Lumichrome
(Synonyms: 光色素) 目录号 : GC44090
A natural metabolite of riboflavin
Cas No.:1086-80-2
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >90.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Lumichrome is a natural metabolite of riboflavin. It can be made by photolysis of riboflavin or it can be produced enzymatically in certain microbes and plants. Lumichrome produced by Rhizobium and other bacterial species induces major developmental changes in plants at nanomolar concentrations. Lumichrome can stimulate larval metamorphosis in ascidians and activate the LasR quorum sensing receptor of bacteria. Lumichrome competitively inhibits the uptake of riboflavin by riboflavin transporters from prokaryotes and eukaryotes.
| Cas No. | 1086-80-2 | SDF | |
| 别名 | 光色素 | ||
| Canonical SMILES | CC1=C(C)C=C(NC(C2=N3)=NC(NC2=O)=O)C3=C1 | ||
| 分子式 | C12H10N4O2 | 分子量 | 242.2 |
| 溶解度 | Soluble in DMSO | 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 | 4.1288 mL | 20.6441 mL | 41.2882 mL |
| 5 mM | 0.8258 mL | 4.1288 mL | 8.2576 mL |
| 10 mM | 0.4129 mL | 2.0644 mL | 4.1288 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。
Rhizosphere ecology of Lumichrome and riboflavin, two bacterial signal molecules eliciting developmental changes in plants
Front Plant Sci 2015 Sep 14;6:700.PMID:26442016DOI:10.3389/fpls.2015.00700.
Lumichrome and riboflavin are novel molecules from rhizobial exudates that stimulate plant growth. Reported studies have revealed major developmental changes elicited by Lumichrome at very low nanomolar concentrations (5 nM) in plants, which include early initiation of trifoliate leaves, expansion of unifoliate and trifoliate leaves, increased stem elongation and leaf area, and consequently greater biomass accumulation in monocots and dicots. But higher Lumichrome concentration (50 nM) depressed root development and reduced growth of unifoliate and second trifoliate leaves. While the mechanisms remain unknown, it is possible that Lumichrome released by rhizobia induced the biosynthesis of classical phytohormones that caused the observed developmental changes in plants. We also showed in earlier studies that applying either 10 nM Lumichrome, 10 nM ABA, or 10 ml of infective rhizobial cells (0.2 OD600) to roots of monocots and dicots for 44 h produced identical effects, which included decreased stomatal conductance and leaf transpiration in Bambara groundnut, soybean, and maize, increased stomatal conductance and transpiration in cowpea and lupin, and elevated root respiration in maize (19% by rhizobia and 20% by Lumichrome). Greater extracellular exudation of Lumichrome, riboflavin and indole acetic acid by N2-fixing rhizobia over non-fixing bacteria is perceived to be an indication of their role as symbiotic signals. This is evidenced by the increased concentration of Lumichrome and riboflavin in the xylem sap of cowpea and soybean plants inoculated with infective rhizobia. In fact, greater xylem concentration of Lumichrome in soybean and its correspondingly increased accumulation in leaves was found to result in dramatic developmental changes than in cowpea. Furthermore, Lumichrome and riboflavin secreted by soil rhizobia are also known to function as (i) ecological cues for sensing environmental stress, (ii) growth factors for microbes, plants, and humans, (iii) signals for stomatal functioning in land plants, and (iv) protectants/elicitors of plant defense. The fact that exogenous application of ABA to plant roots caused the same effect as Lumichrome on leaf stomatal functioning suggests molecular cross-talk in plant response to environmental stimuli.
Initial Excited State Dynamics of Lumichrome upon Ultraviolet Excitation
Photochem Photobiol 2022 Nov;98(6):1270-1283.PMID:35380739DOI:10.1111/php.13631.
Lumichrome (LC) is the major photodegradation product of biologically important flavin cofactors. Since LC serves as a structural comparison with the flavins; understanding excited states of LC is fundamentally important to establish a connection with photophysics of different flavins, such as lumiflavin (LF), riboflavin (RF), flavin mononucleotide (FMN) and flavin adenine dinucleotide (FAD). Herein, we deduce the initial excited state structural dynamics of LC using UV resonance Raman (UVRR) intensity analysis. The UVRR spectra at wavelengths across the 260 nm absorption band of LC were measured and resulting Raman excitation profiles and absorption spectrum were self-consistently simulated using a time-dependent wave packet formalism to extract the initial excited state structural and solvent broadening parameters. These results are compared with those obtained for other flavins following UV excitations. We find that LC undergoes a very distinct instantaneous charge redistribution than flavins, which is attributed to the extended π-conjugation present in flavins but missing in LC. The homogeneous broadening linewidth of LC appears to be lower than that of LF, while the inhomogeneous broadening values are comparable, indicating greater solvent interaction with excited flavin on ultrafast timescale compared with LC, whereas on longer timescale these interactions are almost similar.
