LCL-161-phenol | CAS#2095244-42-9 | IAP ligand

MedKoo Cat#: 462863 | Name: LCL161-phenol

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

LCL-161-phenol is a functionalized IAP ligand for PROTACs.

Chemical Structure

LCL161-phenol

CAS#2095244-42-9 (phenol)

Theoretical Analysis

MedKoo Cat#: 462863

Name: LCL161-phenol

CAS#: 2095244-42-9 (phenol)

Chemical Formula: C31H42N4O6S

Exact Mass: 598.2825

Molecular Weight: 598.76

Elemental Analysis: C, 62.19; H, 7.07; N, 9.36; O, 16.03; S, 5.35

Price and Availability

Size	Price	Availability	Quantity
25mg	USD 550.00	2 Weeks
50mg	USD 950.00	2 Weeks

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Related CAS #

1005342-46-0 (free base) 2095244-42-9 (phenol) 1263876-34-1 (hydrate)

Synonym

LCL 161, phenol; LCL-161-phenol; LCL161-phenol; LCL 161-phenol;

IUPAC/Chemical Name

tert-butyl ((S)-1-(((S)-1-cyclohexyl-2-((S)-2-(4-(3-hydroxybenzoyl)thiazol-2-yl)pyrrolidin-1-yl)-2-oxoethyl)amino)-1-oxopropan-2-yl)(methyl)carbamate

InChi Key

SPXBMEKMIPOEMC-LQGLAIQGSA-N

InChi Code

InChI=1S/C31H42N4O6S/c1-19(34(5)30(40)41-31(2,3)4)27(38)33-25(20-11-7-6-8-12-20)29(39)35-16-10-15-24(35)28-32-23(18-42-28)26(37)21-13-9-14-22(36)17-21/h9,13-14,17-20,24-25,36H,6-8,10-12,15-16H2,1-5H3,(H,33,38)/t19-,24-,25-/m0/s1

SMILES Code

OC1=CC(C(C2=CSC([C@@H]3CCCN3C([C@@H](NC([C@H](C)N(C)C(OC(C)(C)C)=O)=O)C4CCCCC4)=O)=N2)=O)=CC=C1

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

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#T21O05R19

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

cIAP1 ligand 1 is the LCL161 derivative based IAP ligand. cIAP1 ligand 1 can be connected to the ABL ligand for protein by a linker to form SNIPER.

In vitro activity:

Through derivatization of the SNIPER(AR) molecule at the AR ligand and IAP ligand and linker, this study developed 42a (SNIPER(AR)-51), which shows effective protein knockdown activity against AR. Consistent with the degradation of the AR protein, 42a inhibits AR-mediated gene expression and proliferation of androgen-dependent prostate cancer cells. In addition, 42a efficiently induces caspase activation and apoptosis in prostate cancer cells, which was not observed in the cells treated with AR antagonists. Reference: J Med Chem. 2018 Jan 25;61(2):543-575. https://pubmed.ncbi.nlm.nih.gov/28594553/

In vivo activity:

This study recently developed a protein knockdown system based on hybrid small molecule SNIPERs (Specific and Nongenetic IAP-dependent Protein Erasers) that recruit inhibitor of the apoptosis protein (IAP) ubiquitin ligases to specifically degrade targeted proteins. By incorporating a high affinity IAP ligand, this study developed a novel SNIPER against estrogen receptor α (ERα), SNIPER(ER)-87, that has a potent protein knockdown activity. The SNIPER(ER) reduced ERα levels in tumor xenografts and suppressed the growth of ERα-positive breast tumors in mice. Reference: J Biol Chem. 2017 Mar 17;292(11):4556-4570. https://pubmed.ncbi.nlm.nih.gov/28154167/

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	167.01

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 598.76 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.

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

Formulation protocol:

1. Shibata N, Nagai K, Morita Y, Ujikawa O, Ohoka N, Hattori T, Koyama R, Sano O, Imaeda Y, Nara H, Cho N, Naito M. Development of Protein Degradation Inducers of Androgen Receptor by Conjugation of Androgen Receptor Ligands and Inhibitor of Apoptosis Protein Ligands. J Med Chem. 2018 Jan 25;61(2):543-575. doi: 10.1021/acs.jmedchem.7b00168. Epub 2017 Jun 23. PMID: 28594553. 2. Shimokawa K, Shibata N, Sameshima T, Miyamoto N, Ujikawa O, Nara H, Ohoka N, Hattori T, Cho N, Naito M. Targeting the Allosteric Site of Oncoprotein BCR-ABL as an Alternative Strategy for Effective Target Protein Degradation. ACS Med Chem Lett. 2017 Sep 14;8(10):1042-1047. doi: 10.1021/acsmedchemlett.7b00247. PMID: 29057048; PMCID: PMC5641955. 3. Ohoka N, Okuhira K, Ito M, Nagai K, Shibata N, Hattori T, Ujikawa O, Shimokawa K, Sano O, Koyama R, Fujita H, Teratani M, Matsumoto H, Imaeda Y, Nara H, Cho N, Naito M. In Vivo Knockdown of Pathogenic Proteins via Specific and Nongenetic Inhibitor of Apoptosis Protein (IAP)-dependent Protein Erasers (SNIPERs). J Biol Chem. 2017 Mar 17;292(11):4556-4570. doi: 10.1074/jbc.M116.768853. Epub 2017 Feb 2. PMID: 28154167; PMCID: PMC5377772.

In vitro protocol:

In vivo protocol:

1. Ohoka N, Okuhira K, Ito M, Nagai K, Shibata N, Hattori T, Ujikawa O, Shimokawa K, Sano O, Koyama R, Fujita H, Teratani M, Matsumoto H, Imaeda Y, Nara H, Cho N, Naito M. In Vivo Knockdown of Pathogenic Proteins via Specific and Nongenetic Inhibitor of Apoptosis Protein (IAP)-dependent Protein Erasers (SNIPERs). J Biol Chem. 2017 Mar 17;292(11):4556-4570. doi: 10.1074/jbc.M116.768853. Epub 2017 Feb 2. PMID: 28154167; PMCID: PMC5377772.