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| | LAVENDUSTIN A Basic information |
| | LAVENDUSTIN A Chemical Properties |
| Melting point | 205-215 °C | | Boiling point | 741.7±60.0 °C(Predicted) | | density | 1.495±0.06 g/cm3(Predicted) | | RTECS | DG8578950 | | storage temp. | −20°C | | solubility | DMSO: soluble | | form | crystalline | | pka | 2.31±0.10(Predicted) | | color | Yellow to brown | | Sensitive | Air Sensitive | | Stability: | Moisture Sensitive: Hygroscopic | | InChI | 1S/C21H19NO6/c23-16-6-8-19(25)14(9-16)12-22(11-13-3-1-2-4-18(13)24)15-5-7-20(26)17(10-15)21(27)28/h1-10,23-26H,11-12H2,(H,27,28) | | InChIKey | ULTTYPMRMMDONC-UHFFFAOYSA-N | | SMILES | N(Cc3c(ccc(c3)O)O)(Cc2c(cccc2)O)c1cc(c(cc1)O)C(=O)O | | CAS DataBase Reference | 125697-92-9(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 37/39-26 | | WGK Germany | 3 | | HS Code | 29225000 | | Storage Class | 11 - Combustible Solids |
| | LAVENDUSTIN A Usage And Synthesis |
| Description | Lavendustin A is a selective inhibitor of epidermal growth factor (EGF) receptor-associated tyrosine kinase (IC50 = 11 nM) that was first isolated from a Streptomyces culture filtrate. It does not inhibit protein kinase A (PKA), PKC, or PI3K (IC50s > 100 μM). It has been used to differentiate rat mesenchymal stem cells, to inhibit NMDA-stimulated cGMP production, and to inhibit VEGF-induced angiogenesis. | | Chemical Properties | Off-White Solid | | Uses | A potent tyrosine kinase inhibitor. Inhibition is competitive with ATP and is noncompetitive with the peptide. | | Definition | ChEBI: 5-[(2,5-dihydroxyphenyl)methyl-[(2-hydroxyphenyl)methyl]amino]-2-hydroxybenzoic acid is an aromatic amine. | | Biological Activity | Potent, cell-permeable inhibitor of epidermal growth factor receptor (EGFR) tyrosine kinase (IC 50 = 11 nM). Inhibits p60 c-src with an IC 50 of 500 nM and is selective over PKA, PKC and PI 3-kinase (IC 50 > 100 μ M). | | target | EGFR | PKC | PI3K | Calcium Channel | | References | [1] TOSHIHIKO ONODA. Isolation of a Novel Tyrosine Kinase Inhibitor, Lavendustin A, from Streptomyces griseolavendus[J]. Journal of Natural Products , 1989, 52 6: 1252-1257. DOI: 10.1021/np50066a009
[2] C Y HSU. Kinetic analysis of the inhibition of the epidermal growth factor receptor tyrosine kinase by Lavendustin-A and its analogue.[J]. The Journal of Biological Chemistry, 1991, 266 31: 21105-21112.
[3] KI-CHUL HWANG. Chemicals that modulate stem cell differentiation.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2008: 7467-7471. DOI: 10.1073/pnas.0802825105
[4] THOMAS J. O’’DELL Seth G N G Eric R Kandel. Long-term potentiation in the hippocampus is blocked by tyrosine kinase inhibitors[J]. Nature, 1991, 353 6344: 558-560. DOI: 10.1038/353558a0
[5] T P FAN R B R Jaggar. Controlling the vasculature: angiogenesis, anti-angiogenesis and vascular targeting of gene therapy.[J]. Trends in pharmacological sciences, 1995, 16 2: 57-66. DOI: 10.1016/s0165-6147(00)88979-8 |
| | LAVENDUSTIN A Preparation Products And Raw materials |
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