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MedKoo Cat#: 406449 | Name: Poloxin
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Description:

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

Poloxin is the first small-molecule inhibitor specifically targeting the function of the Plk1 PBD. Poloxin induces centrosome fragmentation and abnormal spindle and chromosome misalignment, which activate the spindle assembly checkpoint and prolong mitosis. Notably, centrosomal fragmentation induced by Poloxin is partially attributable to dysfunctional Kizuna, a key substrate of Plk1 at centrosomes. Moreover, Poloxin strongly inhibits proliferation of a panel of cancer cells by inducing mitotic arrest, followed by a surge of apoptosis. More important, we report, for the first time to our knowledge, that the PBD inhibitor, Poloxin , significantly suppresses tumor growth of cancer cell lines in xenograft mouse models by lowering the proliferation rate and triggering apoptosis in treated tumor tissues. Targeting the PBD by Poloxin is a powerful approach for selectively inhibiting Plk1 function in vitro and in vivo. ( Am J Pathol. 2011 Oct;179(4):2091-9. ). (2/18/2014)

Chemical Structure

Poloxin
Poloxin
CAS#321688-88-4

Theoretical Analysis

MedKoo Cat#: 406449

Name: Poloxin

CAS#: 321688-88-4

Chemical Formula: C18H17NO4

Exact Mass: 311.1158

Molecular Weight: 311.33

Elemental Analysis: C, 69.44; H, 5.50; N, 4.50; O, 20.56

Price and Availability

Size Price Availability Quantity
10mg USD 285.00 2 Weeks
25mg USD 565.00 2 Weeks
50mg USD 950.00 2 Weeks
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Related CAS #
No Data
Synonym
Poloxin
IUPAC/Chemical Name
(E)-4-isopropyl-3,6-dioxocyclohexa-1,4-dienecarbaldehyde O-(2-methylbenzoyl) oxime.
InChi Key
KRHMAJOTJVOLBI-VXLYETTFSA-N
InChi Code
InChI=1S/C18H17NO4/c1-11(2)15-9-16(20)13(8-17(15)21)10-19-23-18(22)14-7-5-4-6-12(14)3/h4-11H,1-3H3/b19-10+
SMILES Code
O=C(C(/C=N/OC(C1=CC=CC=C1C)=O)=C2)C=C(C(C)C)C2=O
Appearance
white 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
More Info
        

