IWP 2

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Description: PORCN inhibitor; inhibits Wnt processing and secretion
Chemical Name: N-(6-Methyl-2-benzothiazolyl)-2-[(3,4,6,7-tetrahydro-4-oxo-3-phenylthieno[3,2-d]pyrimidin-2-yl)thio]-acetamide
Purity: ≥98% (HPLC)
Datasheet
Citations (102)
Reviews (2)

Biological Activity for IWP 2

IWP 2 is a potent inhibitor of Wnt processing and secretion (IC50 = 27nM). IWP 2 inactivates PORCN, a membrane-bound O-acyltransferase (MBOAT), and selectively inhibits palmitoylation of Wnt. Blocks Wnt-dependent phosphorylation of Lrp6 receptor and Dvl2, and β-catenin accumulation. IWP 2 suppresses self-renewal in R1 embryonic stem cells and promotes cardiomyocyte differentiation from hPSCs. The compound has also been used in protocols to reprogram human somatic cells to chemically-induced PSCs.

Technical Data for IWP 2

M. Wt 466.6
Formula C22H18N4O2S3
Storage Store at +4°C
Purity ≥98% (HPLC)
CAS Number 686770-61-6
PubChem ID 2155128
InChI Key WRKPZSMRWPJJDH-UHFFFAOYSA-N
Smiles O=C1C3=C(CCS3)N=C(SCC(NC4=NC(C=CC(C)=C5)=C5S4)=O)N1C2=CC=CC=C2

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility Data for IWP 2

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 2.33 5 with gentle warming

Preparing Stock Solutions for IWP 2

The following data is based on the product molecular weight 466.6. 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.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
0.05 mM 42.86 mL 214.32 mL 428.63 mL
0.25 mM 8.57 mL 42.86 mL 85.73 mL
0.5 mM 4.29 mL 21.43 mL 42.86 mL
2.5 mM 0.86 mL 4.29 mL 8.57 mL

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Product Datasheets for IWP 2

Certificate of Analysis / Product Datasheet
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References for IWP 2

References are publications that support the biological activity of the product.

Chen et al (2009) Small molecule-mediated disruption of wnt-dependent signaling in tissue regeneration and cancer. Nature Chem.Biol. 5 100 PMID: 19125156

ten Berge et al (2011) Embryonic stem cells require Wnt proteins to prevent differentiation to epiblast stem cells. Nat.Cell.Biol. 13 1070 PMID: 21841791

Lian et al (2012) Robust cardiomyocyte differentiation from human pluripotent stem cells via temporal modulation of canonical Wnt signaling. Proc.Natl.Acad.Sci.U S A 109 E1848 PMID: 22645348

Noor et al (2019) 3D printing of personalized thick and perfusable cardiac patches and hearts. Adv Sci (Weinh) 6 1900344 PMID: 31179230

Hoang et al (2018) Generation of spatial-patterned early-developing cardiac organoids using human pluripotent stem cells. Nat.Protoc. 13 723 PMID: 29543795

Guan et al (2022) Chemical reprogramming of human somatic cells to pluripotent stem cells. Nature 605 325 PMID: 35418683


If you know of a relevant reference for IWP 2, please let us know.

View Related Products by Product Action

View all PORCN Inhibitors

Keywords: IWP 2, IWP 2 supplier, MBOAT, membrane-bound, o-acyltransferases, Porcupine, porcn, wnt, secretion, production, signaling, signalling, inhibitors, inhibits, inactivators, inactivates, IWP2, beta-catenin, β-catenin, b-catenin, stem, cells, proliferation, reprogramming, ciPSC, pluirpotent, Stem, Cell, Signaling, Proliferation, PORCN, Organoids, Cardiomyocyte, Cells, Reprogramming, 3533, Tocris Bioscience

102 Citations for IWP 2

Citations are publications that use Tocris products. Selected citations for IWP 2 include:

Yang et al (2020) A Human Pluripotent Stem Cell-based Platform to Study SARS-CoV-2 Tropism and Model Virus Infection in Human Cells and Organoids Cell Stem Cell 27 125 PMID: 32579880

