MC2590 is a potent pyridine-containing histone deacetylase (HDAC) inhibitor. MC2590 is an inhibitor (blocker/antagonist) of HDAC1-3, -6, -8 and -10 (class I/IIb selective inhibitor) with IC50 of 0.015 μM-0.156 μM. MC2590 also inhibits other HDAC isoforms, HDAC4, HDAC5, HDAC7, HDAC9, HDAC11, with IC50 of 1.35 μM-3.98 μM. MC2625 induces G2/M cell cycle arrest and modulates pro- and anti-apoptotic microRNAs to cause apoptosis.

Physicochemical Properties

Molecular Formula	C20H17N3O3
Molecular Weight	347.367284536362
Exact Mass	347.126
CAS #	2284460-01-9
PubChem CID	155555345
Appearance	Typically exists as solid at room temperature
LogP	2.1
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	5
Heavy Atom Count	26
Complexity	522
Defined Atom Stereocenter Count	0
SMILES	C1=CC=C2C(=C1)C=CC=C2CC(=O)NC3=CN=C(C=C3)/C=C/C(=O)NO
InChi Key	DTNVLAIWDVXDJR-ZHACJKMWSA-N
InChi Code	InChI=1S/C20H17N3O3/c24-19(23-26)11-10-16-8-9-17(13-21-16)22-20(25)12-15-6-3-5-14-4-1-2-7-18(14)15/h1-11,13,26H,12H2,(H,22,25)(H,23,24)/b11-10+
Chemical Name	(E)-N-hydroxy-3-[5-[(2-naphthalen-1-ylacetyl)amino]pyridin-2-yl]prop-2-enamide
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	HDAC1 0.098 μM (IC50) HDAC2 0.156 μM (IC50) HDAC3 0.039 μM (IC50) HDAC6 0.015 μM (IC50) HDAC8 0.047 μM (IC50) HDAC10 0.071 μM (IC50) HDAC4 2.73 μM (IC50) HDAC5 1.35 μM (IC50) HDAC7 2.06 μM (IC50) HDAC9 2.79 μM (IC50) HDAC11 3.98 μM (IC50)
ln Vitro	Compound 5e, MC2625, has a 72-hour half-life of 0.07 μM for colorectal cancer cells, 0.32 μM for lung adenocarcinoma cells, and 0.05 μM for chronic myelogenous leukemia cells [1]. The G2/M cell cycle arrest is induced by MC2625 (1, 5 μM; 24, 48 hours) [1]. Acetyl-α-tubulin levels rise, H3K9/14 hyperacetylation activity is induced, and p21 protein is dramatically upregulated by MC2625 (1, 5 μM; 24, 48 hours) [1]. Inducing apoptosis, MC2625 (1, 5 μM; 48 hours) downregulates cyclin D1 and BCL-2, enhances the mRNA expression of p21, BAX, and BAK, and modifies pro- and anti-apoptotic microRNA [1].
Cell Assay	Cell Cycle Analysis[1] Cell Types: Human acute myeloid leukaemia U937 cells Tested Concentrations: 1, 5 μM Incubation Duration: 24, 48 h Experimental Results: At 24 h, demonstrated very low increase of the pre-G1 peak and led to a G2/M phase arrest at 1 μM; induced a 10% pre-G1 increase and displayed a block at the G2/M phase at 5 μM. At 48 h, induced a 70-85% block of the cell cycle at the G1 phase. Western Blot Analysis[1] Cell Types: Human acute myeloid leukaemia U937 cells Tested Concentrations: 1, 5 μM Incubation Duration: 24, 48 h Experimental Results: At 1 μM revealed H3K9/14 hyperacetylation activity, increased the acetyl-α-tubulin level, markedly upregulated the p21 protein. RT-PCR[1] Cell Types: Human acute myeloid leukaemia U937 cells Tested Concentrations: 1, 5 μM Incubation Duration: 48 h Experimental Results: At 1 μM Dramatically induced the expression of BAX and BAK, dose-dependently downregulated the antiapoptotic factor BCL-2. Downregulated miRNAs with antiapoptotic activity (miR-17-5p, miR-18-5p, miR-19b-3p, miR-20a-5p,miR-21-5p); induced the proapoptotic miRNAs (miR-let7a-5p, miR-125b-5p, miR-181a-5p, miR-181b-5p, miR-769-5p, miR-122-5p).
References	[1]. Elisabetta Di Bello, et al. Novel pyridine-containing histone deacetylase inhibitors strongly arrest proliferation, induce apoptosis and modulate miRNAs in cancer cells. Eur J Med Chem. 2022 Dec 15;247:115022.

Solubility Data

Solubility (In Vitro)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.8788 mL	14.3939 mL	28.7877 mL
	5 mM	0.5758 mL	2.8788 mL	5.7575 mL
	10 mM	0.2879 mL	1.4394 mL	2.8788 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.