3PO
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MedKoo CAT#: 407325

CAS#: 18550-98-6

Description: 3PO is a PFKFB3 (6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase) inhibitor. 3PO reduces glycolytic flux and suppresses glucose uptake. 3PO may be useful agents in combination with other drugs that inhibit cancer cell proliferation. PFKFB3 inhibitors suppress glucose uptake, which in turn causes an increase in autophagy. The addition of selective inhibitors of autophagy to 3PO and its more potent derivatives may prove useful as rational combinations for the treatment of cancer. Note: this product has been assigned 2 CAS#: 18550-98-6 and 13309-08-5,


Chemical Structure

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3PO
CAS# 18550-98-6

Theoretical Analysis

MedKoo Cat#: 407325
Name: 3PO
CAS#: 18550-98-6
Chemical Formula: C13H10N2O
Exact Mass: 210.0793
Molecular Weight: 210.236
Elemental Analysis: C, 74.27; H, 4.79; N, 13.33; O, 7.61

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200.0mg USD 250.0 Same day
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Related CAS #: 18550-98-6   13309-08-5    

Synonym: 3PO

IUPAC/Chemical Name: 3-(3-Pyridinyl)-1-(4-pyridinyl)-2-propen-1-one

InChi Key: UOWGYMNWMDNSTL-ONEGZZNKSA-N

InChi Code: InChI=1S/C13H10N2O/c16-13(12-5-8-14-9-6-12)4-3-11-2-1-7-15-10-11/h1-10H/b4-3+

SMILES Code: O=C(C1=CC=NC=C1)/C=C/C2=CC=CN=C2

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, not in water

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

Biological target: 3PO is an inhibitor of the PFKFB3 isozyme (IC50, 1.4-24 μM).
In vitro activity: The ability of 3PO to inhibit glycolysis was confirmed in the present study. Indeed, by using Seahorse technology, 3PO inhibits glycolysis in a concentration-dependent manner in HUVECs, resulting in an up to 50% reduction in glycolytic rate. Moreover, 3PO inhibits capillary tube formation, migration of ECs, and formation of aortic sprouts, which are all processes that heavily depend on glycolysis. Reference: FEBS Lett. 2020 Sep;594(18):3067-3075. https://febs.onlinelibrary.wiley.com/doi/10.1002/1873-3468.13878
In vivo activity: In line with this statement, experimental evidence from the present study indicates that treatment of ApoE−/− mice with 3PO for 4 weeks caused neither substantial adverse effects nor changes in general metabolism. Reduced food intake was observed, yet circulating liver enzymes, blood glucose, insulin, and total cholesterol were not affected. Also a glucose and insulin tolerance test was perfectly normal. However, 3PO caused a decrease in the level of circulating triglycerides and a significant rise in β-hydroxybutyrate levels, indicating a metabolic switch from glucose to fatty acid–derived ketones to provide sufficient energy. Reference: Arterioscler Thromb Vasc Biol. 2020 May; 40(5): 1168–1181. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7176341/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 42.33 201.35
DMSO:PBS (pH 7.2) (1:10) 0.09 0.43
DMF 5.0 23.78
Ethanol 2.0 9.51

