QUINOMYCIN A
QUINOMYCIN A Basic information
- Product Name:
- QUINOMYCIN A
- Synonyms:
-
- echinomycina
- nsc526417
- ECHINOMYCIN
- Echinomycin Streptomyces sp. - CAS 512-64-1 - Calbiochem
- N-(2-Quinoxalinylcarbonyl)-O-[N-(2-quinoxalinylcarbonyl)-D-seryl-L-alanyl-3-mercapto-N,S-dimethylcysteinyl-N-methyl-L-valyl]-D-seryl-L-alanyl-N-methylcysteinyl-N-methyl-L-valine-(81)-lactone-cyclic (37)-thioether
- N-[(1R,4S,8R,11S,14R,17S,21R,24S)-3,11,13,16,24,26-hexamethyl-27-methylsulfanyl-2,5,9,12,15,18,22,25-octaoxo-4,17-di(propan-2-yl)-8-(quinoxaline-2-carbonylamino)-6,19-dioxa-28-thia-3,10,13,16,23,26-hexazabicyclo[12.12.3]nonacosan-21-yl]quinoxaline-2-carbo
- N-(2-Quinoxalinylcarbonyl)cyclo(D-Ser*-Ala-N-methyl-L-Cys(1)-N-methyl-L-Val-N-(quinoxaline-2-ylcarbonyl)-D-Ser*-Ala-N-methyl-3-methylthio-L-Ala(1)-N-methyl-L-Val-)
- SK-302B
- CAS:
- 512-64-1
- MF:
- C51H64N12O12S2
- MW:
- 1101.26
- Product Categories:
-
- Antitumour
- Antibiotic
- Mol File:
- 512-64-1.mol
QUINOMYCIN A Chemical Properties
- Melting point:
- 217-218℃
- alpha
- D20 -310° (c = 0.86 in chloroform)
- Boiling point:
- 1427.2±65.0 °C(Predicted)
- Density
- 1.0964 (rough estimate)
- refractive index
- 1.6700 (estimate)
- storage temp.
- -20°C
- solubility
- Soluble in DMSO (up to 5 mg/ml)
- pka
- 9.38±0.70(Predicted)
- form
- White solid
- color
- white to beige
- Merck
- 13,3531
- Stability:
- Stable for 1 year as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months
Safety Information
- Hazard Codes
- T
- Risk Statements
- 46-23/24/25
- Safety Statements
- 53-36/37/39-45
- RIDADR
- UN 3462 6.1/PG 2
- WGK Germany
- 3
- RTECS
- JW5250000
- F
- 10
- HazardClass
- 6.1(b)
- PackingGroup
- III
- HS Code
- 2941900000
MSDS
- Language:English Provider:SigmaAldrich
QUINOMYCIN A Usage And Synthesis
Description
Hypoxia-
Uses
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.
Uses
Quinomycin A is a cyclic depsipeptide metabolite. Quinomycin A has broad activity against bacteria, fungi and viruses, and has found application as an antitumor 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 tumor progression and metastasis.
Uses
Echinomycin has been used for inhibition of hypoxia-inducible factor 1.
Biochem/physiol Actions
Echinomycin is an antitumor antibiotic and potent hypoxia inducible factor 1α (HIF-1α) inhibitor. It binds to DNA via bifunctional intercalation, blocking the binding of HIF-1α, a transcription factor important in tumor growth. Echinomycin selectively eliminated cancer stem cells in a study with mouse lymphoma and human AML xenogeneic models, eradicating the lymphomas. Recently, echinomycin was also found to act as an antibiotic adjuvant having synergistic effects with novobiocin in gram negative bacteria.
in vivo
Echinomycin (10 μg/kg; intravenous injection; for 40 days; NOD-SCID mice) treatment efficiently eradicates mouse lymphoma and serially transplantable human acute myeloid leukemia (AML) in xenogeneic model by preferential elimination of cancer stem cells (CSCs). HIF1α maintains mouse lymphoma CSCs by repressing a negative feedback loop in the Notch pathway[2].
Animal Model: | NOD-SCID mice received 1.8Gy of irradiation and i.v. injection with peripheral blood cells from patients AML-71 and AML-150[2] |
Dosage: | 10 μg/kg |
Administration: | Intravenous injection; for 40 days |
Result: | Efficiently eradicated mouse lymphoma and serially transplantable human AML in xenogeneic model by preferential elimination of CSCs. |
storage
Store at -20°C
References
1) Kong?et al.?(2005),?Echinomycin, a small-molecule inhibitor of hypoxia-inducible factor-1 DNA-binding activity; Cancer Res.,?65?9047 2) Wang?et al. (2014),?Echinomycin protects mice against relapsed acute myeloid leukemia without adverse effect on hematopoietic stem cells; Blood,?124?1127 3) Wang?et al. (2011),?Targeting HIF1α eliminates cancer stem cells in hematological malignancies; Cell Stem Cell.,?8?399 4) Li?et al. (2015),?Hypoxia-inducible factor-1α regulates the expression of L-type voltage-dependent Ca(2+) channels in PC12 cells under hypoxia; Cell Stress Chaperones,?20?507
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