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IWP 2

Catalog #: 3533
102 Citations 1 Review Datasheet
Catalog # Availability Size / Price Qty
3533/10
3533/50
IWP 2 | CAS No. 686770-61-6 | PORCN Inhibitors
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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%

Product Details
Citations (102)
Reviews (1)
Biological Activity Scientific Data Technical Data Background Product Datasheets Calculators

Biological Activity

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.

Scientific Data

Cell Culture iPSC-derived heart organoids differentiated with IWP 2 and CHIR 99021 View Larger

iPSC-derived Human Heart-forming Organoids Human iPSCs were embedded in Cultrex™ UltiMatrix RGF Basement Membrane Extract (R&D Systems, Catalog # BME001-05) and differentiated with CHIR 99021 (Tocris Bioscience, Catalog # TB4423-GMP) and IWP 2 (Tocris Bioscience, Catalog # 3533) into heart-forming organoids based on a protocol from Drakhlis, L. et al. (2021) Nat. Biotechnol. 39:737. Successful differentiation was demonstrated by staining the cells with A) a Rabbit Anti-Human Cardiac Troponin T Antigen Affinity-purified Polyclonal Antibody (green; Novus Biologicals, Catalog # NBP3-13391) to detect cardiomyocytes and a Goat Anti-Human CD31/PECAM-1 Antigen Affinity-purified Polyclonal Antibody (red; R&D Systems, Catalog # AF3628) to detect endothelial cells. The cells were counterstained with DAPI (blue; Tocris Bioscience, Catalog # 5748). As formation of early embryonic heart anlagen is associated with nascent foregut endoderm development, cells were also stained with B) a Goat Anti-Human SOX2 Antigen Affinity-purified Polyclonal Antibody (red; R&D Systems, Catalog # AF2018) and a Mouse Anti-Human HNF-4 alpha/NR2A1 Monoclonal Antibody (green; R&D Systems, Catalog # PP-K9218-00) to detect anterior and posterior foregut endoderm cells, respectively. The cells were counterstained with DAPI (blue; Tocris Bioscience, Catalog # 5748).

Technical Data

M.Wt:
466.6
Formula:
C22H18N4O2S3
Solubility:
Soluble to 5 mM in DMSO with gentle warming
Purity:
≥98%
Storage:
Store at +4°C
CAS No:
686770-61-6

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.

Background References

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  2. 3D Modeling of Esophageal Development using Human PSC-Derived Basal Progenitors Reveals a Critical Role for Notch Signaling
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    Cell Stem Cell, 2018;0(0):.
  3. Robust derivation of epicardium and its differentiated smooth muscle cell progeny from human pluripotent stem cells.
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    Development, 2015;142(8):1528-41.
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  5. Differential Sarcomere and Electrophysiological Maturation of Human iPSC-Derived Cardiac Myocytes in Monolayer vs. Aggregation-Based Differentiation Protocols
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  7. Activin-A and Bmp4 levels modulate cell type specification during CHIR-induced cardiomyogenesis.
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    Hojo, Hironori, Ohba, Shinsuke, Taniguchi, Kiyomi, Shirai, Masataka, Yano, Fumiko, Saito, Taku, Ikeda, Toshiyuk, Nakajima, Keiji, Komiyama, Yuske, Nakagata, Naomi, Suzuki, Kentaro, Mishina, Yuji, Yamada, Masahisa, Konno, Tomohiro, Takato, Tsuyoshi, Kawaguchi, Hiroshi, Kambara, Hideki, Chung, Ung-il
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Product Datasheets

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Citations for IWP 2

The citations listed below are publications that use Tocris products. Selected citations for IWP 2 include:

