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CAS No. :	478336-92-4
Formula :	C₁₂H₁₃NO₄
M.W :	235.24
SMILES Code :	O=C(OC)CC1CC(C2=CC=C(O)C=C2)=NO1
Synonyms :	MIF Antagonist; Macrophage Migration Inhibitory Factor
MDL No. :	MFCD22376813
InChI Key :	AIXMJTYHQHQJLU-UHFFFAOYSA-N
Pubchem ID :	4633677

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P280-P305+P351+P338

Human peripheral blood monocytes	50 µM	0.5-4 hours	ISO-1 profoundly inhibited LPS-induced TNF-α, CXCL8, and IL-1β release. When the interval between ISO-1 and LPS was 4 hr, IL-1β release was no longer inhibited, while TNF-α and CXCL8 release remained blocked.	Immunology. 2008 Sep;125(1):101-10.
PC12 cells	7 µM	1 hour	To evaluate the protective effect of ISO-1 against AGEs and Aβ1-40-induced PC12 cell injury, results showed that ISO-1 significantly improved the survival rate and reduced the expression of inflammatory mediators in the AD cell model.	Mol Med Rep. 2019 Sep;20(3):2135-2142.
Human cartilage end plate chondrocytes	100 µg/mL	12 hours	To evaluate the inhibitory effect of ISO-1 on MIF-induced inflammatory cytokine secretion, results showed that ISO-1 significantly downregulated the secretion of IL-6, IL-8, and PGE2.	Clin Orthop Relat Res. 2014 Jun;472(6):1943-54.
Human monocyte-derived macrophages (MDM)	50 µM	1-24 hours	ISO-1 had no significant effect on LPS-induced TNF-α and CXCL8 release in MDM.	Immunology. 2008 Sep;125(1):101-10.
Human neuroblastoma cells SH-SY5Y	50 µM	24 hours	To evaluate the effect of ISO-1 on cell survival and expression of apoptosis-related proteins in an oxygen-glucose deprivation/reperfusion (OGD/R) model. Results showed that compared to the OGD/R group, the ISO-1 group had significantly lower cell survival rates, increased expression of pro-apoptotic proteins Caspase-3 and Bax, and decreased expression of anti-apoptotic protein Bcl2 and neuronal marker MAP2.	Neural Regen Res. 2020 Aug;15(8):1483-1489.
NRK-52E cells	50 µM	24 hours	To evaluate the inhibitory effect of ISO-1 on AA-induced EMT and matrix deposition. The results showed that ISO-1 significantly decreased the levels of MIF in AA-treated TECs and reversed AA-induced upregulation of α-SMA expression and downregulation of E-cadherin expression. Furthermore, ISO-1 also reduced the expression of type III collagen and the levels of TGF-β1.	Mediators Inflamm. 2016;2016:2174682.
MKN-45 cells	100 nMol	24 hours	To investigate the effect of ISO-1 on LPS-induced MKN-45 cell proliferation, results showed that ISO-1 significantly inhibited LPS-induced cell proliferation.	World J Gastroenterol. 2012 May 14;18(18):2253-61.
Hippocampal neurons	10 µM and 100 µM	48 hours	To investigate the effect of ISO-1 on neurite outgrowth. Results showed that 10 μM and 100 μM ISO-1 significantly reduced the length of the longest neurites and the number of terminal tips of neurites in cultured neurons.	Front Mol Neurosci. 2020 Aug 12;13:147.
Gallbladder cancer cell lines (TGBC24TKB, OCUG-1, NOZ, GB-d1)	0 to 500 µM	48 hours	To evaluate the effect of ISO-1 and 4-IPP on the viability of gallbladder cancer cells, results showed both inhibitors significantly reduced cell viability.	BMC Cancer. 2015 Nov 4;15:843.
PlMDCK cells	10 µM and 100 µM	5 days	To test the effect of the MIF inhibitor ISO-1 on in vitro cyst growth, results showed that ISO-1 significantly inhibited cAMP-dependent cyst enlargement in a dose-dependent manner.	J Mol Med (Berl). 2020 Nov;98(11):1547-1559.
THP-1 monocytic cell line	50 µM		Preliminary data suggested that the effects of ISO-1 might be transient.	Immunology. 2008 Sep;125(1):101-10.
Hs 683 cells	100 or 1000 µM		ISO-1 could restore dexamethasone sensitivity in these cells	J Biol Chem. 2009 Nov 20;284(47):32483-92.
U373 MG cells	100 or 1000 µM		ISO-1 could restore dexamethasone sensitivity in these cells	J Biol Chem. 2009 Nov 20;284(47):32483-92.

