DIMBOA |
Catalog No.GC60138
One-Click Copy Product Info
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DIMBOA (2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one) is a benzoxazinoid (BX), is a secondary metabolite in grasses.
Products are for research use only. Not for human use. We do not sell to patients.
Cas No.: 15893-52-4
Sample solution is provided at 25 µL, 10mM.
DIMBOA (2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one) is a benzoxazinoid (BX), is a secondary metabolite in grasses [1]. DIMBOA act as antibiotic and allelochemical, part of the chemical defense system of graminaceous plants such as maize, wheat, and rye [1,2]. DIMBOA possess growth inhibitory properties against many strains of studied bacteria and fungi, such as Staphylococcus aureus, Escherichia coli as well as against Saccharomyces cerevisiae [2]. Once released, BXs degrade relatively quickly in aqueous environments with a half-life of less than 24 hours [1].
DIMBOA is weak bacterial mutagens and furthermore caused aneuploidy in human-derived liver cells (HepG2 cells) [3]. DIMBOA showed genotoxic effects in HepG2 cell line [4].
DIMBOA showed the antibacterial activity against Ralstonia solanacearum with minimum inhibitory concentrations (MICs) of 50, 100 and 200 mg/L. DIMBOA also significantly affect bacterial growth, reduce biofilm formation, and inhibit swarming motility within 24 h [5].
References:
[1]. Neal A L, Ahmad S, Gordon-Weeks R, et al. Benzoxazinoids in root exudates of maize attract Pseudomonas putida to the rhizosphere[J]. PloS one, 2012, 7(4): e35498.
[2]. Gleńsk M, Gajda B, Franiczek R, et al. In vitro evaluation of the antioxidant and antimicrobial activity of DIMBOA [2, 4-dihydroxy-7-methoxy-2 H-1, 4-benzoxazin-3 (4 H)-one][J]. Natural product research, 2016, 30(11): 1305-1308.
[3]. Buchmann C A, Nersesyan A, Kopp B, et al. Dihydroxy-7-methoxy-1, 4-benzoxazin-3-one (DIMBOA) and 2, 4-dihydroxy-1, 4-benzoxazin-3-one (DIBOA), two naturally occurring benzoxazinones contained in sprouts of Gramineae are potent aneugens in human-derived liver cells (HepG2)[J]. Cancer letters, 2007, 246(1-2): 290-299.
[4]. Buchmann C, Nersesyan A, Kopp B, et al. DIMBOA and DIBOA, two naturally occuring benzoxazinoides, cause aneuploidy in a human-derived liver cell line (HepG2)[C]//BMC Pharmacology. BioMed Central, 2007, 7(2): 1-1.
[5]. Guo B, Zhang Y, Li S, et al. Extract from maize (Zea mays L.): antibacterial activity of DIMBOA and its derivatives against Ralstonia solanacearum[J]. Molecules, 2016, 21(10): 1397.
| Cell experiment [1]: | |
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Cell lines |
Pseudomonas putida KT2440 |
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Preparation Method |
P. putida KT2440 cells were grown to mid-exponential phase in 100 mL M9 medium before DIMBOA was added to a final concentration of 5 µg mL-1. After 1 hour of exposure, cells were harvested by centrifugation at 4°C. |
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Reaction Conditions |
5 µg mL-1, 1h |
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Applications |
P. putida KT2440 appears relatively tolerant to DIMBOA in comparison to other soil bacteria. For all subsequent experiments, DIMBOA was employed at concentrations of 5 µg mL-1 (0.023 mM). |
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References: [1]: Neal A L, Ahmad S, Gordon-Weeks R, et al. Benzoxazinoids in root exudates of maize attract Pseudomonas putida to the rhizosphere[J]. PloS one, 2012, 7(4): e35498. |
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| Cas No. | 15893-52-4 | SDF | |
| Canonical SMILES | O=C1C(O)OC2=CC(OC)=CC=C2N1O | ||
| Formula | C9H9NO5 | M.Wt | 211.17 |
| Solubility | DMSO: 125 mg/mL (591.94 mM) | Storage | Store at -20°C |
| General tips | Please select the appropriate solvent to prepare the stock solution according to the
solubility of the product in different solvents; once the solution is prepared, please store it in
separate packages to avoid product failure caused by repeated freezing and thawing.Storage method
and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored
at -20°C, please use it within 1 month. To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time. |
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| Shipping Condition | Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request. | ||
| Prepare stock solution | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 4.7355 mL | 23.6776 mL | 47.3552 mL |
| 5 mM | 947.1 μL | 4.7355 mL | 9.471 mL |
| 10 mM | 473.6 μL | 2.3678 mL | 4.7355 mL |
Step 1: Enter information below (Recommended: An additional animal making an allowance for loss during the experiment)
g
μL
Step 2: Enter the in vivo formulation (This is only the calculator, not formulation. Please contact us first if there is no in vivo formulation at the solubility Section.)
Calculation results:
Working concentration: mg/ml;
Method for preparing DMSO master liquid: mg drug pre-dissolved in μL DMSO ( Master liquid 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 master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL saline, mix and clarify.
Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.
Note: 1. Please make sure the liquid is clear before adding the next solvent.
2. Be sure to add the solvent(s) in order. You must ensure that the solution obtained, in the previous addition, is a clear solution before proceeding to add the next solvent. Physical methods such as vortex, ultrasound or hot water bath can be used to aid dissolving.
3. All of the above co-solvents are available for purchase on the GlpBio website.
Quality Control & SDS
- View current batch:
- Purity: >98.00% Appearance: A solid
- COA (Certificate of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Average Rating: 5 (Based on Reviews and 13 reference(s) in Google Scholar.)