102 Citations: Showing 1 - 10

  1. Pluripotent stem cell-derived committed cardiac progenitors remuscularize damaged ischemic hearts and improve their function in pigs.
    Authors: Jing Et al.
    NPJ Regen Med  2023;8:26
  2. Systematic discovery of transcription factors that improve hPSC-derived cardiomyocyte maturation via temporal analysis of bioengineered cardiac tissues.
    Authors: Aditya Et al.
    APL Bioeng  2023;7:026109
  3. Reduced Cell-ECM Interactions in the EpiSC Colony Center Cause Heterogeneous Differentiation.
    Authors: Arpan Et al.
    Cells  2023;12
  4. A distal lung organoid model to study interstitial lung disease, viral infection and human lung development.
    Authors: Nadine Et al.
    Nat Protoc  2023;
  5. FUCCI-Based Live Imaging Platform Reveals Cell Cycle Dynamics and Identifies Pro-proliferative Compounds in Human iPSC-Derived Cardiomyocytes.
    Authors: Olaf Et al.
    Front Cardiovasc Med  2022;9:840147
  6. Differentiating Human Pluripotent Stem Cells to Cardiomyocytes Using Purified Extracellular Matrix Proteins.
    Authors: Teisha J Et al.
    Bioengineering (Basel)  2022;9
  7. Retrograde movements determine effective stem cell numbers in the intestine.
    Authors: David J Et al.
    Nature  2022;607:548-554
  8. Tomatidine-stimulated maturation of human embryonic stem cell-derived cardiomyocytes for modeling mitochondrial dysfunction.
    Authors: Jae Boum Et al.
    Exp Mol Med  2022;54:493-502
  9. Autologous humanized mouse models of iPSC-derived tumors enable characterization and modulation of cancer-immune cell interactions.
    Authors: Benjamin Et al.
    Cell Rep Methods  2022;2:100153
  10. Bizonal cardiac engineered tissues with differential maturation features in a mid-throughput multimodal bioreactor.
    Authors: Gregory Et al.
    iScience  2022;25:104297
  11. A dual SHOX2:GFP; MYH6:mCherry knockin hESC reporter line for derivation of human SAN-like cells.
    Authors: Xiaolu Et al.
    iScience  2022;25:104153
  12. In Vitro Generation of Heart Field Specific Cardiomyocytes.
    Authors: Reza Et al.
    Methods Mol Biol  2022;2429:257-267
  13. Effects of Hypocalcemic Vitamin D Analogs in the Expression of DNA Damage Induced in Minilungs from hESCs: Implications for Lung Fibrosis.
    Authors: Alberto Et al.
    Int J Mol Sci  2022;23
  14. The Human Induced Pluripotent Stem Cell Test as an Alternative Method for Embryotoxicity Testing.
    Authors: Leo Et al.
    Int J Mol Sci  2022;23
  15. A Bionic Testbed for Cardiac Ablation Tools.
    Authors: Brenda M Et al.
    Int J Mol Sci  2022;23
  16. Autophagy modulates cell fate decisions during lineage commitment.
    Authors: Elisabeth Et al.
    Autophagy  2022;18:1915-1931
  17. The Biphasic Effect of Retinoic Acid Signaling Pathway on the Biased Differentiation of Atrial-like and Sinoatrial Node-like Cells from hiPSC.
    Authors: Feng Et al.
    Int J Stem Cells  2022;15:247-257
  18. iPSCs derived from esophageal atresia patients reveal SOX2 dysregulation at the anterior foregut stage.
    Authors: Martin A Et al.
    Dis Model Mech  2022;15
  19. Isolation and characterization of human embryonic stem cell-derived heart field-specific cardiomyocytes unravels new insights into their transcriptional and electrophysiological profiles.
    Authors: Peng Et al.
    Cardiovasc Res  2022;118:828-843
  20. Efficient differentiation of human primordial germ cells through geometric control reveals a key role for Nodal signaling.
    Authors: Ran Et al.
    Elife  2022;11
  21. An iPS-derived in vitro model of human atrial conduction.