Shi et al (2017) Genome Editing in hPSCs Reveals GATA6 Haploinsufficiency and a Genetic Interaction with GATA4 in Human Pancreatic Development. Cell Stem Cell 20 675 PMID: 28196600

Lin et al (2017) Culture in Glucose-Depleted Medium Supplemented with Fatty Acid and 3,3',5-Triiodo-l-Thyronine Facilitates Purification and Maturation of Human Pluripotent Stem Cell-Derived Cardiomyocytes. Front Endocrinol (Lausanne) 8 253 PMID: 29067001

Kumar et al (2015) Generation of an expandable intermediate mesoderm restricted progenitor cell line from human pluripotent stem cells. Elife 4 PMID: 26554899

Kim et al (2015) Act.-A and Bmp4 levels modulate cell type specification during CHIR-induced cardiomyogenesis. PLoS One 10 e0118670 PMID: 25706534

Heylman et al (2015) Supervised Machine Learning for Classification of the Electrophysiological Effects of Chronotropic Drugs on Human Induced Pluripotent Stem Cell-Derived Cardiomyocytes. PLoS One 10 e0144572 PMID: 26695765

Lee et al (2015) Machine learning plus optical flow: a simple and sensitive method to detect cardioactive drugs. Sci Rep 5 11817 PMID: 26139150

Huebsch et al (2015) Automated Video-Based Analysis of Contractility and Calcium Flux in Human-Induced Pluripotent Stem Cell-Derived Cardiomyocytes Cultured over Different Spatial Scales. Tissue Eng Part C Methods 21 467 PMID: 25333967

Skelton et al (2014) SIRPA, VCAM1 and CD34 identify discrete lineages during early human cardiovascular development. Nat Genet 13 172 PMID: 24968096

Vahdat et al (2019) Establishment of A Protocol for In Vitro Culture of Cardiogenic Mesodermal Cells Derived from Human Embryonic Stem Cells. Cell J 20 496 PMID: 30123995

Xiang et al (2019) Long-term functional maintenance of primary human hepatocytes in vitro. Science 364 399 PMID: 31023926

Yap et al (2019) In Vivo Generation of Post-infarct Human Cardiac Muscle by Laminin-Promoted Cardiovascular Progenitors. Cell Rep 26 3231 PMID: 30893597

Lee and Evans (2019) TMEM88 Inhibits Wnt Signaling by Promoting Wnt Signalosome Localization to Multivesicular Bodies. iScience 19 267 PMID: 31401350

Nakanishi et al (2019) Geometrical Patterning and Constituent Cell Heterogeneity Facilitate Electrical Conduction Disturbances in a Human Induced Pluripotent Stem Cell-Based Platform: An In vitro Disease Model of Atrial Arrhythmias. Front Physiol 10 818 PMID: 31316396

Walko et al (2017) A genome-wide screen identifies YAP/WBP2 interplay conferring growth advantage on human epidermal stem cells. Nat Commun 8 14744 PMID: 28332498

Lee et al (2017) Human Pluripotent Stem Cell-Derived Atrial and Ventricular Cardiomyocytes Develop from Distinct Mesoderm Populations. Cell Stem Cell 21 179 PMID: 28777944

Tong (2017) Degree of tissue differentiation dictates susceptibility to BRAF-driven colorectal cancer. Cell Rep 21 3833 PMID: 29281831

Ying et al (2021) QKI is a critical pre-mRNA alternative splicing regulator of cardiac myofibrillogenesis and contractile function. Nat Commun 12 89 PMID: 33397958

Duanqing et al (2021) Identification of New Transcription Factors that Can Promote Pluripotent Reprogramming. Stem Cell Rev Rep 17 2223-2234 PMID: 34448118

Bin et al (2021) Myogenin suppresses apoptosis induced by angiotensin II in human induced pluripotent stem cell-derived cardiomyocytes. Biochem Biophys Res Commun 552 84-90 PMID: 33743352

Sara et al (2021) Gender-specific characteristics of hypertrophic response in cardiomyocytes derived from human embryonic stem cells. J Cardiovasc Thorac Res 13 146-155 PMID: 34326969

