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MedKoo Cat#: 523112 | Name: Centrinone
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Description:

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

Centrinone, also known as LCR-263, is a reversible inhibitor of Polo-like kinase 4 (PLK4).

Chemical Structure

Centrinone
Centrinone
CAS#1798871-30-3

Theoretical Analysis

MedKoo Cat#: 523112

Name: Centrinone

CAS#: 1798871-30-3

Chemical Formula: C26H25F2N7O6S2

Exact Mass: 633.1276

Molecular Weight: 633.65

Elemental Analysis: C, 49.28; H, 3.98; F, 6.00; N, 15.47; O, 15.15; S, 10.12

Price and Availability

Size Price Availability Quantity
25mg USD 450.00 2 Weeks
50mg USD 750.00 2 Weeks
100mg USD 1,350.00 2 Weeks
200mg USD 2,350.00 2 Weeks
500mg USD 3,250.00 2 Weeks
1g USD 4,650.00 2 Weeks
2g USD 7,950.00 2 Weeks
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Related CAS #
No Data
Synonym
Centrinone; LCR-263; LCR 263; LCR263.
IUPAC/Chemical Name
{2-[2-Fluoro-4-(2-fluoro-3-nitro-phenylmethanesulfonyl)-phenylsulfanyl]-5-methoxy-6-morpholin-4-yl-pyrimidin-4-yl}-(5-methyl-1H-pyrazol-3-yl)-amine
InChi Key
HHJSKDRCUMVWKF-UHFFFAOYSA-N
InChi Code
InChI=1S/C26H25F2N7O6S2/c1-15-12-21(33-32-15)29-24-23(40-2)25(34-8-10-41-11-9-34)31-26(30-24)42-20-7-6-17(13-18(20)27)43(38,39)14-16-4-3-5-19(22(16)28)35(36)37/h3-7,12-13H,8-11,14H2,1-2H3,(H2,29,30,31,32,33)
SMILES Code
CC1=CC(NC2=NC(SC3=CC=C(S(=O)(CC4=CC=CC([N+]([O-])=O)=C4F)=O)C=C3F)=NC(N5CCOCC5)=C2OC)=NN1
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
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
PLK4 inhibitor
In vitro activity:
To investigate the importance of centrosomes in the proliferation of normal and cancer cells, a centrinone was developed, a reversible inhibitor of Polo-like kinase 4 (Plk4), a serine-threonine protein kinase that initiates centriole assembly. Centrinone treatment caused centrosome depletion in human and other vertebrate cells. Centrosome loss irreversibly arrested normal cells in a senescence-like G1 state by a p53-dependent mechanism that was independent of DNA damage, stress, Hippo signaling, extended mitotic duration, or segregation errors. In contrast, cancer cell lines with normal or amplified centrosome numbers could proliferate indefinitely after centrosome loss. Upon centrinone washout, each cancer cell line returned to an intrinsic centrosome number "set point." Thus, cells with cancer-associated mutations fundamentally differ from normal cells in their response to centrosome loss. Reference: Wong YL, Anzola JV, Davis RL, Yoon M, Motamedi A, Kroll A, Seo CP, Hsia JE, Kim SK, Mitchell JW, Mitchell BJ, Desai A, Gahman TC, Shiau AK, Oegema K. Cell biology. Reversible centriole depletion with an inhibitor of Polo-like kinase 4. Science. 2015 Jun 5;348(6239):1155-60. doi: 10.1126/science.aaa5111. Epub 2015 Apr 30. PMID: 25931445; PMCID: PMC4764081.
In vivo activity:
TBD
Solvent mg/mL mM
Solubility
DMSO 31.7 49.99
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 633.65 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:
