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Merck
CN

SML2916

Sigma-Aldrich

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)

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关于此项目

经验公式(希尔记法):
C18H31NO2
化学文摘社编号:
分子量:
293.44
UNSPSC代码:
41106300
NACRES:
NA.77
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质量水平

方案

≥98% (HPLC)

表单

powder

颜色

white to beige

溶解性

DMSO: 2 mg/mL, clear

储存温度

2-8°C

SMILES字符串

C[C@](N)(CO)CCC1=CC=C(C=C1)OCCCCCCC

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

相关类别

生化/生理作用

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).
More phosphorylatable FTY720 (fingolimod) analog with greater SphK2-dependent sphingosine 1-phosphate receptor (S1P) agonist efficacy in vitro and in vivo.

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable


历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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Ciaran Skerry et al.
The Journal of infectious diseases, 215(2), 278-286 (2016-11-07)
Recent data have demonstrated the potential of sphingosine 1-phosphate (S1P) receptor (S1PR) agonism in the treatment of infectious diseases. A previous study used a murine model of Bordetella pertussis infection to demonstrate that treatment with the S1PR agonist AAL-R reduces
David R Gendron et al.
Frontiers in pharmacology, 8, 78-78 (2017-03-09)
In asthma, excessive bronchial narrowing associated with thickening of the airway smooth muscle (ASM) causes respiratory distress. Numerous pharmacological agents prevent experimental airway hyperresponsiveness (AHR) when delivered prophylactically. However, most fail to resolve this feature after disease is instated. Although
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
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

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