Preparing Stock Solutions

The following data is based on the product molecular weight 210.236 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
Formulation protocol: 1. Emini Veseli B, Perrotta P, Van Wielendaele P, Lambeir AM, Abdali A, Bellosta S, Monaco G, Bultynck G, Martinet W, De Meyer GRY. Small molecule 3PO inhibits glycolysis but does not bind to 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase-3 (PFKFB3). FEBS Lett. 2020 Sep;594(18):3067-3075. doi: 10.1002/1873-3468.13878. Epub 2020 Jul 20. PMID: 32620030. 2. Wik JA, Lundbäck P, la Cour Poulsen L, Haraldsen G, Skålhegg BS, Hol J. 3PO inhibits inflammatory NFκB and stress-activated kinase signaling in primary human endothelial cells independently of its target PFKFB3. PLoS One. 2020 Mar 4;15(3):e0229395. doi: 10.1371/journal.pone.0229395. PMID: 32130250; PMCID: PMC7055879. 3. Perrotta P, Van der Veken B, Van Der Veken P, Pintelon I, Roosens L, Adriaenssens E, Timmerman V, Guns PJ, De Meyer GRY, Martinet W. Partial Inhibition of Glycolysis Reduces Atherogenesis Independent of Intraplaque Neovascularization in Mice. Arterioscler Thromb Vasc Biol. 2020 May;40(5):1168-1181. doi: 10.1161/ATVBAHA.119.313692. Epub 2020 Mar 19. PMID: 32188275; PMCID: PMC7176341. 4. Rao TN, Hansen N, Hilfiker J, Rai S, Majewska JM, Leković D, Gezer D, Andina N, Galli S, Cassel T, Geier F, Delezie J, Nienhold R, Hao-Shen H, Beisel C, Di Palma S, Dimeloe S, Trebicka J, Wolf D, Gassmann M, Fan TW, Lane AN, Handschin C, Dirnhofer S, Kröger N, Hess C, Radimerski T, Koschmieder S, Čokić VP, Skoda RC. JAK2-mutant hematopoietic cells display metabolic alterations that can be targeted to treat myeloproliferative neoplasms. Blood. 2019 Nov 21;134(21):1832-1846. doi: 10.1182/blood.2019000162. PMID: 31511238; PMCID: PMC6872961.
In vitro protocol: 1. Emini Veseli B, Perrotta P, Van Wielendaele P, Lambeir AM, Abdali A, Bellosta S, Monaco G, Bultynck G, Martinet W, De Meyer GRY. Small molecule 3PO inhibits glycolysis but does not bind to 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase-3 (PFKFB3). FEBS Lett. 2020 Sep;594(18):3067-3075. doi: 10.1002/1873-3468.13878. Epub 2020 Jul 20. PMID: 32620030. 2. Wik JA, Lundbäck P, la Cour Poulsen L, Haraldsen G, Skålhegg BS, Hol J. 3PO inhibits inflammatory NFκB and stress-activated kinase signaling in primary human endothelial cells independently of its target PFKFB3. PLoS One. 2020 Mar 4;15(3):e0229395. doi: 10.1371/journal.pone.0229395. PMID: 32130250; PMCID: PMC7055879.
In vivo protocol: 1. Perrotta P, Van der Veken B, Van Der Veken P, Pintelon I, Roosens L, Adriaenssens E, Timmerman V, Guns PJ, De Meyer GRY, Martinet W. Partial Inhibition of Glycolysis Reduces Atherogenesis Independent of Intraplaque Neovascularization in Mice. Arterioscler Thromb Vasc Biol. 2020 May;40(5):1168-1181. doi: 10.1161/ATVBAHA.119.313692. Epub 2020 Mar 19. PMID: 32188275; PMCID: PMC7176341. 2. Rao TN, Hansen N, Hilfiker J, Rai S, Majewska JM, Leković D, Gezer D, Andina N, Galli S, Cassel T, Geier F, Delezie J, Nienhold R, Hao-Shen H, Beisel C, Di Palma S, Dimeloe S, Trebicka J, Wolf D, Gassmann M, Fan TW, Lane AN, Handschin C, Dirnhofer S, Kröger N, Hess C, Radimerski T, Koschmieder S, Čokić VP, Skoda RC. JAK2-mutant hematopoietic cells display metabolic alterations that can be targeted to treat myeloproliferative neoplasms. Blood. 2019 Nov 21;134(21):1832-1846. doi: 10.1182/blood.2019000162. PMID: 31511238; PMCID: PMC6872961.

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1: Lea MA, Guzman Y, Desbordes C. Inhibition of Growth by Combined Treatment with Inhibitors of Lactate Dehydrogenase and either Phenformin or Inhibitors of 6-Phosphofructo-2-kinase/Fructose-2,6-bisphosphatase 3. Anticancer Res. 2016 Apr;36(4):1479-88. PubMed PMID: 27069123.

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5: Lea MA, Altayyar M, desBordes C. Inhibition of Growth of Bladder Cancer Cells by 3-(3-Pyridinyl)-1-(4-pyridinyl)-2-propen-1-one in Combination with Other Compounds Affecting Glucose Metabolism. Anticancer Res. 2015 Nov;35(11):5889-99. PubMed PMID: 26504012.

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13: Klarer AC, O'Neal J, Imbert-Fernandez Y, Clem A, Ellis SR, Clark J, Clem B, Chesney J, Telang S. Inhibition of 6-phosphofructo-2-kinase (PFKFB3) induces autophagy as a survival mechanism. Cancer Metab. 2014 Jan 23;2(1):2. doi: 10.1186/2049-3002-2-2. PubMed PMID: 24451478; PubMed Central PMCID: PMC3913946.

14: Schoors S, De Bock K, Cantelmo AR, Georgiadou M, Ghesquière B, Cauwenberghs S, Kuchnio A, Wong BW, Quaegebeur A, Goveia J, Bifari F, Wang X, Blanco R, Tembuyser B, Cornelissen I, Bouché A, Vinckier S, Diaz-Moralli S, Gerhardt H, Telang S, Cascante M, Chesney J, Dewerchin M, Carmeliet P. Partial and transient reduction of glycolysis by PFKFB3 blockade reduces pathological angiogenesis. Cell Metab. 2014 Jan 7;19(1):37-48. doi: 10.1016/j.cmet.2013.11.008. Epub 2013 Dec 12. PubMed PMID: 24332967.

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(Last updated: 4/20/2016).

3PO

100.0mg / USD 150.0