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MedKoo Cat#: 462789 | Name: Tyrphostin AG17

Description:

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

Tyrphostin AG17 is a biochemical that promotes adipocyte apoptosis in vivo and is an effective modulator of adipocyte differentiation and WAT hypertrophy in vitro and in vivo. It is thought to possibly be useful as a pharmacological obesity treatment. It is a tyrosine kinase antagonist that has also been found to inhibit tumor cell growth.

Chemical Structure

Tyrphostin AG17
Tyrphostin AG17
CAS#71308-35-5

Theoretical Analysis

MedKoo Cat#: 462789

Name: Tyrphostin AG17

CAS#: 71308-35-5

Chemical Formula: C12H10N2O

Exact Mass: 198.0793

Molecular Weight: 198.23

Elemental Analysis: C, 72.71; H, 5.09; N, 14.13; O, 8.07

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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Related CAS #
No Data
Synonym
Tyrphostin-AG17; Tyrphostin 9;
IUPAC/Chemical Name
2-(4-hydroxy-3,5-dimethylbenzylidene)malononitrile
InChi Key
OEDSJMUPYHBZAL-UHFFFAOYSA-N
InChi Code
InChI=1S/C12H10N2O/c1-8-3-10(4-9(2)12(8)15)5-11(6-13)7-14/h3-5,15H,1-2H3
SMILES Code
Cc1c(O)c(C)cc(/C=C(C#N)/C#N)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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 198.23 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: Camacho A, Segoviano-Ramírez JC, Sánchez-Garcia A, de Jesus Herrera-de la Rosa J, García-Juarez J, Hernandez-Puente CA, Calvo-Anguiano G, Maltos-Uro SR, Olguin A, Gojon-Romanillos G, Gojon-Zorrilla G, Ortiz-Lopez R. Tyrphostin AG17 inhibits adipocyte differentiation in vivo and in vitro. Lipids Health Dis. 2018 May 29;17(1):128. doi: 10.1186/s12944-018-0784-7. PMID: 29843731; PMCID: PMC5975476. 2: Liang BC, Ullyatt E. Chemosensitization of glioblastoma cells to bis- dichloroethyl-nitrosourea with tyrphostin AG17. Clin Cancer Res. 1998 Mar;4(3):773-81. PMID: 9533547. 3: Hori H, Nagasawa H, Uto Y, Ohkura K, Kirk KL, Uehara Y, Shimamura M. Design of hypoxia-targeting protein tyrosine kinase inhibitor using an innovative pharmacophore 2-methylene-4-cyclopentene-1,3-dione. Biochim Biophys Acta. 2004 Mar 11;1697(1-2):29-38. doi: 10.1016/j.bbapap.2003.11.011. PMID: 15023348. 4: Holtick U, Vockerodt M, Pinkert D, Schoof N, Stürzenhofecker B, Kussebi N, Lauber K, Wesselborg S, Löffler D, Horn F, Trümper L, Kube D. STAT3 is essential for Hodgkin lymphoma cell proliferation and is a target of tyrphostin AG17 which confers sensitization for apoptosis. Leukemia. 2005 Jun;19(6):936-44. doi: 10.1038/sj.leu.2403750. PMID: 15912144. 5: Burger AM, Kaur G, Alley MC, Supko JG, Malspeis L, Grever MR, Sausville EA. Tyrphostin AG17, [(3,5-Di-tert-butyl-4-hydroxybenzylidene)- malononitrile], inhibits cell growth by disrupting mitochondria. Cancer Res. 1995 Jul 1;55(13):2794-9. Erratum in: Cancer Res 1995 Aug 15;55(16):3684. PMID: 7796405. 6: Sausville EA. Correspondence re: G. Palumbo et al., the tyrphostin AG17 induces apoptosis and inhibition of cdk2 activity in a lymphoma cell line that overexpresses bcl-2. Cancer Res., 57: 2434-2439, 1997. Cancer Res. 1997 Dec 15;57(24):5610. PMID: 9407975. 7: Palumbo GA, Yarom N, Gazit A, Sandalon Z, Baniyash M, Kleinberger-Doron N, Levitzki A, Ben-Yehuda D. The tryphostin AG17 induces apoptosis and inhibition of cdk2 activity in a lymphoma cell line that overexpresses bcl-2. Cancer Res. 1997 Jun 15;57(12):2434-9. PMID: 9192822. 