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FKBP12 PROTAC dTAG-7 - CAS 2064175-32-0

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FKBP12 PROTAC dTAG-7 is a bifunctional PROTAC® degrader inducing the selective degradation of FKBP12F36V fusion proteins and BET BRD4, consisting of a ligand selective for F36V single-point mutated FKBP12 conjugated to a cereblon ligand by a linker.

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Molecular Formula

C63H79N5O19

Molecular Weight

1210.32

FKBP12 PROTAC dTAG-7

- Specification
  - Purity
    
    ≥95%
    
    Solubility
    
    Soluble in DMSO, Ethanol
    
    Appearance
    
    Off-white Solid
    
    Storage
    
    Store at -20°C
    
    Shipping
    
    Room temperature in continental US; may vary elsewhere.
    
    IUPAC Name
    
    [(1R)-3-(3,4-dimethoxyphenyl)-1-[2-[2-[3-[2-[2-[3-[[2-[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]oxyacetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-2-oxoethoxy]phenyl]propyl] (2S)-1-[(2S)-2-(3,4,5-trimethoxyphenyl)butanoyl]piperidine-2-carboxylate
    
    Synonyms
    
    (1R)-3-(3,4-Dimethoxyphenyl)-1-(2-((19-((2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)oxy)-2,18-dioxo-7,10,13-trioxa-3,17-diazanonadecyl)oxy)phenyl)propyl (2S)-1-((S)-2-(3,4,5-trimethoxyphenyl)butanoyl)piperidine-2-carboxylate; 2-Piperidinecarboxylic acid, 1-[(2S)-1-oxo-2-(3,4,5-trimethoxyphenyl)butyl]-, (1R)-3-(3,4-dimethoxyphenyl)-1-[2-[[19-[[2-(2,6-dioxo-3-piperidinyl)-2,3-dihydro-1,3-dioxo-1H-isoindol-4-yl]oxy]-2,18-dioxo-7,10,13-trioxa-3,17-diazanonadec-1-yl]oxy]phenyl]propyl ester, (2S)-; (1R)-3-(3,4-Dimethoxyphenyl)-1-[2-[[19-[[2-(2,6-dioxo-3-piperidinyl)-2,3-dihydro-1,3-dioxo-1H-isoindol-4-yl]oxy]-2,18-dioxo-7,10,13-trioxa-3,17-diazanonadec-1-yl]oxy]phenyl]propyl (2S)-1-[(2S)-1-oxo-2-(3,4,5-trimethoxyphenyl)butyl]-2-piperidinecarboxylate; dTAG-7
- Properties
  - Boiling Point
    
    1242.1±65.0°C at 760 Torr
    
    Density
    
    1.265±0.06 g/cm3
    
    InChI Key
    
    IFCAWDLUIZXIPI-FJDAOBEISA-N
    
    InChI
    
    InChI=1S/C63H79N5O19/c1-7-42(41-36-52(79-4)58(81-6)53(37-41)80-5)60(73)67-28-11-10-17-46(67)63(76)87-48(23-20-40-21-24-49(77-2)51(35-40)78-3)43-15-8-9-18-47(43)85-38-55(70)64-26-13-29-82-31-33-84-34-32-83-30-14-27-65-56(71)39-86-50-19-12-16-44-57(50)62(75)68(61(44)74)45-22-25-54(69)66-59(45)72/h8-9,12,15-16,18-19,21,24,35-37,42,45-46,48H,7,10-11,13-14,17,20,22-23,25-34,38-39H2,1-6H3,(H,64,70)(H,65,71)(H,66,69,72)/t42-,45?,46-,48+/m0/s1
    
    Canonical SMILES
    
    O=C(OC(C=1C=CC=CC1OCC(=O)NCCCOCCOCCOCCCNC(=O)COC2=CC=CC=3C(=O)N(C(=O)C23)C4C(=O)NC(=O)CC4)CCC5=CC=C(OC)C(OC)=C5)C6N(C(=O)C(C7=CC(OC)=C(OC)C(OC)=C7)CC)CCCC6
    
    Pub Chem ID
    
    131954816
- Reference Reading
  - 1. The dTAG system for immediate and target-specific protein degradation.
    
    Nabet, B., Roberts, J.M., Buckley, D.L., Paulk, J., Dastjerdi, S., Yang, A., Leggett, A.L., Erb, M.A., Lawlor, M.A., Souza, A. and Scott, T.G., 2018. Nature chemical biology, 14(5), pp.431-441.
    
    Dissection of complex biological systems requires target-specific control of the function or abundance of proteins. Genetic perturbations are limited by off-target effects, multicomponent complexity, and irreversibility. Most limiting is the requisite delay between modulation to experimental measurement. To enable the immediate and selective control of single protein abundance, we created a chemical biology system that leverages the potency of cell-permeable heterobifunctional degraders. The dTAG system pairs a novel degrader of FKBP12F36V with expression of FKBP12F36V in-frame with a protein of interest. By transgene expression or CRISPR-mediated locus-specific knock-in, we exemplify a generalizable strategy to study the immediate consequence of protein loss. Using dTAG, we observe an unexpected superior antiproliferative effect of pan-BET bromodomain degradation over selective BRD4 degradation, characterize immediate effects of KRASG12V loss on proteomic signaling, and demonstrate rapid degradation in vivo. This technology platform will confer kinetic resolution to biological investigation and provide target validation in the context of drug discovery.
- Preparing Stock Solutions
  - ConcentrationVolumeMass 1 mg 5 mg 10 mg
    
    1 mM 0.83 mL 4.13 mL 8.26 mL
    
    5 mM 0.17 mL 0.83 mL 1.65 mL
    
    10 mM 0.08 mL 0.41 mL 0.83 mL
    
    50 mM 0.02 mL 0.08 mL 0.17 mL

ConcentrationVolumeMass	1 mg	5 mg	10 mg
1 mM	0.83 mL	4.13 mL	8.26 mL
5 mM	0.17 mL	0.83 mL	1.65 mL
10 mM	0.08 mL	0.41 mL	0.83 mL
50 mM	0.02 mL	0.08 mL	0.17 mL

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It is commonly abbreviated as: C₁V₁ = C₂V₂

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