C57BL/6 mice	ICV-STZ-induced sporadic AD model	Intraperitoneal injection	20 mg/kg	Daily for 4 weeks	To evaluate the effect of ISO-1 on ICV-STZ-induced cognitive impairment. Results showed that ISO-1 significantly improved STZ-induced impairment in contextual memory performance.	Mol Med. 2020 Apr 17;26(1):34
B10.RIII mice	Experimental autoimmune uveitis (EAU) model	Intraperitoneal injection	20 mg/kg	Once daily for 14 days	ISO-1 attenuated intraocular inflammation and inhibited the differentiation of Th1 and Th17 in EAU mice.	Clin Exp Immunol. 2016 Feb;183(2):280-93
C57BL/6 mice	OVA-sensitized/challenged murine model of chronic asthma	Intraperitoneal injection	35 mg/kg	0.5 h before each OVA challenge, 3 days per week for 6 weeks	ISO-1 significantly mitigated all symptoms caused by OVA treatment, including airway inflammation, airway wall thickening, airway smooth muscle hypertrophy, subepithelial fibrosis, and goblet cell hyperplasia. Additionally, ISO-1 significantly reduced TGF-β1 mRNA levels in pulmonary tissue and its protein level in bronchial alveolar lavage fluid supernatants.	Mol Med. 2010 Sep-Oct;16(9-10):400-8
Mice	Polycystic kidney disease Mice model	Intraperitoneal injection	40 mg/kg	5 days per week for 12 weeks	To test the effect of ICA on MIF and ABCA1 expression, results showed that ICA significantly increased MIF and ABCA1 expression, while deletion of HIF-1α prevented this upregulation.	J Mol Med (Berl). 2020 Nov;98(11):1547-1559.
NZB/NZW F1 and MRL/lpr mice	Systemic lupus erythematosus (SLE) models	Intraperitoneal injection	40 mg/kg	NZB/NZW F1 mice were treated for 12 weeks, MRL/lpr mice for 10 weeks	ISO-1 reduced functional and histological indices of glomerulonephritis, decreased recruitment of CD74+ and CXCR4+ leukocytes, and lowered pro-inflammatory cytokine and chemokine expression.	J Immunol. 2011 Jan 1;186(1):527-38
Kunming mice	Developing hippocampus	Intraperitoneal injection	7 mg/kg	Once daily for 9 consecutive days	To investigate the effect of ISO-1 on hippocampal cell proliferation. Results showed that ISO-1 significantly reduced the number of BrdU-positive cells in the subgranular zone (SGZ) of the dentate gyrus.	Front Mol Neurosci. 2020 Aug 12;13:147.

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CAS No.: 478336-92-4

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CAS No.: 478336-92-4

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NCT02204202	-		Recruiting	May 2019	United States, Missouri ... More >> Washington University School of Medicine / Barnes-Jewish Hospital Recruiting Saint Louis, Missouri, United States, 63110 Contact: Delphine L Chen, MD 314-362-7029 chend@mir.wustl.edu Principal Investigator: Delphine L Chen, MD Less <<
NCT03057743	-		Recruiting	April 5, 2020	United States, Pennsylvania ... More >> Abramson Cancer Center of the University of Pennsylvania Recruiting Philadelphia, Pennsylvania, United States, 19004 Contact: Elizabeth McDonald, MD, Ph.D 855-216-0098 PennCancerTrials@emergingmed.com Less <<
NCT00968656	Breast Cancer ... More >> Head and Neck Cancer Diffuse Large B-cell Lymphoma Less <<	Phase 1	Completed	-	United States, Missouri ... More >> Washington University / Barnes Jewish Hospital Saint Louis, Missouri, United States, 63110 Less <<
NCT02284919	Breast Cancer ... More >> Breast Neoplasm Less <<	Phase 1	Active, not recruiting	November 2019	United States, Pennsylvania ... More >> University of Pennsylvania Hospital Philadelphia, Pennsylvania, United States, 19104 Less <<

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