CAS No. :	136164-66-4
Formula :	C₂₁H₃₀O₆
M.W :	378.46
SMILES Code :	CCCCCCCCC/C(C(O)=O)=C\C1=C(C)C(C(OC)=C(OC)C1=O)=O
Synonyms :	APX-3330
MDL No. :	MFCD00901331

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H411
Precautionary Statements:	P273-P312-P501

XPA1 cells	20-30 µM	72 hours	E3330 significantly inhibits the growth of XPA1 cells	Mol Cancer Ther. 2008 Jul;7(7):2012-21.
PANC1 cells	20-30 µM	72 hours	E3330 significantly inhibits the growth of PANC1 cells	Mol Cancer Ther. 2008 Jul;7(7):2012-21.
Dental Papilla Cells (DPCs)	10 µM	1 day, 3 days, 6 days, 9 days	E3330 promotes the osteo/odontogenic differentiation capacity of DPCs by inhibiting the redox function of Ape1 and activating the canonical Wnt signaling pathway.	Sci Rep. 2015 Dec 7;5:17483.
HepG2 cells	10-100 µM	12 hours	E3330 synergistically increased cytotoxicity when combined with TRAIL, TNFα, and Fas ligand	World J Gastroenterol. 2005 Oct 28;11(40):6258-61.
SKHep1 cells	10-100 µM	12 hours	E3330 synergistically increased cytotoxicity when combined with TRAIL, TNFα, and Fas ligand	World J Gastroenterol. 2005 Oct 28;11(40):6258-61.
HLE cells	10-100 µM	12 hours	E3330 decreased NFκB levels in a dose-dependent manner in HLE cells stimulated by TNFα and TRAIL	World J Gastroenterol. 2005 Oct 28;11(40):6258-61.
Retinal vascular endothelial cells (RVECs)	10, 25, 50, 100 µM	2 days	Evaluated the effect of E3330 on RVEC proliferation, showing dose-dependent inhibition of RVEC growth	Antioxid Redox Signal. 2008 Nov;10(11):1853-67.
FLO-1 cells	40 µM	20 minutes	To investigate the effect of E3330 on ABS-induced E-cadherin cleavage and EMT, results showed that E3330 downregulated MMP14 and abrogated ABS-induced EMT.	Gut. 2023 Dec 7;73(1):47-62.
OE19 cells	40 µM	20 minutes	To investigate the effect of E3330 on ABS-induced E-cadherin cleavage and EMT, results showed that E3330 downregulated MMP14 and abrogated ABS-induced EMT.	Gut. 2023 Dec 7;73(1):47-62.
OE33 cells	40 µM	20 minutes	To investigate the effect of E3330 on ABS-induced E-cadherin cleavage and EMT, results showed that E3330 downregulated MMP14 and abrogated ABS-induced EMT.	Gut. 2023 Dec 7;73(1):47-62.
OE33 cells	100 µM	20 minutes	To investigate the inhibitory effect of E3330 on APE1 redox function, it was found that E3330 treatment led to a significant decrease in NRF2 transcriptional activity.	Redox Biol. 2021 Jul;43:101970.
FLO1 cells	100 µM	20 minutes	To investigate the inhibitory effect of E3330 on APE1 redox function, it was found that E3330 treatment led to a significant decrease in NRF2 transcriptional activity.	Redox Biol. 2021 Jul;43:101970.
CPB cells	100 µM	20 minutes	To investigate the inhibitory effect of E3330 on APE1 redox function, it was found that E3330 treatment led to a significant decrease in NRF2 transcriptional activity.	Redox Biol. 2021 Jul;43:101970.
Bone marrow-derived dendritic cells (BMDCs)	50 µM	24 hours	E3330 up-regulated IL-12 p35 and p40 gene expression but decreased IL-12 secretion	J Biol Chem. 2016 Nov 4;291(45):23672-23680.
Primate choroid endothelial cells (CECs)	25-100 µM	24 hours	E3330 dose-dependently suppressed CEC proliferation, migration, and tube formation without noticeable cell toxicity.	Invest Ophthalmol Vis Sci. 2014 Jun 26;55(7):4461-9.
3T3-L1 cells	50 µM	24 hours	E3330 inhibited the redox function of APE1/Ref-1, increasing the mRNA and protein levels of C/EBP-α, PPAR-γ, and aP2, promoting adipocyte differentiation.	Int J Mol Sci. 2023 Feb 7;24(4):3251.