Shukry J et al (2021) Assessing the Wnt-reactivity of cytonemes of mouse embryonic stem cells using a bioengineering approach. STAR Protoc 2 100813 PMID: 34568840

Feng et al (2021) p53 Promotes Differentiation of Cardiomyocytes from hiPSC through Wnt Signaling-Mediated Mesendodermal Differentiation. Int J Stem Cells 14 410-422 PMID: 34158418

Yingqiong et al (2021) A simple protocol to produce mature human-induced pluripotent stem cell-derived cardiomyocytes. STAR Protoc 2 100912 PMID: 34755117

Schneider et al (2019) User-Friendly and Parallelized Generation of Human Induced Pluripotent Stem Cell-Derived Microtissues in a Centrifugal Heart-on-a-Chip. Tissue Eng Part A 25 786 PMID: 30968738

Wang et al (2019) Point mutations in the PDX1 transactivation domain impair human β-cell development and function. Mol Metab 24 80 PMID: 30930126

George A et al (2018) Efficient transdifferentiation of human dermal fibroblasts into skeletal muscle. J Tissue Eng Regen Med 12 e918-e936 PMID: 28101909

Ying et al (2018) 3D Modeling of Esophageal Development using Human PSC-Derived Basal Progenitors Reveals a Critical Role for Notch Signaling. Cell Stem Cell 23 516-529.e5 PMID: 30244870

Liam R et al (2017) Use of Human Pluripotent Stem Cell Derived-Cardiomyocytes to Study Drug-Induced Cardiotoxicity. Curr Protoc Toxicol 73 22.5.1-22.5.22 PMID: 28777443

Wen et al (2017) Heparin Promotes Cardiac Differentiation of Human Pluripotent Stem Cells in Chemically Defined Albumin-Free Medium, Enabling Consistent Manufacture of Cardiomyocytes. Stem Cells Transl Med 6 527-538 PMID: 28191759

Heinrich et al (2017) WNT ligands contribute to the immune response during septic shock and amplify endotoxemia-driven inflammation in mice. Blood Adv 1 1274-1286 PMID: 29296769

Ulrich et al (2015) Cardiac differentiation of human pluripotent stem cells in scalable suspension culture. Nat Protoc 10 1345-61 PMID: 26270394

Richard P et al (2015) A Universal and Robust Integrated Platform for the Scalable Production of Human Cardiomyocytes From Pluripotent Stem Cells. Stem Cells Transl Med 4 1482-94 PMID: 26511653

Hojo et al (2013) Hedgehog-Gli activators direct osteo-chondrogenic function of bone morphogenetic protein toward osteogenesis in the perichondrium. J Biol Chem 288 9924 PMID: 23423383

Elisabeth et al (2022) Autophagy modulates cell fate decisions during lineage commitment. Autophagy 18 1915-1931 PMID: 34923909

David J et al (2022) Retrograde movements determine effective stem cell numbers in the intestine. Nature 607 548-554 PMID: 35831497

Teisha J et al (2022) Differentiating Human Pluripotent Stem Cells to Cardiomyocytes Using Purified Extracellular Matrix Proteins. Bioengineering (Basel) 9 PMID: 36550926

Ran et al (2022) Efficient differentiation of human primordial germ cells through geometric control reveals a key role for Nodal signaling. Elife 11 PMID: 35394424

Brenda M et al (2022) A Bionic Testbed for Cardiac Ablation Tools. Int J Mol Sci 23 PMID: 36430922

Reza et al (2022) In Vitro Generation of Heart Field Specific Cardiomyocytes. Methods Mol Biol 2429 257-267 PMID: 35507167

Peng et al (2022) Isolation and characterization of human embryonic stem cell-derived heart field-specific cardiomyocytes unravels new insights into their transcriptional and electrophysiological profiles. Cardiovasc Res 118 828-843 PMID: 33744937

Kentaro et al (2022) An iPS-derived in vitro model of human atrial conduction. Physiol Rep 10 e15407 PMID: 36117385

Martin A et al (2022) iPSCs derived from esophageal atresia patients reveal SOX2 dysregulation at the anterior foregut stage. Dis Model Mech 15 PMID: 36317486

