Structure of SM-164
CAS No.: 957135-43-2
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
SM-164 is a cell-permeable Smac mimetic compound that binds to XIAP protein containing both the BIR2 and BIR3 domains with an IC50 value of 1.39 nM, functioning as an extremely potent XIAP antagonist.
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Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 957135-43-2 |
Formula : | C62H84N14O6 |
M.W : | 1121.42 |
SMILES Code : | C[C@H](NC)C(N[C@H]1CCCC[C@](CC[C@H]2C(N[C@@H](C3=CC=CC=C3)C4=CN(CCCCC5=CC=C(CCCCN6N=NC([C@@H](NC([C@@H]7CC[C@@](CCCC[C@@H]8NC([C@@H](NC)C)=O)([H])N7C8=O)=O)C9=CC=CC=C9)=C6)C=C5)N=N4)=O)([H])N2C1=O)=O |
MDL No. : | MFCD28167763 |
InChI Key : | LGYDZXNSSLRFJS-IOQQVAQYSA-N |
Pubchem ID : | 17756618 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
In Vitro:
Cell Line
|
Concentration | Treated Time | Description | References |
bone-marrow-derived macrophages (BMDMs) | 50 nM to 5 µM | 4 hours to 24 hours | SM-164 induces macrophage death by degrading cIAP1 and cIAP2, with the mechanism being prograμMed necrosis (necroptosis). | PMC3469059 |
MDA-MB-231 breast cancer cells | 1 nmol/L | 12 hours | induced 32% of the cells to undergo apoptosis | PMC2784911 |
SK-OV-3 ovarian cancer cells | 1 nmol/L | 12 hours | induced 33% of the cells to undergo apoptosis | PMC2784911 |
MALME-3M melanoma cells | 1 nmol/L | 12 hours | induced 37% of the cells to undergo apoptosis | PMC2784911 |
MDA-MB-231 | 5 nM | 16 hours | To evaluate the effect of SM-164 on apoptosis, results showed that SM-164 induced cleavage of caspase-3 and PARP, indicating apoptosis. | PMC3294058 |
SKOV-3 | 5 nM | 16 hours | To evaluate the effect of SM-164 on apoptosis, results showed that SM-164 induced cleavage of caspase-3 and PARP, indicating apoptosis. | PMC3294058 |
MDA-MB-231 cells | 3 nM | 16 hours | To evaluate the effect of SM-164 combined with LPS on the apoptosis of MDA-MB-231 cells. Results showed that SM-164 combined with LPS significantly increased the apoptosis rate. | PMC9471085 |
MCF7 cells | 3 nM | 16 hours | To evaluate the effect of SM-164 combined with LPS on the apoptosis of MCF7 cells. Results showed that SM-164 combined with LPS did not significantly increase the apoptosis rate, but combined with TNFα, it induced apoptosis. | PMC9471085 |
MDA-MB-231 cells | 3 nM | 24 hours | SM-164 alone slightly but significantly increased the percentage of early and late apoptosis and dead cells in MDA-MB-231 cells, but when combined with the conditioned medium from M-DCsTNF, it significantly induced cell apoptosis and death. | PMC11303651 |
UMSCC-1 | 10 nM or 200 nM | 2 hours | SM-164 showed dose-dependent radiosensitization in UMSCC-1 cells with SERs of 1.4 and 1.5, respectively. | PMC3073022 |
UMSCC-17B | 200 nM | 2 hours | SM-164 showed radiosensitization in UMSCC-17B cells with an SER of 1.6. | PMC3073022 |
UMSCC-12 | 200 nM | 2 hours | SM-164 showed no significant radiosensitization in UMSCC-12 cells. | PMC3073022 |
UMSCC-74B | 200 nM | 2 hours | SM-164 showed no significant radiosensitization in UMSCC-74B cells. | PMC3073022 |
MDA-MB-231 cells | 3 nM | overnight | SM-164 in combination with TNFα induced apoptosis of MDA-MB-231 cells | PMC7181667 |
In Vivo:
Species
|
Animal Model
|
Administration | Dosage | Frequency | Description | References |
mice | intraperitoneal injection | 50 mg/kg | Every other day for 2 months | SM-164 treatment leads to increased macrophage death in vivo and compromised control of the bacterial pathogen Listeria monocytogenes. | PMC3469059 | |
mice | MDA-MB-231 xenograft tumor model | intravenous injection | 5 mg/kg | daily for 4 days | induced rapid cIAP-1 degradation and robust apoptosis in tumor tissues and achieved tumor regression | PMC2784911 |
SCID mice | MDA-MB-231 xenograft model | Intravenous injection | 130 mg/kg | Single dose, 12 hours duration | To evaluate the tumor growth inhibitory effect of SM-164 alone or in combination with GSK1363089, results showed that the combination significantly inhibited tumor growth. | PMC3294058 |
NSG mice | Breast cancer model | Intraperitoneal injection | 5 mg/kg | single dose | To evaluate the effect of SM-164 combined with LPS on tumor growth in a breast cancer mouse model. Results showed that SM-164 alone significantly inhibited tumor growth, and combined with LPS, it exhibited a stronger inhibitory effect in advanced tumors. | PMC9471085 |
NSG mice | Breast cancer bone metastasis model | Intraperitoneal injection | 3 mg/kg | Twice daily for 4 weeks | SM-164 alone had no significant effect on tumor size or weight, but when combined with M-DCsTNF, it significantly inhibited tumor growth. | PMC11303651 |
Nude mice | UMSCC-1 xenograft model | Intravenous injection | 200 mg/kg/day | once daily for 4 weeks | SM-164 significantly suppressed the growth of UMSCC-1 xenograft tumors and was well-tolerated by the animals. | PMC3073022 |
nude mice | triple-negative breast cancer metastasis to bone and lung model | intraperitoneal injection | 3 mg/kg | Twice daily for 10 days | SM-164 significantly reduced the progression of advanced bone and lung metastases from the triple-negative human breast cancer cell line, MDA-MB-231, in a mouse model | PMC7181667 |
Tags: SM-164 | SM164 | SM 164 | IAP | Apoptosis | Smac mimetic | XIAP antagonist | BIR domains | cell-permeable | apoptosis | BIR2 domain | BIR3 domain | 957135-43-2
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H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
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H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
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Health hazards | |
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H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
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H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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