Roseoflavin
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MedKoo CAT#: 562256

CAS#: 51093-55-1

Description: Roseoflavin is an antibiotic agent. Roseoflavin is an analog of flavin mononucleotide (FMN) and riboflavin that is synthesized by the soil bacterium S. davawensis.

Chemical Structure

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Roseoflavin
CAS# 51093-55-1
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 562256
Name: Roseoflavin
CAS#: 51093-55-1
Chemical Formula: C18H23N5O6
Exact Mass: 405.16
Molecular Weight: 405.410
Elemental Analysis: C, 53.33; H, 5.72; N, 17.28; O, 23.68

Price and Availability

Size Price Availability Quantity
5mg USD 200
10mg USD 320
25mg USD 600
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Synonym: Roseoflavin;

IUPAC/Chemical Name: 8-(Dimethylamino)-7-methyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]benzo[g]pteridine-2,4-dione

InChi Key: IGQLDUYTWDABFK-GUTXKFCHSA-N

InChi Code: 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)/t12-,13+,15-/m0/s1

SMILES Code: O=C(N1)N=C2N(C[C@H](O)[C@H](O)[C@H](O)CO)C3=CC(N(C)C)=C(C)C=C3N=C2C1=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: Roseoflavin has been shown to bind directly to FMN riboswitch aptamers (KD = ~100 nM), downregulating the expression of genes responsible for the synthesis and transport of riboflavin.
In vitro activity: Roseoflavin can block growth of the bacterial pathogen Listeria monocytogenes, but also enhances its virulence. Roseoflavin stimulated L. monocytogenes virulence gene expression and infection abilities in a mechanism independent of the FMN riboswitch. Reference: RNA Biol. 2011 Jul-Aug;8(4):674-80. https://pubmed.ncbi.nlm.nih.gov/21593602/
In vivo activity: This study tested the antimalarial activity of roseoflavin against Plasmodium vinckei vinckei in mice. Roseoflavin decreased the parasitemia by 46-fold and, on average, increased the survival of mice by 4 to 5 days. These data indicate that roseoflavin could serve as a potential starting point for the development of new antimalarials. Reference: Antimicrob Agents Chemother. 2022 Oct 18;66(10):e0054022. https://pubmed.ncbi.nlm.nih.gov/36094195/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 0.3 0.74
DMSO 10.0 24.67

Preparing Stock Solutions

The following data is based on the product molecular weight 405.41 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Kao HJ, Balasubramaniam A, Chen CC, Huang CM. Extracellular electrons transferred from honey probiotic Bacillus circulans inhibits inflammatory acne vulgaris. Sci Rep. 2022 Nov 10;12(1):19217. doi: 10.1038/s41598-022-23848-9. PMID: 36357775; PMCID: PMC9649788. 2. Mansjö M, Johansson J. The riboflavin analog roseoflavin targets an FMN-riboswitch and blocks Listeria monocytogenes growth, but also stimulates virulence gene-expression and infection. RNA Biol. 2011 Jul-Aug;8(4):674-80. doi: 10.4161/rna.8.4.15586. Epub 2011 Jul 1. PMID: 21593602; PMCID: PMC3225981. 3. Hemasa AL, Mack M, Saliba KJ. Roseoflavin, a Natural Riboflavin Analogue, Possesses In Vitro and In Vivo Antiplasmodial Activity. Antimicrob Agents Chemother. 2022 Oct 18;66(10):e0054022. doi: 10.1128/aac.00540-22. Epub 2022 Sep 12. PMID: 36094195; PMCID: PMC9578400.
In vitro protocol: 1. Kao HJ, Balasubramaniam A, Chen CC, Huang CM. Extracellular electrons transferred from honey probiotic Bacillus circulans inhibits inflammatory acne vulgaris. Sci Rep. 2022 Nov 10;12(1):19217. doi: 10.1038/s41598-022-23848-9. PMID: 36357775; PMCID: PMC9649788. 2. Mansjö M, Johansson J. The riboflavin analog roseoflavin targets an FMN-riboswitch and blocks Listeria monocytogenes growth, but also stimulates virulence gene-expression and infection. RNA Biol. 2011 Jul-Aug;8(4):674-80. doi: 10.4161/rna.8.4.15586. Epub 2011 Jul 1. PMID: 21593602; PMCID: PMC3225981.
In vivo protocol: 1. Hemasa AL, Mack M, Saliba KJ. Roseoflavin, a Natural Riboflavin Analogue, Possesses In Vitro and In Vivo Antiplasmodial Activity. Antimicrob Agents Chemother. 2022 Oct 18;66(10):e0054022. doi: 10.1128/aac.00540-22. Epub 2022 Sep 12. PMID: 36094195; PMCID: PMC9578400.

