1. Anti-infection
  2. Influenza Virus
  3. 3-Deoxysappanchalcone

3-Deoxysappanchalcone is a kinase inhibitor and antiviral agent. 3-Deoxysappanchalcone directly targets MET, EGFR, AKT, mTOR, p38 MAPK, JNK, thrombin, FXa, and influenza virus neuraminidase, thereby regulating related signaling pathways. 3-Deoxysappanchalcone induces cell cycle arrest, ROS production, and apoptosis. 3-Deoxysappanchalcone exhibits anti-inflammatory, anti-allergic, anticoagulant, and antithrombotic activities. 3-Deoxysappanchalcone is applicable to research related to gefitinib-resistant lung cancer, esophageal squamous cell carcinoma, thrombosis, and influenza virus infection.

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3-Deoxysappanchalcone

3-Deoxysappanchalcone Chemical Structure

CAS No. : 112408-67-0

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Based on 2 publication(s) in Google Scholar

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Description

3-Deoxysappanchalcone is a kinase inhibitor and antiviral agent. 3-Deoxysappanchalcone directly targets MET, EGFR, AKT, mTOR, p38 MAPK, JNK, thrombin, FXa, and influenza virus neuraminidase, thereby regulating related signaling pathways. 3-Deoxysappanchalcone induces cell cycle arrest, ROS production, and apoptosis. 3-Deoxysappanchalcone exhibits anti-inflammatory, anti-allergic, anticoagulant, and antithrombotic activities. 3-Deoxysappanchalcone is applicable to research related to gefitinib-resistant lung cancer, esophageal squamous cell carcinoma, thrombosis, and influenza virus infection[1][3][4][5].

IC50 & Target

IC50: 1.06 μM (H3N2)[2]

Cellular Effect
Cell Line Type Value Description References
3T3-L1 IC50
41.8 μM
Compound: 6
Antiadipogenic activity against mouse 3T3L1 cells assessed as inhibition of differentiation after 7 days by oil-red O staining
Antiadipogenic activity against mouse 3T3L1 cells assessed as inhibition of differentiation after 7 days by oil-red O staining
[PMID: 19757853]
A549 IC50
32.6 μM
Compound: 11
Cytotoxicity against human A549 cells after 3 days by MTT assay
Cytotoxicity against human A549 cells after 3 days by MTT assay
[PMID: 21800859]
A549 IC50
62.1 μM
Compound: 29
Cytotoxicity against human A549 cells after 72 hrs by MTT assay
Cytotoxicity against human A549 cells after 72 hrs by MTT assay
[PMID: 18440233]
A549 IC50
66.5 μM
Compound: 26
Cytotoxicity against human A549 cells after 72 hrs by MTT assay
Cytotoxicity against human A549 cells after 72 hrs by MTT assay
[PMID: 19689125]
B16-BL6 IC50
49.9 μM
Compound: 26
Cytotoxicity against mouse B16-BL6 cells after 72 hrs by MTT assay
Cytotoxicity against mouse B16-BL6 cells after 72 hrs by MTT assay
[PMID: 19689125]
B16-BL6 IC50
56.3 μM
Compound: 29
Cytotoxicity against mouse B16-BL6 cells after 72 hrs by MTT assay
Cytotoxicity against mouse B16-BL6 cells after 72 hrs by MTT assay
[PMID: 18440233]
Ca9-22 IC50
57.56 μM
Compound: 11
Cytotoxicity against human Ca9-22 cells after 3 days by MTT assay
Cytotoxicity against human Ca9-22 cells after 3 days by MTT assay
[PMID: 21800859]
HT-1080 IC50
26.7 μM
Compound: 26
Cytotoxicity against human HT1080 cells after 72 hrs by MTT assay
Cytotoxicity against human HT1080 cells after 72 hrs by MTT assay
[PMID: 19689125]
HT-1080 IC50
51.2 μM
Compound: 29
Cytotoxicity against human HT1080 cells after 72 hrs by MTT assay
Cytotoxicity against human HT1080 cells after 72 hrs by MTT assay
[PMID: 18440233]
HeLa IC50
33.3 μM
Compound: 26
Cytotoxicity against human HeLa cells after 72 hrs by MTT assay
Cytotoxicity against human HeLa cells after 72 hrs by MTT assay
[PMID: 19689125]
HeLa IC50
67.9 μM
Compound: 29
Cytotoxicity against human HeLa cells after 72 hrs by MTT assay
Cytotoxicity against human HeLa cells after 72 hrs by MTT assay
[PMID: 18440233]
Hep 3B2 IC50
17.89 μM
Compound: 11
Cytotoxicity against human Hep3B cells after 3 days by MTT assay
Cytotoxicity against human Hep3B cells after 3 days by MTT assay
[PMID: 21800859]
HepG2 IC50
7.37 μM
Compound: 11
Cytotoxicity against human HepG2 cells after 3 days by MTT assay
Cytotoxicity against human HepG2 cells after 3 days by MTT assay
[PMID: 21800859]
MCF7 IC50
51.41 μM
Compound: 11
Cytotoxicity against human MCF7 cells after 3 days by MTT assay
Cytotoxicity against human MCF7 cells after 3 days by MTT assay
[PMID: 21800859]
MDA-MB-231 IC50
44.44 μM
Compound: 11
Cytotoxicity against human MDA-MB-231 cells after 3 days by MTT assay
Cytotoxicity against human MDA-MB-231 cells after 3 days by MTT assay
[PMID: 21800859]
RAW264.7 IC50
8.1 μM
Compound: 13
Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced NO production after 24 hrs by Griess method
Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced NO production after 24 hrs by Griess method
[PMID: 23127886]
In Vitro

3-Deoxysappanchalcone (12 h) directly binds to EGFR and MET proteins in HCC827GR gefitinib-resistant human lung adenocarcinoma cells[1].
3-Deoxysappanchalcone (3-12 μM; 1 h) inhibits purified EGFR kinase activity with dose-dependent efficacy[1].
3-Deoxysappanchalcone (3-12 μM; 24-48 h) reduces HCC827GR gefitinib-resistant human lung adenocarcinoma cell viability in a dose- and time-dependent manne[1].
3-Deoxysappanchalcone (6-12 μM; 48 h) induces apoptotic cell death in HCC827GR gefitinib-resistant human lung adenocarcinoma cells in a dose-dependent manner[1].
3-Deoxysappanchalcone (6-12 μM; 48 h) induces G2/M cell cycle arrest and increases apoptotic sub-G1 cell population in HCC827GR gefitinib-resistant human lung adenocarcinoma cells[1].
3-Deoxysappanchalcone (6-12 μM; 48 h) inhibits phosphorylation of EGFR, MET, AKT, and ERK in HCC827GR gefitinib-resistant human lung adenocarcinoma cells, reducing p-EGFR to 0.31-fold and p-MET to 0.24-fold of control at 12 μM after 48 h[1].
3-Deoxysappanchalcone (6-12 μM; 48 h) increases intracellular ROS levels and induces ER stress in HCC827GR gefitinib-resistant human lung adenocarcinoma cells, and ROS scavenger NAC abrogates 3-DSC-induced cell death[1].
3-Deoxysappanchalcone (6-12 μM; 48 h) induces mitochondrial depolarization and intrinsic mitochondrial apoptosis in HCC827GR gefitinib-resistant human lung adenocarcinoma cells, and modulating Bcl-2 family proteins and cytochrome C translocation[1].
3-Deoxysappanchalcone (3-DSC) (5-20 μM; 48 h) induces concentration-dependent multi-caspase activation and upregulation of cleaved caspase-3 and cleaved caspase-7 expression in KYSE 30 and KYSE 410 ESCC cells, and this caspase activation is reversed by pretreatment with the ROS scavenger NAC (6 mM; 3 h prior to 3-DSC treatment)[3].
3-Deoxysappanchalcone (1-20 μM; 1 min) significantly prolongs aPTT and PT in human plasma at concentrations of 5 μM and higher, with concentrations of 18.7 μM and 17.3 μM required to double aPTT and PT, respectively[4].
3-Deoxysappanchalcone (2-20 μM; 20 min) dose-dependently reduces the maximum rate of thrombin-catalyzed fibrin polymerization in human plasma at concentrations of 2, 3, 5, 10, and 20 μM[4].
3-Deoxysappanchalcone (5-50 μM; 48 h) exhibits no cytotoxicity in HUVECs at concentrations up to 50 μM following 48 h of incubation[4].
3-Deoxysappanchalcone (0.001-10 μM; 1 min) dose-dependently inhibits the amidolytic activity of thrombin in a cell-free system at concentrations of 0.001, 0.01, 0.1, 1, and 10 μM, with significant inhibition at 1 μM and higher[4].
3-Deoxysappanchalcone (0.001-10 μM; 1 min) dose-dependently inhibits the amidolytic activity of FXa in a cell-free system at concentrations of 0.001, 0.01, 0.1, 1, and 10 μM, with significant inhibition at 1 μM and higher[4].
3-Deoxysappanchalcone (1-20 μM; 10 min preincubation) dose-dependently inhibits thrombin production from prothrombin in HUVECs at concentrations of 1, 2, 3, 5, 10, and 20 μM following a 10 min preincubation[4].
3-Deoxysappanchalcone (1-20 μM; 10 min preincubation) dose-dependently inhibits TNF-α-stimulated FXa production in HUVECs at concentrations of 1, 2, 3, 5, 10, and 20 μM following a 10 min preincubation[4].
3-Deoxysappanchalcone (2-20 μM; 18 h) dose-dependently suppresses TNF-α-stimulated PAI-1 secretion in HUVECs at concentrations of 2, 3, 5, 10, and 20 μM over 18 h, mitigating the TNF-α-induced increase in the PAI-1/t-PA ratio without significantly affecting t-PA secretion[4].
3-Deoxysappanchalcone inhibits influenza virus A/PR/8/34 (H1N1) NA with an IC50 of 14.6 μg/mL[5].
3-Deoxysappanchalcone inhibits influenza virus A/Guangdong/243/72 (H3N2) NA with an IC50 of 17.4 μg/mL[5].
3-Deoxysappanchalcone inhibits influenza virus B/Jiangsu/10/2003 NA with an IC50 of 18.6 μg/mL[5].
3-Deoxysappanchalcone inhibits influenza virus A/Guangdong/243/72 (H3N2)-induced cytopathic effects in MDCK cells with an IC50 of 1.06 μg/mL, a CC50 of 17.25 μg/mL, and a selective index of 16.27[5].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Cell Viability Assay[1]

Cell Line: HCC827GR gefitinib-resistant human lung adenocarcinoma cells
Concentration: 3-12 μM (24 h incubation); 3-12 μM (48 h incubation)
Incubation Time: 24 h; 48 h
Result: Reduced HCC827GR cell viability in a dose- and time-dependent manner.

Apoptosis Analysis[1]

Cell Line: HCC827GR gefitinib-resistant human lung adenocarcinoma cells
Concentration: 6-12 μM
Incubation Time: 48 h
Result: Induced apoptotic cell death in a dose-dependent manner.

Cell Cycle Analysis[1]

Cell Line: HCC827GR gefitinib-resistant human lung adenocarcinoma cells
Concentration: 6-12 μM
Incubation Time: 48 h
Result: Increased the sub-G1 (apoptotic) cell population and induced G2/M cell cycle arrest.

Western Blot Analysis[1]

Cell Line: HCC827GR gefitinib-resistant human lung adenocarcinoma cells
Concentration: 6-12 μM
Incubation Time: 48 h
Result: Reduced phosphorylation of EGFR (Tyr1068) to 0.88-, 0.76-, and 0.31-fold of control at 6, 9, and 12 μM, respectively, without altering total EGFR protein levels.
Reduced phosphorylation of MET (Tyr1234/1235) to 0.94-, 0.27-, and 0.24-fold of control at 6, 9, and 12 μM, respectively, without altering total MET protein levels.
Reduced phosphorylation of downstream AKT (Ser473) to 0.72-, 0.39-, and 0.32-fold of control, and phosphorylation of ERK (Thr202/Tyr204) to 0.88-, 0.85-, and 0.68-fold of control at 6, 9, and 12 μM, respectively, without altering total AKT or ERK protein levels.

ELISA Assay[4]

Cell Line: Human umbilical vein endothelial cells (HUVECs)
Concentration: 2-20 μM
Incubation Time: 18 h (with TNF-α)
Result: Markedly suppressed TNF-α-stimulated PAI-1 release in a concentration-dependent fashion, with significant inhibition observed from 5 μM onward.
Did not significantly affect t-PA secretion from HUVECs.
Mitigated the TNF-α-induced increase in the PAI-1/t-PA ratio.
In Vivo

3-Deoxysappanchalcone (3-DSC) (50 mg/kg; i.p.; single dose 1 hour prior to LPS challenge) provides 100% survival protection against LPS-induced lethal systemic inflammation in male C57BL/6 mice[2].
3-Deoxysappanchalcone (0.02-0.4 mg/kg; i.v.) significantly prolongs tail bleeding time in male C57BL/6 mice at doses of 0.1 mg/kg, 0.2 mg/kg, and 0.4 mg/kg, with the highest tested dose (0.4 mg/kg) extending bleeding time to 82.3 s[4].
3-Deoxysappanchalcone (0.02-0.4 mg/kg; i.v.) significantly prolongs ex vivo aPTT and PT in male C57BL/6 mice at doses of 0.1 mg/kg, 0.2 mg/kg, and 0.4 mg/kg, with the highest tested dose (0.4 mg/kg) increasing aPTT to 47.9 ± 0.8 s and PT to 29.4 ± 1.2 s[4].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model: C57BL/6 (male, 20-22 g, LPS-induced systemic inflammation)[2]
Dosage: 50 mg/kg
Administration: i.p.; single dose (1 hour prior to LPS challenge)
Result: Achieved 100% survival rate over 6 days.
Animal Model: C57BL/6 (male, 6-7 weeks old, 27 g)[4]
Dosage: 0.02 mg/kg; 0.04 mg/kg; 0.06 mg/kg; 0.1 mg/kg; 0.2 mg/kg; 0.4 mg/kg
Administration: i.v.
Result: Prolonged tail bleeding time to 48.1 s at 0.1 mg/kg, 63.1 s at 0.2 mg/kg, and 82.3 s at 0.4 mg/kg.
Prolonged ex vivo aPTT to 35.4 s and PT to 23.8 s at 0.1 mg/kg, aPTT to 38.5 s and PT to 28.7 s at 0.2 mg/kg, and aPTT to 47.9 s and PT to 29.4 s at 0.4 mg/kg.
Molecular Weight

270.28

Formula

C16H14O4

CAS No.
Appearance

Solid

Color

Light yellow to yellow

SMILES

O=C(/C=C/C1=CC=C(C=C1)O)C2=CC=C(C=C2OC)O

Structure Classification
Initial Source
Shipping

Room temperature in continental US; may vary elsewhere.

Storage

4°C, protect from light

*In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)

Solvent & Solubility
In Vitro: 

DMSO : 50 mg/mL (184.99 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

Preparing
Stock Solutions
Concentration Solvent Mass 1 mg 5 mg 10 mg
1 mM 3.6999 mL 18.4993 mL 36.9987 mL
5 mM 0.7400 mL 3.6999 mL 7.3997 mL
View the 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 (protect from light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

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Purity & Documentation

Purity: 99.77%

References

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 (protect from light). 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 3.6999 mL 18.4993 mL 36.9987 mL 92.4967 mL
5 mM 0.7400 mL 3.6999 mL 7.3997 mL 18.4993 mL
10 mM 0.3700 mL 1.8499 mL 3.6999 mL 9.2497 mL
15 mM 0.2467 mL 1.2333 mL 2.4666 mL 6.1664 mL
20 mM 0.1850 mL 0.9250 mL 1.8499 mL 4.6248 mL
25 mM 0.1480 mL 0.7400 mL 1.4799 mL 3.6999 mL
30 mM 0.1233 mL 0.6166 mL 1.2333 mL 3.0832 mL
40 mM 0.0925 mL 0.4625 mL 0.9250 mL 2.3124 mL
50 mM 0.0740 mL 0.3700 mL 0.7400 mL 1.8499 mL
60 mM 0.0617 mL 0.3083 mL 0.6166 mL 1.5416 mL
80 mM 0.0462 mL 0.2312 mL 0.4625 mL 1.1562 mL
100 mM 0.0370 mL 0.1850 mL 0.3700 mL 0.9250 mL
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