S-426-S (Lepetit)
ECHINOMYCIN · SK-302B · nsc526417 · NSC 13502 · echinomycina · QUINOMYCIN A · Echinomycin >97% · Antibiotic A 654I
Identifikatoren & physikalische Daten
| CAS No. | 512-64-1 |
|---|---|
| Summenformel | C51H64N12O12S2 |
| Durchschnittliche Molmasse | 1.101,3 g/mol |
| Monoisotopische Masse | 1.100,42080787 g/mol |
| SMILES | CSC1SC[C@H]2C(=O)N(C)[C@@H](C(C)C)C(=O)OC[C@@H](NC(=O)c3cnc4ccccc4n3)C(=O)N[C@H](C)C(=O)N(C)[C@@H]1C(=O)N(C)[C@@H](C(C)C)C(=O)OC[C@@H](NC(=O)c1cnc3ccccc3n1)C(=O)N[C@H](C)C(=O)N2C |
| InChIKey | AUJXLBOHYWTPFV-CVLRASHMSA-N |
| PubChem CID | 458034 |
Chemische & physikalische Eigenschaften
| XLogP | 2,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 352 |
| H-Brücken-Donoren | 4 |
| H-Brücken-Akzeptoren | 18 |
| Frei drehbare Bindungen | 7 |
| Schwere Atome | 77 |
| Formalladung | 0 |
| Komplexität | 2.200 |
| Schmelzpunkt | 217-218℃ |
| Siedepunkt | 1427.2±65.0 °C(Predicted) |
| Dichte | 1.0964 (rough estimate) |
| Brechungsindex | 1.6700 (estimate) |
| Lagerbedingungen | -20°C |
| Löslichkeit | Soluble in DMSO (up to 5 mg/ml) |
| pKa (Säurekonstante) | 9.38±0.70(Predicted) |
| Aggregatzustand | White solid |
| Farbe | white to beige |
| Merck | 13,3531 |
| Stabilität | Stable for 1 year as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months |
| InChIKey | AUJXLBOHYWTPFV-UHFFFAOYSA-N |
| SMILES | S1C(C2N(C(=O)C(NC(=O)C(COC(=O)C(N(C(=O)C(N(C(=O)C(NC(=O)C(COC(=O)C(N(C2=O)C)C(C)C)NC(=O)c5nc6c(nc5)cccc6)C)C)C1)C)C(C)C)NC(=O)c3nc4c(nc3)cccc4)C)C)SC |
Sicherheit & Vorschriften
| F | 10 |
|---|---|
| Wassergefährdungsklasse (WGK) | 3 |
| UN-Transportnummer | UN 3462 6.1/PG 2 |
| Zollcode | 2941900000 |
| RTECS-Nr. | JW5250000 |
| R-Sätze (R) | 46-23/24/25 |
| Gefahrensymbole | T |
| Sicherheitshinweise (S) | 53-36/37/39-45 |
| Gefahrenklasse | 6.1(b)Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralRepr. 2 |
| Verpackungsgruppe | III |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
Anwendungen & Verwendung
Beschreibung
Hypoxia-inducible factor-1 (HIF-1) is a transcription factor that controls genes involved in glycolysis, angiogenesis, migration, and invasion. Echinomycin is a cell-permeable inhibitor of HIF-1-mediated gene transcription. It acts by intercalating into DNA in a sequence-specific manner, blocking the binding of either HIF-1α or HIF-1β to the hypoxia-responsive element. Echinomycin reversibly inhibits hypoxia-induced HIF-1 transcription activity in U215 cells with an EC50 value of 1.2 nM. It inhibits hypoxia-induced expression of vascular endothelial growth factor, blocking angiogenesis and altering excitatory synaptic transmission in hippocampal neurons. Echinomycin also impairs expression of survivin, enhancing the sensitivity of multiple myeloma cells to melphalan.
Verwenden
Quiniomycin A is a cyclic depsipeptide metabolite. Quinomycin A has broad activity against bacteria, fungi and viruses, and has found application as an antitumour agent. Quinomycin A acts by bifunctional intercalation of nucleic acids. Recent research has shown quinomycin A to be an extremely potent inhibitor of hypoxia-inducible factor-1 (HIF-1). This transcription factor plays an essential role in tumour progression and metastasis.