PP2
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MedKoo CAT#: 401706

CAS#: 172889-27-9

Description: PP2, also known as AG 1879, is a substance that has frequently been used in cancer research as a "selective" inhibitor for Src-family kinases. It strongly inhibits the kinases Lck (IC50=4 nM), Fyn (5 nM) and Hck (5 nM), shows weaker inhibition of EGFR (480 nM) and practically no inhibition of ZAP-70 (100 µM) and JAK2 (50 µM). Despite its extensive use as a Src-selective inhibitor, recent research has shown that PP2 is non-selective and inhibits many other kinases with similar affinities.

Chemical Structure

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PP2
CAS# 172889-27-9
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 401706
Name: PP2
CAS#: 172889-27-9
Chemical Formula: C15H16ClN5
Exact Mass: 301.11
Molecular Weight: 301.778
Elemental Analysis: C, 59.70; H, 5.34; Cl, 11.75; N, 23.21

Price and Availability

Size Price Availability Quantity
100mg USD 750
200mg USD 1250
500mg USD 1950
1g USD 2450
2g USD 4250
5g USD 6950
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Synonym: PP2; PP-2; PP 2; AG 1879; AG-1879; AG1879.

IUPAC/Chemical Name: 1-(tert-butyl)-3-(4-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

InChi Key: PBBRWFOVCUAONR-UHFFFAOYSA-N

InChi Code: InChI=1S/C15H16ClN5/c1-15(2,3)21-14-11(13(17)18-8-19-14)12(20-21)9-4-6-10(16)7-5-9/h4-8H,1-3H3,(H2,17,18,19)

SMILES Code: NC1=C2C(N(C(C)(C)C)N=C2C3=CC=C(Cl)C=C3)=NC=N1

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: >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

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Product Data:
Product Data
Instruction:
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Biological target: PP2 is a reversible and ATP-competitive Src family kinases inhibitor with IC50s of 4 and 5 nM for Lck and Fyn.
In vitro activity: In this regard, the study’s aims are to explore the mechanism of PP2 on cervical cancer cell growth inhibition by investigating the suppressive divergence among PP1, PP2, and a negative control compound PP3. MTT results showed that three compounds had different inhibitory effects on proliferation of two cervical cancer cells, HeLa and SiHa, and PP2 was most efficient in a time- and dose-dependent manner. Moreover, this study found 10 μM PP2 down-regulated pSrc-Y416 (P < 0.05), pEGFR-Y845 (P < 0.05), and -Y1173 (P < 0.05) expression levels, while 10 μM PP1 down-regulated pSrc-Y416 (P < 0.05) and pEGFR-Y845 (P < 0.05), but not pEGFR-Y1173; 10 μM PP3 down-regulated only pEGFR-Y1173 (P < 0.05). Reference: Mol Cell Biochem. 2011 Feb;348(1-2):11-9. https://pubmed.ncbi.nlm.nih.gov/21052789/
In vivo activity: PP2-treated rats showed approximately 50% reduction of infarct size on T2-weighted MRI and in TTC staining compared with controls (P < 0.05). Moreover, the neurological score was better in the PP2 group than controls (P < 0.05). PP2 is a potential neuroprotective agent in cerebral ischemia-reperfusion. The interference of PP2 with SFKs and/or other pathways remains to be elucidated. Reference: Acta Neurol Scand. 2004 Sep;110(3):175-9. https://pubmed.ncbi.nlm.nih.gov/15285775/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 3.0 9.94
DMF:PBS (pH 7.2) (1:9) 0.1 0.33
DMSO 37.1 123.05
Ethanol 1.1 3.56