Wong YL, Anzola JV, Davis RL, Yoon M, Motamedi A, Kroll A, Seo CP, Hsia JE, Kim SK, Mitchell JW, Mitchell BJ, Desai A, Gahman TC, Shiau AK, Oegema K. Cell biology. Reversible centriole depletion with an inhibitor of Polo-like kinase 4. Science. 2015 Jun 5;348(6239):1155-60. doi: 10.1126/science.aaa5111. Epub 2015 Apr 30. PMID: 25931445; PMCID: PMC4764081.
In vitro protocol:
Wong YL, Anzola JV, Davis RL, Yoon M, Motamedi A, Kroll A, Seo CP, Hsia JE, Kim SK, Mitchell JW, Mitchell BJ, Desai A, Gahman TC, Shiau AK, Oegema K. Cell biology. Reversible centriole depletion with an inhibitor of Polo-like kinase 4. Science. 2015 Jun 5;348(6239):1155-60. doi: 10.1126/science.aaa5111. Epub 2015 Apr 30. PMID: 25931445; PMCID: PMC4764081.
In vivo protocol:
TBD
1: Meitinger F, Ohta M, Lee KY, Watanabe S, Davis RL, Anzola JV, Kabeche R, Jenkins DA, Shiau AK, Desai A, Oegema K. TRIM37 controls cancer-specific vulnerability to PLK4 inhibition. Nature. 2020 Sep;585(7825):440-446. doi: 10.1038/s41586-020-2710-1. Epub 2020 Sep 9. PMID: 32908304; PMCID: PMC7501188. 2: Mu XR, Ma MM, Lu ZY, Liu J, Xue YT, Cao J, Zeng LY, Li F, Xu KL, Wu QY. Effects of the PLK4 inhibitor Centrinone on the biological behaviors of acute myeloid leukemia cell lines. Front Genet. 2022 Aug 16;13:898474. doi: 10.3389/fgene.2022.898474. PMID: 36051696; PMCID: PMC9424683. 3: Takeda Y, Kuroki K, Chinen T, Kitagawa D. Centrosomal and Non-centrosomal Functions Emerged through Eliminating Centrosomes. Cell Struct Funct. 2020 May 23;45(1):57-64. doi: 10.1247/csf.20007. Epub 2020 Apr 9. PMID: 32269206. 4: Jin B, Zhang Y, Miller HD, He L, Ge D, Wang AR, You Z. Defect of IL17 Signaling, but Not Centrinone, Inhibits the Development of Psoriasis and Skin Papilloma in Mouse Models. Biomedicines. 2022 Aug 15;10(8):1976. doi: 10.3390/biomedicines10081976. PMID: 36009523; PMCID: PMC9405709. 5: Kerschner-Morales SL, Kühne M, Becker S, Beck JF, Sonnemann J. Anticancer effects of the PLK4 inhibitors CFI-400945 and centrinone in Ewing's sarcoma cells. J Cancer Res Clin Oncol. 2020 Nov;146(11):2871-2883. doi: 10.1007/s00432-020-03346-z. Epub 2020 Aug 8. PMID: 32770382; PMCID: PMC7519924. 6: Byrne DP, Clarke CJ, Brownridge PJ, Kalyuzhnyy A, Perkins S, Campbell A, Mason D, Jones AR, Eyers PA, Eyers CE. Use of the Polo-like kinase 4 (PLK4) inhibitor centrinone to investigate intracellular signalling networks using SILAC-based phosphoproteomics. Biochem J. 2020 Jul 17;477(13):2451-2475. doi: 10.1042/BCJ20200309. PMID: 32501498; PMCID: PMC7338032. 7: Domínguez-Calvo A, Gönczy P, Holland AJ, Balestra FR. TRIM37: a critical orchestrator of centrosome function. Cell Cycle. 2021 Dec;20(23):2443-2451. doi: 10.1080/15384101.2021.1988289. Epub 2021 Oct 21. PMID: 34672905; PMCID: PMC8794516. 8: Suri A, Bailey AW, Tavares MT, Gunosewoyo H, Dyer CP, Grupenmacher AT, Piper DR, Horton RA, Tomita T, Kozikowski AP, Roy SM, Sredni ST. Evaluation of Protein Kinase Inhibitors with PLK4 Cross-Over Potential in a Pre-Clinical Model of Cancer. Int J Mol Sci. 2019 Apr 29;20(9):2112. doi: 10.3390/ijms20092112. PMID: 31035676; PMCID: PMC6540285. 9: Wong YL, Anzola JV, Davis RL, Yoon M, Motamedi A, Kroll A, Seo CP, Hsia JE, Kim SK, Mitchell JW, Mitchell BJ, Desai A, Gahman TC, Shiau AK, Oegema K. Cell biology. Reversible centriole depletion with an inhibitor of Polo-like kinase 4. Science. 2015 Jun 5;348(6239):1155-60. doi: 10.1126/science.aaa5111. Epub 2015 Apr 30. PMID: 25931445; PMCID: PMC4764081. 