UT-155
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MedKoo CAT#: 558752

CAS#: 2031161-35-8

Description: UT-155 is a potent selective androgen receptor degrader (SARD), markedly reducing the activity of wild-type and splice variant isoforms of AR, binding the amino-terminal transcriptional activation domain AF-1 and the carboxy-terminal ligand binding domain.


Chemical Structure

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UT-155
CAS# 2031161-35-8

Theoretical Analysis

MedKoo Cat#: 558752
Name: UT-155
CAS#: 2031161-35-8
Chemical Formula: C20H15F4N3O2
Exact Mass: 405.11
Molecular Weight: 405.35
Elemental Analysis: C, 59.26; H, 3.73; F, 18.75; N, 10.37; O, 7.89

Price and Availability

Size Price Availability Quantity
5.0mg USD 90.0 Ready to ship
10.0mg USD 150.0 Ready to ship
25.0mg USD 250.0 Ready to ship
50.0mg USD 450.0 Ready to ship
100.0mg USD 750.0 Ready to ship
200.0mg USD 1350.0 Ready to ship
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Synonym: (S)-UT 155; (S) UT-155; (S)-UT-155; UT155; UT 155; UT-155

IUPAC/Chemical Name: (S)-N-(4-cyano-3-(trifluoromethyl)phenyl)-3-(5-fluoro-1H-indol-1-yl)-2-hydroxy-2-methylpropanamide

InChi Key: CFSAYQVTXBMPRF-IBGZPJMESA-N

InChi Code: InChI=1S/C20H15F4N3O2/c1-19(29,11-27-7-6-12-8-14(21)3-5-17(12)27)18(28)26-15-4-2-13(10-25)16(9-15)20(22,23)24/h2-9,29H,11H2,1H3,(H,26,28)/t19-/m0/s1

SMILES Code: O=C(NC1=CC=C(C#N)C(C(F)(F)F)=C1)[C@@](C)(O)CN2C=CC3=C2C=CC(F)=C3

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Biological target: UT-155 is a selective and potent androgen receptor (AR) antagonist, with a Ki of 267 nM for UT-155 binding to AR-LBD.
In vitro activity: The effect of UT-155 on the protein level of closely related receptors, PR and estrogen receptor (ER) was tested in T47D breast cancer cells. Although UT-155 blocked PR-dependent transactivation (Figure 1), it had no effect on PR or ER protein levels in T47D cells (Figure 3D). The effect of UT-155 on glucocorticoid receptor (GR) protein levels was tested in PC-3 cells transiently transfected with an expression construct. While UT-155 inhibited the AR protein under similar conditions, it had no effect on GR (Figure S2A). Second, the effect of UT-155 on the fluorescence signal emitted by GFP-AR, GFP, or GFP-ANGPTL4, a protein that has no homology to nuclear receptors, was tested in HeLa cells. Treatment of HeLa cells transfected with the GFP-tagged constructs with 10 μM UT-155 resulted in down-regulation of the GFP signal in GFP-AR-transfected cells, but not in cells expressing GFP or GFP-ANGPTL4 (Figure S2B). Additionally, mass spectrometry was performed in LNCaP cells treated with vehicle or 10 μM UT-155. The results show that UT-155 did not inhibit the expression of the proteins identified, other than the AR. Some of the proteins identified are shown in Figure S2C. Finally, a study to determine the cross-reactivity of UT-155 with a panel of kinases demonstrated no significant inhibition of kinase activity. These results provide strong evidence for the selectivity of UT-155 to the AR. Reference: Cancer Res. 2017 Nov 15;77(22):6282-6298. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/28978635/
In vivo activity: To determine the effects in vivo, UT-155 was tested in xenograft models. UT-155 inhibited the growth of the LNCaP tumors with a 65% tumor growth inhibition (TGI) (Figure 7C). Consistent with the inhibition of tumor volume, tumor weights and tumor PSA were also significantly lower by 50–75% in UT-155-treated animals (Figure 7C). UT-155 significantly inhibited the growth of 22RV1 xenograft by 53% (Figure 7D). In the measurement of drug concentration in the tumors to determine the drug exposure, UT-155 was extracted from tumors and was detected by mass spectrometry. UT-155 accumulated in the tumors and the concentration of 562 nM was above its IC50 concentration (Figure S8F). Consistent with the observations made in 22RV1 xenografts, UT-155 inhibited the growth of Pr-3001 by 40–60% over the course of 14 days (Figure 7E). Reference: Cancer Res. 2017 Nov 15;77(22):6282-6298. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/28978635/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 100.0 246.7

Preparing Stock Solutions

The following data is based on the product molecular weight 405.35 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
In vitro protocol: 1. Ponnusamy S, Coss CC, Thiyagarajan T, Watts K, Hwang DJ, He Y, Selth LA, McEwan IJ, Duke CB, Pagadala J, Singh G, Wake RW, Ledbetter C, Tilley WD, Moldoveanu T, Dalton JT, Miller DD, Narayanan R. Novel Selective Agents for the Degradation of Androgen Receptor Variants to Treat Castration-Resistant Prostate Cancer. Cancer Res. 2017 Nov 15;77(22):6282-6298. doi: 10.1158/0008-5472.CAN-17-0976. Epub 2017 Oct 4. PMID: 28978635; PMCID: PMC5890913.
In vivo protocol: 1. Ponnusamy S, Coss CC, Thiyagarajan T, Watts K, Hwang DJ, He Y, Selth LA, McEwan IJ, Duke CB, Pagadala J, Singh G, Wake RW, Ledbetter C, Tilley WD, Moldoveanu T, Dalton JT, Miller DD, Narayanan R. Novel Selective Agents for the Degradation of Androgen Receptor Variants to Treat Castration-Resistant Prostate Cancer. Cancer Res. 2017 Nov 15;77(22):6282-6298. doi: 10.1158/0008-5472.CAN-17-0976. Epub 2017 Oct 4. PMID: 28978635; PMCID: PMC5890913.

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1: Ponnusamy S, Coss CC, Thiyagarajan T, Watts K, Hwang DJ, He Y, Selth LA, McEwan IJ, Duke CB, Pagadala J, Singh G, Wake RW, Ledbetter C, Tilley WD, Moldoveanu T, Dalton JT, Miller DD, Narayanan R. Novel Selective Agents for the Degradation of Androgen Receptor Variants to Treat Castration-Resistant Prostate Cancer. Cancer Res. 2017 Nov 15;77(22):6282-6298. doi: 10.1158/0008-5472.CAN-17-0976. Epub 2017 Oct 4. PubMed PMID: 28978635; PubMed Central PMCID: PMC5890913.