Roseoflavin

Names

[ Name ]:
Roseoflavin

[Synonym ]:
Roseoflavine
Riboflavin,8-demethyl-8-(dimethylamino)
C18H23N5O6
8-Dimethylaminoriboflavin
D-Ribitol, 1-deoxy-1-[8-(dimethylamino)-3,4-dihydro-7-methyl-2,4-dioxopyrimido[4,5-b]quinolin-10(2H)-yl]-
8-(dimethylamino)-7-methyl-10-(2,3,4,5-tetrahydroxypentyl)benzo[g]pteridine-2,4-dione
7-Methyl-8-dimethylamino-10-(1'-D-ribityl)isoalloxazin
8-(dimethylamino)-7-methyl-10-((2S,3S,4R)-2,3,4,5-tetrahydroxypentyl)benzo[g]pteridine-2,4(3H,10H)-dione
8-demethyl-8-(dimethylamino)riboflavin
8-dimethylamino-7-methyl-10-D-ribitol-1-yl-10H-benzo[g]pteridine-2,4-dione
1-Deoxy-1-[8-(dimethylamino)-7-methyl-2,4-dioxo-3,4-dihydropyrimido[4,5-b]quinolin-10(2H)-yl]-D-ribitol
Roseoflavin

Biological Activity

[Description]:

Roseoflavin, a natural pigment originally isolated from Streptomyces davawensis, is an antimetabolite analog of Riboflavin and flavin mononucleotide that has antimicrobial properties[1].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Bacterial

[In Vitro]

Roseoflavin, a chemical analog of flavin mononucleotide (FMN) and riboflavin that has antimicrobial activity, can directly bind to FMN riboswitch (Kd~100 nM) aptamers and downregulate the expression of an FMN riboswitch-lacZ reporter gene in B. subtilis[1].

[References]

[1]. Lee ER, et al. Roseoflavin is a natural antibacterial compound that binds to FMN riboswitches and regulates gene expression. RNA Biol. 2009;6(2):187-194.

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Melting Point ]:
276-278ºC

[ Molecular Formula ]:
C₁₈H₂₃N₅O₆

[ Molecular Weight ]:
404.417

[ Exact Mass ]:
404.169586

[ PSA ]:
151.91000

[ LogP ]:
-0.55

[ Index of Refraction ]:
1.688

[ Storage condition ]:
-20°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: VJ1300000

CHEMICAL NAME :: Riboflavin, 8-demethyl-8-(dimethylamino)-

CAS REGISTRY NUMBER :: 51093-55-1

LAST UPDATED :: 199309

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C18-H23-N5-O6

MOLECULAR WEIGHT :: 405.46

WISWESSER LINE NOTATION :: T C666 BN DNVMV INJ B1YQYQYQ1Q L1 MN1&1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85ERAY "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978 Volume(issue)/page/year: 1,277,1978

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 400 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 27,88,1974