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MedKoo Cat#: 562256 | Name: Roseoflavin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Roseoflavin
Roseoflavin
CAS#51093-55-1

Theoretical Analysis

MedKoo Cat#: 562256

Name: Roseoflavin

CAS#: 51093-55-1

Chemical Formula: C18H23N5O6

Exact Mass: 405.1648

Molecular Weight: 405.41

Elemental Analysis: C, 53.33; H, 5.72; N, 17.28; O, 23.68

Price and Availability

Size Price Availability Quantity
5mg USD 300.00
10mg USD 450.00
25mg USD 750.00
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Related CAS #
No Data
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/
Solvent mg/mL mM
Solubility
DMF 0.3 0.74
DMSO 10.0 24.67
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.
1: Joshi T, Demmer U, Schneider C, Glaser T, Warkentin E, Ermler U, Mack M. The Phosphatase RosC from Streptomyces davaonensis is Used for Roseoflavin Biosynthesis and has Evolved to Largely Prevent Dephosphorylation of the Important Cofactor Riboflavin-5'-phosphate. J Mol Biol. 2024 Oct 15;436(20):168734. doi: 10.1016/j.jmb.2024.168734. Epub 2024 Aug 2. PMID: 39097184. 2: Hemasa A, Spry C, Mack M, Saliba KJ. Mutation of the Plasmodium falciparum Flavokinase Confers Resistance to Roseoflavin and 8-Aminoriboflavin. ACS Infect Dis. 2024 Aug 9;10(8):2939-2949. doi: 10.1021/acsinfecdis.4c00289. Epub 2024 Jun 26. PMID: 38920250. 3: Liunardo JJ, Messerli S, Gregotsch AK, Lang S, Schlosser K, Rückert-Reed C, Busche T, Kalinowski J, Zischka M, Weller P, Nouioui I, Neumann-Schaal M, Risdian C, Wink J, Mack M. Isolation, characterisation and description of the roseoflavin producer Streptomyces berlinensis sp. nov. Environ Microbiol Rep. 2024 Apr;16(2):e13266. doi: 10.1111/1758-2229.13266. PMID: 38653477; PMCID: PMC11039241. 4: Langa S, Peirotén Á, Rodríguez S, Calzada J, Prieto-Paredes R, Curiel JA, Landete JM. Riboflavin bio-enrichment of soy beverage by selected roseoflavin- resistant and engineered lactic acid bacteria. Int J Food Microbiol. 2024 Feb 2;411:110547. doi: 10.1016/j.ijfoodmicro.2023.110547. Epub 2023 Dec 21. PMID: 38150774. 5: Dmytruk KV, Ruchala J, Fayura LR, Chrzanowski G, Dmytruk OV, Tsyrulnyk AO, Andreieva YA, Fedorovych DV, Motyka OI, Mattanovich D, Marx H, Sibirny AA. Efficient production of bacterial antibiotics aminoriboflavin and roseoflavin in eukaryotic microorganisms, yeasts. Microb Cell Fact. 2023 Jul 20;22(1):132. doi: 10.1186/s12934-023-02129-8. PMID: 37474952; PMCID: PMC10357625. 6: Charoenwongpaiboon T, Klaewkla M, Chaiyen P, Tongsook C. Mechanistic Insights into Roseoflavin Synthesis by N,N-8-Demethyl-8-aminoriboflavin Dimethyltransferase (RosA): Molecular Dynamics Simulations and Residue Conservation Analysis. J Chem Inf Model. 2023 Jun 26;63(12):3903-3910. doi: 10.1021/acs.jcim.3c00655. Epub 2023 Jun 13. PMID: 37310018. 7: Diez-Ozaeta I, Martín-Loarte L, Mohedano ML, Tamame M, Ruiz-Masó JÁ, Del Solar G, Dueñas MT, López P. A methodology for the selection and characterization of riboflavin-overproducing Weissella cibaria strains after treatment with roseoflavin. Front Microbiol. 2023 Apr 6;14:1154130. doi: 10.3389/fmicb.2023.1154130. PMID: 37089563; PMCID: PMC10116070. 8: 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. 