MedKoo Cat#: 407135 | Name: WEHI-539 free base

Description:

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

WEHI-539 is a highly potent and selective BCL-XL inhibitor. The prosurvival BCL-2 family protein BCL-X(L) is often overexpressed in solid tumors and renders malignant tumor cells resistant to anticancer therapeutics. WEHI-539 has high affinity (subnanomolar) and selectivity for BCL-X(L) and potently kills cells by selectively antagonizing its prosurvival activity. WEHI-539 will be an invaluable tool for distinguishing the roles of BCL-X(L) from those of its prosurvival relatives, both in normal cells and notably in malignant tumor cells, many of which may prove to rely upon BCL-X(L) for their sustained.

Chemical Structure

WEHI-539 free base
WEHI-539 free base
CAS#1431866-33-9 (free base)

Theoretical Analysis

MedKoo Cat#: 407135

Name: WEHI-539 free base

CAS#: 1431866-33-9 (free base)

Chemical Formula: C31H29N5O3S2

Exact Mass: 583.1712

Molecular Weight: 583.72

Elemental Analysis: C, 63.79; H, 5.01; N, 12.00; O, 8.22; S, 10.98

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Synonym
WEHI-539; WEHI 539; WEHI539; WEHI-539 free base
IUPAC/Chemical Name
(E)-5-(3-(4-(aminomethyl)phenoxy)propyl)-2-(8-(2-(benzo[d]thiazol-2-yl)hydrazono)-5,6,7,8-tetrahydronaphthalen-2-yl)thiazole-4-carboxylic acid
InChi Key
JKMWZKPAXZBYEH-JWHWKPFMSA-N
InChi Code
InChI=1S/C31H29N5O3S2/c32-18-19-10-14-22(15-11-19)39-16-4-9-27-28(30(37)38)34-29(40-27)21-13-12-20-5-3-7-24(23(20)17-21)35-36-31-33-25-6-1-2-8-26(25)41-31/h1-2,6,8,10-15,17H,3-5,7,9,16,18,32H2,(H,33,36)(H,37,38)/b35-24+
SMILES Code
O=C(C1=C(CCCOC2=CC=C(CN)C=C2)SC(C(C=C/34)=CC=C4CCCC3=N/NC5=NC6=CC=CC=C6S5)=N1)O
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

