ChemicalBook > CAS DataBase List > QUINOMYCIN A

QUINOMYCIN A

Product Name: QUINOMYCIN A
CAS No.: 512-64-1
Chemical Name: QUINOMYCIN A
Synonyms: SK-302B;nsc526417;NSC 13502;ECHINOMYCIN;echinomycina;QUINOMYCIN A;Echinomycin >97%;Antibiotic A 654I;Echinomycin (NSC-13502);Echinomycin, HIF-1alpha inhibitor
CBNumber: CB6394145
Molecular Formula: C51H64N12O12S2
Formula Weight: 1101.26
MOL File: 512-64-1.mol

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QUINOMYCIN A Property

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

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Safety

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

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H361Suspected of damaging fertility or the unborn child

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SML0477
Product name: Echinomycin
Purity: ≥98% (HPLC)
Packaging: 1mg
Price: $146
Updated: 2025/07/31

Cayman Chemical

Product number: 11049
Product name: Echinomycin
Purity: ≥98%
Packaging: 1mg
Price: $97
Updated: 2024/03/01

Cayman Chemical

Product number: 11049
Product name: Echinomycin
Purity: ≥98%
Packaging: 5mg
Price: $360
Updated: 2024/03/01

Sigma-Aldrich

Product number: SML0477
Product name: Echinomycin
Purity: ≥98% (HPLC)
Packaging: 5mg
Price: $605
Updated: 2025/07/31

Tocris

Product number: 5520
Product name: Echinomycin
Purity: ≥98%(HPLC)
Packaging: 1
Price: $118
Updated: 2021/12/16

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QUINOMYCIN A Chemical Properties,Usage,Production

Description

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.

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] DEHE KONG. Echinomycin, a small-molecule inhibitor of hypoxia-inducible factor-1 DNA-binding activity.[J]. Cancer research, 2005, 65 19: 9047-9055. DOI:10.1158/0008-5472.can-05-1235
[2] YIN WANG. Echinomycin protects mice against relapsed acute myeloid leukemia without adverse effect on hematopoietic stem cells.[J]. Blood, 2014, 124 7: 1127-1135. DOI:10.1182/blood-2013-12-544221
[3] YIN WANG. Targeting HIF1α eliminates cancer stem cells in hematological malignancies.[J]. Cell stem cell, 2011, 8 4: 399-411. DOI:10.1016/j.stem.2011.02.006
[4] RAN LI . Hypoxia-inducible factor-1α regulates the expression of L-type voltage-dependent Ca2+ channels in PC12 cells under hypoxia[J]. Cell Stress & Chaperones, 2015, 20 3: Pages 507-516. DOI:10.1007/s12192-015-0575-2

QUINOMYCIN A Preparation Products And Raw materials

Raw materials

Preparation Products

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512-64-1, QUINOMYCIN ARelated Search:

Chrysin Anifostine trihydrate CHAETOMIN BISPHENOL A DIMETHYL ETHER Sunitinib Malate Geldanamycin Imatinib mesylate Azithromycin 4-OXO-1,4-DIHYDRO-[1,10]PHENANTHROLINE-3-CARBOXYLIC ACID 2-QUINOXALINECARBALDEHYDE AC-VAL-OME QUINOMYCIN A DIMETHYLAMINOETHOXY PROPYLAMINE quinomycin N,N-DIMETHYL-L-VALINE 2-QUINOXALINYLMETHYLAMINE,97% 2-Quinoxalinemethanamine,N-methyl-(9CI) 3-[(3-AMINO-3-OXOPROPYL)THIO]PROPANAMIDE

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

Echinomycin >97%

Echinomycin (NSC-13502)

N-[2,4,12,15,17,25-hexamethyl-29-methylsulfanyl-3,6,10,13,16,19,23,26-octaoxo-11,24-di(propan-2-yl)-7-(quinoxaline-2-carbonylamino)-9,22-dioxa-28-thia-2,5,12,15,18,25-hexazabicyclo[12.12.3]nonacosan-20-yl]quinoxaline-2-carboxamide

QUINOMYCIN A

EchinoMycin, Actinoleukin, 1491, 59266, X 948, X 53III

9,22-Dioxa-28-thia-2,5,12,15,18,25-hexaazabicyclo[12.12.3]nonacosane cyclic peptide deriv.

Antibiotic A 654I

NSC 13502

L-Valine, 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-, (8→1)-lactone, cyclic (3→7)-thioether

Echinomycin, HIF-1alpha inhibitor

Echinomycin <i>Streptomyces</i> sp.

N-[(1R,4S,7R,11S,14R,17S,20R,24S)-2,4,12,15,17,25-hexamethyl-27-methylsulfanyl-3,6,10,13,16,19,23,26-octaoxo-11,24-di(propan-2-yl)-20-(quinoxaline-2-carbonylamino)-9,22-dioxa-28-thia-2,5,12,15,18,25-hexazabicyclo[12.12.3]nonacosan-7-yl]quinoxaline-2-carboxamide

512-64-1

C51H64N12O12S2

Antibiotics

Antibiotics A-F

Antibiotics A to Z

BioChemical

Antitumour

Antibiotic