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SML1583

Sigma-Aldrich

Roseoflavin

≥95% (HPLC)

Synonym(s):

8-Demethyl-8-(dimethylamino)-riboflavin, 8-Dimethylaminoriboflavin

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About This Item

Empirical Formula (Hill Notation):
C18H23N5O6
CAS Number:
51093-55-1
Molecular Weight:
405.41
UNSPSC Code:
12352200
NACRES:
NA.77
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Quality Level

100

Assay

≥95% (HPLC)

form

powder

storage condition

protect from light

color

faint red to very dark brown-red

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

−20°C

SMILES string

[n]1(c2n[c]([nH][c](c2nc3c1cc(c(c3)C)N(C)C)=O)=O)CC(O)C(O)C(O)CO

InChI

1S/C18H23N5O6/c1-8-4-9-11(5-10(8)22(2)3)23(6-12(25)15(27)13(26)7-24)16-14(19-9)17(28)21-18(29)20-16/h4-5,12-13,15,24-27H,6-7H2,1-3H3,(H,21,28,29)

InChI key

IGQLDUYTWDABFK-UHFFFAOYSA-N

Biochem/physiol Actions

Roseoflavin is an analog of flavin mononucleotide (FMN) and riboflavin with antimicrobial activity.
Roseoflavin is an analog of flavin mononucleotide (FMN) and riboflavin with antimicrobial activity. Roseoflavin is converted to the flavin mononucleotide (FMN) analog roseoflavin mononucleotide (RoFMN) by flavokinase and to the flavin adenine dinucleotide (FAD) analog roseoflavin adenine dinucleotide (RoFAD) by FAD synthetase, and acts as a riboflavin antagonist. Roseoflavin is an inhibitor of bacterial riboflavin riboswitches, cis regulatory elements present in non-coding RNA that specifically bind to natural ligands to regulate gene expression. Roseoflavin, converted to RoFMN, blocks the flavin mononucleotide riboswitch-mediated expression of the ribB gene, which is required for riboflavin biosynthesis.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000221629
0000221628
0000218537
0000221629
0000221628

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Maira Rivera et al.
Nucleic acids research, 52(6), 3164-3179 (2024-02-20)
The capacity of riboswitches to undergo conformational changes in response to binding their native ligands is closely tied to their functional roles and is an attractive target for antimicrobial drug design. Here, we established a probe-based fluorescence anisotropy assay to

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