SML2916
AAL-R
≥98% (HPLC)
Synonym(s):
(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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About This Item
Empirical Formula (Hill Notation):
C18H31NO2
CAS Number:
Molecular Weight:
293.44
UNSPSC Code:
41106300
NACRES:
NA.77
Assay:
≥98% (HPLC)
Form:
powder
Quality Segment
assay
≥98% (HPLC)
form
powder
color
white to beige
solubility
DMSO: 2 mg/mL, clear
storage temp.
2-8°C
SMILES string
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
Biochem/physiol Actions
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.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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