(-)-Parthenolide - CAS 20554-84-1
Catalog number: 20554-84-1
Category: Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C15H20O3
Molecular Weight:
248.32
COA:
Inquire
Targets:
HDAC
Description:
(-)-Parthenolide is a sesquiterpene lactone which occurs naturally in the plant feverfew(Tanacetum parthenium) and also promotes the ubiquitination of MDM2 and activates p53 cellular functions.
Purity:
>98%
MSDS:
Inquire
InChIKey:
KTEXNACQROZXEV-PVLRGYAZSA-N
InChI:
InChI=1S/C15H20O3/c1-9-5-4-8-15(3)13(18-15)12-11(7-6-9)10(2)14(16)17-12/h5,11-13H,2,4,6-8H2,1,3H3/b9-5+/t11-,12-,13+,15+/m0/s1
Canonical SMILES:
CC1=CCCC2(C(O2)C3C(CC1)C(=C)C(=O)O3)C
1.Anticancer activity and radiosensitization effect of methyleneisoxazolidin-5-ones in hepatocellular carcinoma HepG2 cells.
Gach K1, Grądzka I2, Wasyk I2, Męczyńska-Wielgosz S2, Iwaneńko T2, Szymański J3, Koszuk J4, Janecki T4, Kruszewski M5, Janecka A6. Chem Biol Interact. 2016 Mar 25;248:68-73. doi: 10.1016/j.cbi.2016.01.011. Epub 2016 Feb 9.
Parthenolide (PTL), a well-known sesquiterpene lactone of natural origin with α,β-unsaturated carbonyl structure, has proven to show promising anti-cancer properties. In this report, anti-proliferative potential of two synthetic methyleneisoxazolidin-5-ones, MZ-6 and MZ-14, with the same structural motif, has been investigated in human hepatoma HepG2 cells. The effects on apoptosis induction and DNA damage were evaluated. All compounds decreased the number of live cells and increased the number of late apoptotic cells. However, only MZ-14 was able to induce DNA damage. Both synthetic compounds increased intracellular reactive oxygen species (ROS) generation and mitochondrial membrane potential changes at the same level as PTL. Additionally, cell survival was analyzed after a combined treatment, in which HepG2 cells were preincubated for 24 h with MZ-6, MZ-14 or PTL and irradiated with different doses of X-rays. The inhibition of cell survival was assessed by the clonogenic assay.
2.The clerodane diterpene casearin J induces apoptosis of T-ALL cells through SERCA inhibition, oxidative stress, and interference with Notch1 signaling.
De Ford C1,2,3, Heidersdorf B3, Haun F2,4, Murillo R5, Friedrich T2,6, Borner C2,4,7, Merfort I1,2,3. Cell Death Dis. 2016 Jan 28;7:e2070. doi: 10.1038/cddis.2015.413.
T-cell acute lymphoblastic leukemia (T-ALL) is an aggressive hematologic malignancy that preferentially affects children and adolescents. Over 50% of human T-ALLs possess activating mutations of Notch1. The clerodane diterpene casearin J (CJ) is a natural product that inhibits the sarcoendoplasmatic reticulum calcium ATPase (SERCA) pump and induces cell death in leukemia cells, but the molecular mechanism of cytotoxicity remains poorly understood. Here we show that owing to SERCA pump inhibition, CJ induces depletion of the endoplasmic reticulum calcium pools, oxidative stress, and apoptosis via the intrinsic signaling pathway. Moreover, Notch1 signaling is reduced in T-ALL cells with auto-activating mutations in the HD-domain of Notch1, but not in cells that do not depend on Notch1 signaling. CJ also provoked a slight activation of NF-κB, and consistent with this notion a combined treatment of CJ and the NF-κB inhibitor parthenolide (Pt) led to a remarkable synergistic cell death in T-ALL cells.
3.Crystal structure of (E)-13-(pyrimidin-5-yl)parthenolide.
Bommagani S1, Penthala NR1, Parkin S2, Crooks PA1. Acta Crystallogr E Crystallogr Commun. 2015 Nov 28;71(Pt 12):1536-8. doi: 10.1107/S2056989015021507. eCollection 2015.
The title compound, C19H22N2O3, {systematic name (1aR,4E,7aS,8E,10aS,10bR)-1a,5-dimethyl-8-[(pyrimidin-5-yl)-methylid-ene]-2,3,6,7,7a,8,10a,10b-octa-hydro-oxireno[2',3':9,10]cyclo-deca-[1,2-b]furan-9(1aH)-one} was obtained from the reaction of parthenolide [systematic name (1aR,7aS,10aS,10bR,E)-1a,5-dimethyl-8-methyl-ene-2,3,6,7,7a,8,10a,10b-octa-hydro-oxireno[2',3':9,10]cyclodeca-[1,2-b]furan-9(1aH)-one] with 5-bromo-pyrimidine under Heck reaction conditions, and was identified as an E isomer. The mol-ecule possesses ten-, five- (lactone) and three-membered (epoxide) rings with a pyrimidine group as a substituent. The ten-membered ring displays an approximate chair-chair conformation, while the lactone ring shows a flattened envelope-type conformation. The dihedral angle between the pyrimidine moiety and the lactone ring system is 29.43 (7)°.
4.Relative In Vitro Potentials of Parthenolide to Induce Apoptosis and Cell Cycle Arrest in Skin Cancer Cells.
George VC, Kumar DR, Kumar RA1. Curr Drug Discov Technol. 2016;13(1):34-40.
BACKGROUND: Parthenolide (PN) has been reported to inhibit proliferation and induces apoptosis in a variety of cancer cells with different mechanisms. Nevertheless, to the best of our knowledge, its relative anticancer activity at lower doses has not been reported in HaCaT immortalized keratinocytes and A375 melanoma cells.
Molecular Weight Calculator Molarity Calculator Solution Dilution Calculator

Related HDAC Products


CAS 251456-60-7 M344

M344
(CAS: 251456-60-7)

M344 is a potent HDAC inhibitor, which can also induced expression of the pro-apoptotic genes, Puma and Bax, together with the morphological features of apoptos...