8: Ohkura K, Hori H. Modification of cell response to insulin by membrane-acting agents in rat white adipocytes: analysis of structural features by computational simulation. Bioorg Med Chem. 2001 Nov;9(11):3023-33. doi: 10.1016/s0968-0896(01)00199-7. PMID: 11597485. 9: Yura Y, Kusaka J, Tsujimoto H, Yoshioka Y, Yoshida H, Sato M. Effects of protein tyrosine kinase inhibitors on the replication of herpes simplex virus and the phosphorylation of viral proteins. Intervirology. 1997;40(1):7-14. doi: 10.1159/000150515. PMID: 9268765. 10: Hori H, Nagasawa H, Ishibashi M, Uto Y, Hirata A, Saijo K, Ohkura K, Kirk KL, Uehara Y. TX-1123: an antitumor 2-hydroxyarylidene-4-cyclopentene-1,3-dione as a protein tyrosine kinase inhibitor having low mitochondrial toxicity. Bioorg Med Chem. 2002 Oct;10(10):3257-65. doi: 10.1016/s0968-0896(02)00160-8. PMID: 12150871. 11: Ghorab MM, Ragab FA, Heiba HI, Elsayed MSA, Ghorab WM. Design, synthesis and molecular modeling study of certain 4-Methylbenzenesulfonamides with CDK2 inhibitory activity as anticancer and radio-sensitizing agents. Bioorg Chem. 2018 Oct;80:276-287. doi: 10.1016/j.bioorg.2018.06.010. Epub 2018 Jun 5. PMID: 29966874. 12: Ohkura K, Kawaguchi Y, Tatematsu Y, Uto Y, Hori H. An Antitumor 2-Hydroxyarylidene-4-cyclopentene-1,3-Dione as a Protein Tyrosine Kinase Inhibitor: Interaction Between TX-1123 Derivatives and Src Kinase. Anticancer Res. 2016 Jul;36(7):3645-9. PMID: 27354635. 13: Lama Z, Gaudin Y, Blondel D, Lagaudrière-Gesbert C. Kinase inhibitors tyrphostin 9 and rottlerin block early steps of rabies virus cycle. Antiviral Res. 2019 Aug;168:51-60. doi: 10.1016/j.antiviral.2019.04.014. Epub 2019 May 7. PMID: 31071352. 14: Gillespie J, Dye JF, Schachter M, Guillou PJ. Inhibition of pancreatic cancer cell growth in vitro by the tyrphostin group of tyrosine kinase inhibitors. Br J Cancer. 1993 Dec;68(6):1122-6. doi: 10.1038/bjc.1993.491. Erratum in: Br J Cancer 1994 Oct;70(4):780. PMID: 8260363; PMCID: PMC1968666. 15: Yura Y, Kusaka J, Kondo Y, Tsujimoto H, Yoshida H, Sato M. Inhibitory effect of tyrphostin on the replication of herpes simplex virus type 1. Arch Virol. 1995;140(7):1181-94. doi: 10.1007/BF01322745. PMID: 7544112. 16: Lander HM, Levine DM, Novogrodsky A. Agonistic effects of tyrphostins on human peripheral mononuclear cells. Cell Immunol. 1992 Oct 1;144(1):155-68. doi: 10.1016/0008-8749(92)90233-f. PMID: 1394436. 17: Starkov AA. "Mild" uncoupling of mitochondria. Biosci Rep. 1997 Jun;17(3):273-9. doi: 10.1023/a:1027380527769. PMID: 9337482. 18: Terada H. Uncouplers of oxidative phosphorylation. Environ Health Perspect. 1990 Jul;87:213-8. doi: 10.1289/ehp.9087213. PMID: 2176586; PMCID: PMC1567840. 19: Tatematsu Y, Hayashi H, Taguchi R, Fujita H, Yamamoto A, Ohkura K. Effect of N-Phenylanthranilic Acid Scaffold Nonsteroidal Anti-inflammatory Drugs on the Mitochondrial Permeability Transition. Biol Pharm Bull. 2016;39(2):278-84. doi: 10.1248/bpb.b15-00717. PMID: 26830486. 20: Uto Y, Nagasawa H, Jin CZ, Nakayama S, Tanaka A, Kiyoi S, Nakashima H, Shimamura M, Inayama S, Fujiwara T, Takeuchi Y, Uehara Y, Kirk KL, Nakata E, Hori H. Design of antiangiogenic hypoxic cell radiosensitizers: 2-nitroimidazoles containing a 2-aminomethylene-4-cyclopentene-1,3-dione moiety. Bioorg Med Chem. 2008 Jun 1;16(11):6042-53. doi: 10.1016/j.bmc.2008.04.041. Epub 2008 Apr 24. PMID: 18474428; PMCID: PMC3113482.

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