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Cayman Chemical Item Number 10007974

Synthetic Ligand of FKBP (CAS 195513-96-3)

SLF (CAS 195513-96-3)

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Description

FK-506 is a potent immunosuppressant that forms a high affinity complex (Ki = 0.2 nM) with FK-506 binding protein 12 (FKBP12). This complex inhibits the activity of the calcium/calmodulin-dependent protein phosphatase, calcineurin, leading to disruption of T-cell activation.1 Synthetic ligand of FKBP (SLF) is a cell-permeable analog of FK-506 that binds tightly to FKBP but lacks the ability to inhibit calcineurin.2 By itself, SLF does not exhibit a significant cellular response. However, homodimers of SLF or heterodimers with another protein ligand, provide a method to promote the dimerization of ligand-specific fusion proteins to induce signaling events within a cellular environment.3,2 For example, SLF monomers connected with a 10-atom linker activates Fas signaling via Fas-FKBP fusion proteins with an EC50 of 6 nM.3

1 Dumont, F.J. FK506, An immunosuppressant targeting calcineurin function. Curr Med Chem 7 731-748 (2000).

2 Braun, P.D., Barglow, K.T., Lin, Y., et al. A bifunctional molecule that displays context-dependent cellular activity. J Am Chem Soc 125 7575-7580 (2003).

3 Amara, J.F., Clackson, T., Rivera, V.M., et al. A versatile synthetic dimerizer for the regulation of protein-protein interactions. Proc Natl Acad Sci USA 94 10618-10623 (1997).

Synonyms
  • Synthetic Ligand of FKBP
Formal Name (1R)-​1-​(3-​aminophenyl)-​3-​(3,​4-​dimethoxyphenyl)propyl ester-​1-​(3,​3-​dimethyl-​1,​2-​dioxopentyl)-​2S-​piperidinecarboxylic acid
CAS Number 195513-96-3
Molecular Formula C30H40N2O6
Formula Weight 524.7
Formulation A solution in methyl acetate
Purity ≥98%
λmax 205, 232, 281 nm
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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COc1cc(CCC(OC(=O)​[C@@H]​2CCCCN2C(=O)​C(=O)​C(C)​(C)​CC)​c2cccc(N)​c2)​ccc1OC
InCHI Code
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​1S/C30H40N2O6/c1-6-30(2,3)​27(33)​28(34)​32-17-8-7-12-23(32)​29(35)​38-24(21-10-9-11-22(31)​19-21)​15-13-20-14-16-25(36-4)​26(18-20)​37-5/h9-11,14,16,18-19,23-24H,6-8,12-13,15,17,31H2,1-5H3/t23-,24+/m0/s1
InCHI Key
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IIDSDBBDZNDWCN-BJKOFHAPSA-N

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SLF is available in the following screening library:

Size Price Quantity Subtotal
5 mg $74.00 $0.00
10 mg $141.00 $0.00
50 mg $592.00 $0.00
100 mg $1,036.00 $0.00
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Cart Total $0.00

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Pricing updated 2014-04-17. Prices are subject to change without notice.

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