TW-37
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MedKoo CAT#: 205939

CAS#: 877877-35-5

Description: TW-37 is a small-molecule inhibitor of Bcl-2 family proteins, inhibited cell growth and induced apoptosis in pancreatic cancer. TW-37 induces cell growth inhibition and S-phase cell cycle arrest, with regulation of several important cell cycle-related genes like p27, p57, E2F-1, cdc25A, CDK4, cyclin A, cyclin D1, and cyclin E. The cell growth inhibition was accompanied by increased apoptosis with concomitant attenuation of Notch-1, Jagged-1, and its downstream genes such as Hes-1 in vitro and in vivo.


Chemical Structure

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TW-37
CAS# 877877-35-5

Theoretical Analysis

MedKoo Cat#: 205939
Name: TW-37
CAS#: 877877-35-5
Chemical Formula: C33H35NO6S
Exact Mass: 573.21851
Molecular Weight: 573.7
Elemental Analysis: C, 69.09; H, 6.15; N, 2.44; O, 16.73; S, 5.59

Price and Availability

Size Price Availability Quantity
5.0mg USD 235.0 2 Weeks
10.0mg USD 400.0 2 Weeks
25.0mg USD 740.0 2 Weeks
Bulk inquiry

Synonym: TW37; TW 37; TW-37.

IUPAC/Chemical Name: 5-(2-isopropylbenzyl)-N-(4-(2-tert-butylphenylsulfonyl)phenyl)-2,3,4-trihydroxybenzamide

InChi Key: PQAPVTKIEGUPRN-UHFFFAOYSA-N

InChi Code: InChI=1S/C33H35NO6S/c1-20(2)25-11-7-6-10-21(25)18-22-19-26(30(36)31(37)29(22)35)32(38)34-23-14-16-24(17-15-23)41(39,40)28-13-9-8-12-27(28)33(3,4)5/h6-17,19-20,35-37H,18H2,1-5H3,(H,34,38)

SMILES Code: O=C(NC1=CC=C(S(=O)(C2=CC=CC=C2C(C)(C)C)=O)C=C1)C3=CC(CC4=CC=CC=C4C(C)C)=C(O)C(O)=C3O

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: >5 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

Preparing Stock Solutions

The following data is based on the product molecular weight 573.7 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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1: Skommer J, Brittain T. Extended survival of SH-SY5Y cells following overexpression of Lys67Glu neuroglobin is associated with stabilization of ΔψM. Cytometry A. 2012 Jul;81(7):602-10. doi: 10.1002/cyto.a.22046. Epub 2012 Mar 29. PubMed PMID: 22467552.

2: Lieber J, Ellerkamp V, Wenz J, Kirchner B, Warmann SW, Fuchs J, Armeanu-Ebinger S. Apoptosis sensitizers enhance cytotoxicity in hepatoblastoma cells. Pediatr Surg Int. 2012 Feb;28(2):149-59. doi: 10.1007/s00383-011-2988-z. PubMed PMID: 21971946.

3: Zeitlin BD, Spalding AC, Campos MS, Ashimori N, Dong Z, Wang S, Lawrence TS, Nör JE. Metronomic small molecule inhibitor of Bcl-2 (TW-37) is antiangiogenic and potentiates the antitumor effect of ionizing radiation. Int J Radiat Oncol Biol Phys. 2010 Nov 1;78(3):879-87. doi: 10.1016/j.ijrobp.2010.04.024. Epub 2010 Aug 1. PubMed PMID: 20675079; PubMed Central PMCID: PMC2946486.

4: Tchernev G, Nenoff P. [Dissecting the pathways of tumour escape: " question of life and death?"]. An Bras Dermatol. 2010 Mar-Apr;85(2):248-59. Review. Portuguese. PubMed PMID: 20520947.

5: Buron N, Porceddu M, Brabant M, Desgué D, Racoeur C, Lassalle M, Péchoux C, Rustin P, Jacotot E, Borgne-Sanchez A. Use of human cancer cell lines mitochondria to explore the mechanisms of BH3 peptides and ABT-737-induced mitochondrial membrane permeabilization. PLoS One. 2010 Mar 31;5(3):e9924. doi: 10.1371/journal.pone.0009924. PubMed PMID: 20360986; PubMed Central PMCID: PMC2847598.

6: Ni Chonghaile T, Letai A. Mimicking the BH3 domain to kill cancer cells. Oncogene. 2008 Dec;27 Suppl 1:S149-57. doi: 10.1038/onc.2009.52. Review. PubMed PMID: 19641500.