Feng et al (2022) The Biphasic Effect of Retinoic Acid Signaling Pathway on the Biased Differentiation of Atrial-like and Sinoatrial Node-like Cells from hiPSC. Int J Stem Cells 15 247-257 PMID: 35220280

Leo et al (2022) The Human Induced Pluripotent Stem Cell Test as an Alternative Method for Embryotoxicity Testing. Int J Mol Sci 23 PMID: 35328717

Jae Boum et al (2022) Tomatidine-stimulated maturation of human embryonic stem cell-derived cardiomyocytes for modeling mitochondrial dysfunction. Exp Mol Med 54 493-502 PMID: 35379934

Xiaolu et al (2022) A dual SHOX2:GFP; MYH6:mCherry knockin hESC reporter line for derivation of human SAN-like cells. iScience 25 104153 PMID: 35434558

Benjamin et al (2022) Autologous humanized mouse models of iPSC-derived tumors enable characterization and modulation of cancer-immune cell interactions. Cell Rep Methods 2 100153 PMID: 35474871

Olaf et al (2022) FUCCI-Based Live Imaging Platform Reveals Cell Cycle Dynamics and Identifies Pro-proliferative Compounds in Human iPSC-Derived Cardiomyocytes. Front Cardiovasc Med 9 840147 PMID: 35548410

Alberto et al (2022) Effects of Hypocalcemic Vitamin D Analogs in the Expression of DNA Damage Induced in Minilungs from hESCs: Implications for Lung Fibrosis. Int J Mol Sci 23 PMID: 35563311

Gregory et al (2022) Bizonal cardiac engineered tissues with differential maturation features in a mid-throughput multimodal bioreactor. iScience 25 104297 PMID: 35586070

Stefan et al (2021) Distinct properties of Ca2+ efflux from brain, heart and liver mitochondria: The effects of Na+, Li+ and the mitochondrial Na+/Ca2+ exchange inhibitor CGP37157. Cell Calcium 96 102382 PMID: 33684833

Kenneth R et al (2021) Isolation of human ESC-derived cardiac derivatives and embryonic heart cells for population and single-cell RNA-seq analysis. STAR Protoc 2 100339 PMID: 33644774

Ling et al (2021) Commitment and oncogene-induced plasticity of human stem cell-derived pancreatic acinar and ductal organoids. Cell Stem Cell 28 1090-1104.e6 PMID: 33915081

Varda et al (2021) Principles of signaling pathway modulation for enhancing human naive pluripotency induction. Cell Stem Cell 28 1549-1565.e12 PMID: 33915080

Cecilia et al (2021) Mapping the temporal and spatial dynamics of the human endometrium in vivo and in vitro. Nat Genet 53 1698-1711 PMID: 34857954

Arun et al (2021) Responsiveness to perturbations is a hallmark of transcription factors that maintain cell identity in vitro. Cell Syst 12 885-899.e8 PMID: 34352221

Matteo et al (2021) The in vitro multilineage differentiation and maturation of lung and airway cells from human pluripotent stem cell-derived lung progenitors in 3D. Nat Protoc 16 1802-1829 PMID: 33649566

Jianping et al (2021) A microfluidics-based stem cell model of early post-implantation human development. Nat Protoc 16 309-326 PMID: 33311712

Robert et al (2021) Generation of heart-forming organoids from human pluripotent stem cells. Nat Protoc 16 5652-5672 PMID: 34759383

Ruili et al (2021) Human Pluripotent Stem Cells for High-Throughput Drug Screening and Characterization of Small Molecules. Methods Mol Biol 2454 811-827 PMID: 34128205

Rostovskaya et al (2019) Capacitation of human naïve pluripotent stem cells for multi-lineage differentiation. Development 146 PMID: 30944104

Kennedy et al (2016) Sp5 and Sp8 recruit β-catenin and Tcf1-Lef1 to select enhancers to activate Wnt target gene transcription. Proc Natl Acad Sci U S A 113 3545 PMID: 26969725

Michael A et al (2020) Differentiation of PTH-Expressing Cells From Human Pluripotent Stem Cells. Endocrinology 161 PMID: 32810225

