(-)-DHMEQ
Based on 35 publication(s) in Google Scholar
(-)-DHMEQ (Dehydroxymethylepoxyquinomicin) is a potent, selective and irreversible NF-κB inhibitor that covalently binds to a cysteine residue. (-)-DHMEQ inhibits nuclear translocation of NF-κB and shows anti-inflammatory and anticancer activity.
For research use only. We do not sell to patients.
- Purity: 99.81%
- CAS No.: 287194-40-5
- Formula: C13H11NO5
- Molecular Weight:261.23
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Storage:
-20°C, stored under nitrogen
* In solvent : -80°C, 6 months; -20°C, 1 month (stored under nitrogen)
Publications Citing Use of MedChemExpress (MCE) (-)-DHMEQ
More- Cancer Cell. 2025 Mar 10;43(3):413-427.e9. [Abstract]
- Kidney Int. 2023 Nov;104(5):943-955. [Abstract]
- Sci Bull. 2023 Dec 30;68(24):3207-3224. [Abstract]
- Redox Biol. 2021 Nov:47:102157. [Abstract]
- Theranostics. 2023 Apr 23;13(8):2588-2604. [Abstract]
- Theranostics. 2019 Jan 1;9(2):436-448. [Abstract]
- Sci Adv. 2024 Feb 16;10(7):eadj1290. [Abstract]
- Cancer Lett. 2026 May 1:645:218395. [Abstract]
- Biosens Bioelectron. 2021 Mar 15:176:112942. [Abstract]
- Int J Biol Sci. 2023 Sep 4;19(15):4744-4762. [Abstract]
- J Transl Med. 2020 Dec 3;18(1):460. [Abstract]
- Sens Actuators B Chem. 2018 Nov 20;274:481-490.
- Mol Cells. 2018 Dec 31;41(12):1008-1015. [Abstract]
- Br J Cancer. 2021 Nov;125(10):1399-1407. [Abstract]
- Anal Chem. 2017 Jul 18;89(14):7316-7323. [Abstract]
- Mol Cancer Ther. 2018 Jun;17(6):1303-1314. [Abstract]
- J Neuroimmune Pharmacol. 2019 Mar;14(1):94-109. [Abstract]
- Anal Chim Acta. 2019 Feb 7:1048:168-177. [Abstract]
- Hepatol Commun. 2026 Apr 13;10(5):e0941. [Abstract]
- Cell Oncol (Dordr). 2025 Jun;48(3):637-654. [Abstract]
- Toxicology. 2018 Jul 1:404-405:49-58. [Abstract]
- Biomedicines. 2022 Jan 13;10(1):165. [Abstract]
- BMC Vet Res. 2019 Oct 25;15(1):365. [Abstract]
- PLoS One. 2025 Nov 6;20(11):e0336333. [Abstract]
- Neurosci Lett. 2023 Feb 6:796:137064. [Abstract]
- Int J Hematol. 2023 Jul;118(1):75-87. [Abstract]
- Biol Pharm Bull. 2017;40(10):1669-1677. [Abstract]
- University of Bonn. 2025.
- Res Sq. 2025 Nov 5.
- bioRxiv. 2025 April 24.
- Université de Lausanne. 2024 Feb 7.
- bioRxiv. 2023 Jan 3:2023.01.03.522642. [Abstract]
- Biomed Pharmacother. 2022 Sep:153:113363. [Abstract]
- Bioengineered. 2022 Feb;13(2):3395-3409. [Abstract]
- bioRxiv. 2020 Apr.
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Biological Activity
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RelA |
RelB |
(-)-DHMEQ (Dehydroxymethylepoxyquinomicin; 2-10 μg/mL; 12-48 hours) treatment significantly reduces the viability of all cell lines in a dose- and time-dependent manner, whereas the effect is not significant in a control cell line K562 without constitutive NF-κB activity[2].
(-)-DHMEQ (10 μg/mL; 0-48 hours; TL-Om1, MT-1 and K562 cells) treatment significantly increases the Annexin V-positive cells in MT-1 and TL-Om1 cell lines[2].
(-)-DHMEQ (10 μg/mL; 4-16 hours; MT-1 cells) treatment down-regulates Bcl-xL, Bcl-2, c-myc, cyclin D1, Rb, and p53, and up-regulates proapoptotic genes such as caspase-3, -8, and-9[2].
(-)-DHMEQ treatment increases cells in G0 /G1 phase in a time-dependent manner, demonstrating antiproliferative effects of (-)-DHMEQ[2].
(-)-DHMEQ binds to p65, cRel, RelB, and p50, but not to p52 at specific cysteine residues. (-)-DHMEQ inhibits not only DNA-binding of RelB, but also its interaction to importin. (-)-DHMEQ also induces instability of RelB[1].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:TL-Om1, MT-1, KK-1, ST-1 and K562 cells
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Concentration:2 μg/mL, 5 μg/mL, 10 μg/mL
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Incubation Time:12 hours, 24 hours, 48 hours
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Result:Significantly reduced the viability of all cell lines in a dose- and time-dependent manner.
