AP-III-a4 | CAS#1177827-73-4 | enolase inhibitor

MedKoo Cat#: 527872 | Name: AP-III-a4

Description:

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

AP-III-a4, also known as ENOblock, is the first, nonsubstrate inhibitor of enolase, blocking cancer cell metastasis in vivo. biochemical analysis showed that the half maximal inhibitory concentration (IC50) of enolase inhibition by ENOblock is 0.576 μM. ENOblock can inhibit cancer cell metastasis in vivo. Moreover, an unexpected role for enolase in glucose homeostasis was revealed by in vivo analysis. ENOblock is the first reported enolase inhibitor that is suitable for biological assays.

Chemical Structure

AP-III-a4

CAS#1177827-73-4

Theoretical Analysis

MedKoo Cat#: 527872

Name: AP-III-a4

CAS#: 1177827-73-4

Chemical Formula: C31H43FN8O3

Exact Mass: 594.3442

Molecular Weight: 594.74

Elemental Analysis: C, 62.61; H, 7.29; F, 3.19; N, 18.84; O, 8.07

Price and Availability

Size	Price	Availability
5mg	USD 150.00	Ready to ship
10mg	USD 250.00	Ready to ship
25mg	USD 450.00	Ready to ship
50mg	USD 750.00	Ready to ship
100mg	USD 1,250.00	Ready to ship
200mg	USD 2,150.00	Ready to ship
500mg	USD 2,650.00	Ready to ship
1g	USD 4,650.00	Ready to ship

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Synonym

AP-III-a4; ENOblock;

IUPAC/Chemical Name

N-[2-[2-(2-Aminoethoxy)ethoxy]ethyl]-4-[[4-[(cyclohexylmethyl)amino]-6-[[(4-fluorophenyl)methyl]amino]-1,3,5-triazin-2-yl]amino]benzeneacetamide

InChi Key

MOVYITHKOHMLHC-UHFFFAOYSA-N

InChi Code

InChI=1S/C31H43FN8O3/c32-26-10-6-25(7-11-26)22-36-30-38-29(35-21-24-4-2-1-3-5-24)39-31(40-30)37-27-12-8-23(9-13-27)20-28(41)34-15-17-43-19-18-42-16-14-33/h6-13,24H,1-5,14-22,33H2,(H,34,41)(H3,35,36,37,38,39,40)

SMILES Code

O=C(NCCOCCOCCN)CC1=CC=C(NC2=NC(NCC3CCCCC3)=NC(NCC4=CC=C(F)C=C4)=N2)C=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

>2 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

ENOblock is a testament to the power of forward chemical genetics to provide new chemical probes, drug targets, and candidate therapeutics for previously uncharacterized cellular mechanisms regulating human disease.

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#A21T12K13

QC Data

View QC data: current batch, Lot#A21T12K13

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

ENOblock(AP-III-a4) is a novel small molecule which is the first, nonsubstrate analogue that directly binds to enolase and inhibits its activity (IC50=0.576 uM); inhibit cancer cell metastasis in vivo.

In vitro activity:

ENOblock was used to inhibit the activity of ENO1 in PAMC-82 and SNU16 cells and then investigated the changes of stemness in GCs. It was found that treatment with ENOblock (10 or 20 μM) could reduce the glycolysis level, that is, ENOblock could decrease glucose consumption and lactic acid production. Moreover, ENOblock treatment (10 or 20 μM) significantly decreased the ECAR levels of these cells. Furthermore, ENOblock treatment at 10 or 20 μM could significantly inhibit GCs’ self-renewal capacity. The function of ENOblock on cell migration and invasion was then explored. The results indicated that treatment with ENOblock (10 or 20 μM) could strongly reduce cells’ migration and invasion rates. Moreover, cells’ cisplatin sensitivities were markedly increased by treatment with ENOblock at 10 or 20 μM. These results suggested that the function of inhibition by ENOblock was in consistent with the function of ENO1-knockdown. Reference: Cell Death Dis. 2020 Oct 16;11(10):870. https://pubmed.ncbi.nlm.nih.gov/33067426/

In vivo activity:

TBD

	Solvent	mg/mL	mM
Solubility
	DMSO	81.3	136.71

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 594.74 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. Yang T, Shu X, Zhang HW, Sun LX, Yu L, Liu J, Sun LC, Yang ZH, Ran YL. Enolase 1 regulates stem cell-like properties in gastric cancer cells by stimulating glycolysis. Cell Death Dis. 2020 Oct 16;11(10):870. doi: 10.1038/s41419-020-03087-4. PMID: 33067426; PMCID: PMC7567818.

