8-11,20H,3-7,12-15,19H2,1-2H3/t18-/m1/s1
InChI key
ITJCKQTXCLGXHE-GOSISDBHSA-N
SMILES string
C[C@](N)(CO)CCC1=CC=C(C=C1)OCCCCCCC
assay
≥98% (HPLC)
form
powder
color
white to beige
solubility
DMSO: 2 mg/mL, clear
storage temp.
2-8°C
Quality Level
Biochem/physiol Actions
More phosphorylatable FTY720 (fingolimod) analog with greater SphK2-dependent sphingosine 1-phosphate receptor (S1P) agonist efficacy in vitro and in vivo.
AAL-R [AAL(R)] is a FTY720 (fingolimod) analog and a much more rapidly activated sphingosine 1-phosphate receptor (S1P) agonist by sphingosine kinase 2 (SphK2)-mediated phosphorylation in vitro and in vivo. AAL-R triggers lymphocytes apoptosis in a SphK2-dependent manner (34%/84% remaining parental/SphK2-deficient Jurkat; 24 h 5 μM) with a significantly higher efficacy than its S-enantiomer AAL-S or FTY720 (%PI- mouse splenocytes = 27/ALL-R vs 56/FTY720 or ALL-S; 24 h 4 μM). AAL-R (0.1-0.3 mg/kg intratracheally), but not ALL-S, inhibits T-cell response to influenza infection and reduces pulmonary inflammation during Bordetella pertussis infection in mice (0.5 mg/kg intranasally).
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Peter Ettmayer et al.
Bioorganic & medicinal chemistry letters, 16(1), 84-87 (2005-10-21)
Fluorescently labeled chiral analogs of the immunomodulatory drug FTY720 and its corresponding phosphates with variable aliphatic spacers between the aromatic ring and the NBD label have been synthesized. Determining the influence of the spacer on the in vitro phosphorylation rate
Ciaran Skerry et al.
Infection and immunity, 87(2) (2018-12-05)
Incidence of whooping cough (pertussis), a bacterial infection of the respiratory tract caused by the bacterium Bordetella pertussis, has reached levels not seen since the 1950s. Antibiotics fail to improve the course of disease unless administered early in infection. Therefore
Jeremy Ardanuy et al.
Journal of immunology (Baltimore, Md. : 1950), 204(8), 2192-2202 (2020-03-11)
Type I and III IFNs play diverse roles in bacterial infections, being protective for some but deleterious for others. Using RNA-sequencing transcriptomics we investigated lung gene expression responses to Bordetella pertussis infection in adult mice, revealing that type I and
Eve Jary et al.
Molecular pharmacology, 78(4), 685-692 (2010-07-09)
The new immunosuppressant FTY720 (fingolimod), an analog of the endogenous lipid sphingosine, induces transient lymphopenia through the sequestration of lymphocytes in secondary lymphoid organs. Phosphorylation of FTY720 by sphingosine kinase 2 (SphK2) yields the active metabolite FTY720-phosphate (FTY-P), which induces
David Marsolais et al.
Molecular pharmacology, 74(3), 896-903 (2008-06-26)
The mechanism by which locally delivered sphingosine analogs regulate host response to localized viral infection has never been addressed. In this report, we show that intratracheal delivery of the chiral sphingosine analog (R)-2-amino-4-(4-heptyloxyphenyl)-2-methylbutanol (AAL-R) or its phosphate ester inhibits the
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