Carissa et al (2020) Potently Cytotoxic Natural Killer Cells Initially Emerge from Erythro-Myeloid Progenitors during Mammalian Development. Dev Cell 53 229-239.e7 PMID: 32197069

Feng et al (2020) Enrichment differentiation of human induced pluripotent stem cells into sinoatrial node-like cells by combined modulation of BMP, FGF, and RA signaling pathways. Stem Cell Res Ther 11 284 PMID: 32678003

Jizhong et al (2020) Differentiation of Cardiomyocytes from Human Pluripotent Stem Cells in Fully Chemically Defined Conditions. STAR Protoc 1 PMID: 32734277

Elena et al (2019) Coculture with noncardiac cells promoted maturation of human stem cell-derived cardiomyocyte microtissues. J Cell Biochem 120 16681-16691 PMID: 31090105

Nasser et al (2019) TBX18 transcription factor overexpression in human-induced pluripotent stem cells increases their differentiation into pacemaker-like cells. J Cell Physiol 234 1534-1546 PMID: 30078203

Puspa R et al (2019) End-to-End Platform for Human Pluripotent Stem Cell Manufacturing. Int J Mol Sci 21 PMID: 31877727

Kenneth R et al (2019) Population and Single-Cell Analysis of Human Cardiogenesis Reveals Unique LGR5 Ventricular Progenitors in Embryonic Outflow Tract. Dev Cell 48 475-490.e7 PMID: 30713072

Peidong et al (2019) Canonical Wnt5b Signaling Directs Outlying Nkx2.5+ Mesoderm into Pacemaker Cardiomyocytes. Dev Cell 50 729-743.e5 PMID: 31402282

Magro-Lopez et al (2018) Effects of lung and airway epithelial maturation cocktail on the structure of lung bud organoids. Stem Cell Res.Ther. 9 186 PMID: 29996941

Kling et al (2018) Temporal Regulation of Natural Killer T Cell Interferon Gamma Responses by β-Catenin-Dependent and -Independent Wnt Signaling. Front Immunol 9 483 PMID: 29616022

Xu et al (2016) Wnt/β-catenin signaling promotes self-renewal and inhibits the primed state transition in naïve human embryonic stem cells. Proc Natl Acad Sci U S A 113 E6382 PMID: 27698112

Faisy et al (2014) Wnt/β-catenin signaling modulates human airway sensitization induced by β2-adrenoceptor stimulation. PLoS One 9 e111350 PMID: 25360795

Kelly A et al (2020) In vitro Differentiation of Human iPSC-derived Cardiovascular Progenitor Cells (iPSC-CVPCs). Bio Protoc 10 e3755 PMID: 33659414

Ting et al (2020) Protocol for the Generation of Human Pluripotent Reporter Cell Lines Using CRISPR/Cas9. STAR Protoc 1 PMID: 33073252

Hui et al (2020) Protocol to Generate and Characterize Potent and Selective WNT Mimetic Molecules. STAR Protoc 1 100043 PMID: 33111090

Gareth et al (2020) A method for differentiating human induced pluripotent stem cells toward functional cardiomyocytes in 96-well microplates. Sci Rep 10 18498 PMID: 33116175

Ludovic et al (2020) Naive Pluripotent Stem Cells Exhibit Phenotypic Variability that Is Driven by Genetic Variation. Cell Stem Cell 27 470-481.e6 PMID: 32795399

Jae Ho et al (2020) Cardiotoxicity induced by the combination therapy of chloroquine and azithromycin in human embryonic stem cell-derived cardiomyocytes. BMB Rep 53 545-550 PMID: 32958120

Stefania et al (2020) CRISPR/Cas9-mediated introduction of the sodium/iodide symporter gene enables noninvasive in?vivo tracking of induced pluripotent stem cell-derived cardiomyocytes. Stem Cells Transl Med 9 1203-1217 PMID: 32700830

Jason et al (2020) Generation and trapping of a mesoderm biased state of human pluripotency. Nat Commun 11 4989 PMID: 33020476

Ingo et al (2020) Generation of an INSULIN-H2B-Cherry reporter human iPSC line. Stem Cell Res 45 101797 PMID: 32361463

