| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
|
||
| 10mg |
|
||
| 50mg |
|
||
| 100mg | |||
| Other Sizes |
| Targets |
Roseoflavin targets flavin-dependent enzymes and FMN riboswitches. It acts as an antimetabolite analog of riboflavin and FMN. It directly binds to FMN riboswitch aptamers with a Kd of 100 nM. By binding to these RNA elements, it downregulates the expression of FMN riboswitch-lacZ reporter genes in B. subtilis. This mechanism disrupts key metabolic processes in bacteria.
|
|---|---|
| ln Vitro |
The chemical analogue of riboflavin and flavin mononucleotide (FMN) is called roseoflavin. It may directly bind to the FMN riboswitch (Kd~100 nM) aptamer and downregulate the FMN riboswitch-lacZ in Bacillus subtilis. It also possesses antimicrobial properties. Reporter gene expression[1].
In vitro, roseoflavin shows antimicrobial activity. It directly binds to FMN riboswitch aptamers (Kd=100 nM) and downregulates the expression of an FMN riboswitch-lacZ reporter gene in B. subtilis. As an antimetabolite, it mimics riboflavin in flavin biosynthesis but leads to the formation of inactive flavin co-factors. Its antibacterial activity is linked to its disruption of riboflavin metabolism. |
| ln Vivo |
In vivo, roseoflavin's antibacterial properties make it a valuable tool for studying bacterial resistance and riboflavin biosynthesis pathways. It has been shown to be an important regulator of bacterial gene expression by binding to RNA untranslated regions, so-called riboswitching sites. Its activity is dependent on its ability to interfere with essential metabolic processes in bacteria.
|
| Enzyme Assay |
Cell-free assays for roseoflavin measure its binding affinity to FMN riboswitch aptamers, which is Kd = 100 nM. Its interaction with flavin-dependent enzymes can also be studied in vitro. Its molecular weight (405.41) and formula (C18H23N5O6) are confirmed by mass spectrometry. Its purity is confirmed by HPLC. Its solubility in DMSO (55 mg/mL) is documented.
|
| Cell Assay |
Cellular assays for roseoflavin are performed in bacterial cells, such as B. subtilis, to measure its effect on gene expression. It is used to study the regulation of FMN riboswitch-lacZ reporter genes. Its antibacterial activity is assessed in standard antimicrobial susceptibility tests. These assays confirm its mechanism of action as a riboswitch-targeting antibiotic.
|
| Animal Protocol |
In vivo animal experiments for roseoflavin are not detailed in the provided information. Its primary use is in bacterial models to study riboswitch function and antibiotic resistance. Its in vivo efficacy as an antibiotic would be assessed in animal models of infection, but such studies are not mentioned in the available data.
|
| ADME/Pharmacokinetics |
Roseoflavin has a molecular weight of 405.41 and a molecular formula of C18H23N5O6. It is a naturally occurring pigment. It is soluble in DMSO (55 mg/mL). For storage, the powder can be kept at -20°C for 3 years, and in solvent at -80°C for 1 year. It is recommended to be stored at low temperature and away from moisture.
|
| Toxicity/Toxicokinetics |
The toxicological profile of roseoflavin is not extensively detailed. As an antibiotic and an analog of riboflavin, its toxicity is likely related to its disruption of flavin metabolism. It is considered a research compound, and its safety for human use has not been established. It should be handled with care.
|
| 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.
|
| Additional Infomation |
Roseoflavin is a benzo[a]pteroidine compound, a derivative of riboflavin in which the 8-methyl group is replaced by a dimethylamino group. It possesses antibacterial activity and is a bacterial metabolite. Its function is related to riboflavin; it is the conjugate acid of Roseoflavin (1-). Roseoflavin has been reported to be present in Streptomyces, Streptomyces leucopsis, and Streptomyces azureense, and relevant data are available.
Roseoflavin is a naturally occurring antibiotic and riboflavin analog produced by Streptomyces davawensis. It acts as an antimetabolite, interfering with riboflavin metabolism by binding to FMN riboswitches and inhibiting flavin-dependent enzymes. It is a valuable tool for studying bacterial gene regulation, riboswitch function, and antibiotic resistance. It is a research compound not intended for human use. |
| Molecular Formula |
C18H23N5O6
|
|---|---|
| Molecular Weight |
405.40512
|
| Exact Mass |
404.169
|
| CAS # |
51093-55-1
|
| PubChem CID |
49867612
|
| Appearance |
Typically exists as solid at room temperature
|
| Density |
1.5±0.1 g/cm3
|
| Melting Point |
276-278ºC
|
| Index of Refraction |
1.688
|
| LogP |
-0.55
|
| Hydrogen Bond Donor Count |
5
|
| Hydrogen Bond Acceptor Count |
8
|
| Rotatable Bond Count |
6
|
| Heavy Atom Count |
29
|
| Complexity |
726
|
| Defined Atom Stereocenter Count |
3
|
| SMILES |
CC1=CC2=C(N(C3=NC(NC(C3=N2)=O)=O)CC(O)C(O)C(O)CO)C=C1N(C)C
|
| 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
|
| Chemical Name |
8-(dimethylamino)-7-methyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]benzo[g]pteridine-2,4-dione
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO : ~50 mg/mL (~123.33 mM)
|
|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.4666 mL | 12.3332 mL | 24.6664 mL | |
| 5 mM | 0.4933 mL | 2.4666 mL | 4.9333 mL | |
| 10 mM | 0.2467 mL | 1.2333 mL | 2.4666 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
