158792-24-6

Basic information

• Product Name: COLLISMYCIN A
• Synonyms: COLLISMYCIN A;Collismycin;(E)-4-Methoxy-5-(methylthio)-[2,2'-bipyridine]-6-carbaldehyde oxime
• CAS NO: 158792-24-6
• Molecular Formula: C13H13N3O2S
• Molecular Weight: 275.33
• Mol File: 158792-24-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 173-174 °C
• Boiling Point: 381.2 °C at 760 mmHg
• Flash Point: 184.3 °C
• Appearance: /
• Density: 1.27 g/cm³
• Vapor Pressure: 5.16E-06mmHg at 25°C
• Refractive Index: 1.624
• Storage Temp.: 2-8°C
• PKA: 9.75±0.50(Predicted)
• CAS DataBase Reference: COLLISMYCIN A(CAS DataBase Reference)
• NIST Chemistry Reference: COLLISMYCIN A(158792-24-6)
• EPA Substance Registry System: COLLISMYCIN A(158792-24-6)

Safety Data

• Hazardous Substances Data: 158792-24-6(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 158792-24-6 differently. You can refer to the following data:
1. Collismycin is a rare and unusual antibiotic belonging to the caerulomycin class, containing a core 2,2’-bispyridyl with an oxime substituent, produced by a strain of Streptomyces and discovered by researchers from Kirin, Japan in 1994. Collismycin was discovered as a potent inhibitor of glucocorticoid receptor binding. Collismycin has weak to moderate activity against bacteria, fungi and tumor cell lines. More recently, collismycin has been found to be a potent and selective neuroprotective agent against oxidative stress. Other recent publications have focused on the biosynthesis of collismycin as a route to the production of related analogues.
2. Collismycin A is a microbial product that exhibits anti-proliferative activity against cancer cells. Collismycin A is also an iron chelator and used to develop neuroprotective compounds.

InChI:InChI=1/C13H13N3O2S/c1-18-12-7-10(9-5-3-4-6-14-9)16-11(8-15-17)13(12)19-2/h3-8,16H,1-2H3/b11-8+

Upstream product

• 98-98-6 2-Picolinic acid 
• 14163-00-9 4-nitro-2,2'-bipyridine N-oxide 
• 14163-05-4 4-methoxy-2,2’-bipyridine N-oxide 
• 33421-43-1 2,2'-bipyridyl N-oxide 
• 366-18-7 [2,2]bipyridinyl 
• 205053-07-2 4-methoxy-5-methylsulfanyl-[2,2′]bipyridinyl-6-carbaldehyde 
• 205052-97-7 6-bromo-4-nitro-2,2'-bipyridine N-oxide 
• 205053-05-0 6-bromo-4-methoxy-5-(methylthio)-2,2'-bipyridine 
• 205052-91-1 6-bromo-4-methoxy-2,2'-bipyridine N-oxide 
• 205052-93-3 6-bromo-4-methoxy-2,2'-bipyridine 
• 205052-95-5 6-bromo-2,2'-bipyridine N-oxide 
• 1416512-50-9 4-methoxy-[2,2']bipyridinyl-6-carboxylic acid diisopropylamide 
• 1416512-49-6 sodium 4-methoxy-[2,2']bipyridinyl-6-carboxylate 
• 14761-58-1 4-methoxy-2,2'-bipyridyl-6-carboxamidoxime 

Downstream Products

• 158792-25-7 collismycin B 

Relevant articles and documents

Generation by mutasynthesis of potential neuroprotectant derivatives of the bipyridyl collismycin A

Collismycin A is a member of the 2,2′-bipyridyl family of natural products and structurally belongs to the hybrid polyketides-nonribosomal peptides. A gene coding for a lysine 2-aminotransferase of Streptomyces sp. CS40 (collismycin A producer) was inactivated by gene replacement. The mutant was unable of synthesizing collismycin A but it recovered this capability when picolinic acid was added to the culture medium. By feeding different picolinic acid analogs to this mutant, two new collismycin A derivatives were obtained with a methyl group at the 4 and 6 position of the first pyridine ring of collismycin A, respectively. The two compounds showed effective neuroprotective action against an oxidative stress inducer in a zebra fish model, one of them showing higher neuroprotectant activity than that of collismycin A and that of the control lipoic acid.

First Syntheses of Caerulomycin E and Collismycins A and C. A New Synthesis of Caerulomycin A

Caerulomycins produced by Streptomyces caeruleus, and collismycins more recently isolated from Streptomyces species, are bipyridinic molecules endowed with antibiotic and cytotoxic activities. The first syntheses of caerulomycin E (1), as well as new synt