Timothy J et al (2020) Human Induced Pluripotent Stem Cell-Derived Non-Cardiomyocytes Modulate Cardiac Electrophysiological Maturation Through Connexin 43-Mediated Cell-Cell Interactions. Stem Cells Dev 29 75-89 PMID: 31744402

Capowski et al (2016) Regulation of WNT Signaling by VSX2 During Optic Vesicle Patterning in Human Induced Pluripotent Stem Cells. Stem Cells 34 2625 PMID: 27301076

Perales-Clemente et al (2016) Natural underlying mtDNA heteroplasmy as a potential source of intra-person hiPSC variability. EMBO J 35 1979 PMID: 27436875

Datta et al (2016) Label-free imaging of metabolism and oxidative stress in human induced pluripotent stem cell-derived cardiomyocytes. Biomed Opt Express 7 1690 PMID: 27231614

Lin et al (2016) HP Promotes Cardiac Differentiation of Human Pluripotent Stem Cells in Chemically Defined Albumin-Free Medium, Enabling Consistent Manufacture of Cardiomyocytes. Stem Cells Transl Med PMID: 27591141

Kempf et al (2014) Controlling expansion and cardiomyogenic differentiation of human pluripotent stem cells in scalable suspension culture. Stem Cell Reports 3 1132 PMID: 25454631

Huang et al (2014) Efficient generation of lung and airway epithelial cells from human pluripotent stem cells. Nat Biotechnol 32 84 PMID: 24291815

Arpan et al (2023) Reduced Cell-ECM Interactions in the EpiSC Colony Center Cause Heterogeneous Differentiation. Cells 12 PMID: 36672261

Nadine et al (2023) A distal lung organoid model to study interstitial lung disease, viral infection and human lung development. Nat Protoc PMID: 37165073

Jing et al (2023) Pluripotent stem cell-derived committed cardiac progenitors remuscularize damaged ischemic hearts and improve their function in pigs. NPJ Regen Med 8 26 PMID: 37236990

Aditya et al (2023) Systematic discovery of transcription factors that improve hPSC-derived cardiomyocyte maturation via temporal analysis of bioengineered cardiac tissues. APL Bioeng 7 026109 PMID: 37252678

Shekhar et al (2018) ETV1 activates a rapid conduction transcriptional program in rodent and human cardiomyocytes. Sci Rep 8 9944 PMID: 29967479

Lin et al (2018) Efficient differentiation of cardiomyocytes and generation of calcium-sensor reporter lines from nonhuman primate iPSCs. Sci Rep 8 5907 PMID: 29651156

Huang et al (2015) The in vitro generation of lung and airway progenitor cells from human pluripotent stem cells. Sci Rep 10 413 PMID: 25654758

Lee et al (2015) A systems-biological study on the identification of safe and effective molecular targets for the reduction of ultraviolet B-induced skin pigmentation. Nat Commun 5 10305 PMID: 25980672

Freedman et al (2015) Modelling kidney disease with CRISPR-mutant kidney organoids derived from human pluripotent epiblast spheroids. Nat Cell Biol 6 8715 PMID: 26493500

Ditadi et al (2015) Human definitive haemogenic endothelium and arterial vascular endothelium represent distinct lineages. Stem Cell Res 17 580 PMID: 25915127


Do you know of a great paper that uses IWP 2 from Tocris? Please let us know.

Reviews for IWP 2

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IWP2 for small molecule pathway.
By Anonymous on 07/23/2021
Assay Type: In Vitro
Species: Human

IWP2 was used for cardiomyocyte differentiation of pluripotent stem cells. IWP2 was used at a concentration of 5 uM on day 3 of the differentiation schedule. The image shows differentiated cardiomyocytes.

review image

IWP2 for cardiac differentiation..
By Anonymous on 02/01/2018
Assay Type: In Vitro
Species: Human
Cell Line/Tissue: human foreskin fibroblasts-derived-IPS

I use it as a blocking molecule of the WNT pathway for cardiac differentiation in foreskin fibroblast-derive IPS cells. I obtained succesfully cardiomyocytes in a 5uM concentration.

review image