In vitro protocol:

In vivo protocol:

TBD

1: McCoy HM, Polcyn R, Banik NL, Haque A. Regulation of enolase activation to promote neural protection and regeneration in spinal cord injury. Neural Regen Res. 2023 Jul;18(7):1457-1462. doi: 10.4103/1673-5374.361539. PMID: 36571342. 2: Wang D, Fu Y, Fan J, Wang Y, Li C, Xu Y, Chen H, Hu Y, Cao H, Zhao RC, He W, Zhang J. Identification of alpha-enolase as a potential immunogenic molecule during allogeneic transplantation of human adipose-derived mesenchymal stromal cells. Cytotherapy. 2022 Apr;24(4):393-404. doi: 10.1016/j.jcyt.2021.10.004. Epub 2021 Dec 2. PMID: 34863626. 3: Yang T, Shu X, Zhang HW, Sun LX, Yu L, Liu J, Sun LC, Yang ZH, Ran YL. Enolase 1 regulates stem cell-like properties in gastric cancer cells by stimulating glycolysis. Cell Death Dis. 2020 Oct 16;11(10):870. doi: 10.1038/s41419-020-03087-4. PMID: 33067426; PMCID: PMC7567818. 4: Polcyn R, Capone M, Matzelle D, Hossain A, Chandran R, Banik NL, Haque A. Enolase inhibition alters metabolic hormones and inflammatory factors to promote neuroprotection in spinal cord injury. Neurochem Int. 2020 Oct;139:104788. doi: 10.1016/j.neuint.2020.104788. Epub 2020 Jul 8. PMID: 32650031; PMCID: PMC7483987. 5: Li L, Zhang T, Xu J, Wu J, Wang Y, Qiu X, Zhang Y, Hou W, Yan L, An M, Jiang Y. The Synergism of the Small Molecule ENOblock and Fluconazole Against Fluconazole-Resistant Candida albicans. Front Microbiol. 2019 Sep 6;10:2071. doi: 10.3389/fmicb.2019.02071. PMID: 31555252; PMCID: PMC6742966. 6: Cho H, Lee JH, Um J, Kim S, Kim Y, Kim WH, Kim YS, Pagire HS, Ahn JH, Ahn Y, Chang YT, Jung DW, Williams DR. ENOblock inhibits the pathology of diet-induced obesity. Sci Rep. 2019 Jan 24;9(1):493. doi: 10.1038/s41598-018-36715-3. PMID: 30679508; PMCID: PMC6346001. 7: Haque A, Capone M, Matzelle D, Cox A, Banik NL. Targeting Enolase in Reducing Secondary Damage in Acute Spinal Cord Injury in Rats. Neurochem Res. 2017 Oct;42(10):2777-2787. doi: 10.1007/s11064-017-2291-z. Epub 2017 May 15. PMID: 28508172; PMCID: PMC5685929. 8: Cho H, Um J, Lee JH, Kim WH, Kang WS, Kim SH, Ha HH, Kim YC, Ahn YK, Jung DW, Williams DR. ENOblock, a unique small molecule inhibitor of the non-glycolytic functions of enolase, alleviates the symptoms of type 2 diabetes. Sci Rep. 2017 Mar 8;7:44186. doi: 10.1038/srep44186. PMID: 28272459; PMCID: PMC5341156. 9: Satani N, Lin YH, Hammoudi N, Raghavan S, Georgiou DK, Muller FL. ENOblock Does Not Inhibit the Activity of the Glycolytic Enzyme Enolase. PLoS One. 2016 Dec 28;11(12):e0168739. doi: 10.1371/journal.pone.0168739. PMID: 28030597; PMCID: PMC5193436. 10: Jung DW, Kim WH, Park SH, Lee J, Kim J, Su D, Ha HH, Chang YT, Williams DR. A unique small molecule inhibitor of enolase clarifies its role in fundamental biological processes. ACS Chem Biol. 2013;8(6):1271-82. doi: 10.1021/cb300687k. Epub 2013 Apr 22. PMID: 23547795.