Preparing Stock Solutions

The following data is based on the product molecular weight 583.72 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
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PMID: 36381235; PMCID: PMC9648413. 7: Vera MB, Morris-Hanon O, Nogueiras GI, Ripari LB, Esquivel MI, Perez-Castro C, Romorini L, Sevlever GE, Scassa ME, Videla-Richardson GA. Noxa and Mcl-1 expression influence the sensitivity to BH3-mimetics that target Bcl-xL in patient-derived glioma stem cells. Sci Rep. 2022 Oct 22;12(1):17729. doi: 10.1038/s41598-022-20910-4. PMID: 36273072; PMCID: PMC9587994. 8: Hoffmeister-Wittmann P, Mock A, Nichetti F, Korell F, Heilig CE, Scherr AL, Günther M, Albrecht T, Kelmendi E, Xu K, Nader L, Kessler A, Schmitt N, Fritzsche S, Weiler S, Sobol B, Stenzinger A, Boeck S, Westphalen CB, Schulze- Osthoff K, Trojan J, Kindler T, Weichert W, Spiekermann K, Bitzer M, Folprecht G, Illert AL, Boerries M, Klauschen F, Ochsenreither S, Siveke J, Bauer S, Glimm H, Brors B, Hüllein J, Hübschmann D, Uhrig S, Horak P, Kreutzfeldt S, Banales JM, Springfeld C, Jäger D, Schirmacher P, Roessler S, Ormanns S, Goeppert B, Fröhling S, Köhler BC. Bcl-xL as prognostic marker and potential therapeutic target in cholangiocarcinoma. Liver Int. 2022 Dec;42(12):2855-2870. doi: 10.1111/liv.15392. Epub 2022 Sep 14. PMID: 35983950. 9: Albalawi YA, Narasipura SD, Al-Harthi L. Wnt/β-Catenin Protects Lymphocytes from HIV-Mediated Apoptosis via Induction of Bcl-xL. Viruses. 2022 Jul 2;14(7):1469. doi: 10.3390/v14071469. PMID: 35891449; PMCID: PMC9324643. 10: Sobol B, Azzam Nieto O, Eberlein EL, Scherr AL, Ismail L, Kessler A, Nader L, Schwab M, Hoffmeister P, Schmitt N, Jäger D, Welte S, Seidensaal K, Christopoulos P, Heilig C, Kriegsmann K, Fröhling S, Kriegsmann M, Hess J, Köhler BC. Specific Targeting of Antiapoptotic Bcl-2 Proteins as a Radiosensitizing Approach in Solid Tumors. Int J Mol Sci. 2022 Jul 16;23(14):7850. doi: 10.3390/ijms23147850. PMID: 35887198; PMCID: PMC9319836. 11: Chiou JT, Lee YC, Wang LJ, Chang LS. BCL2 inhibitor ABT-199 and BCL2L1 inhibitor WEHI-539 coordinately promote NOXA-mediated degradation of MCL1 in human leukemia cells. Chem Biol Interact. 2022 Jul 1;361:109978. doi: 10.1016/j.cbi.2022.109978. Epub 2022 May 11. PMID: 35561756. 12: Bekker GJ, Fukuda I, Higo J, Fukunishi Y, Kamiya N. Cryptic-site binding mechanism of medium-sized Bcl-xL inhibiting compounds elucidated by McMD-based dynamic docking simulations. Sci Rep. 2021 Mar 3;11(1):5046. doi: 10.1038/s41598-021-84488-z. PMID: 33658550; PMCID: PMC7930018. 13: Shang E, Nguyen TTT, Shu C, Westhoff MA, Karpel-Massler G, Siegelin MD. Epigenetic Targeting of Mcl-1 Is Synthetically Lethal with Bcl-xL/Bcl-2 Inhibition in Model Systems of Glioblastoma. Cancers (Basel). 2020 Aug 1;12(8):2137. doi: 10.3390/cancers12082137. PMID: 32752193; PMCID: PMC7464325. 14: Loo LSW, Soetedjo AAP, Lau HH, Ng NHJ, Ghosh S, Nguyen L, Krishnan VG, Choi H, Roca X, Hoon S, Teo AKK. BCL-xL/BCL2L1 is a critical anti-apoptotic protein that promotes the survival of differentiating pancreatic cells from human pluripotent stem cells. Cell Death Dis. 2020 May 18;11(5):378. doi: 10.1038/s41419-020-2589-7. PMID: 32424151; PMCID: PMC7235254. 15: Bessou M, Lopez J, Gadet R, Deygas M, Popgeorgiev N, Poncet D, Nougarède A, Billard P, Mikaelian I, Gonzalo P, Rimokh R, Gillet G. The apoptosis inhibitor Bcl-xL controls breast cancer cell migration through mitochondria-dependent reactive oxygen species production. Oncogene. 2020 Apr;39(15):3056-3074. doi: 10.1038/s41388-020-1212-9. Epub 2020 Feb 17. PMID: 32066881. 16: Rohner L, Reinhart R, Iype J, Bachmann S, Kaufmann T, Fux M. Impact of BH3-mimetics on Human and Mouse Blood Leukocytes: A Comparative Study. Sci Rep. 2020 Jan 14;10(1):222. doi: 10.1038/s41598-019-57000-x. PMID: 31937836; PMCID: PMC6959258. 17: Vallet S, Fan F, Malvestiti S, Pecherstorfer M, Sattler M, Schneeweiss A, Schulze-Bergkamen H, Opferman JT, Cardone MH, Jäger D, Podar K. Rationally derived drug combinations with the novel Mcl-1 inhibitor EU-5346 in breast cancer. Breast Cancer Res Treat. 2019 Feb;173(3):585-596. doi: 10.1007/s10549-018-5022-5. Epub 2018 Oct 29. PMID: 30374681. 18: de Jong Y, Monderer D, Brandinelli E, Monchanin M, van den Akker BE, van Oosterwijk JG, Blay JY, Dutour A, Bovée JVMG. Bcl-xl as the most promising Bcl-2 family member in targeted treatment of chondrosarcoma. Oncogenesis. 2018 Sep 21;7(9):74. doi: 10.1038/s41389-018-0084-0. PMID: 30242253; PMCID: PMC6155044. 19: Lucantoni F, Düssmann H, Llorente-Folch I, Prehn JHM. BCL2 and BCL(X)L selective inhibitors decrease mitochondrial ATP production in breast cancer cells and are synthetically lethal when combined with 2-deoxy-D-glucose. Oncotarget. 2018 May 25;9(40):26046-26063. doi: 10.18632/oncotarget.25433. PMID: 29899841; PMCID: PMC5995245. 20: Lucantoni F, Lindner AU, O'Donovan N, Düssmann H, Prehn JHM. Systems modeling accurately predicts responses to genotoxic agents and their synergism with BCL-2 inhibitors in triple negative breast cancer cells. Cell Death Dis. 2018 Jan 19;9(2):42. doi: 10.1038/s41419-017-0039-y. PMID: 29352235; PMCID: PMC5833806.