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Cell Line:TL-Om1, MT-1 and K562 cells
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Concentration:10 μg/mL
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Incubation Time:0 hours, 24 hours, 48 hours
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Result:Annexin V-positive cells were significantly increased after 24 to 48 hours.
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Cell Line:MT-1 cells
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Concentration:10 μg/mL
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Incubation Time:4 hours, 8 hours, 16 hours
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Result:Annexin V-positive cells were significantly increased after 24 to 48 hours.
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:Male C.B17-scid/scid (5 weeks old) mice injected with MT-2 cells[2]
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Dosage:4 mg/kg or 12 mg/kg
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Administration:Intraperitoneal injection; on day 0 and 3 times a week; for one month
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Result:Showed a significant increase in the survival rate in mice.
Chemical Information
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CAS No. 287194-40-5
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Appearance Solid
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Molecular Weight 261.23
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Formula C13H11NO5
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Color Off-white to gray
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SMILES
O=C1[C@@H](O2)[C@@H]2[C@@H](O)C(NC(C3=C(O)C=CC=C3)=O)=C1
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Synonyms
Dehydroxymethylepoxyquinomicin
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
-20°C, stored under nitrogen
* In solvent : -80°C, 6 months; -20°C, 1 month (stored under nitrogen)
Publications (35)
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Journal Impact Factor
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Most Recent
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Cancer Cell
Microglial reprogramming enhances antitumor immunity and immunotherapy response in melanoma brain metastases. [Abstract]2025 Mar 10;43(3):413-427.e9. PMID: 39919736 -
Kidney Int
The nucleotide-sensing Toll-Like Receptor 9/Toll-Like Receptor 7 system is a potential therapeutic target for IgA nephropathy. [Abstract]2023 Nov;104(5):943-955. PMID: 37648155 -
Sci Bull
Engineering redirected NF-κB/OIP5 expression programs to enhance tumor responses to chemotherapy in bladder cancer. [Abstract]2023 Dec 30;68(24):3207-3224. PMID: 37993335 -
Redox Biol
Reactive oxygen species trigger NF-κB-mediated NLRP3 inflammasome activation involvement in low-dose CdTe QDs exposure-induced hepatotoxicity. [Abstract]2021 Nov:47:102157. PMID: 34614473 -
Theranostics
Inactivating IL34 promotes regenerating muscle stem cell expansion and attenuates Duchenne muscular dystrophy in mouse models. [Abstract]2023 Apr 23;13(8):2588-2604. PMID: 37215564 -
Theranostics
MSC-Delivered Soluble TRAIL and Paclitaxel as Novel Combinatory Treatment for Pancreatic Adenocarcinoma. [Abstract]2019 Jan 1;9(2):436-448. PMID: 30809285 -
Sci Adv
Nutrient availability regulates the secretion and function of immune cell-derived extracellular vesicles through metabolic rewiring. [Abstract]2024 Feb 16;10(7):eadj1290. PMID: 38354238 -
Cancer Lett
DysUFMylation reprograms immunosuppressive neutrophils to potentiate anti-PD-1 therapy in hepatocellular carcinoma. [Abstract]2026 May 1:645:218395. PMID: 41780840 -
Biosens Bioelectron
Entropy-driven electrochemiluminescence ultra-sensitive detection strategy of NF-κB p50 as the regulator of cytokine storm. [Abstract]2021 Mar 15:176:112942. PMID: 33401144 -
Int J Biol Sci
Hypoxia-induced exosomes facilitate lung pre-metastatic niche formation in hepatocellular carcinoma through the miR-4508-RFX1-IL17A-p38 MAPK-NF-κB pathway. [Abstract]2023 Sep 4;19(15):4744-4762. PMID: 37781522 -
J Transl Med
Association of carbamylated high-density lipoprotein with coronary artery disease in type 2 diabetes mellitus: carbamylated high-density lipoprotein of patients promotes monocyte adhesion. [Abstract]2020 Dec 3;18(1):460. PMID: 33272295 -
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Mol Cells
Proteasome Inhibitor-Induced IκB/NF-κB Activation is Mediated by Nrf2-Dependent Light Chain 3B Induction in Lung Cancer Cells. [Abstract]2018 Dec 31;41(12):1008-1015. PMID: 30396235
(-)-DHMEQ purchased from MedChemExpress. Usage Cited in: Mol Cells. 2018 Dec 31;41(12):1008-1015. [Abstract]
NCI-H157 cells are pretreated with DHMEQ (10 or 20 μg/mL) for 2 h and then stimulated with PS-341 for 6 or 24 h. Nuclear proteins (6 h) and whole cell proteins (24 h) are isolated and subjected to Western blot analysis for p65, Lamin A/C, COX-2, and GAPDH.
