Daidzin | CAS#552-66-9 | aldehyde dehydrogenase 2 inhibitor

Daidzin
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 561538

CAS#: 552-66-9

Description: Daidzin is an aldehyde dehydrogenase 2 inhibitor. It decreases DNA damage but does not alter transmitter release by cisplatin. Daidzin is also an antidipsotropic agent, and shows potential for the treatment of alcohol dependency.

Chemical Structure

Daidzin

CAS# 552-66-9

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 561538
Name: Daidzin
CAS#: 552-66-9
Chemical Formula: C21H20O9
Exact Mass: 416.11
Molecular Weight: 416.382
Elemental Analysis: C, 60.58; H, 4.84; O, 34.58

Price and Availability

Size	Price	Availability
100mg	USD 350	2 Weeks
250mg	USD 650	2 weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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

Appearance: Solid powder

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

More Info:

Product Data:

Product Data

Instruction:

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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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	48.0	115.28

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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