| Field | Specification |
|---|---|
| Target | |
| CAS no. | |
| Applications | |
| Molecular weight | |
| Molecular formula | C34H45N5O4 |
| Purity | |
| SMILES | |
| Form | Solid |
| Storage | |
| Shipping | |
| Catalog no. (Mfr.) | |
| Main SKU |
Compound Overview
XIAP degrader-1 is a PROTAC-like degrader with a Kd of 1 μM for XIAP. It is metabolized to an active aldehyde species that covalently binds Cys326 of FBXO22, forming a ternary complex with the BIR2 domain of XIAP, and it drives polyubiquitination and proteasomal degradation of XIAP through the ubiquitin-proteasome system. This process depends on NEDD8 conjugation, the SCFFBXO22 ligase complex, and the functional activities of the XIAP ligase, E1, and the proteasome[1][2]. It is supplied as an off-white to light yellow solid (C34H45N5O4, MW 587.75) at 98.11% purity.
Physical & Chemical Properties
| CAS Number | 2803617-91-4 |
|---|---|
| Molecular Formula | C34H45N5O4 |
| Molecular Weight | 587.75 g/mol |
| Purity | 98.11% |
| Appearance | Solid |
| Color | Off-white to light yellow |
| SMILES | CN[C@H](C(N[C@@H]1C(N(C2=C(N([C@H]1C)C(CCCCCCCN)=O)C=CC=C2)CC3=C(C=CC=C4)C4=CC=C3OC)=O)=O)C |
| Target | XIAP |
| Signaling Pathway | PROTAC; Apoptosis |
| Solubility | In Vitro: DMSO: 100 mg/mL (170.14 mM; Requires sonication; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO) |
| Storage | Powder: -20°C, 3 years; 4°C, 2 years. In solvent: -80°C, 6 months; -20°C, 1 month. |
| Shipping | Room temperature in continental US; may vary elsewhere. |
Biological Activity
IC50 & Target[1]
|
XIAP 1 μM (Kd) |
Literature Cited
Sources cited in this description and in the In Vitro & In Vivo Data tab. Peer-reviewed publications that used this product are listed under References.
Safety
For Research Use Only. Not for use in diagnostic or therapeutic procedures, and not for human or veterinary use. Handle in accordance with the Safety Data Sheet and your institution's chemical hygiene plan.
In Vitro
| Solvent | Solubility | Notes |
|---|---|---|
| DMSO | 100 mg/mL (170.14 mM) | requires sonication; use freshly opened DMSO (absorbed moisture lowers solubility) |
Aliquot the stock solution and store it at -80°C (up to 6 months) or -20°C (up to 1 month); avoid repeated freeze-thaw cycles.
Data provided by the manufacturer.
In Vitro
In MCF7 cells, XIAP degrader-1 (0.01-10 μM; 8-16 h) potently lowers XIAP protein levels, reaching 98% degradation after 16 h at 1 μM; the mechanism depends on binding to XIAP but not on cIAP[2]. In MCF7 cells, a primary amine is critical for the degradation activity of XIAP degrader-1 (0.01-10 μM; 16 h): modifications of this group that block ubiquitylation abolish the reduction in XIAP protein levels[2]. In transfected 293T cells, XIAP degrader-1 (0.01-10 μM; 16 h) lowers wild-type HA-XIAP levels but does not degrade the RING-deficient HA-XIAPH467A mutant, showing that it depends on XIAP ligase function[2]. In a recombinant in vitro system, XIAP degrader-1 (1 μM; 0-16 h) undergoes XIAP-dependent ubiquitylation, forming monoubiquitylated and polyubiquitylated species that are blocked by excess XIAP antagonist[2].
Western Blot Analysis[2]
| Cell Line | MCF7 human breast cancer cells |
|---|---|
| Concentration | 0.01 μM, 0.1 μM, 1 μM, 10 μM |
| Incubation Time | 16 h, 8 h |
| Result | Reduced XIAP levels to 2% of DMSO control levels after 16 h incubation with 1 μM reagent. Induced maximal XIAP loss after 8 h incubation with 1 μM reagent. Had its XIAP degradation effect blocked when co-incubated with 0.1 μM reagent and excess XIAP antagonist 1. Maintained its XIAP degradation effect after pretreatment with 1 μM BV6. |
Data provided by the manufacturer. Numbered citations refer to the Literature Cited list in the product description.
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Alkylamine-tethered molecules recruit FBXO22 for targeted protein degradation. Nat Commun 2024 Jun 26;15(1):5409. PMID: 38926334