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1: Landwehr W, Kämpfer P, Glaeser SP, Rückert C, Kalinowski J, Blom J, Goesmann A, Mack M, Schumann P, Atasayar E, Hahnke RL, Rohde M, Martin K, Stadler M, Wink J. Taxonomic analyses of members of the Streptomyces cinnabarinus cluster, description of Streptomyces cinnabarigriseus sp. nov. and Streptomyces davaonensis sp. nov. Int J Syst Evol Microbiol. 2018 Jan;68(1):382-393. doi: 10.1099/ijsem.0.002519. Epub 2017 Dec 11. PubMed PMID: 29227220.

2: Chen J, Vestergaard M, Jensen TG, Shen J, Dufva M, Solem C, Jensen PR. Finding the Needle in the Haystack-the Use of Microfluidic Droplet Technology to Identify Vitamin-Secreting Lactic Acid Bacteria. MBio. 2017 May 30;8(3). pii: e00526-17. doi: 10.1128/mBio.00526-17. PubMed PMID: 28559484; PubMed Central PMCID: PMC5449655.

3: Krajewski SS, Ignatov D, Johansson J. Two Are Better Than One: Dual Targeting of Riboswitches by Metabolite Analogs. Cell Chem Biol. 2017 May 18;24(5):535-537. doi: 10.1016/j.chembiol.2017.05.004. PubMed PMID: 28525764.

4: Wang H, Mann PA, Xiao L, Gill C, Galgoci AM, Howe JA, Villafania A, Barbieri CM, Malinverni JC, Sher X, Mayhood T, McCurry MD, Murgolo N, Flattery A, Mack M, Roemer T. Dual-Targeting Small-Molecule Inhibitors of the Staphylococcus aureus FMN Riboswitch Disrupt Riboflavin Homeostasis in an Infectious Setting. Cell Chem Biol. 2017 May 18;24(5):576-588.e6. doi: 10.1016/j.chembiol.2017.03.014. Epub 2017 Apr 20. PubMed PMID: 28434876.

5: Balcazar DE, Vanrell MC, Romano PS, Pereira CA, Goldbaum FA, Bonomi HR, Carrillo C. The superfamily keeps growing: Identification in trypanosomatids of RibJ, the first riboflavin transporter family in protists. PLoS Negl Trop Dis. 2017 Apr 13;11(4):e0005513. doi: 10.1371/journal.pntd.0005513. eCollection 2017 Apr. PubMed PMID: 28406895; PubMed Central PMCID: PMC5404878.

6: Thakur K, Tomar SK, Wei ZJ. Comparative mRNA Expression Profiles of Riboflavin Biosynthesis Genes in Lactobacilli Isolated from Human Feces and Fermented Bamboo Shoots. Front Microbiol. 2017 Mar 17;8:427. doi: 10.3389/fmicb.2017.00427. eCollection 2017. PubMed PMID: 28367143; PubMed Central PMCID: PMC5356473.

7: Konjik V, Brünle S, Demmer U, Vanselow A, Sandhoff R, Ermler U, Mack M. The Crystal Structure of RosB: Insights into the Reaction Mechanism of the First Member of a Family of Flavodoxin-like Enzymes. Angew Chem Int Ed Engl. 2017 Jan 19;56(4):1146-1151. doi: 10.1002/anie.201610292. Epub 2016 Dec 16. PubMed PMID: 27981706.

8: Juarez Del Valle M, Laiño JE, Savoy de Giori G, LeBlanc JG. Factors stimulating riboflavin produced by Lactobacillus plantarum CRL 725 grown in a semi-defined medium. J Basic Microbiol. 2017 Mar;57(3):245-252. doi: 10.1002/jobm.201600573. Epub 2016 Dec 14. PubMed PMID: 27966212.

