(R)-(-)-Gossypol (AT-101) acetic acid | Bcl-2 Inhibitor

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CAS No. :	866541-93-7
Formula :	C₃₂H₃₄O₁₀
M.W :	578.61
SMILES Code :	O=CC1=C(C(O)=C(C(C)C)C2=CC(C)=C(C3=C(C4=C(C(O)=C(C(C(C)C)=C4C=C3C)O)C=O)O)C(O)=C12)O.O=C(C)O
Synonyms :	AT-101 (acetic acid); AT-101 acetic acid; (R)-Gossypol acetic acid
MDL No. :	MFCD00058385

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H361
Precautionary Statements:	P501-P202-P201-P280-P308+P313-P405

U937 leukemia cells	20 μM	12 hours	AT-101 significantly increased apoptosis and mitochondrial injury in U937 leukemia cells, accompanied by caspase-3, caspase-9, and PARP cleavage, and cytochrome c release.	PMC4040709
Jurkat T-lymphoblastic leukemia cells	20 μM	12 hours	AT-101 significantly increased apoptosis in Jurkat T-lymphoblastic leukemia cells, accompanied by caspase-3, caspase-9, and PARP cleavage, and cytochrome c release.	PMC4040709
HL-60 promyelocytic leukemia cells	20 μM	12 hours	AT-101 significantly increased apoptosis in HL-60 promyelocytic leukemia cells, accompanied by caspase-3, caspase-9, and PARP cleavage, and cytochrome c release.	PMC4040709
HUVECs	5 µM	18 hours	AT-101 significantly enhanced the inhibitory effect of CDDP on the migration of HUVECs	PMC4467754
A2780	5 µM	24 h	GAA significantly reduced mitochondrial activity in A2780 cells, including basal OCR, ATP production, and Maximal OCR.	PMC10373366
SKOV3	5 µM	24 h	GAA significantly reduced mitochondrial activity in SKOV3 cells, including basal OCR, ATP production, and Maximal OCR.	PMC10373366
Primary human leukemia cells	20 μM	24 hours	AT-101 significantly increased apoptosis in primary human leukemia cells, accompanied by caspase-3, caspase-9, and PARP cleavage, and cytochrome c release.	PMC4040709
MM-B1	1.56–25 μM	24, 48, and 72 h	AT-101 significantly inhibited the survival of MM-B1 cells, with IC50 values of 9.30 μM at 48 hours and 5.59 μM at 72 hours.	PMC6232343
H-Meso-1	1.56–25 μM	24, 48, and 72 h	AT-101 significantly inhibited the survival of H-Meso-1 cells, with IC50 values of 9.24 μM at 48 hours and 2.66 μM at 72 hours.	PMC6232343
MM-F1	1.56–25 μM	24, 48, and 72 h	AT-101 significantly inhibited the survival of MM-F1 cells, with IC50 values of 9.32 μM at 48 hours and 5.10 μM at 72 hours.	PMC6232343
U87MG	15 µM	48 h	To investigate the effects of AT-101 on protein expression in U87MG cells, results showed a significant downregulation of mitochondrial-related proteins.	PMC6135628
U343	15 µM	48 h	To investigate the effects of AT-101 on protein expression in U343 cells, results showed a significant downregulation of mitochondrial-related proteins.	PMC6135628
A549 cells	5 µM	48 hours	AT-101 significantly enhanced the inhibitory effect of CDDP on the proliferation of A549 cells	PMC4467754
human non-small cell lung cancer A549 cells	5 µM	6 hours	To evaluate the effects of sequential treatment with AT-101 and cisplatin (CDDP) on the proliferation, migration, and apoptosis of A549 cells. The results showed that the sequential treatment significantly inhibited cell proliferation and migration and induced apoptosis.	PMC4271790
VCaP cells	1-10 µM	72 hours	To evaluate the effect of AT-101 on VCaP cell viability, results showed that AT-101 dose-dependently decreased VCaP cell viability after 72 hours	PMC2134900
PC-3 cells	1-10 µM	72 hours	To evaluate the effect of AT-101 on PC-3 cell viability, results showed that AT-101 dose-dependently decreased PC-3 cell viability after 72 hours	PMC2134900
PC-3 (prostate cancer cells)	8.72 ± 0.30 μM (IC50)	72 hours	Evaluate the cytotoxicity of Gos/cRGD-LP on PC-3 cells, results showed that the IC50 of Gos/cRGD-LP was 9.53 ± 0.26 μM, significantly higher than that of free drug, indicating stronger cytotoxicity.	PMC8766252
HCT-116 (colon cancer cells)	6.32 ± 0.40 μM (IC50)	72 hours	Evaluate the cytotoxicity of Gos/cRGD-LP on HCT-116 cells, results showed that the IC50 of Gos/cRGD-LP was 8.93 ± 0.41 μM, significantly higher than that of free drug, indicating stronger cytotoxicity.	PMC8766252

SCID mice	VCaP prostate cancer xenograft model	Oral	15 mg/kg	5 days per week, continuous treatment	To evaluate the efficacy of AT-101 in combination with surgical castration in delaying the onset of androgen-independent prostate cancer growth, results showed that AT-101 combined with surgical castration significantly delayed the onset of androgen-independent prostate cancer growth	PMC2134900
BALB/c Nude mice	PC-3 tumor model	Intravenous injection	15 mg/kg	Once every three days, for 6 times in total	Evaluate the antitumor effect of Gos/cRGD-LP in the PC-3 tumor model, results showed that Gos/cRGD-LP significantly inhibited tumor growth, with a tumor inhibition rate of over 74%.	PMC8766252
BALB/c Nude mice	A549 xenograft model	Oral gavage	35 mg/kg/day	for 10 consecutive days	To evaluate the effects of sequential treatment with AT-101 and cisplatin (CDDP) on tumor growth in the A549 xenograft model. The results showed that the sequential treatment significantly inhibited tumor growth and enhanced the expressions of Bcl-2 and Bcl-xL by downregulating the APE1/STAT3 signaling pathway.	PMC4271790
NOD/SCID mice	U937 xenograft model	Intraperitoneal injection	50 mg/kg	Five times per week for 60 days	AT-101 significantly inhibited tumor growth in the U937 xenograft mouse model, accompanied by RhoA/ROCK1/PTEN signaling activation and Akt inactivation.	PMC4040709
BALB/c Nude mice	A2780 cell subcutaneous xenograft model	intraperitoneal injection	30 mg/kg	every other day for 3 weeks	GAA significantly inhibited the growth of A2780 cell subcutaneous xenografts and did not cause weight loss or liver and kidney function impairment in mice.	PMC10373366
BALB/c Nude mice	A549 xenograft model	Oral and intraperitoneal injection	35 mg/kg/day	10 days	Combination therapy of AT-101 and CDDP significantly inhibited tumor angiogenesis and tumor cell proliferation	PMC4467754
C57BL/6 mice	mouse model intraperitoneally transplanted with #40a cells	intraperitoneal injection	0.1 mg	once a week, up to 17 weeks	AT-101 significantly increased the median survival time of mice (7 weeks vs. 4.5 weeks) and reduced the risk of tumor development.	PMC6232343

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CAS No.: 866541-93-7

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CAS No.: 866541-93-7

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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