9: Hernández-Alcántara AM, Chiva R, Mohedano ML, Russo P, Ruiz-Masó JÁ, Del Solar G, Spano G, Tamame M, López P. Weissella cibaria riboflavin- overproducing and dextran-producing strains useful for the development of functional bread. Front Nutr. 2022 Oct 4;9:978831. doi: 10.3389/fnut.2022.978831. PMID: 36267909; PMCID: PMC9577222. 10: 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. 11: Crielaard S, Maassen R, Vosman T, Rempkens I, Velema WA. Affinity-Based Profiling of the Flavin Mononucleotide Riboswitch. J Am Chem Soc. 2022 Jun 15;144(23):10462-10470. doi: 10.1021/jacs.2c02685. Epub 2022 Jun 6. PMID: 35666649; PMCID: PMC9204756. 12: Ripa I, Ruiz-Masó JÁ, De Simone N, Russo P, Spano G, Del Solar G. A single change in the aptamer of the Lactiplantibacillus plantarum rib operon riboswitch severely impairs its regulatory activity and leads to a vitamin B2 - overproducing phenotype. Microb Biotechnol. 2022 Apr;15(4):1253-1269. doi: 10.1111/1751-7915.13919. Epub 2021 Oct 2. PMID: 34599851; PMCID: PMC8966005. 13: Muramatsu MK, Zhou J, Fitzgerald BL, Deka RK, Belisle JT, Norgard MV. An rfuABCD-Like Operon and Its Relationship to Riboflavin Utilization and Mammalian Infectivity by Borrelia burgdorferi. Infect Immun. 2021 Sep 16;89(10):e0030721. doi: 10.1128/IAI.00307-21. Epub 2021 Jul 12. PMID: 34310888; PMCID: PMC8445183. 14: Schneider C, Mack M. A second riboflavin import system is present in flavinogenic Streptomyces davaonensis and supports roseoflavin biosynthesis. Mol Microbiol. 2021 Aug;116(2):470-482. doi: 10.1111/mmi.14726. Epub 2021 May 6. PMID: 33829573. 15: Russo P, De Simone N, Capozzi V, Mohedano ML, Ruiz-Masó JÁ, Del Solar G, López P, Spano G. Selection of Riboflavin Overproducing Strains of Lactic Acid Bacteria and Riboflavin Direct Quantification by Fluorescence. Methods Mol Biol. 2021;2280:3-14. doi: 10.1007/978-1-0716-1286-6_1. PMID: 33751425. 16: Zhou LF, Wu J, Li S, Li Q, Jin LP, Yin CP, Zhang YL. Antibacterial Potential of Termite-Associated Streptomyces spp. ACS Omega. 2021 Feb 5;6(6):4329-4334. doi: 10.1021/acsomega.0c05580. PMID: 33623843; PMCID: PMC7893633. 17: Kachel B, Mack M. Engineering of Synechococcus sp. strain PCC 7002 for the photoautotrophic production of light-sensitive riboflavin (vitamin B2). Metab Eng. 2020 Nov;62:275-286. doi: 10.1016/j.ymben.2020.09.010. Epub 2020 Sep 28. PMID: 32992032. 18: Schneider C, Konjik V, Kißling L, Mack M. The novel phosphatase RosC catalyzes the last unknown step of roseoflavin biosynthesis in Streptomyces davaonensis. Mol Microbiol. 2020 Oct;114(4):609-625. doi: 10.1111/mmi.14567. Epub 2020 Jul 21. PMID: 32621340. 19: Kißling L, Schneider C, Seibel K, Dorjjugder N, Busche T, Kalinowski J, Mack M. The roseoflavin producer Streptomyces davaonensis has a high catalytic capacity and specific genetic adaptations with regard to the biosynthesis of riboflavin. Environ Microbiol. 2020 Aug;22(8):3248-3265. doi: 10.1111/1462-2920.15066. Epub 2020 Jun 18. PMID: 32410282. 20: Tong J, Zhang P, Zhang L, Zhang D, Beratan DN, Song H, Wang Y, Li T. A Robust Bioderived Wavelength-Specific Photosensor Based on BLUF Proteins. Sens Actuators B Chem. 2020 May 1;310:127838. doi: 10.1016/j.snb.2020.127838. Epub 2020 Feb 6. PMID: 32296265; PMCID: PMC7157799.

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