Preparing Stock Solutions

The following data is based on the product molecular weight 301.78 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: 1. Kong L, Deng Z, Shen H, Zhang Y. Src family kinase inhibitor PP2 efficiently inhibits cervical cancer cell proliferation through down-regulating phospho-Src-Y416 and phospho-EGFR-Y1173. Mol Cell Biochem. 2011 Feb;348(1-2):11-9. doi: 10.1007/s11010-010-0632-1. Epub 2010 Nov 4. PMID: 21052789. 2. Nam JS, Ino Y, Sakamoto M, Hirohashi S. Src family kinase inhibitor PP2 restores the E-cadherin/catenin cell adhesion system in human cancer cells and reduces cancer metastasis. Clin Cancer Res. 2002 Jul;8(7):2430-6. PMID: 12114449. 3. Li P, Maitra D, Kuo N, Kwan R, Song Y, Tang W, Chen L, Xie Q, Liu L, Omary MB. PP2 protects from keratin mutation-associated liver injury and filament disruption via SRC kinase inhibition in male but not female mice. Hepatology. 2023 Jan 1;77(1):144-158. doi: 10.1002/hep.32574. Epub 2022 Jun 13. PMID: 35586977. 4. Lennmyr F, Ericsson A, Gerwins P, Akterin S, Ahlström H, Terént A. Src family kinase-inhibitor PP2 reduces focal ischemic brain injury. Acta Neurol Scand. 2004 Sep;110(3):175-9. doi: 10.1111/j.1600-0404.2004.00306.x. PMID: 15285775.
In vitro protocol: 1. Kong L, Deng Z, Shen H, Zhang Y. Src family kinase inhibitor PP2 efficiently inhibits cervical cancer cell proliferation through down-regulating phospho-Src-Y416 and phospho-EGFR-Y1173. Mol Cell Biochem. 2011 Feb;348(1-2):11-9. doi: 10.1007/s11010-010-0632-1. Epub 2010 Nov 4. PMID: 21052789. 2. Nam JS, Ino Y, Sakamoto M, Hirohashi S. Src family kinase inhibitor PP2 restores the E-cadherin/catenin cell adhesion system in human cancer cells and reduces cancer metastasis. Clin Cancer Res. 2002 Jul;8(7):2430-6. PMID: 12114449.
In vivo protocol: 1. Li P, Maitra D, Kuo N, Kwan R, Song Y, Tang W, Chen L, Xie Q, Liu L, Omary MB. PP2 protects from keratin mutation-associated liver injury and filament disruption via SRC kinase inhibition in male but not female mice. Hepatology. 2023 Jan 1;77(1):144-158. doi: 10.1002/hep.32574. Epub 2022 Jun 13. PMID: 35586977. 2. Lennmyr F, Ericsson A, Gerwins P, Akterin S, Ahlström H, Terént A. Src family kinase-inhibitor PP2 reduces focal ischemic brain injury. Acta Neurol Scand. 2004 Sep;110(3):175-9. doi: 10.1111/j.1600-0404.2004.00306.x. PMID: 15285775.

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1: Seltana A, Guezguez A, Lepage M, Basora N, Beaulieu JF. Src family kinase inhibitor PP2 accelerates differentiation in human intestinal epithelial cells. Biochem Biophys Res Commun. 2012 Dec 27. doi:pii: S0006-291X(12)02433-3. 10.1016/j.bbrc.2012.12.085. [Epub ahead of print] PubMed PMID: 23274493.

2: Wallet MA, Reist CM, Williams JC, Appelberg S, Guiulfo GL, Gardner B, Sleasman JW, Goodenow MM. The HIV-1 protease inhibitor nelfinavir activates PP2 and inhibits MAPK signaling in macrophages: a pathway to reduce inflammation. J Leukoc Biol. 2012 Oct;92(4):795-805. doi: 10.1189/jlb.0911447. Epub 2012 Jul 11. PubMed PMID: 22786868; PubMed Central PMCID: PMC3441314.

3: Bartscht T, Lehnert H, Gieseler F, Ungefroren H. The Src family kinase inhibitors PP2 and PP1 effectively block TGF-beta1-induced cell migration and invasion in both established and primary carcinoma cells. Cancer Chemother Pharmacol. 2012 Aug;70(2):221-30. doi: 10.1007/s00280-012-1904-0. Epub 2012 Jun 15. PubMed PMID: 22699812.

4: Dubey KV, Charde PN, Meshram SU, Shendre LP, Dubey VS, Juwarkar AA. Surface-active potential of biosurfactants produced in curd whey by Pseudomonas aeruginosa strain-PP2 and Kocuria turfanesis strain-J at extreme environmental conditions. Bioresour Technol. 2012 Dec;126:368-74. doi: 10.1016/j.biortech.2012.05.024. Epub 2012 May 12. PubMed PMID: 22683199.

5: Gong J, Gu HY, Wang X, Liang Y, Sun T, Liu PJ, Wang Y, Yan JC, Jiao ZJ. SRC kinase family inhibitor PP2 promotes DMSO-induced cardiac differentiation of P19 cells and inhibits proliferation. Int J Cardiol. 2012 May 8. [Epub ahead of print] PubMed PMID: 22575628.