Lin-negative bone marrow cells	0.5 µM	36~48 hours	E3330 treatment of Tet2-KO Lin-negative bone marrow cells inhibits IL-6 induced cell survival	Cell Stem Cell. 2018 Dec 6;23(6):833-849.e5.
Non-small cell lung cancer (NSCLC) cell lines	1.55 µM	4 days	To evaluate the sensitivity of NSCLC cell lines to 6-thio-dG, finding 73/77 cell lines were sensitive and 4/77 were resistant.	Mol Cancer Ther. 2017 Jul;16(7):1401-1411.
U937 monocyte-like cells	100 µM	4 hours	To investigate the effects of E3330 on inflammatory response in U937 cells, results showed that E3330 treatment reduced cell viability and expression of pro-inflammatory cytokines.	Front Cell Dev Biol. 2021 Sep 20;9:731588.
SKOV-3X ovarian cancer cells	80 µM (IC50)	40 hours	To evaluate the inhibitory effect of E3330 and its analogues on NF-κB activity, results showed that E3330 and its analogues could inhibit NF-κB activation in a dose-dependent manner	Antioxid Redox Signal. 2011 Apr 15;14(8):1387-401.
H1693 NSCLC cells	10 µM	4-7 days	Overexpression of SLC43A3 in H1693 cells increased sensitivity to 6-thio-dG.	Mol Cancer Ther. 2017 Jul;16(7):1401-1411.
HCC4017 NSCLC cells	10 µM	4-7 days	Knockdown of SLC43A3 by siRNA resulted in resistance to 6-thio-dG in HCC4017 cells.	Mol Cancer Ther. 2017 Jul;16(7):1401-1411.
Panc-1 cells	87 µM (ED50)	48 hours	To evaluate the effect of E3330 on the proliferation of pancreatic cancer cells, results showed that E3330 significantly slowed cell growth in a dose-dependent manner.	Mol Cancer Ther. 2011 Sep;10(9):1698-708.
CD4+ T cells	50 µM	72 hours	E3330 had no significant effect on the induction of IFN-γ-producing T cells in the absence of APCs	J Biol Chem. 2016 Nov 4;291(45):23672-23680.
OT-II mouse splenocytes	50 µM	72 hours	E3330 significantly increased the induction of IFN-γ-producing OT-II T cells	J Biol Chem. 2016 Nov 4;291(45):23672-23680.
PaCa-2 cells	135 µM (ED50)	72 hours	To evaluate the effect of E3330 on the proliferation of pancreatic cancer cells, results showed that E3330 significantly slowed cell growth in a dose-dependent manner.	Mol Cancer Ther. 2011 Sep;10(9):1698-708.
HPNE cells	50 µM	72 hours	E3330 has no suppressive effects on the growth of HPNE cells	Mol Cancer Ther. 2008 Jul;7(7):2012-21.
Panc-1 cells	67.5 µM	8-12 hours	To evaluate the effect of E3330 on the adhesion ability of pancreatic cancer cells, results showed that E3330 significantly inhibited cell adhesion.	Mol Cancer Ther. 2011 Sep;10(9):1698-708.
PaCa-2 cells	67.5 µM	8-12 hours	To evaluate the effect of E3330 on the adhesion ability of pancreatic cancer cells, results showed that E3330 significantly inhibited cell adhesion.	Mol Cancer Ther. 2011 Sep;10(9):1698-708.
H2087 NSCLC cells	3 µM	9-18 days	Established acquired resistance model in H2087 cells, finding downregulation of SLC43A3 in resistant clones.	Mol Cancer Ther. 2017 Jul;16(7):1401-1411.
OE33 cells	100 µM	Overnight	E3330 inhibited ABS-mediated increase in YAP1 protein levels	J Exp Clin Cancer Res. 2022 Sep 1;41(1):264.
FLO-1 cells	100 µM	Overnight	E3330 inhibited ABS-mediated increase in YAP1 protein levels	J Exp Clin Cancer Res. 2022 Sep 1;41(1):264.
Hey-C2 ovarian cancer cells	38.9 µM (LD50)		To evaluate the effect of E3330 and its analogues on cell growth, results showed that E3330 and its analogues could inhibit cell growth	Antioxid Redox Signal. 2011 Apr 15;14(8):1387-401.