    Authors: Kentaro Et al.
    Physiol Rep  2022;10:e15407
  22. Distinct properties of Ca2+ efflux from brain, heart and liver mitochondria: The effects of Na+, Li+ and the mitochondrial Na+/Ca2+ exchange inhibitor CGP37157.
    Authors: Stefan Et al.
    Cell Calcium  2021;96:102382
  23. Myogenin suppresses apoptosis induced by angiotensin II in human induced pluripotent stem cell-derived cardiomyocytes.
    Authors: Bin Et al.
    Biochem Biophys Res Commun  2021;552:84-90
  24. Mapping the temporal and spatial dynamics of the human endometrium in vivo and in vitro.
    Authors: Cecilia Et al.
    Nat Genet  2021;53:1698-1711
  25. A simple protocol to produce mature human-induced pluripotent stem cell-derived cardiomyocytes.
    Authors: Yingqiong Et al.
    STAR Protoc  2021;2:100912
  26. Assessing the Wnt-reactivity of cytonemes of mouse embryonic stem cells using a bioengineering approach.
    Authors: Shukry J Et al.
    STAR Protoc  2021;2:100813
  27. Isolation of human ESC-derived cardiac derivatives and embryonic heart cells for population and single-cell RNA-seq analysis.
    Authors: Kenneth R Et al.
    STAR Protoc  2021;2:100339
  28. Principles of signaling pathway modulation for enhancing human naive pluripotency induction.
    Authors: Varda Et al.
    Cell Stem Cell  2021;28:1549-1565.e12
  29. Commitment and oncogene-induced plasticity of human stem cell-derived pancreatic acinar and ductal organoids.
    Authors: Ling Et al.
    Cell Stem Cell  2021;28:1090-1104.e6
  30. Human Pluripotent Stem Cells for High-Throughput Drug Screening and Characterization of Small Molecules.
    Authors: Ruili Et al.
    Methods Mol Biol  2021;2454:811-827
  31. Identification of New Transcription Factors that Can Promote Pluripotent Reprogramming.
    Authors: Duanqing Et al.
    Stem Cell Rev Rep  2021;17:2223-2234
  32. Generation of heart-forming organoids from human pluripotent stem cells.
    Authors: Robert Et al.
    Nat Protoc  2021;16:5652-5672
  33. A microfluidics-based stem cell model of early post-implantation human development.
    Authors: Jianping Et al.
    Nat Protoc  2021;16:309-326
  34. The in vitro multilineage differentiation and maturation of lung and airway cells from human pluripotent stem cell-derived lung progenitors in 3D.
    Authors: Matteo Et al.
    Nat Protoc  2021;16:1802-1829
  35. p53 Promotes Differentiation of Cardiomyocytes from hiPSC through Wnt Signaling-Mediated Mesendodermal Differentiation.
    Authors: Feng Et al.
    Int J Stem Cells  2021;14:410-422
  36. Gender-specific characteristics of hypertrophic response in cardiomyocytes derived from human embryonic stem cells.
    Authors: Sara Et al.
    J Cardiovasc Thorac Res  2021;13:146-155
  37. QKI is a critical pre-mRNA alternative splicing regulator of cardiac myofibrillogenesis and contractile function.
    Authors: Ying Et al.
    Nat Commun  2021;12:89
  38. Responsiveness to perturbations is a hallmark of transcription factors that maintain cell identity in vitro.
    Authors: Arun Et al.
    Cell Syst  2021;12:885-899.e8
  39. CRISPR/Cas9-mediated introduction of the sodium/iodide symporter gene enables noninvasive in?vivo tracking of induced pluripotent stem cell-derived cardiomyocytes.
    Authors: Stefania Et al.
    Stem Cells Transl Med  2020;9:1203-1217
  40. Cardiotoxicity induced by the combination therapy of chloroquine and azithromycin in human embryonic stem cell-derived cardiomyocytes.
    Authors: Jae Ho Et al.
    BMB Rep  2020;53:545-550
  41. Potently Cytotoxic Natural Killer Cells Initially Emerge from Erythro-Myeloid Progenitors during Mammalian Development.
