Tyrphostin AG957 | CAS#140674-76-6 | tyrosine kinase inhibitor

MedKoo Cat#: 563556 | Name: Tyrphostin AG957

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Description:

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

Tyrphostin AG957 is a tyrosine kinase inhibitor that specifically targets the BCR/ABL fusion protein, a constitutively active kinase responsible for the pathogenesis of chronic myelogenous leukemia (CML). By inhibiting p210^BCR/ABL^ kinase activity, AG957 restores normal β1 integrin-mediated adhesion and signaling in CML hematopoietic progenitors, thereby reducing their uncontrolled proliferation.

Chemical Structure

Tyrphostin AG957

CAS#140674-76-6

Theoretical Analysis

MedKoo Cat#: 563556

Name: Tyrphostin AG957

CAS#: 140674-76-6

Chemical Formula: C15H15NO4

Exact Mass: 273.1001

Molecular Weight: 273.28

Elemental Analysis: C, 65.92; H, 5.53; N, 5.13; O, 23.42

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 400.00	2 Weeks
10mg	USD 650.00	2 Weeks

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Related CAS #

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Synonym

Tyrphostin AG957; Tyrphostin-AG957; TyrphostinAG957; Tyrphostin AG-957; Tyrphostin AG 957; AG-957; AG 957; AG957;

IUPAC/Chemical Name

methyl 4-((2,5-dihydroxybenzyl)amino)benzoate

InChi Key

QSFREBZMBNRGOK-UHFFFAOYSA-N

InChi Code

InChI=1S/C15H15NO4/c1-20-15(19)10-2-4-12(5-3-10)16-9-11-8-13(17)6-7-14(11)18/h2-8,16-18H,9H2,1H3

SMILES Code

OC1=C(CNC2=CC=C(C(OC)=O)C=C2)C=C(O)C=C1

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

Shelf Life

>3 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

2934.99.03.00

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Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 273.28 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.