6: Congleton J, MacDonald R, Yen A. Src inhibitors, PP2 and dasatinib, increase retinoic acid-induced association of Lyn and c-Raf (S259) and enhance MAPK-dependent differentiation of myeloid leukemia cells. Leukemia. 2012 Jun;26(6):1180-8. doi: 10.1038/leu.2011.390. Epub 2011 Dec 19. PubMed PMID: 22182854; PubMed Central PMCID: PMC3310950.

7: Ahn JH, Lee M. Suppression of autophagy sensitizes multidrug resistant cells towards Src tyrosine kinase specific inhibitor PP2. Cancer Lett. 2011 Nov 28;310(2):188-97. doi: 10.1016/j.canlet.2011.06.034. Epub 2011 Jul 3. PubMed PMID: 21775053.

8: Ungefroren H, Sebens S, Groth S, Gieseler F, Fändrich F. The Src family kinase inhibitors PP2 and PP1 block TGF-beta1-mediated cellular responses by direct and differential inhibition of type I and type II TGF-beta receptors. Curr Cancer Drug Targets. 2011 May;11(4):524-35. PubMed PMID: 21395548.

9: Kong L, Deng Z, Shen H, Zhang Y. Src family kinase inhibitor PP2 efficiently inhibits cervical cancer cell proliferation through down-regulating phospho-Src-Y416 and phospho-EGFR-Y1173. Mol Cell Biochem. 2011 Feb;348(1-2):11-9. doi: 10.1007/s11010-010-0632-1. Epub 2010 Nov 4. PubMed PMID: 21052789.

10: Hishiki T, Saito T, Sato Y, Mitsunaga T, Terui E, Matsuura G, Saito E, Shibata R, Mise N, Yokoyama Y, Yoshida H. Src kinase family inhibitor PP2 induces aggregation and detachment of neuroblastoma cells and inhibits cell growth in a PI3 kinase/Akt pathway-independent manner. Pediatr Surg Int. 2011 Feb;27(2):225-30. doi: 10.1007/s00383-010-2775-2. PubMed PMID: 21046121.

11: Liu X, Feng R, Du L. The role of enoyl-CoA hydratase short chain 1 and peroxiredoxin 3 in PP2-induced apoptosis in human breast cancer MCF-7 cells. FEBS Lett. 2010 Jul 16;584(14):3185-92. doi: 10.1016/j.febslet.2010.06.002. Epub 2010 Jun 10. PubMed PMID: 20541551.

12: Beneteau J, Renard D, Marché L, Douville E, Lavenant L, Rahbé Y, Dupont D, Vilaine F, Dinant S. Binding properties of the N-acetylglucosamine and high-mannose N-glycan PP2-A1 phloem lectin in Arabidopsis. Plant Physiol. 2010 Jul;153(3):1345-61. doi: 10.1104/pp.110.153882. Epub 2010 May 4. PubMed PMID: 20442276; PubMed Central PMCID: PMC2899916.

13: Daoud G, Le bellego F, Lafond J. PP2 regulates human trophoblast cells differentiation by activating p38 and ERK1/2 and inhibiting FAK activation. Placenta. 2008 Oct;29(10):862-70. doi: 10.1016/j.placenta.2008.07.011. Epub 2008 Sep 9. PubMed PMID: 18783823.

14: Schuster IG, Busch DH, Eppinger E, Kremmer E, Milosevic S, Hennard C, Kuttler C, Ellwart JW, Frankenberger B, Nössner E, Salat C, Bogner C, Borkhardt A, Kolb HJ, Krackhardt AM. Allorestricted T cells with specificity for the FMNL1-derived peptide PP2 have potent antitumor activity against hematologic and other malignancies. Blood. 2007 Oct 15;110(8):2931-9. Epub 2007 Jul 12. PubMed PMID: 17626842.

15: Hou XY, Liu Y, Zhang GY. PP2, a potent inhibitor of Src family kinases, protects against hippocampal CA1 pyramidal cell death after transient global brain ischemia. Neurosci Lett. 2007 Jun 15;420(3):235-9. Epub 2007 Mar 25. PubMed PMID: 17556100.

16: Lee M. Raf-1 kinase activation is uncoupled from downstream MEK/ERK pathway in cells treated with Src tyrosine kinase inhibitor PP2. Biochem Biophys Res Commun. 2006 Nov 17;350(2):450-6. Epub 2006 Sep 22. PubMed PMID: 17010316.

17: Kanda S, Kanetake H, Miyata Y. Role of Src in angiopoietin 1-induced capillary morphogenesis of endothelial cells: Effect of chronic hypoxia on Src inhibition by PP2. Cell Signal. 2007 Mar;19(3):472-80. Epub 2006 Sep 1. PubMed PMID: 16949254.