    Authors: Carissa Et al.
    Dev Cell  2020;53:229-239.e7
  42. Generation of an INSULIN-H2B-Cherry reporter human iPSC line.
    Authors: Ingo Et al.
    Stem Cell Res  2020;45:101797
  43. Human Induced Pluripotent Stem Cell-Derived Non-Cardiomyocytes Modulate Cardiac Electrophysiological Maturation Through Connexin 43-Mediated Cell-Cell Interactions.
    Authors: Timothy J Et al.
    Stem Cells Dev  2020;29:75-89
  44. Naive Pluripotent Stem Cells Exhibit Phenotypic Variability that Is Driven by Genetic Variation.
    Authors: Ludovic Et al.
    Cell Stem Cell  2020;27:470-481.e6
  45. A Human Pluripotent Stem Cell-based Platform to Study SARS-CoV-2 Tropism and Model Virus Infection in Human Cells and Organoids
    Authors: Yang Et al.
    Cell Stem Cell  2020;27:125
  46. Protocol to Generate and Characterize Potent and Selective WNT Mimetic Molecules.
    Authors: Hui Et al.
    STAR Protoc  2020;1:100043
  47. Differentiation of PTH-Expressing Cells From Human Pluripotent Stem Cells.
    Authors: Michael A Et al.
    Endocrinology  2020;161
  48. Generation and trapping of a mesoderm biased state of human pluripotency.
    Authors: Jason Et al.
    Nat Commun  2020;11:4989
  49. Enrichment differentiation of human induced pluripotent stem cells into sinoatrial node-like cells by combined modulation of BMP, FGF, and RA signaling pathways.
    Authors: Feng Et al.
    Stem Cell Res Ther  2020;11:284
  50. In vitro Differentiation of Human iPSC-derived Cardiovascular Progenitor Cells (iPSC-CVPCs).
    Authors: Kelly A Et al.
    Bio Protoc  2020;10:e3755
  51. A method for differentiating human induced pluripotent stem cells toward functional cardiomyocytes in 96-well microplates.
    Authors: Gareth Et al.
    Sci Rep  2020;10:18498
  52. Differentiation of Cardiomyocytes from Human Pluripotent Stem Cells in Fully Chemically Defined Conditions.
    Authors: Jizhong Et al.
    STAR Protoc  2020;1
  53. Protocol for the Generation of Human Pluripotent Reporter Cell Lines Using CRISPR/Cas9.
    Authors: Ting Et al.
    STAR Protoc  2020;1
  54. Canonical Wnt5b Signaling Directs Outlying Nkx2.5+ Mesoderm into Pacemaker Cardiomyocytes.
    Authors: Peidong Et al.
    Dev Cell  2019;50:729-743.e5
  55. Population and Single-Cell Analysis of Human Cardiogenesis Reveals Unique LGR5 Ventricular Progenitors in Embryonic Outflow Tract.
    Authors: Kenneth R Et al.
    Dev Cell  2019;48:475-490.e7
  56. Long-term functional maintenance of primary human hepatocytes in vitro.
    Authors: Xiang Et al.
    Science  2019;364:399
  57. In Vivo Generation of Post-infarct Human Cardiac Muscle by Laminin-Promoted Cardiovascular Progenitors.
    Authors: Yap Et al.
    Cell Rep  2019;26:3231
  58. User-Friendly and Parallelized Generation of Human Induced Pluripotent Stem Cell-Derived Microtissues in a Centrifugal Heart-on-a-Chip.
    Authors: Schneider Et al.
    Tissue Eng Part A  2019;25:786
  59. Point mutations in the PDX1 transactivation domain impair human β-cell development and function.
    Authors: Wang Et al.
    Mol Metab  2019;24:80
  60. TBX18 transcription factor overexpression in human-induced pluripotent stem cells increases their differentiation into pacemaker-like cells.
    Authors: Nasser Et al.
    J Cell Physiol  2019;234:1534-1546
  61. End-to-End Platform for Human Pluripotent Stem Cell Manufacturing.
    Authors: Puspa R Et al.
    Int J Mol Sci  2019;21
  62. Establishment of A Protocol for In Vitro Culture of Cardiogenic Mesodermal Cells Derived from Human Embryonic Stem Cells.
    Authors: Vahdat Et al.