7: Ashimori N, Zeitlin BD, Zhang Z, Warner K, Turkienicz IM, Spalding AC, Teknos TN, Wang S, Nör JE. TW-37, a small-molecule inhibitor of Bcl-2, mediates S-phase cell cycle arrest and suppresses head and neck tumor angiogenesis. Mol Cancer Ther. 2009 Apr;8(4):893-903. doi: 10.1158/1535-7163.MCT-08-1078. PubMed PMID: 19372562; PubMed Central PMCID: PMC2709836.

8: Wang Z, Azmi AS, Ahmad A, Banerjee S, Wang S, Sarkar FH, Mohammad RM. TW-37, a small-molecule inhibitor of Bcl-2, inhibits cell growth and induces apoptosis in pancreatic cancer: involvement of Notch-1 signaling pathway. Cancer Res. 2009 Apr 1;69(7):2757-65. doi: 10.1158/0008-5472.CAN-08-3060. Epub 2009 Mar 24. PubMed PMID: 19318573.

9: Al-Katib AM, Sun Y, Goustin AS, Azmi AS, Chen B, Aboukameel A, Mohammad RM. SMI of Bcl-2 TW-37 is active across a spectrum of B-cell tumors irrespective of their proliferative and differentiation status. J Hematol Oncol. 2009 Feb 16;2:8. doi: 10.1186/1756-8722-2-8. PubMed PMID: 19220884; PubMed Central PMCID: PMC2651908.

10: Azmi AS, Wang Z, Burikhanov R, Rangnekar VM, Wang G, Chen J, Wang S, Sarkar FH, Mohammad RM. Critical role of prostate apoptosis response-4 in determining the sensitivity of pancreatic cancer cells to small-molecule inhibitor-induced apoptosis. Mol Cancer Ther. 2008 Sep;7(9):2884-93. doi: 10.1158/1535-7163.MCT-08-0438. PubMed PMID: 18790769.

11: Azmi AS, Mohammad RM. Non-peptidic small molecule inhibitors against Bcl-2 for cancer therapy. J Cell Physiol. 2009 Jan;218(1):13-21. doi: 10.1002/jcp.21567. Review. PubMed PMID: 18767026; PubMed Central PMCID: PMC2577714.

12: Wang Z, Song W, Aboukameel A, Mohammad M, Wang G, Banerjee S, Kong D, Wang S, Sarkar FH, Mohammad RM. TW-37, a small-molecule inhibitor of Bcl-2, inhibits cell growth and invasion in pancreatic cancer. Int J Cancer. 2008 Aug 15;123(4):958-66. doi: 10.1002/ijc.23610. PubMed PMID: 18528859.

13: Mohammad RM, Goustin AS, Aboukameel A, Chen B, Banerjee S, Wang G, Nikolovska-Coleska Z, Wang S, Al-Katib A. Preclinical studies of TW-37, a new nonpeptidic small-molecule inhibitor of Bcl-2, in diffuse large cell lymphoma xenograft model reveal drug action on both Bcl-2 and Mcl-1. Clin Cancer Res. 2007 Apr 1;13(7):2226-35. PubMed PMID: 17404107.

14: Verhaegen M, Bauer JA, Martín de la Vega C, Wang G, Wolter KG, Brenner JC, Nikolovska-Coleska Z, Bengtson A, Nair R, Elder JT, Van Brocklin M, Carey TE, Bradford CR, Wang S, Soengas MS. A novel BH3 mimetic reveals a mitogen-activated protein kinase-dependent mechanism of melanoma cell death controlled by p53 and reactive oxygen species. Cancer Res. 2006 Dec 1;66(23):11348-59. PubMed PMID: 17145881.

15: Wang G, Nikolovska-Coleska Z, Yang CY, Wang R, Tang G, Guo J, Shangary S, Qiu S, Gao W, Yang D, Meagher J, Stuckey J, Krajewski K, Jiang S, Roller PP, Abaan HO, Tomita Y, Wang S. Structure-based design of potent small-molecule inhibitors of anti-apoptotic Bcl-2 proteins. J Med Chem. 2006 Oct 19;49(21):6139-42. PubMed PMID: 17034116.

16: Zeitlin BD, Joo E, Dong Z, Warner K, Wang G, Nikolovska-Coleska Z, Wang S, Nör JE. Antiangiogenic effect of TW37, a small-molecule inhibitor of Bcl-2. Cancer Res. 2006 Sep 1;66(17):8698-706. PubMed PMID: 16951185.
  

TW-37

5.0mg / USD 235.0


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