Synonym
Daidzin; Daidzein 7-O-glucoside;
IUPAC/Chemical Name
3-(4-Hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
InChi Key
KYQZWONCHDNPDP-QNDFHXLGSA-N
InChi Code
InChI=1S/C21H20O9/c22-8-16-18(25)19(26)20(27)21(30-16)29-12-5-6-13-15(7-12)28-9-14(17(13)24)10-1-3-11(23)4-2-10/h1-7,9,16,18-23,25-27H,8H2/t16-,18-,19+,20-,21-/m1/s1
SMILES Code
O=C1C(C2=CC=C(O)C=C2)=COC3=C1C=CC(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)=C3
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Daidzin is an isoflavone that has anti-oxidant, anti-carcinogenic, and anti-atherosclerotic activities; it directly inhibits mitochondrial aldehyde dehydrogenase 2 (IC50 = 80 nM) and is an effective anti-dipsotropic isoflavone.
In vitro activity:
It was next determined if DDZ could alter STAT3 activation in U266 cells. As depicted in Figure 1C, DDZ substantially suppressed the constitutive activation of both p-STAT3 (Tyr705) and p-STAT3(Ser727) in U266 cells. It was next examined whether DDZ could affect the ability of STAT3 to bind to DNA, and it was noted that DDZ could effectively modify the DNA-binding activity of STAT3 (Figure 1D). Additionally, the effect of DDZ to regulate the nuclear localization of STAT3 in U266 cells was examined by immunocytochemistry. Figure 1E,F demonstrate that DDZ could reduce the translocation of phospho-STAT3 and total STAT3 to the nucleus.
Reference: Biomolecules. 2020 Jan; 10(1): 23. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7022648/
In vivo activity:
To determine whether or not daidzin inhibits acetaldehyde metabolism in vivo, plasma acetaldehyde in daidzin-treated hamsters was measured after the administration of a test dose of ethanol. Daidzin treatment (150 mg/kg per day i.p. for 6 days) significantly suppresses (> 70%) hamster ethanol intake. Before ethanol challenge, the residual acetaldehyde concentrations found in the plasma of these hamsters were 1.2, 2.5,and 3 ,AM, respectively (Fig. 2A, t = 0)-i.e., in the range of background values normally found in untreated hamsters kept in our animal facility. After injection of a test ethanol dose (1.3 g/kg i.p.), there is a 4-fold increase in plasma acetaldehyde concentration in all hamsters. These results indicate that (i) the action of daidzin differs from that proposed for the classic, broad-acting ALDH inhibitors (e.g., disulfiram), and (ii) the daidzin-sensitive mitochondrial ALDH is not the one and only enzyme that is essential for acetaldehyde metabolism in golden hamsters.
Reference: Proc Natl Acad Sci U S A. 1995 Sep 12;92(19):8990-3. https://pubmed.ncbi.nlm.nih.gov/7568058/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
48.0 |
115.28 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
416.38
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Yang MH, Jung SH, Chinnathambi A, Alahmadi TA, Alharbi SA, Sethi G, Ahn KS. Attenuation of STAT3 Signaling Cascade by Daidzin Can Enhance the Apoptotic Potential of Bortezomib against Multiple Myeloma. Biomolecules. 2019 Dec 23;10(1):23. doi: 10.3390/biom10010023. PMID: 31878046; PMCID: PMC7022648. 2. Keung WM, Lazo O, Kunze L, Vallee BL. Daidzin suppresses ethanol consumption by Syrian golden hamsters without blocking acetaldehyde metabolism. Proc Natl Acad Sci U S A. 1995 Sep 12;92(19):8990-3. doi: 10.1073/pnas.92.19.8990. PMID: 7568058; PMCID: PMC41093.
3. Wu KC, Lin WY, Sung YT, Wu WY, Cheng YH, Chen TS, Chiang BJ, Chien CT. Glycine tomentella hayata extract and its ingredient daidzin ameliorate cyclophosphamide-induced hemorrhagic cystitis and oxidative stress through the action of antioxidation, anti-fibrosis, and anti-inflammation. Chin J Physiol. 2019 Sep-Oct;62(5):188-195. doi: 10.4103/CJP.CJP_60_19. PMID: 31670282
In vitro protocol:
1. Yang MH, Jung SH, Chinnathambi A, Alahmadi TA, Alharbi SA, Sethi G, Ahn KS. Attenuation of STAT3 Signaling Cascade by Daidzin Can Enhance the Apoptotic Potential of Bortezomib against Multiple Myeloma. Biomolecules. 2019 Dec 23;10(1):23. doi: 10.3390/biom10010023. PMID: 31878046; PMCID: PMC7022648. 2. Keung WM, Lazo O, Kunze L, Vallee BL. Daidzin suppresses ethanol consumption by Syrian golden hamsters without blocking acetaldehyde metabolism. Proc Natl Acad Sci U S A. 1995 Sep 12;92(19):8990-3. doi: 10.1073/pnas.92.19.8990. PMID: 7568058; PMCID: PMC41093.
In vivo protocol:
1. Wu KC, Lin WY, Sung YT, Wu WY, Cheng YH, Chen TS, Chiang BJ, Chien CT. Glycine tomentella hayata extract and its ingredient daidzin ameliorate cyclophosphamide-induced hemorrhagic cystitis and oxidative stress through the action of antioxidation, anti-fibrosis, and anti-inflammation. Chin J Physiol. 2019 Sep-Oct;62(5):188-195. doi: 10.4103/CJP.CJP_60_19. PMID: 31670282. 2. Keung WM, Lazo O, Kunze L, Vallee BL. Daidzin suppresses ethanol consumption by Syrian golden hamsters without blocking acetaldehyde metabolism. Proc Natl Acad Sci U S A. 1995 Sep 12;92(19):8990-3. doi: 10.1073/pnas.92.19.8990. PMID: 7568058; PMCID: PMC41093.
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