10: Zhu W, Xie B. PLK4 inhibitor exhibits antitumor effect and synergizes sorafenib via arresting cell cycle and inactivating Wnt/β-catenin pathway in anaplastic thyroid cancer. Cancer Biol Ther. 2023 Dec 31;24(1):2223383. doi: 10.1080/15384047.2023.2223383. PMID: 37351847; PMCID: PMC10292002. 11: Gavilan MP, Gandolfo P, Balestra FR, Arias F, Bornens M, Rios RM. The dual role of the centrosome in organizing the microtubule network in interphase. EMBO Rep. 2018 Nov;19(11):e45942. doi: 10.15252/embr.201845942. Epub 2018 Sep 17. PMID: 30224411; PMCID: PMC6216252. 12: Feng M, Tang Y, Yao S, Zhang H, Xu D, Wei K. PLK inhibitors identified by high content phenotypic screening promote maturation of human PSC-derived cardiomyocytes. Biochem Biophys Res Commun. 2022 Sep 10;620:113-120. doi: 10.1016/j.bbrc.2022.06.074. Epub 2022 Jun 25. PMID: 35780579. 13: Chen S, Zhong L, Chu X, Wan P, Liu Z, Lu Y, Zhang Z, Wang X, Zhou Z, Shao X, Liu B. Downregulation of Polo-like kinase 4 induces cell apoptosis and G2/M arrest in acute myeloid leukemia. Pathol Res Pract. 2023 Mar;243:154376. doi: 10.1016/j.prp.2023.154376. Epub 2023 Feb 12. PMID: 36821942. 14: Denu RA, Shabbir M, Nihal M, Singh CK, Longley BJ, Burkard ME, Ahmad N. Centriole Overduplication is the Predominant Mechanism Leading to Centrosome Amplification in Melanoma. Mol Cancer Res. 2018 Mar;16(3):517-527. doi: 10.1158/1541-7786.MCR-17-0197. Epub 2018 Jan 12. PMID: 29330283; PMCID: PMC5835182. 15: Tkach JM, Philip R, Sharma A, Strecker J, Durocher D, Pelletier L. Global cellular response to chemical perturbation of PLK4 activity and abnormal centrosome number. Elife. 2022 Jun 27;11:e73944. doi: 10.7554/eLife.73944. PMID: 35758262; PMCID: PMC9236612. 16: Meitinger F, Anzola JV, Kaulich M, Richardson A, Stender JD, Benner C, Glass CK, Dowdy SF, Desai A, Shiau AK, Oegema K. 53BP1 and USP28 mediate p53 activation and G1 arrest after centrosome loss or extended mitotic duration. J Cell Biol. 2016 Jul 18;214(2):155-66. doi: 10.1083/jcb.201604081. PMID: 27432897; PMCID: PMC4949453. 17: Singh CK, Denu RA, Nihal M, Shabbir M, Garvey DR, Huang W, Iczkowski KA, Ahmad N. PLK4 is upregulated in prostate cancer and its inhibition reduces centrosome amplification and causes senescence. Prostate. 2022 Jun;82(9):957-969. doi: 10.1002/pros.24342. Epub 2022 Mar 25. PMID: 35333404; PMCID: PMC9090996. 18: Huang RL, Liu C, Fu R, Yan Y, Yang J, Wang X, Li Q. Downregulation of PLK4 expression induces apoptosis and G0/G1-phase cell cycle arrest in keloid fibroblasts. Cell Prolif. 2022 Jul;55(7):e13271. doi: 10.1111/cpr.13271. Epub 2022 Jun 7. PMID: 35670224; PMCID: PMC9251049. 19: Fujimoto M, Bo T, Yamamoto K, Yasui H, Yamamori T, Inanami O. Radiation- induced abnormal centrosome amplification and mitotic catastrophe in human cervical tumor HeLa cells and murine mammary tumor EMT6 cells. J Clin Biochem Nutr. 2020 Nov;67(3):240-247. doi: 10.3164/jcbn.19-80. Epub 2020 Apr 9. PMID: 33293764; PMCID: PMC7705082. 20: Guizzunti G, Seemann J. Mitotic Golgi disassembly is required for bipolar spindle formation and mitotic progression. Proc Natl Acad Sci U S A. 2016 Oct 25;113(43):E6590-E6599. doi: 10.1073/pnas.1610844113. Epub 2016 Oct 10. PMID: 27791030; PMCID: PMC5087019.