Lumichrome Inhibits Human Lung Cancer Cell Growth and Induces Apoptosis via a p53-Dependent Mechanism
Nutr Cancer 2019;71(8):1390-1402.PMID:31074646DOI:10.1080/01635581.2019.1610183.
Lumichrome, a major derivative of riboflavin, may exhibit pharmacological activity against cancer cells. Riboflavin is a vitamin found in food, however, certain evidence has suggested its possible potentiating effects on cancer progression. Here, we have shown for the first time that unlike riboflavin, Lumichrome can suppress lung cancer cell growth and reduce survival in both normal and anchorage-independent conditions. In addition, Lumichrome induced apoptosis in lung cancer cells via a p53-dependent mitochondrial mechanism with substantial selectivity, shown by its lesser toxicity to the normal primary dermal papilla cells. The potency of Lumichrome in killing lung cancer cells was found to be comparable to that of cisplatin, a standard chemotherapeutic drug for lung cancer treatment. With regard to the mechanism, Lumichrome significantly upregulated p53 and decreased its downstream target BCL-2. Such a shift of BCL-2 family protein balance further activated caspase-9 and -3 and finally executed apoptosis. Furthermore, Lumichrome potentially suppressed cancer stem cells (CSCs) in lung cancer by dramatically suppressing CSC markers together with the CSC-maintaining cell signaling namely protein kinase B (AKT) and β-catenin. To conclude, the present study has unraveled a novel role and mechanism of Lumichrome against lung cancer that may benefit the development of the compound for management of the disease.
Efficient production of Lumichrome by Microbacterium sp. strain TPU 3598
Appl Environ Microbiol 2015 Nov;81(21):7360-7.PMID:26253661DOI:10.1128/AEM.02166-15.
Lumichrome is a photodegradation product of riboflavin and is available as a photosensitizer and fluorescent dye. To develop new efficient methods of Lumichrome production, we isolated bacterial strains with high Lumichrome productivity from soil. The strain with highest productivity was identified as Microbacterium sp. strain TPU 3598. Since this strain inductively produced Lumichrome when cultivated with riboflavin, we developed two different methods, a cultivation method and a resting cell method, for the production of large amounts of Lumichrome using the strain. In the cultivation method, 2.4 g (9.9 mmol) of Lumichrome was produced from 3.8 g (10.1 mmol) of riboflavin at the 500-ml scale (98% yield). The strain also produced 4.7 g (19.4 mmol) of Lumichrome from 7.6 g (20.2 mmol) of riboflavin (96% yield) by addition of riboflavin during cultivation at the 500-ml scale. In the resting cell method, 20 g of cells (wet weight) in 100 ml of potassium phosphate buffer, pH 7.0, produced 2.4 g of Lumichrome from 3.8 g of riboflavin (98% yield). Since the Lumichrome production by these methods was carried out in suspension, the resulting Lumichrome was easily purified from the cultivation medium or reaction mixture by centrifugation and crystallization. Thus, the biochemical methods we describe here are a significant improvement in terms of simplicity and yield over the existing chemical, photolytic, and other biochemical methods of Lumichrome production.
Lumichrome from the photolytic riboflavin acts as an electron shuttle in microbial photoelectrochemical systems
Bioelectrochemistry 2023 Apr 7;152:108439.PMID:37060705DOI:10.1016/j.bioelechem.2023.108439.
Riboflavin has been proposed to serve as an electron shuttle in photoelectrochemical systems. However, riboflavin was also observed for abiotic photolysis under illumination. Such conflicting reports raise the necessity for further investigation. In this study, riboflavin secreted by Rhodopseudomonas palustris was studied to clarify its stability and electron shuttle function under illumination. The data of high-performance liquid chromatography-mass spectrometry showed that the riboflavin was photolyzed to Lumichrome in microbial photoelectrochemical systems. In addition, the anodic current increased by 75% after adding Lumichrome compared with that of the control; it further demonstrated that Lumichrome, not riboflavin, as an electron shuttle could facilitate microbial electron transfer. This study clarifies the mechanism of the interface process in microbial photoelectrochemical systems.