SM1-176 | 4-Hydroxythalidomide | CAS#5054-59-1

MedKoo Cat#: 408152 | Name: SM1-176

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Description:

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

SM1-176, also known as 4-hydroxy thalidomide, is an active metabolite of thalidomide. SM1-176 is formed from thalidomide via hydroxylation. It is a E3 ligase ligand.

Chemical Structure

SM1-176

CAS#5054-59-1

Theoretical Analysis

MedKoo Cat#: 408152

Name: SM1-176

CAS#: 5054-59-1

Chemical Formula: C13H10N2O5

Exact Mass: 274.0590

Molecular Weight: 274.23

Elemental Analysis: C, 56.94; H, 3.68; N, 10.22; O, 29.17

Price and Availability

Size	Price	Availability
5g	USD 350.00	2 Weeks
10g	USD 550.00	2 Weeks
25g	USD 950.00	2 Weeks

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Related CAS #

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Synonym

4-Hydroxythalidomide; thalidomide-4-OH; SM1-176; SM1 176; SM1176; SM-1176; SM 1176; E3 ligase Ligand 2

IUPAC/Chemical Name

2-(2,6-Dioxopiperidin-3-yl)-4-hydroxyisoindoline-1,3-dione

InChi Key

XMPJICVFSDYOEG-UHFFFAOYSA-N

InChi Code

InChI=1S/C13H10N2O5/c16-8-3-1-2-6-10(8)13(20)15(12(6)19)7-4-5-9(17)14-11(7)18/h1-3,7,16H,4-5H2,(H,14,17,18)

SMILES Code

O=C1N(C(CC2)C(NC2=O)=O)C(C3=C1C=CC=C3O)=O

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

Instruction

View handling instruction

Biological target:

SM1-176 decreases the production of TNF-α induced by 12-O-tetradecanoylphorbol 13-acetate in THP-1 cells when used at a concentration of 30 µM. SM1-176 (333 µM) completely inhibits the proliferation of human umbilical vein endothelial cells (HUVECs). It inhibits VEGF- and FGF2-induced angiogenesis by 14% in a chicken chorioallantoic membrane (CAM) assay in utero when administered at a dose of 100 µg/embryo.

In vitro activity:

Thalidomide shows limited anti-proliferative activity on cancer cells, but its hydroxylated analogs (such as SM1-176), based on putative metabolites, demonstrate significant anti-angiogenic potential. Further exploration of these derivatives as anti-angiogenic agents is warranted. Reference: Biol Pharm Bull. 2002 May;25(5):597-604. https://pubmed.ncbi.nlm.nih.gov/12033499/

In vivo activity:

To be determined

	Solvent	mg/mL	mM
Solubility
	DMF	12.0	43.76
	DMSO	10.0	36.47

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 274.23 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. Marks MG, Shi J, Fry MO, Xiao Z, Trzyna M, Pokala V, Ihnat MA, Li PK. Effects of putative hydroxylated thalidomide metabolites on blood vessel density in the chorioallantoic membrane (CAM) assay and on tumor and endothelial cell proliferation. Biol Pharm Bull. 2002 May;25(5):597-604. doi: 10.1248/bpb.25.597. PMID: 12033499. 2. Robb CM, Contreras JI, Kour S, Taylor MA, Abid M, Sonawane YA, Zahid M, Murry DJ, Natarajan A, Rana S. Chemically induced degradation of CDK9 by a proteolysis targeting chimera (PROTAC). Chem Commun (Camb). 2017 Jul 4;53(54):7577-7580. doi: 10.1039/c7cc03879h. PMID: 28636052; PMCID: PMC5555382.

In vitro protocol:

In vivo protocol:

To be determined