18: Li Z, Hosoi Y, Cai K, Tanno Y, Matsumoto Y, Enomoto A, Morita A, Nakagawa K, Miyagawa K. Src tyrosine kinase inhibitor PP2 suppresses ERK1/2 activation and epidermal growth factor receptor transactivation by X-irradiation. Biochem Biophys Res Commun. 2006 Mar 10;341(2):363-8. Epub 2006 Jan 18. PubMed PMID: 16414009.

19: Shyu KG, Jow GM, Lee YJ, Wang SJ. PP2 inhibits glutamate release from nerve endings by affecting vesicle mobilization. Neuroreport. 2005 Nov 28;16(17):1969-72. PubMed PMID: 16272889.

20: Chiang GJ, Billmeyer BR, Canes D, Stoffel J, Moinzadeh A, Austin CA, Kosakowski M, Rieger-Christ KM, Libertino JA, Summerhayes IC. The src-family kinase inhibitor PP2 suppresses the in vitro invasive phenotype of bladder carcinoma cells via modulation of Akt. BJU Int. 2005 Aug;96(3):416-22. PubMed PMID: 16042741.

21: Calcagno AM, Fostel JM, Orchekowski RP, Alston JT, Mattes WB, Siahaan TJ, Ware JA. Modulation of cell adhesion molecules in various epithelial cell lines after treatment with PP2. Mol Pharm. 2005 May-Jun;2(3):170-84. PubMed PMID: 15934778.

22: Guo H, Chen X, Zhang H, Fang R, Yuan Z, Zhang Z, Tian Y. Characterization and activity enhancement of the phloem-specific pumpkin PP2 gene promoter. Transgenic Res. 2004 Dec;13(6):559-66. PubMed PMID: 15672837.

23: Krishnan S, Prabhu Y, Phale PS. O-phthalic acid, a dead-end product in one of the two pathways of phenanthrene degradation in Pseudomonas sp. strain PP2. Indian J Biochem Biophys. 2004 Oct;41(5):227-32. PubMed PMID: 22900278.

24: Wu SS, Yamauchi K, Rozengurt E. Bombesin and angiotensin II rapidly stimulate Src phosphorylation at Tyr-418 in fibroblasts and intestinal epithelial cells through a PP2-insensitive pathway. Cell Signal. 2005 Jan;17(1):93-102. PubMed PMID: 15451029.

25: Lee M, Kim JY, Koh WS. Apoptotic effect of PP2 a Src tyrosine kinase inhibitor, in murine B cell leukemia. J Cell Biochem. 2004 Oct 15;93(3):629-38. PubMed PMID: 15378599.

26: Lee M, Kim JY, Anderson WB. Src tyrosine kinase inhibitor PP2 markedly enhances Ras-independent activation of Raf-1 protein kinase by phorbol myristate acetate and H2O2. J Biol Chem. 2004 Nov 19;279(47):48692-701. Epub 2004 Sep 8. PubMed PMID: 15356004.

27: Lennmyr F, Ericsson A, Gerwins P, Akterin S, Ahlström H, Terént A. Src family kinase-inhibitor PP2 reduces focal ischemic brain injury. Acta Neurol Scand. 2004 Sep;110(3):175-9. PubMed PMID: 15285775.

28: Prabhu Y, Phale PS. Biodegradation of phenanthrene by Pseudomonas sp. strain PP2: novel metabolic pathway, role of biosurfactant and cell surface hydrophobicity in hydrocarbon assimilation. Appl Microbiol Biotechnol. 2003 May;61(4):342-51. Epub 2003 Feb 11. PubMed PMID: 12743764.

29: Carlomagno F, Vitagliano D, Guida T, Basolo F, Castellone MD, Melillo RM, Fusco A, Santoro M. Efficient inhibition of RET/papillary thyroid carcinoma oncogenic kinases by 4-amino-5-(4-chloro-phenyl)-7-(t-butyl)pyrazolo[3,4-d]pyrimidine (PP2). J Clin Endocrinol Metab. 2003 Apr;88(4):1897-902. PubMed PMID: 12679489.

30: Nam JS, Ino Y, Sakamoto M, Hirohashi S. Src family kinase inhibitor PP2 restores the E-cadherin/catenin cell adhesion system in human cancer cells and reduces cancer metastasis. Clin Cancer Res. 2002 Jul;8(7):2430-6. PubMed PMID: 12114449.