Preparing Stock Solutions

The following data is based on the product molecular weight 311.33 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
1: Warmington E, Smith G, Chortis V, Liang R, Lippert J, Steinhauer S, Landwehr LS, Hantel C, Kiseljak-Vassiliades K, Wierman ME, Altieri B, Foster PA, Ronchi CL. PLK1 inhibitors as a new targeted treatment for adrenocortical carcinoma. Endocr Connect. 2023 Dec 14;13(1):e230403. doi: 10.1530/EC-23-0403. PMID: 37992487; PMCID: PMC10762563. 2: Kolosenko I, Palm-Apergi C. Small-molecule inhibitors for targeting polo-like kinase 1. Future Med Chem. 2020 Aug;12(16):1457-1460. doi: 10.4155/fmc-2020-0128. Epub 2020 Jul 8. PMID: 32638616. 3: Rubner S, Schubert S, Berg T. Poloxin-2HT+: changing the hydrophobic tag of Poloxin-2HT increases Plk1 degradation and apoptosis induction in tumor cells. Org Biomol Chem. 2019 Mar 20;17(12):3113-3117. doi: 10.1039/c9ob00080a. PMID: 30848278. 4: Rubner S, Scharow A, Schubert S, Berg T. Selective Degradation of Polo-like Kinase 1 by a Hydrophobically Tagged Inhibitor of the Polo-Box Domain. Angew Chem Int Ed Engl. 2018 Dec 21;57(52):17043-17047. doi: 10.1002/anie.201809640. Epub 2018 Nov 27. PMID: 30351497. 5: Archambault V, Normandin K. Several inhibitors of the Plk1 Polo-Box Domain turn out to be non-specific protein alkylators. Cell Cycle. 2017 Jun 18;16(12):1220-1224. doi: 10.1080/15384101.2017.1325043. Epub 2017 May 19. PMID: 28521657; PMCID: PMC5499904. 6: Normandin K, Lavallée JF, Futter M, Beautrait A, Duchaine J, Guiral S, Marinier A, Archambault V. Identification of Polo-like kinase 1 interaction inhibitors using a novel cell-based assay. Sci Rep. 2016 Nov 22;5:37581. doi: 10.1038/srep37581. PMID: 27874094; PMCID: PMC5118709. 7: Ritter A, Friemel A, Kreis NN, Louwen F, Yuan J. Impact of Polo-like kinase 1 inhibitors on human adipose tissue-derived mesenchymal stem cells. Oncotarget. 2016 Dec 20;7(51):84271-84285. doi: 10.18632/oncotarget.12482. PMID: 27713178; PMCID: PMC5356661. 8: Scharow A, Knappe D, Reindl W, Hoffmann R, Berg T. Development of Bifunctional Inhibitors of Polo-Like Kinase 1 with Low-Nanomolar Activities Against the Polo-Box Domain. Chembiochem. 2016 Apr 15;17(8):759-67. doi: 10.1002/cbic.201500535. Epub 2015 Dec 4. PMID: 26634982. 9: Scharow A, Raab M, Saxena K, Sreeramulu S, Kudlinzki D, Gande S, Dötsch C, Kurunci-Csacsko E, Klaeger S, Kuster B, Schwalbe H, Strebhardt K, Berg T. Optimized Plk1 PBD Inhibitors Based on Poloxin Induce Mitotic Arrest and Apoptosis in Tumor Cells. ACS Chem Biol. 2015 Nov 20;10(11):2570-9. doi: 10.1021/acschembio.5b00565. Epub 2015 Aug 27. PMID: 26279064. 10: Liu X. Targeting Polo-Like Kinases: A Promising Therapeutic Approach for Cancer Treatment. Transl Oncol. 2015 Jun;8(3):185-95. doi: 10.1016/j.tranon.2015.03.010. PMID: 26055176; PMCID: PMC4486469. 11: Shin SB, Woo SU, Yim H. Differential Cellular Effects of Plk1 Inhibitors Targeting the ATP-binding Domain or Polo-box Domain. J Cell Physiol. 2015 Dec;230(12):3057-67. doi: 10.1002/jcp.25042. PMID: 25975351. 12: Stehle A, Hugle M, Fulda S. Eribulin synergizes with Polo-like kinase 1 inhibitors to induce apoptosis in rhabdomyosarcoma. Cancer Lett. 2015 Aug 28;365(1):37-46. doi: 10.1016/j.canlet.2015.04.011. Epub 2015 Apr 23. PMID: 25917079. 13: Kreis NN, Louwen F, Zimmer B, Yuan J. Loss of p21Cip1/CDKN1A renders cancer cells susceptible to Polo-like kinase 1 inhibition. Oncotarget. 2015 Mar 30;6(9):6611-26. doi: 10.18632/oncotarget.2844. PMID: 25483104; PMCID: PMC4466638. 14: Sanhaji M, Louwen F, Zimmer B, Kreis NN, Roth S, Yuan J. Polo-like kinase 1 inhibitors, mitotic stress and the tumor suppressor p53. Cell Cycle. 2013 May 1;12(9):1340-51. doi: 10.4161/cc.24573. Epub 2013 Apr 10. PMID: 23574746; PMCID: PMC3674062. 15: Weiß L, Efferth T. Polo-like kinase 1 as target for cancer therapy. Exp Hematol Oncol. 2012 Dec 10;1(1):38. doi: 10.1186/2162-3619-1-38. PMID: 23227884; PMCID: PMC3533518. 16: Sanhaji M, Kreis NN, Zimmer B, Berg T, Louwen F, Yuan J. p53 is not directly relevant to the response of Polo-like kinase 1 inhibitors. Cell Cycle. 2012 Feb 1;11(3):543-53. doi: 10.4161/cc.11.3.19076. Epub 2012 Feb 1. PMID: 22262171. 17: Yuan J, Sanhaji M, Krämer A, Reindl W, Hofmann M, Kreis NN, Zimmer B, Berg T, Strebhardt K. Polo-box domain inhibitor poloxin activates the spindle assembly checkpoint and inhibits tumor growth in vivo. Am J Pathol. 2011 Oct;179(4):2091-9. doi: 10.1016/j.ajpath.2011.06.031. Epub 2011 Aug 10. PMID: 21839059; PMCID: PMC3181368. 18: Liao C, Park JE, Bang JK, Nicklaus MC, Lee KS. Exploring Potential Binding Modes of Small Drug-like Molecules to the Polo-Box Domain of Human Polo-like Kinase 1. ACS Med Chem Lett. 2010;1(3):110-114. doi: 10.1021/ml100020e. PMID: 20625469; PMCID: PMC2898210. 19: Reindl W, Yuan J, Krämer A, Strebhardt K, Berg T. Inhibition of polo-like kinase 1 by blocking polo-box domain-dependent protein-protein interactions. Chem Biol. 2008 May;15(5):459-66. doi: 10.1016/j.chembiol.2008.03.013. PMID: 18482698. 20: Lee KS, Idle JR. Pinning down the polo-box domain. Chem Biol. 2008 May;15(5):415-6. doi: 10.1016/j.chembiol.2008.04.009. PMID: 18482691.

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