    Cell J  2019;20:496
  63. TMEM88 Inhibits Wnt Signaling by Promoting Wnt Signalosome Localization to Multivesicular Bodies.
    Authors: Lee and Evans
    iScience  2019;19:267
  64. Capacitation of human na�ve pluripotent stem cells for multi-lineage differentiation.
    Authors: Rostovskaya Et al.
    Development  2019;146
  65. Coculture with noncardiac cells promoted maturation of human stem cell-derived cardiomyocyte microtissues.
    Authors: Elena Et al.
    J Cell Biochem  2019;120:16681-16691
  66. 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.
    Authors: Nakanishi Et al.
    Front Physiol  2019;10:818
  67. Temporal Regulation of Natural Killer T Cell Interferon Gamma Responses by β-Catenin-Dependent and -Independent Wnt Signaling.
    Authors: Kling Et al.
    Front Immunol  2018;9:483
  68. Effects of lung and airway epithelial maturation cocktail on the structure of lung bud organoids.
    Authors: Magro-Lopez Et al.
    Stem Cell Res.Ther.  2018;9:186
  69. ETV1 activates a rapid conduction transcriptional program in rodent and human cardiomyocytes.
    Authors: Shekhar Et al.
    Sci Rep  2018;8:9944
  70. Efficient differentiation of cardiomyocytes and generation of calcium-sensor reporter lines from nonhuman primate iPSCs.
    Authors: Lin Et al.
    Sci Rep  2018;8:5907
  71. 3D Modeling of Esophageal Development using Human PSC-Derived Basal Progenitors Reveals a Critical Role for Notch Signaling.
    Authors: Ying Et al.
    Cell Stem Cell  2018;23:516-529.e5
  72. Efficient transdifferentiation of human dermal fibroblasts into skeletal muscle.
    Authors: George A Et al.
    J Tissue Eng Regen Med  2018;12:e918-e936
  73. 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.
    Authors: Lin Et al.
    Front Endocrinol (Lausanne)  2017;8:253
  74. A genome-wide screen identifies YAP/WBP2 interplay conferring growth advantage on human epidermal stem cells.
    Authors: Walko Et al.
    Nat Commun  2017;8:14744
  75. Use of Human Pluripotent Stem Cell Derived-Cardiomyocytes to Study Drug-Induced Cardiotoxicity.
    Authors: Liam R Et al.
    Curr Protoc Toxicol  2017;73:22.5.1-22.5.22
  76. Heparin Promotes Cardiac Differentiation of Human Pluripotent Stem Cells in Chemically Defined Albumin-Free Medium, Enabling Consistent Manufacture of Cardiomyocytes.
    Authors: Wen Et al.
    Stem Cells Transl Med  2017;6:527-538
  77. Human Pluripotent Stem Cell-Derived Atrial and Ventricular Cardiomyocytes Develop from Distinct Mesoderm Populations.
    Authors: Lee Et al.
    Cell Stem Cell  2017;21:179
  78. Degree of tissue differentiation dictates susceptibility to BRAF-driven colorectal cancer.
    Authors: Tong
    Cell Rep  2017;21(13):3833
  79. Genome Editing in hPSCs Reveals GATA6 Haploinsufficiency and a Genetic Interaction with GATA4 in Human Pancreatic Development.
    Authors: Shi Et al.
    Cell Stem Cell  2017;20:675
  80. WNT ligands contribute to the immune response during septic shock and amplify endotoxemia-driven inflammation in mice.
    Authors: Heinrich Et al.
    Blood Adv  2017;1:1274-1286
  81. Label-free imaging of metabolism and oxidative stress in human induced pluripotent stem cell-derived cardiomyocytes.
    Authors: Datta Et al.
    Biomed Opt Express  2016;7:1690
  82. Natural underlying mtDNA heteroplasmy as a potential source of intra-person hiPSC variability.
    Authors: Perales-Clemente Et al.
    EMBO J  2016;35:1979
  83. Regulation of WNT Signaling by VSX2 During Optic Vesicle Patterning in Human Induced Pluripotent Stem Cells.
    Authors: Capowski Et al.
    Stem Cells  2016;34:2625
