C2659

Chromomycin A₃

from Streptomyces griseus, ≥95% (HPLC), powder, RNA synthesis inhibitor

• Synonym(s): Aburamycin B, CMA₃, NSC 58514
• Empirical Formula (Hill Notation): C₅₇H₈₂O₂₆
• CAS Number: 7059-24-7
• Molecular Weight: 1183.25
• EC Number: 230-348-0
• MDL number: MFCD00043151
• UNSPSC Code: 41106305
• PubChem Substance ID: 24892514
• NACRES: NA.77

Properties

• Product Name: Chromomycin A₃ from Streptomyces griseus, ≥95% (HPLC)
• Quality Level: 200
• Assay: ≥95% (HPLC)
• form: powder
• antibiotic activity spectrum: Gram-positive bacteria; fungi; neoplastics
• Mode of action: DNA synthesis | interferes
• storage temp.: −20°C
• SMILES string: CO[C@H]1[C@@H](O)CC(O[C@H]1C)O[C@H]2CC(O[C@@H](C)[C@H]2OC(C)=O)Oc3cc4cc5C[C@@H]([C@@H](OC)C(=O)[C@@H](O)[C@H](C)O)[C@H](OC6C[C@@H](OC7C[C@H](OC8C[C@](C)(O)[C@@H](OC(C)=O)[C@H](C)O8)[C@@H](O)[C@H](C)O7)[C@H](O)[C@@H](C)O6)C(=O)c5c(O)c4c(O)c3C
• InChI: 1S/C57H82O26/c1-21-34(79-40-19-37(53(26(6)75-40)77-28(8)59)82-38-16-33(61)52(70-11)25(5)74-38)15-31-13-30-14-32(54(71-12)51(68)46(63)22(2)58)55(50(67)44(30)49(66)43(31)45(21)62)83-41-18-35(47(64)24(4)73-41)80-39-17-36(48(65)23(3)72-39)81-42-20-57(10,69)56(27(7)76-42)78-29(9)60/h13,15,22-27,32-33,35-42,46-48,52-56,58,61-66,69H,14,16-20H2,1-12H3/t22-,23-,24+,25-,26-,27-,32-,33-,35+,36-,37-,38?,39?,40?,41?,42?,46-,47+,48-,52+,53+,54+,55-,56-,57-/m0/s1
• InChI key: ZYVSOIYQKUDENJ-MTPXVABGSA-N

Description

General description

Chemical structure: aureolic acid

Application

Chromomycin A3 from Streptomyces griseus has been used as a reagent in flow sorting.[1] It has also been used to stain spermatozoa to evaluate the sperm nuclear chromatin integrity.[2]

Biochem/physiol Actions

Chromomycin A3 from Streptomyces griseus is an antibiotic exhibiting anti-bacterial, anti-fungal and antitumor activities.[3] It serves as a fluorescent DNA stain.[4] It is useful for the detection of protamine deficiency in sperm chromatin. The compound blocks macromolecule synthesis by a specific, reversible interaction with DNA in the presence of bivalent metal ions. Binding to DNA minor groove mediates an efficient competitive inhibition of DNA gyrase and significantly affects topoisomerase II activity.

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Safety Information

• Pictograms: GHS06
• Signal Word: Danger
• Hazard Statements: H300
• Precautionary Statements: P264 - P270 - P301 + P310 - P405 - P501
• Hazard Classifications: Acute Tox. 1 Oral
• Storage Class Code: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves