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Details

Stereochemistry ACHIRAL
Molecular Formula C10H10O5
Molecular Weight 210.1834
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 2,4-DIACETYLPHLOROGLUCINOL

SMILES

CC(=O)C1=C(O)C(C(C)=O)=C(O)C=C1O

InChI

InChIKey=PIFFQYJYNWXNGE-UHFFFAOYSA-N
InChI=1S/C10H10O5/c1-4(11)8-6(13)3-7(14)9(5(2)12)10(8)15/h3,13-15H,1-2H3

HIDE SMILES / InChI

Molecular Formula C10H10O5
Molecular Weight 210.1834
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

2,4-Diacetylphloroglucinol (DAPG) is a secondary metabolite of the P. Fluorescens strain CHAo which inhibits bacteria, fungi, and plants and suppresses pathogens. 2,4-Diacetylphlo roglucinol also displays antiviral activity against DNA and RNA viruses with envelopes. 2,4-Diacetylphloroglucinol exhibited a broad-spectrum of anti-leukemic, anti-lung, and anti-breast cancer properties. The anticancer and antimetastatic activities of DAPG were mediated by the inhibition of ROS, NF-κB, Bcl-2, MMP-2, VEGF and primary inflammatory mediators such as TNF-α, IL-6, IL-1β and NO. The DAPG induced apoptosis in cancer cells by intrinsic and extrinsic pathways via the release of cytochrome-C, upregulation of Bax and the activation of caspases and also, exhibited anti-inflammatory activity by the inhibition of LPS-inflammed cell proliferation of macrophage (Raw 264.7), monocytic cells (THP-1) and peripheral blood mononuclear cells (PBMCs). Results further confirmed that the DAPG inhibited the primary inflammatory mediators in cancer cells and inflammed immune cells through the down regulation of NF-κB.

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
5.82 µM [IC50]
6.74 µM [IC50]
29.8 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
2,4-Diacetylphloroglucinol inhibited MMP-2, MMP-9, and NF-κB activities with the low IC50 concentration of 5.82 ± 1.6, 6.74 ± 1.2, and 10.7 ± 1.5 uM respectively. DAPG inhibited the Bcl-2, Bcl-xL and Bcl-w activities with the high IC50 concentration of 29.8 ± 1.9, 85.9 ± 2.7, and 97.4 ± 1.5 uM, respectively. These results correlate with the relatively high IC50 concentration of 16.3 ± 1.76, 7.67 ± 0.78, and 10.7 ± 0.96 uM in the Bcl-2-overexpressing HL-60, K562 and Raji leukemic cells than the metastatic A549 and MDA MB-231 cancer cells with the low IC50 concentration of 0.06 ± 0.02 and 0.08 ± 0.01 uM, respectively, compared to the healthy, human embryonic kidney (HEK-293) cells with the high IC50 concentration of 54.7 ± 1.43 uM.
Substance Class Chemical
Record UNII
8XV4YYO3WN
Record Status Validated (UNII)
Record Version