  84. Wnt/β-catenin signaling promotes self-renewal and inhibits the primed state transition in na�ve human embryonic stem cells.
    Authors: Xu Et al.
    Proc Natl Acad Sci U S A  2016;113:E6382
  85. Sp5 and Sp8 recruit β-catenin and Tcf1-Lef1 to select enhancers to activate Wnt target gene transcription.
    Authors: Kennedy Et al.
    Proc Natl Acad Sci U S A  2016;113:3545
  86. HP Promotes Cardiac Differentiation of Human Pluripotent Stem Cells in Chemically Defined Albumin-Free Medium, Enabling Consistent Manufacture of Cardiomyocytes.
    Authors: Lin Et al.
    Stem Cells Transl Med  2016;
  87. Modelling kidney disease with CRISPR-mutant kidney organoids derived from human pluripotent epiblast spheroids.
    Authors: Freedman Et al.
    Nat Cell Biol  2015;6:8715
  88. Machine learning plus optical flow: a simple and sensitive method to detect cardioactive drugs.
    Authors: Lee Et al.
    Sci Rep  2015;5:11817
  89. A systems-biological study on the identification of safe and effective molecular targets for the reduction of ultraviolet B-induced skin pigmentation.
    Authors: Lee Et al.
    Nat Commun  2015;5:10305
  90. A Universal and Robust Integrated Platform for the Scalable Production of Human Cardiomyocytes From Pluripotent Stem Cells.
    Authors: Richard P Et al.
    Stem Cells Transl Med  2015;4:1482-94
  91. Generation of an expandable intermediate mesoderm restricted progenitor cell line from human pluripotent stem cells.
    Authors: Kumar Et al.
    Elife  2015;4
  92. Automated Video-Based Analysis of Contractility and Calcium Flux in Human-Induced Pluripotent Stem Cell-Derived Cardiomyocytes Cultured over Different Spatial Scales.
    Authors: Huebsch Et al.
    Tissue Eng Part C Methods  2015;21:467
  93. Human definitive haemogenic endothelium and arterial vascular endothelium represent distinct lineages.
    Authors: Ditadi Et al.
    Stem Cell Res  2015;17:580
  94. Supervised Machine Learning for Classification of the Electrophysiological Effects of Chronotropic Drugs on Human Induced Pluripotent Stem Cell-Derived Cardiomyocytes.
    Authors: Heylman Et al.
    PLoS One  2015;10:e0144572
  95. Act.-A and Bmp4 levels modulate cell type specification during CHIR-induced cardiomyogenesis.
    Authors: Kim Et al.
    PLoS One  2015;10:e0118670
  96. The in vitro generation of lung and airway progenitor cells from human pluripotent stem cells.
    Authors: Huang Et al.
    Sci Rep  2015;10:413
  97. Cardiac differentiation of human pluripotent stem cells in scalable suspension culture.
    Authors: Ulrich Et al.
    Nat Protoc  2015;10:1345-61
  98. Wnt/β-catenin signaling modulates human airway sensitization induced by β2-adrenoceptor stimulation.
    Authors: Faisy Et al.
    PLoS One  2014;9:e111350
  99. Controlling expansion and cardiomyogenic differentiation of human pluripotent stem cells in scalable suspension culture.
    Authors: Kempf Et al.
    Stem Cell Reports  2014;3:1132
  100. Efficient generation of lung and airway epithelial cells from human pluripotent stem cells.
    Authors: Huang Et al.
    Nat Biotechnol  2014;32:84
  101. SIRPA, VCAM1 and CD34 identify discrete lineages during early human cardiovascular development.
    Authors: Skelton Et al.
    Nat Genet  2014;13:172
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Wnt pathway inhibitor that works really well
By Anonymous on 12/09/2019
Species: Human

I used it as a Wnt pathway inhibitor in Hepatocellular Carcinoma Cells. I used the concentration 5uM and it works really well.

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