Mice	PL2-IL1β transgenic Mice model	Intraperitoneal injection	20 mg/kg	28 days	To investigate the effect of E3330 on PDX tumor growth and invasion, results showed that E3330 suppressed tumor growth and invasion and restored E-cadherin expression levels.	Gut. 2023 Dec 7;73(1):47-62.
Mice	Tet2-KO mice	Oral gavage	20 mg/kg	Daily for 12 weeks	Long-term treatment of juvenile Tet2-KO mice with E3330 rescues multiple phenotypic defects associated with Tet2 deficiency	Cell Stem Cell. 2018 Dec 6;23(6):833-849.e5.
Mice	PDX Mice model	Oral gavage	20 mg/kg	Every weekday for 4 weeks	E3330 significantly inhibited PDX tumor volume and enhanced PDX mice survival	J Exp Clin Cancer Res. 2022 Sep 1;41(1):264.
C57BL/6 mice	Laser-induced CNV Mice model	Intravitreal injection	200 μM (1 μL )	Single injection, lasted for 2 weeks	E3330 significantly suppressed laser-induced CNV development without causing tissue toxicity.	Invest Ophthalmol Vis Sci. 2014 Jun 26;55(7):4461-9.
C57BL/6J mice	Laser-induced choroidal neovascularization (CNV) model	Intravitreal injection	200 μM (1 μL )	Single injection, lasted for 2 weeks	A single intravitreal injection of E3330 significantly reduced the area of laser-induced CNV lesions, indicating that E3330 attenuated damage to the RPE-Bruch's membrane complex in vivo.	Redox Biol. 2014 Feb 21;2:485-94
NOD/SCID mice	Pancreatic cancer xenograft model	Intraperitoneal injection	25 mg/kg	Twice daily for 10-12 days	To evaluate the effect of E3330 on tumor growth in pancreatic cancer xenograft models in vivo, results showed that E3330 significantly inhibited tumor growth.	Mol Cancer Ther. 2011 Sep;10(9):1698-708.
Nude mice	T24 subcutaneous tumor model	Intraperitoneal injection	50 mg/kg	Every 12 hours for up to 12 days	Inhibition of tumor growth	Mol Cancer Ther. 2019 Nov;18(11):1947-1960

Bio Calculators
Preparing Stock Solutions		1mg	5mg	10mg
Preparing Stock Solutions	1 mM 5 mM 10 mM	2.64mL 0.53mL 0.26mL	13.21mL 2.64mL 1.32mL	26.42mL 5.28mL 2.64mL
Dissolving Methods	Animal experiment Please choose the appropriate dissolution scheme according to your animal administration guide.For the following dissolution schemes, clear stock solution should be prepared according to in vitro experiments, and then cosolvent should be added in turn: in order to ensure the reliability of the experimental results, the clarified stock solution can be properly preserved according to the storage conditions; The working fluid for in vivo experiment is recommended to be prepared now and used on the same day; The percentage shown in front of the following solvent refers to the volume ratio of the solvent in the final solution; If precipitation or precipitation occurs in the preparation process, it can be assisted by heating and/or ultrasound. Protocol 1 Protocol 2

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CAS No.: 136164-66-4

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CAS No.: 136164-66-4

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed