3PO
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.
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Chemical Information
| Name | 3PO |
|---|---|
| Iupac Chemical Name | 3-(3-Pyridinyl)-1-(4-pyridinyl)-2-propen-1-one |
| Synonyms | 3PO |
| Molecular Formula | C13H10N2O |
| Molecular Weight | 210.236 |
| Smile | O=C(C1=CC=NC=C1)/C=C/C2=CC=CN=C2 |
| InChiKey | UOWGYMNWMDNSTL-ONEGZZNKSA-N |
| InChi | 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+ |
| CAS Number | 18550-98-6 |
| Related CAS |
Ordering Information
| Packaging | Price | Availability | Purity | Shipping Time |
|---|---|---|---|---|
| Bulk | Enquiry | Enquiry | Enquiry |
| Formulation | Solid powder |
|---|---|
| Purity | 98% Min. |
| Storage | 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 |
| Handling | |
| 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. |
| HS Code |
| Targets | |
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| Mechanism | |
| Cell study | |
| Animal study | |
| Clinical study |
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2: Biniecka M, Canavan M, McGarry T, Gao W, McCormick J, Cregan S, Gallagher L, Smith T, Phelan JJ, Ryan J, O'Sullivan J, Ng CT, Veale DJ, Fearon U. Dysregulated bioenergetics: a key regulator of joint inflammation. Ann Rheum Dis. 2016 Mar 24. pii: annrheumdis-2015-208476. doi: 10.1136/annrheumdis-2015-208476. [Epub ahead of print] PubMed PMID: 27013493.
3: Saneei A, Pourayoubi M, Crochet A, Fromm KM. The first phosphoramide-mercury(II) complex with a Cl2Hg-OP[N(C)(C)]3 segment. Acta Crystallogr C Struct Chem. 2016 Mar 1;72(Pt 3):230-3. doi: 10.1107/S2053229616002394. Epub 2016 Feb 25. PubMed PMID: 26942433.
4: Nakajima J, Suganami Y, Tsutsumi N, Hirose A, Kondo A, Sunohara D, Kawashima H. Legal Problems Surrounding Medical Care for Neonates Born to International Students: Report of Two Families in Japan. J Immigr Minor Health. 2016 Feb 24. [Epub ahead of print] PubMed PMID: 26911876.
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.
6: Maeda M, Kayano E, Fujiwara T, Nagare H, Akao S. Nitrous oxide emissions during biological soil disinfestation with different organic matter and plastic mulch films in laboratory-scale tests. Environ Technol. 2015 Oct 23:1-7. [Epub ahead of print] PubMed PMID: 26370049.
7: Xie N, Tan Z, Banerjee S, Cui H, Ge J, Liu RM, Bernard K, Thannickal VJ, Liu G. Glycolytic Reprogramming in Myofibroblast Differentiation and Lung Fibrosis. Am J Respir Crit Care Med. 2015 Dec 15;192(12):1462-74. doi: 10.1164/rccm.201504-0780OC. PubMed PMID: 26284610; PubMed Central PMCID: PMC4731722.
8: Xintaropoulou C, Ward C, Wise A, Marston H, Turnbull A, Langdon SP. A comparative analysis of inhibitors of the glycolysis pathway in breast and ovarian cancer cell line models. Oncotarget. 2015 Sep 22;6(28):25677-95. doi: 10.18632/oncotarget.4499. PubMed PMID: 26259240; PubMed Central PMCID: PMC4694858.
9: Nakajima J, Sunohara D, Kawashima H. Congenital Cytomegalovirus Infection in Monozygotic Twins with Twin-to-twin Transfusion Syndrome. Indian Pediatr. 2015 May;52(5):429-31. PubMed PMID: 26061933.
10: Gupta AK, Yadav A, Srivastava AK, Ramya KR, Paithankar H, Nandi S, Chugh J, Boomishankar R. A neutral cluster cage with a tetrahedral [Pd12(II)L6] framework: crystal structures and host–guest studies. Inorg Chem. 2015 Apr 6;54(7):3196-202. doi: 10.1021/ic502798r. Epub 2015 Mar 17. PubMed PMID: 25781912.
11: Joordens JC, d'Errico F, Wesselingh FP, Munro S, de Vos J, Wallinga J, Ankjærgaard C, Reimann T, Wijbrans JR, Kuiper KF, Mücher HJ, Coqueugniot H, Prié V, Joosten I, van Os B, Schulp AS, Panuel M, van der Haas V, Lustenhouwer W, Reijmer JJ, Roebroeks W. Homo erectus at Trinil on Java used shells for tool production and engraving. Nature. 2015 Feb 12;518(7538):228-31. doi: 10.1038/nature13962. Epub 2014 Dec 3. PubMed PMID: 25470048.
12: Christian BM, Parkinson C, Macrae CN, Miles LK, Wheatley T. When imagining yourself in pain, visual perspective matters: the neural and behavioral correlates of simulated sensory experiences. J Cogn Neurosci. 2015 May;27(5):866-75. doi: 10.1162/jocn_a_00754. Epub 2014 Nov 12. PubMed PMID: 25390204.
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.
15: Schmitz M, Wulf K, Signore SC, Schulz-Schaeffer WJ, Kermer P, Bähr M, Wouters FS, Zafar S, Zerr I. Impact of the cellular prion protein on amyloid-β and 3PO-tau processing. J Alzheimers Dis. 2014;38(3):551-65. doi: 10.3233/JAD-130566. PubMed PMID: 24028865.
16: Gupta AK, Reddy SA, Boomishankar R. Facile formation of stable tris(imido)phosphate trianions as their tri- and hexanuclear Pd(II) complexes in protic solvents. Inorg Chem. 2013 Jul 1;52(13):7608-14. doi: 10.1021/ic400686e. Epub 2013 Jun 10. PubMed PMID: 23750700.
17: Clem BF, O'Neal J, Tapolsky G, Clem AL, Imbert-Fernandez Y, Kerr DA 2nd, Klarer AC, Redman R, Miller DM, Trent JO, Telang S, Chesney J. Targeting 6-phosphofructo-2-kinase (PFKFB3) as a therapeutic strategy against cancer. Mol Cancer Ther. 2013 Aug;12(8):1461-70. doi: 10.1158/1535-7163.MCT-13-0097. Epub 2013 May 14. PubMed PMID: 23674815; PubMed Central PMCID: PMC3742633.
18: Dassie E, Andrews MR, Bensadoun JC, Cacquevel M, Schneider BL, Aebischer P, Wouters FS, Richardson JC, Hussain I, Howlett DR, Spillantini MG, Fawcett JW. Focal expression of adeno-associated viral-mutant tau induces widespread impairment in an APP mouse model. Neurobiol Aging. 2013 May;34(5):1355-68. doi: 10.1016/j.neurobiolaging.2012.11.011. Epub 2012 Dec 25. PubMed PMID: 23273572.
19: Lee S, Shea TB. Caspase-mediated truncation of tau potentiates aggregation. Int J Alzheimers Dis. 2012;2012:731063. doi: 10.1155/2012/731063. Epub 2012 Sep 4. PubMed PMID: 22988541; PubMed Central PMCID: PMC3440879.
20: Telang S, Clem BF, Klarer AC, Clem AL, Trent JO, Bucala R, Chesney J. Small molecule inhibition of 6-phosphofructo-2-kinase suppresses t cell activation. J Transl Med. 2012 May 16;10:95. doi: 10.1186/1479-5876-10-95. PubMed PMID: 22591674; PubMed Central PMCID: PMC3441391.
(Last updated: 4/20/2016).
Chemical Structure