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: 16181795. 4: Yeheskely-Hayon D, Regev R, Eytan GD, Dann EJ. The tyrosine kinase inhibitors imatinib and AG957 reverse multidrug resistance in a chronic myelogenous leukemia cell line. Leuk Res. 2005 Jul;29(7):793-802. doi: 10.1016/j.leukres.2004.12.007. Epub 2005 Feb 26. PMID: 15927675. 5: Ackermann U, Tochon-Danguy HJ, Nerrie M, Nice EC, Sachinidis JI, Scott AM. Synthesis, 11C labeling and biological properties of derivatives of the tyrphostin AG957. Nucl Med Biol. 2005 May;32(4):323-8. doi: 10.1016/j.nucmedbio.2005.02.006. PMID: 15878501. 6: Kaur G, Narayanan VL, Risbood PA, Hollingshead MG, Stinson SF, Varma RK, Sausville EA. Synthesis, structure-activity relationship, and p210(bcr-abl) protein tyrosine kinase activity of novel AG 957 analogs. Bioorg Med Chem. 2005 Mar 1;13(5):1749-61. doi: 10.1016/j.bmc.2004.12.003. PMID: 15698792. 7: Chandra J, Hackbarth J, Le S, Loegering D, Bone N, Bruzek LM, Narayanan VL, Adjei AA, Kay NE, Tefferi A, Karp JE, Sausville EA, Kaufmann SH. Involvement of reactive oxygen species in adaphostin-induced cytotoxicity in human leukemia cells. Blood. 2003 Dec 15;102(13):4512-9. doi: 10.1182/blood-2003-02-0562. Epub 2003 Aug 14. PMID: 12920036. 8: Wang Y, Wagner MB, Kumar R, Cheng J, Joyner RW. Inhibition of fast sodium current in rabbit ventricular myocytes by protein tyrosine kinase inhibitors. Pflugers Arch. 2003 Jul;446(4):485-91. doi: 10.1007/s00424-003-1061-8. Epub 2003 Apr 26. PMID: 12719980. 9: Brisdelli F, Iorio E, Knijn A, Ferretti A, Marcheggiani D, Lenti L, Strom R, Podo F, Bozzi A. Two-step formation of 1H NMR visible mobile lipids during apoptosis of paclitaxel-treated K562 cells. Biochem Pharmacol. 2003 Apr 15;65(8):1271-80. doi: 10.1016/s0006-2952(03)00080-7. PMID: 12694868. 10: Wang Y, Kumar R, Wagner MB, Cheng J, Mishra M, Joyner RW. Regulation of transient outward current in human atrial myocytes by protein tyrosine kinase pathway. J Cardiovasc Electrophysiol. 2002 Sep;13(9):927-35. doi: 10.1046/j.1540-8167.2002.00927.x. PMID: 12380934. 11: Urbano A, Gorgun G, Foss F. Mechanisms of apoptosis by the tyrphostin AG957 in hematopoietic cells. Biochem Pharmacol. 2002 Feb 15;63(4):689-92. doi: 10.1016/s0006-2952(01)00916-9. PMID: 11992636. 12: Bhatia R, Munthe HA, Forman SJ. Abnormal growth factor modulation of beta1-integrin-mediated adhesion in chronic myelogenous leukaemia haematopoietic progenitors. Br J Haematol. 2001 Dec;115(4):845-53. doi: 10.1046/j.1365-2141.2001.03192.x. PMID: 11843818. 13: Deutsch E, Dugray A, AbdulKarim B, Marangoni E, Maggiorella L, Vaganay S, M'Kacher R, Rasy SD, Eschwege F, Vainchenker W, Turhan AG, Bourhis J. BCR-ABL down-regulates the DNA repair protein DNA-PKcs. Blood. 2001 Apr 1;97(7):2084-90. doi: 10.1182/blood.v97.7.2084. PMID: 11264175. 14: Sun X, Layton JE, Elefanty A, Lieschke GJ. Comparison of effects of the tyrosine kinase inhibitors AG957, AG490, and STI571 on BCR-ABL--expressing cells, demonstrating synergy between AG490 and STI571. Blood. 2001 Apr 1;97(7):2008-15. doi: 10.1182/blood.v97.7.2008. PMID: 11264165. 15: Svingen PA, Tefferi A, Kottke TJ, Kaur G, Narayanan VL, Sausville EA, Kaufmann SH. Effects of the bcr/abl kinase inhibitors AG957 and NSC 680410 on chronic myelogenous leukemia cells in vitro. Clin Cancer Res. 2000 Jan;6(1):237-49. PMID: 10656455. 16: Carlo-Stella C, Regazzi E, Sammarelli G, Colla S, Garau D, Gazit A, Savoldo B, Cilloni D, Tabilio A, Levitzki A, Rizzoli V. Effects of the tyrosine kinase inhibitor AG957 and an Anti-Fas receptor antibody on CD34(+) chronic myelogenous leukemia progenitor cells. Blood. 1999 Jun 1;93(11):3973-82. PMID: 10339507. 17: Jamieson L, Carpenter L, Biden TJ, Fields AP. Protein kinase Ciota activity is necessary for Bcr-Abl-mediated resistance to drug-induced apoptosis. J Biol Chem. 1999 Feb 12;274(7):3927-30. doi: 10.1074/jbc.274.7.3927. PMID: 9933579. 18: Losiewicz MD, Kaur G, Sausville EA. Different early effets of tyrphostin AG957 and geldanamycins on mitogen-activated protein kinase and p120cbl phosphorylation in anti CD-3-stimulated T-lymphoblasts. Biochem Pharmacol. 1999 Feb 1;57(3):281-9. doi: 10.1016/s0006-2952(98)00293-7. PMID: 9890555. 19: Bhatia R, Munthe HA, Verfaillie CM. Tyrphostin AG957, a tyrosine kinase inhibitor with anti-BCR/ABL tyrosine kinase activity restores beta1 integrin- mediated adhesion and inhibitory signaling in chronic myelogenous leukemia hematopoietic progenitors. Leukemia. 1998 Nov;12(11):1708-17. doi: 10.1038/sj.leu.2401193. PMID: 9823945. 20: Kaur G, Sausville EA. Altered physical state of p210bcr-abl in tyrphostin AG957-treated K562 cells. Anticancer Drugs. 1996 Nov;7(8):815-24. doi: 10.1097/00001813-199611000-00001. PMID: 8991184.