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Br J Cancer
Tenascin-C expression in the lymph node pre-metastatic niche in muscle-invasive bladder cancer. [Abstract]2021 Nov;125(10):1399-1407. PMID: 34564696 -
Anal Chem
Sensitive and Label-Free Fluorescent Detection of Transcription Factors Based on DNA-Ag Nanoclusters Molecular Beacons and Exonuclease III-Assisted Signal Amplification. [Abstract]2017 Jul 18;89(14):7316-7323. PMID: 28657304 -
Mol Cancer Ther
Nuclear Factor-κB Promotes Urothelial Tumorigenesis and Cancer Progression via Cooperation with Androgen Receptor Signaling. [Abstract]2018 Jun;17(6):1303-1314. PMID: 29592878
(-)-DHMEQ purchased from MedChemExpress. Usage Cited in: Mol Cancer Ther. 2018 Jun;17(6):1303-1314. [Abstract]
Effects of TNF-α/DHMEQ on the expression of NF-κB and AR as well as neoplastic transformation of urothelial cells. Western blotting of NF-κB/p65, p-NF-κB/p65, and AR, using proteins extracted from SVHUC-AR cells cultured with ethanol, TNF-α(20 ng/mL), or DHMEQ (15 µg/mL) for 6 hours.
(-)-DHMEQ purchased from MedChemExpress. Usage Cited in: Mol Cancer Ther. 2018 Jun;17(6):1303-1314. [Abstract]
Effects of NF-κB activation/inhibition on the expression of NF-κB and its downstream targets as well as AR in bladder cancer cells. Western blotting of NF-κB/p65, p-NF-κB/p65, and AR, using proteins extracted from UMUC3 cells cultured with ethanol (mock), TNF-α (20 ng/mL), or DHMEQ (15 µg/mL) for 6 hours.
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J Neuroimmune Pharmacol
The Glucocorticoid Receptor Is a Critical Regulator of HIV Latency in Human Microglial Cells. [Abstract]2019 Mar;14(1):94-109. PMID: 29987742 -
Anal Chim Acta
2019 Feb 7:1048:168-177. PMID: 30598147 -
Hepatol Commun
CD14+CD16- monocytes exhibit NF-κB hyperactivation in biliary atresia: Clinical association and murine therapeutic validation. [Abstract]2026 Apr 13;10(5):e0941. PMID: 41974027 -
Cell Oncol (Dordr)
UBE2Q2 promotes tumor progression and glycolysis of hepatocellular carcinoma through NF-κB/HIF1α signal pathway. [Abstract]2025 Jun;48(3):637-654. PMID: 39833608 -
Toxicology
Exposure to a combination of formaldehyde and DINP aggravated asthma-like pathology through oxidative stress and NF-κB activation. [Abstract]2018 Jul 1:404-405:49-58. PMID: 29758289 -
Biomedicines
Microtubule Affinity-Regulating Kinase 4 Promotes Oxidative Stress and Mitochondrial Dysfunction by Activating NF-κB and Inhibiting AMPK Pathways in Porcine Placental Trophoblasts. [Abstract]2022 Jan 13;10(1):165. PMID: 35052845 -
BMC Vet Res
2019 Oct 25;15(1):365. PMID: 31653220 -
PLoS One
Xiao Qing Long Tang ameliorates neutrophil extracellular trap-dendritic cells-T helper 17 cell axis in Neutrophilic Asthma. [Abstract]2025 Nov 6;20(11):e0336333. PMID: 41196933 -
Neurosci Lett
High-frequency electrical stimulation reduced hyperalgesia and the activation of the Myd88 and NFκB pathways in chronic constriction injury of sciatic nerve-induced neuropathic pain mice. [Abstract]2023 Feb 6:796:137064. PMID: 36638955 -
Int J Hematol
CD30 stimulation induces multinucleation and chromosomal instability in HTLV-1-infected cell lines. [Abstract]2023 Jul;118(1):75-87. PMID: 37014603 -
Biol Pharm Bull
Eudesmane-Type Sesquiterpene Lactones Inhibit Nuclear Translocation of the Nuclear Factor κB Subunit RelB in Response to a Lymphotoxin β Stimulation. [Abstract]2017;40(10):1669-1677. PMID: 28966239
(-)-DHMEQ purchased from MedChemExpress. Usage Cited in: Biol Pharm Bull. 2017;40(10):1669-1677. [Abstract]
A549 transfectants stably expressing RelB WT (A) are preincubated with various concentrations of (–)-DHMEQ for 1 h and then incubated with or without LTβ (25 ng/mL) for 2 h in the presence or absence of (−)-DHMEQ.
(-)-DHMEQ purchased from MedChemExpress. Usage Cited in: Biol Pharm Bull. 2017;40(10):1669-1677. [Abstract]
A549 transfectants stably expressing RelB (C144S) (B) are preincubated with various concentrations of (–)-DHMEQ for 1 h and then incubated with or without LTβ (25 ng/mL) for 2 h in the presence or absence of (−)-DHMEQ.
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bioRxiv
Cooperative NF-κB and Notch1 signaling promotes macrophage-mediated MenaINV expression in breast cancer. [Abstract]2023 Jan 3:2023.01.03.522642. PMID: 36711751 -
Biomed Pharmacother
Iron chelator deferasirox inhibits NF-κB activity in hepatoma cells and changes sorafenib-induced programmed cell deaths. [Abstract]2022 Sep:153:113363. PMID: 35834989 -
Bioengineered
Silencing of specificity protein 1 protects H9c2 cells against lipopolysaccharide-induced injury via binding to the promoter of chemokine CXC receptor 4 and suppressing NF-κB signaling. [Abstract]2022 Feb;13(2):3395-3409. PMID: 35048778 -
Solvent & Solubility
DMSO : 95 mg/mL (363.66 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (stored under nitrogen). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (stored under nitrogen). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Select the appropriate dissolution method based on your experimental animal and administration route.
- For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
- To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
- The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.
Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline
Solubility: 5 mg/mL (19.14 mM); Suspended solution; Need ultrasonic
This protocol yields a suspended solution of 5 mg/mL. Suspended solution can be used for oral and intraperitoneal injection.
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (50.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.
Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
Please enter the basic information of animal experiments:
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Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
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%DMSO +
Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
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%+
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+%Tween-80 + +
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%Saline +
The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).
Working solution concentration: 0.22 mg/mL
Method for preparing stock solution: mg drug dissolved in μL DMSO. Stock solution concentration: mg/mL. * In solvent : -80°C, 6 months; -20°C, 1 month (stored under nitrogen)
1. Take μL DMSO stock solution;
2. Add μL .
μL , mix evenly;
3. Then add μL Tween 80, mix evenly;
4. Then add μL
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
Purity & Documentation
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Data Sheet (282 KB)
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SDS (394 KB)
- English - EN (394 KB)
- Français - FR (394 KB)
- Deutsch - DE (394 KB)
- Norwegian - NO (394 KB)
- Español - ES (394 KB)
- Swedish - SV (394 KB)
- Italian - IT (394 KB)
- Korean - KR (394 KB)
- Portuguese - PT (394 KB)
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Handling Instructions (2659 KB)
References
[1]. Yinzhi Lin, et al. Inhibition of Late and Early Phases of Cancer Metastasis by the NF-κB Inhibitor DHMEQ Derived from Microbial Bioactive Metabolite Epoxyquinomicin: A Review. [Content Brief]
[2]. Mariko Watanabe, et al. Dual targeting of transformed and untransformed HTLV-1-infected T cells by DHMEQ, a potent and selective inhibitor of NF-kappaB, as a strategy for chemoprevention and therapy of adult T-cell leukemia. Blood. 2005 Oct 1;106(7):2462-71. [Content Brief]
[3]. Quach HT, et al. Eudesmane-Type Sesquiterpene Lactones Inhibit Nuclear Translocation of the Nuclear Factor κB Subunit RelB in Response to a Lymphotoxin β Stimulation. Biol Pharm Bull. 2017;40(10):1669-1677. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (stored under nitrogen). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO | 1 mM | 3.8280 mL | 19.1402 mL | 38.2804 mL | 95.7011 mL |
| 5 mM | 0.7656 mL | 3.8280 mL | 7.6561 mL | 19.1402 mL | |
| 10 mM | 0.3828 mL | 1.9140 mL | 3.8280 mL | 9.5701 mL | |
| 15 mM | 0.2552 mL | 1.2760 mL | 2.5520 mL | 6.3801 mL | |
| 20 mM | 0.1914 mL | 0.9570 mL | 1.9140 mL | 4.7851 mL | |
| 25 mM | 0.1531 mL | 0.7656 mL | 1.5312 mL | 3.8280 mL | |
| 30 mM | 0.1276 mL | 0.6380 mL | 1.2760 mL | 3.1900 mL | |
| 40 mM | 0.0957 mL | 0.4785 mL | 0.9570 mL | 2.3925 mL | |
| 50 mM | 0.0766 mL | 0.3828 mL | 0.7656 mL | 1.9140 mL | |
| 60 mM | 0.0638 mL | 0.3190 mL | 0.6380 mL | 1.5950 mL | |
| 80 mM | 0.0479 mL | 0.2393 mL | 0.4785 mL | 1.1963 mL | |
| 100 mM | 0.0383 mL | 0.1914 mL | 0.3828 mL | 0.9570 mL |