| Field | Specification |
|---|---|
| CAS no. | |
| Applications | |
| Molecular weight | |
| Molecular formula | C22H21NO5S2 |
| Purity | |
| SMILES | |
| Form | Solid |
| Storage | |
| Shipping | |
| Catalog no. (Mfr.) | |
| Main SKU |
Compound Overview
KPT-6566 is a selective, covalent inhibitor of the prolyl isomerase PIN1 that binds covalently to the PIN1 catalytic site and selectively inhibits and degrades PIN1. It shows an IC50 of 640 nM and a Ki of 625.2 nM against the PIN1 PPIase domain, and it can be used in cancer research[1]. It is supplied as a white to yellow solid (C22H21NO5S2, MW 443.54) at 98.0% purity.
Physical & Chemical Properties
| CAS Number | 881487-77-0 |
|---|---|
| Molecular Formula | C22H21NO5S2 |
| Molecular Weight | 443.54 g/mol |
| Purity | 98.0% |
| Appearance | Solid |
| Color | White to yellow |
| SMILES | O=C(O)CSC(C1=O)=C/C(C2=C1C=CC=C2)=N\S(=O)(C3=CC=C(C(C)(C)C)C=C3)=O |
| Signaling Pathway | PI3K/Akt/mTOR |
| Solubility | In Vitro: DMSO: 19.23 mg/mL (43.36 mM; Requires sonication; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO) |
| Storage | 4°C, protect from light, stored under nitrogen. In solvent: -80°C, 6 months; -20°C, 1 month (protect from light, stored under nitrogen). |
| Shipping | Room temperature in continental US; may vary elsewhere. |
Biological Activity
IC50 & Target
IC50: 640 nM (PIN1 PPIase)[1] Ki: 625.2 nM (PIN1 PPIase)[1]
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 | 19.23 mg/mL (43.36 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); protect from light, stored under nitrogen; avoid repeated freeze-thaw cycles.
In Vivo
Choose the formulation that suits the animal model and route of administration; percentages are volume ratios of the final working solution. Start from a clear DMSO stock (see In Vitro above), add the co-solvents one at a time in the order listed, mixing after each addition, and prepare the working solution fresh on the day of dosing. If precipitation or phase separation occurs, gentle warming or sonication can help.
Protocol 1
| Composition | 10% DMSO + 40% PEG300 + 5% Tween-80 + 45% saline |
|---|---|
| Result | 1.92 mg/mL (4.33 mM); suspension; requires sonication |
| How to prepare | Gives a suspension at 1.92 mg/mL. The suspension is suitable for oral and intraperitoneal dosing. For 1 mL of working solution: add 100 μL DMSO stock (19.2 mg/mL) to 400 μL PEG300; then 50 μL Tween-80; then 450 μL saline to bring the volume to 1 mL. Saline: dissolve 0.9 g sodium chloride in ddH2O and make up to 100 mL. |
Protocol 2
| Composition | 10% DMSO + 90% (20% SBE-β-CD in saline) |
|---|---|
| Result | ≥ 1 mg/mL (2.25 mM); clear solution |
| How to prepare | Gives a clear solution at ≥ 1 mg/mL (saturation not determined). For 1 mL of working solution: add 100 μL DMSO stock (10.0 mg/mL) to 900 μL 20% SBE-β-CD in saline. 20% SBE-β-CD in saline: dissolve 2 g SBE-β-CD powder in 10 mL saline until clear (4°C, store up to one week). |
Data provided by the manufacturer.
In Vitro
Proliferation of WT fibroblasts is inhibited by KPT-6566 (1-5 μM; 0-8 d)[1]. Viability of normal breast epithelial cells and cancer cells is inhibited by KPT-6566 (0-10 μM; 48 h) in a PIN1-dependent manner[1]. KPT-6566 (0-10 μM; 48 h) affects hyperphosphorylated pRB level and the concentrations of Cyclin D1 and PIN1[1]. The mut-p53, NOTCH1 and NRF2 pathways are inhibited by KPT-6566 (2.5-5 μM; 48 h)[1]. KPT-6566 (0-5 μM; 48 h) causes DNA damage in a PIN1-dependent way[1].
Cell Proliferation Assay[1]
| Cell Line | Immortalized fibroblasts derived from WT and Pin1 KO mouse embryos |
|---|---|
| Concentration | 1 and 5 μM |
| Incubation Time | 0-8 days |
| Result | Dose-dependently inhibited proliferation of WT fibroblasts, while showed no effect on Pin1 KO fibroblasts. |
Cell Viability Assay[1]
| Cell Line | MCF10A, HMEC, HeLa, LNCaP, SKOV-3, PANC-1, PC-3, MDA-MB-468 and MDA-MB-231 cells |
|---|---|
| Concentration | 0-10 μM |
| Incubation Time | 48 hours |
| Result | Inhibited normal breast epithelial cells and cancer cells viability even at a low concentration and increased the concentration of PIN1 in MDA-MB-468, SKOV-3, PC-3, LNCaP and PANC-1. |
Western Blot Analysis[1]
| Cell Line | Immortalized fibroblasts derived from WT and Pin1 KO mouse embryos and PIN1 KO MDA-MB-231 cells |
|---|---|
| Concentration | 0-10 μM |
| Incubation Time | 48 hours |
| Result | Decreased hyperphosphorylated pRB and Cyclin D1 levels, dose- and time-dependently promoted degradation of PIN1. |
Western Blot Analysis[1]
| Cell Line | MDA-MB-231, MCF10A, MDA-MB-468 and MDA-MB-231 cells |
|---|---|
| Concentration | 0, 2.5 and 5 μM |
| Incubation Time | 48 hours |
| Result | Dose-dependently increased H2AX phosphorylation and caused H2AX phosphorylation in MCF10A, MDA-MB-468 and MDA-MB-231 cell lines. Increased H2AX phosphorylation while other inhibitors such as ATRA, PiB and Juglone disabled to induce H2AX phosphorylation at same concentration. Achieved DNA damage through formation of DNA adducts. |
RT-PCR[1]
| Cell Line | MDA-MB-231 cells |
|---|---|
| Concentration | 2.5 and 5 μM |
| Incubation Time | 48 hours |
| Result | Dose-dependently inhibitd the activation of mut-p53 and NOTCH1 pathways which are controlled by PIN1. Inhibitd the expression of cFOS HO1, NQO1, TXNRD1 and DNAJAB, and induced cellular responses to oxidative stress. |
In Vivo
Mice given KPT-6566 (5 mg/kg; i.p. once a day for 26 days) show no toxicity[1].
| Animal Model | 6-week-old female mice with 1 million of MDA-MB-231Luc6 cells injection[1] |
|---|---|
| Dosage | 5 mg/kg |
| Administration | Intraperitoneal injection; 5 mg/kg once a day; for 26 days |
| Result | Exibited no sign of local or systemic and organ toxicity by post mortem morphologic analyses. |
Data provided by the manufacturer. Numbered citations refer to the Literature Cited list in the product description.
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The Prolyl Isomerase PIN1 Impacts Fibroblast Differentiation States and Crosstalk in Pancreatic Cancer. Cancer Res 2025 Sep 18. PMID: 40966318
Pin1 targets phosphorylated NCOA4 for K29/K48-linked ubiquitination to suppress ferritinophagy and ferroptosis in anaplastic thyroid cancer. Cell Death Dis 2026 Jul 1. PMID: 42380121