CAS 149647-78-9 Vorinostat

Vorinostat
(CAS: 149647-78-9)

Vorinostat (suberoylanilide hydroxamic acid, SAHA) is an HDAC inhibitor with IC50 of ~10 nM.

CAS 783355-60-2 Abexinostat

Abexinostat
(CAS: 783355-60-2)

Abexinostat, also known as PCI-24781 or CRA-024781, is novel, broad-spectrum hydroxamic acid-based inhibitor of histone deacetylase (HDAC) with potential antine...

CAS 1688677-89-5 LW479

LW479
(CAS: 1688677-89-5)

LW479 is a HDAC inhibitor with marked cytotoxicity leading to apoptosis and cell cycle arrest in a panel of breast cancer cell lines. LW479 silences EGFR expres...

CAS 848354-66-5 PTACH

PTACH
(CAS: 848354-66-5)

PTACH is a SAHA-based novel inhibitor of histone deacetylase (HDAC). It exerts potent growth inhibition against various human cancer cells, with EC50 values ran...

CAS 404951-53-7 Dacinostat

Dacinostat
(CAS: 404951-53-7)

Dacinostat, also known as LAQ824, is a hydroxamate histone deacetylase inhibitor with potential anticancer activity. LAQ824 sensitized nonsmall cell lung cancer...

CAS 1310693-92-5 Tubastatin A HCl salt

Tubastatin A HCl salt
(CAS: 1310693-92-5)

Tubastatin A is a potent and selective HDAC6 inhibitor. Tubastatin A was substantially more selective than the known HDAC6 inhibitor Tubacin at all isozymes exc...

CAS 414864-00-9 Belinostat

Belinostat
(CAS: 414864-00-9)

Belinostat is a hydroxamic acid-type histone deacetylase (HDAC) inhibitor. Belinostat targets HDAC enzymes to inhibit tumor cell proliferation and angiogenesis,...

CAS 875320-31-3 JNJ 26481585 dihydrochloride

JNJ 26481585 dihydrochloride
(CAS: 875320-31-3)

JNJ 26481585 dihydrochloride is a potent and second-generation pan-HDAC inhibitor (IC50 value 0.11 nM for HDAC1, and sub-nanomolar for HDAC2, HDAC4, HDAC10, and...

CAS 151720-43-3 Oxamflatin

Oxamflatin
(CAS: 151720-43-3)

Oxamflatin, also known as Metacept-3, an aromatic sulfonamide derivative, is a cell-permeable, potent HDAC inhibitor (IC50= 15.7 nM) with antitumor effect.

HDAC-IN-1
(CAS: 1239610-44-6)

HDAC-IN-1, an analogue of MC 1568, is a Iia HDACs inhibitor that could probably influence myogenesis and adipogenesis.

CAS 1622921-15-6 Remodelin

Remodelin
(CAS: 1622921-15-6)

Remodelin, via inhibition of NAT10, mediates nuclear shape rescue of LMNA depleted cells by microtubule reorganization, and improves nuclear shape and fitness o...

CAS 864814-88-0 Resminostat

Resminostat
(CAS: 864814-88-0)

Resminostat is an orally bioavailable inhibitor of histone deacetylases (HDACs) with potential antineoplastic activity. Resminostat binds to and inhibits HDACs ...

ST7612AA1
(CAS: 1428535-92-5)

ST7612AA1 is a potent Histone deacetylase (HDCA) inhibitor. It showed an in vitro activity in the nanomolar range associated with a remarkable in vivo antitumor...

CAS 1187075-34-8 Resminostat hydrochloride

Resminostat hydrochloride
(CAS: 1187075-34-8)

Resminostat is an inhibitor of histone deacetylase (HDAC) with IC50 values of 42.5nM, 50.1nM and 71.8nM, respectively against HDAC1, 3 and 6. As an inhibitor of...

CAS 1236199-60-2 EDO-S101

EDO-S101
(CAS: 1236199-60-2)

EDO-S101 is a pan HDAC inhibitor (IC50= 9, 9 and 25 nM for HDAC1, HDAC2 and HDAC3, respectively). EDO-S101 is a first-in-class fusion molecule that combines DNA...

CAS 20554-84-1 (-)-Parthenolide

(-)-Parthenolide
(CAS: 20554-84-1)

(-)-Parthenolide is a sesquiterpene lactone which occurs naturally in the plant feverfew(Tanacetum parthenium) and also promotes the ubiquitination of MDM2 and ...

CAS 852475-26-4 MC1568

MC1568
(CAS: 852475-26-4)

Givinostat hydrochloride
(CAS: 199657-29-9)

Givinostat hydrochloride is the hydrochloride salt form of Givinostat. Givinostat, also called as GVS or ITF2357, a potent HDAC inhibitor for Maize HD2 (IC50= 1...

CAS 541-15-1 L-carnitine

L-carnitine
(CAS: 541-15-1)

L-carnitine is a constituent striated muscle and liver, and also a cofactor involved in fatty acid metabolism for transporting fatty acids through the inner mit...

Chemical Structure

CAS 20554-84-1 (-)-Parthenolide

Quick Inquiry

Verification code

Featured Items