9: Matern A, Pedrolli D, Großhennig S, Johansson J, Mack M. Uptake and Metabolism of Antibiotics Roseoflavin and 8-Demethyl-8-Aminoriboflavin in Riboflavin-Auxotrophic Listeria monocytogenes. J Bacteriol. 2016 Nov 4;198(23):3233-3243. Print 2016 Dec 1. PubMed PMID: 27672192; PubMed Central PMCID: PMC5105903.

10: Jhulki I, Chanani PK, Abdelwahed SH, Begley TP. A Remarkable Oxidative Cascade That Replaces the Riboflavin C8 Methyl with an Amino Group during Roseoflavin Biosynthesis. J Am Chem Soc. 2016 Jul 13;138(27):8324-7. doi: 10.1021/jacs.6b02469. Epub 2016 Jun 29. PubMed PMID: 27331868; PubMed Central PMCID: PMC5610575.

11: Schwarz J, Konjik V, Jankowitsch F, Sandhoff R, Mack M. Identification of the Key Enzyme of Roseoflavin Biosynthesis. Angew Chem Int Ed Engl. 2016 May 10;55(20):6103-6. doi: 10.1002/anie.201600581. Epub 2016 Apr 9. PubMed PMID: 27062037.

12: Tongsook C, Uhl MK, Jankowitsch F, Mack M, Gruber K, Macheroux P. Structural and kinetic studies on RosA, the enzyme catalysing the methylation of 8-demethyl-8-amino-d-riboflavin to the antibiotic roseoflavin. FEBS J. 2016 Apr;283(8):1531-49. doi: 10.1111/febs.13690. Epub 2016 Mar 17. PubMed PMID: 26913589; PubMed Central PMCID: PMC4982073.

13: Karasulu B, Götze JP, Thiel W. Assessment of Franck-Condon Methods for Computing Vibrationally Broadened UV-vis Absorption Spectra of Flavin Derivatives: Riboflavin, Roseoflavin, and 5-Thioflavin. J Chem Theory Comput. 2014 Dec 9;10(12):5549-66. doi: 10.1021/ct500830a. PubMed PMID: 26583238.

14: Pedrolli D, Langer S, Hobl B, Schwarz J, Hashimoto M, Mack M. The ribB FMN riboswitch from Escherichia coli operates at the transcriptional and translational level and regulates riboflavin biosynthesis. FEBS J. 2015 Aug;282(16):3230-42. doi: 10.1111/febs.13226. Epub 2015 Feb 27. PubMed PMID: 25661987.

15: Karasulu B, Thiel W. Photoinduced intramolecular charge transfer in an electronically modified flavin derivative: roseoflavin. J Phys Chem B. 2015 Jan 22;119(3):928-43. doi: 10.1021/jp506101x. Epub 2014 Sep 26. PubMed PMID: 25214319.

16: Pedrolli DB, Jankowitsch F, Schwarz J, Langer S, Nakanishi S, Mack M. Natural riboflavin analogs. Methods Mol Biol. 2014;1146:41-63. doi: 10.1007/978-1-4939-0452-5_3. Review. PubMed PMID: 24764087.

17: Haase I, Gräwert T, Illarionov B, Bacher A, Fischer M. Recent advances in riboflavin biosynthesis. Methods Mol Biol. 2014;1146:15-40. doi: 10.1007/978-1-4939-0452-5_2. Review. PubMed PMID: 24764086.

18: Russo P, Capozzi V, Arena MP, Spadaccino G, Dueñas MT, López P, Fiocco D, Spano G. Riboflavin-overproducing strains of Lactobacillus fermentum for riboflavin-enriched bread. Appl Microbiol Biotechnol. 2014 Apr;98(8):3691-700. doi: 10.1007/s00253-013-5484-7. Epub 2014 Jan 12. PubMed PMID: 24413973.

19: Pedrolli DB, Mack M. Bacterial flavin mononucleotide riboswitches as targets for flavin analogs. Methods Mol Biol. 2014;1103:165-76. doi: 10.1007/978-1-62703-730-3_13. PubMed PMID: 24318894.

20: Langer S, Hashimoto M, Hobl B, Mathes T, Mack M. Flavoproteins are potential targets for the antibiotic roseoflavin in Escherichia coli. J Bacteriol. 2013 Sep;195(18):4037-45. doi: 10.1128/JB.00646-13. Epub 2013 Jul 8. PubMed PMID: 23836860; PubMed Central PMCID: PMC3754745.