Roseoflavin
(Synonyms: 玫瑰黄色素) 目录号 : GC44850
Antibiotic analog of riboflavin
Cas No.:51093-55-1
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Roseoflavin is an analog of flavin mononucleotide (FMN) and riboflavin that is synthesized by the soil bacterium S. davawensis and possesses antimicrobial activity. It 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.
| Cas No. | 51093-55-1 | SDF | |
| 别名 | 玫瑰黄色素 | ||
| Canonical SMILES | O=C(C1=NC2=CC(C)=C(N(C)C)C=C2N(C[C@H](O)[C@H](O)[C@H](O)CO)C1=N3)NC3=O | ||
| 分子式 | C18H23N5O6 | 分子量 | 405.4 |
| 溶解度 | DMF: 0.3 mg/ml,DMSO: 10 mg/ml,DMSO:PBS(pH7.2) (1:1): 0.5 mg/ml | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.4667 mL | 12.3335 mL | 24.667 mL |
| 5 mM | 0.4933 mL | 2.4667 mL | 4.9334 mL |
| 10 mM | 0.2467 mL | 1.2333 mL | 2.4667 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Roseoflavin, a Natural Riboflavin Analogue, Possesses In Vitro and In Vivo Antiplasmodial Activity
Antimicrob Agents Chemother 2022 Oct 18;66(10):e0054022.PMID:36094195DOI:10.1128/aac.00540-22.
The ability of the human malaria parasite Plasmodium falciparum to access and utilize vital nutrients is critical to its growth and proliferation. Molecules that interfere with these processes could potentially serve as antimalarials. We found that two riboflavin analogues, Roseoflavin and 8-aminoriboflavin, inhibit malaria parasite proliferation by targeting riboflavin metabolism and/or the utilization of the riboflavin metabolites flavin mononucleotide and flavin adenine dinucleotide. An additional eight riboflavin analogues were evaluated, but none were found to be more potent than Roseoflavin, nor was their activity on target. Focusing on Roseoflavin, we tested its antimalarial activity in vivo against Plasmodium vinckei vinckei in mice. We found that Roseoflavin decreased the parasitemia by 46-fold following a 4 day suppression test and, on average, increased the survival of mice by 4 to 5 days. Our data are consistent with riboflavin metabolism and/or the utilization of riboflavin-derived cofactors being viable drug targets for the development of new antimalarials and that Roseoflavin could serve as a potential starting point.
Metabolic engineering of roseoflavin-overproducing microorganisms
Microb Cell Fact 2019 Aug 26;18(1):146.PMID:31451111DOI:10.1186/s12934-019-1181-2.
Background: Roseoflavin, a promising broad-spectrum antibiotic, is naturally produced by the bacteria Streptomyces davaonensis and Streptomyces cinnabarinus. The key enzymes responsible for Roseoflavin biosynthesis and the corresponding genes were recently identified. In this study we aimed to enhance Roseoflavin production in S. davaonensis and to synthesize Roseoflavin in the heterologous hosts Bacillus subtilis and Corynebacterium glutamicum by (over)expression of the Roseoflavin biosynthesis genes. Results: While expression of the Roseoflavin biosynthesis genes from S. davaonensis was not observed in recombinant strains of B. subtilis, overexpression was successful in C. glutamicum and S. davaonensis. Under the culture conditions tested, a maximum of 1.6 ± 0.2 µM (ca. 0.7 mg/l) and 34.9 ± 5.2 µM (ca. 14 mg/l) Roseoflavin was produced with recombinant strains of C. glutamicum and S. davaonensis, respectively. In S. davaonensis the Roseoflavin yield was increased by 78%. Conclusions: The results of this study provide a sound basis for the development of an economical Roseoflavin production process.
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.PMID:32410282DOI:10.1111/1462-2920.15066.
The bacterium Streptomyces davaonensis synthesizes the antibiotic Roseoflavin in the stationary phase of growth. The starting point for Roseoflavin biosynthesis is riboflavin (vitamin B2 ) and four enzymes (RibCF, RosB, RosA and RosC) are necessary to convert a vitamin (riboflavin) into a potent, broad-spectrum antibiotic (Roseoflavin). In S. davaonensis, seven enzymatic functions are required to synthesize the Roseoflavin precursor riboflavin from the central building blocks GTP and ribulose 5-phosphate. When compared with other bacterial and in particular Streptomyces genomes the S. davaonensis genome contains an unusual high number (21) of putative riboflavin biosynthetic genes (rib genes), including a rib gene encoding an additional riboflavin synthase originating from an Archaeon. We show by complementation analyses and enzyme assays that 17 out of these 21 putative rib genes indeed encode for riboflavin biosynthetic enzymes. Biochemical analyses of selected enzymes support this finding. Transcriptome analyses show that all of the rib genes are expressed either in the exponential or in the stationary phase of growth and thus do not represent silent genes. We conclude that the Rib enzymes produced in the stationary phase represent a physiological adaptation to support Roseoflavin biosynthesis.
Roseoflavin is a natural antibacterial compound that binds to FMN riboswitches and regulates gene expression
RNA Biol 2009 Apr-Jun;6(2):187-94.PMID:19246992DOI:10.4161/rna.6.2.7727.
Riboswitches in messenger RNAs carry receptor domains called aptamers that can bind to metabolites and control expression of associated genes. The Gram-positive bacterium Bacillus subtilis has two representatives of a class of riboswitches that bind flavin mononucleotide (FMN). These riboswitches control genes responsible for the biosynthesis and transport of riboflavin, a precursor of FMN. We found that Roseoflavin, a chemical analog of FMN and riboflavin that has antimicrobial activity, can directly bind to FMN riboswitch aptamers and downregulate the expression of an FMN riboswitch-lacZ reporter gene in B. subtilis. A role for the riboswitch in the antimicrobial mechanism of Roseoflavin is supported by our observation that some previously identified roseoflavin-resistant bacteria have mutations within an FMN aptamer. Riboswitch mutations in these resistant bacteria disrupt ligand binding and derepress reporter gene expression in the presence of either riboflavin or Roseoflavin. If FMN riboswitches are a major target for Roseoflavin antimicrobial action, then future efforts to develop compounds that trigger FMN riboswitch function could lead to the identification of new antimicrobial drugs.
Formation of Roseoflavin from guanine through riboflavin
J Biochem 1979 Jul;86(1):167-75.PMID:479119doi
A synthesis of Roseoflavin by Streptomyces davawensis from guanine through riboflavin was demonstrated. The lines of evidence are (1)incorporations of 14C of [2-and U-14C] guanine and [2-14C] riboflavin into Roseoflavin, (2) no incorporation of 14C of [8-14C] guanine into Roseoflavin, (3) localizations of 14C in Roseoflavin, and (4) a decrease of specific radioactivity of Roseoflavin formed from [2-14C]guanine on addition of riboflavin to the culture. The 14C atoms in Roseoflavin formed were localized by radioactivity analysis of the NaOH-hydrolysis products, i.e., urea and 1,2-dihydro-6-methyl-7-dimethylamino-2-keto-1-D-ribityl-3-quinox-alinecarboxylic acid (QC), a new substance. These hydrolysis products were identified by the isolation of dixanthylures, decomposition with urease, and from the properties of QC and QC tetraacetate isolated. These finding suggest that the pyrimidine ring of guanine is conserved in the formation of Roseoflavin from guanine through riboflavin.