| Identification | More | [Name]
LAVENDUSTIN A | [CAS]
125697-92-9 | [Synonyms]
RG14355
NSC 678027
LAVENDUSTIN A
Lavendustin A,98%
RG-14355;NSC 678027
LAVENDUSTIN A USP/EP/BP
Lavendustin A - CAS 125697-92-9 - Calbiochem
5-AMINO-[(N-2,5-DIHYDROXYBENZYL)-N'-2-HYDROXYBENZYL]SALICYLIC ACID
5-[(2,5-Dihydroxybenzyl)(2-hydroxybenzyl)amino]-2-hydroxybenzoic acid
5-[[(2,5-DIHYDROXYPHENYL)METHYL][(2-HYDROXYPHENYL)METHYL]AMINO]-2-HYDROXYBENZOIC ACID
Benzoic acid,5-[[(2,5-dihydroxyphenyl)methyl][(2-hydroxyphenyl)methyl]amino]-2-hydroxy- | [Molecular Formula]
C21H19NO6 | [MDL Number]
MFCD00153822 | [Molecular Weight]
381.38 | [MOL File]
125697-92-9.mol |
| Chemical Properties | Back Directory | [Appearance]
Off-White Solid | [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 | [Usage]
A potent tyrosine kinase inhibitor. Inhibition is competitive with ATP and is noncompetitive with the peptide | [Stability:]
Moisture Sensitive: Hygroscopic | [CAS DataBase Reference]
125697-92-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [HS Code ]
29225000 |
| Hazard Information | Back Directory | [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.1,2 It does not inhibit protein kinase A (PKA), PKC, or PI3K (IC50s > 100 μM).2 It has been used to differentiate rat mesenchymal stem cells, to inhibit NMDA-stimulated cGMP production, and to inhibit VEGF-induced angiogenesis.3,4,5 | [Chemical Properties]
Off-White Solid | [Uses]
A potent tyrosine kinase inhibitor. Inhibition is competitive with ATP and is noncompetitive with the peptide | [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 | [storage]
Desiccate at -20°C | [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 |
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