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Structure of β-Aminopropionitrile
CAS No.: 151-18-8
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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.
β-Aminopropionitrile (BAPN) is a specific, irreversible, orally active lysyl oxidase (LOX) inhibitor targeting the active sites of LOX or LOXL isozymes.
Synonyms: BAPN
4.5
*For Research Use Only !
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| CAS No. : | 151-18-8 |
| Formula : | C3H6N2 |
| M.W : | 70.09 |
| SMILES Code : | N#CCCN |
| Synonyms : |
BAPN
|
| MDL No. : | MFCD00014820 |
| InChI Key : | AGSPXMVUFBBBMO-UHFFFAOYSA-N |
| Pubchem ID : | 1647 |
| GHS Pictogram: |
|
| Signal Word: | Danger |
| Hazard Statements: | H227-H302-H314-H361 |
| Precautionary Statements: | P201-P202-P260-P264-P270-P271-P281-P305+P351+P338-P330-P331-P363-P370+P378-P403+P233-P501 |
| Class: | 8 |
| UN#: | 2735 |
| Packing Group: | Ⅲ |
In Vitro:
|
Cell Line
|
Concentration | Treated Time | Description | References |
| Primary cardiac fibroblasts | 500 µM | 7 days | Inhibit HG-induced collagen protein upregulation | J Adv Res. 2023 Dec;54:223-237 |
| Endothelial cells (C166 cells) | 25 μg/mL BAPN and 10 nM Ang I/Ang II | 24 hours | To investigate the role of MMP8 in Ang I/Ang II-induced VCAM1 expression, results showed Ang I upregulated VCAM1 expression via MMP8 | Cells. 2022 Oct 14;11(20):3218 |
| Vascular smooth muscle cells | 25 μg/mL BAPN | 24-48 hours | To investigate the role of MMP8 in BAPN/Ang II-induced SMC inflammation and apoptosis, results showed MMP8 increased SMC apoptosis via ROS generation | Cells. 2022 Oct 14;11(20):3218 |
| Human valvular interstitial cells (VICs) | 0.5 mM | 24-hours pretreatment followed by continuous culture | To evaluate the effect of BAPN on oxidative stress and calcification in VICs. Results showed that BAPN significantly reduced superoxide anion levels and calcium deposition. | Antioxidants (Basel). 2024 Apr 26;13(5):523 |
| HT22 cells | 1 mM | 30 minutes | Inhibited LysOX activity, reduced glutamate- or erastin-induced neuronal death and lipid ROS accumulation. | Acta Pharm Sin B. 2022 Sep;12(9):3513-3528 |
| LX-2 cells | 1.0 mg/mL | 48 hours | To evaluate the inhibitory effect of BAPN on LOXL2 and α-SMA expression in TGFβ-activated LX-2 cells. Results showed that BAPN significantly downregulated TGFβ-induced LOXL2 and α-SMA expression. | J Nanobiotechnology. 2023 Jun 16;21(1):195 |
| Vascular smooth muscle cells | 25 µg/mL | 48 hours | To investigate the effect of BAPN on vascular smooth muscle cell phenotypic modulation, results showed that NE gene inactivation prevents BAPN-induced SMC phenotypic switching. | Arterioscler Thromb Vasc Biol. 2023 Oct;43(10):1900-1920 |
In Vivo:
|
Species
|
Animal Model
|
Administration | Dosage | Frequency | Description | References |
| Mice | Intervertebral disc herniation injury model | Oral (via drinking water) | ~125 mg/kg/day | From embryonic day 5.5 until postnatal day 5 (p5) or 14 (p14) | To inhibit collagen crosslinking density and evaluate its impact on disc regeneration. Results showed BAPN treatment reduced AF crosslinking density and tissue modulus in p14 mice, leading to fibrotic healing instead of regenerative healing. | iScience. 2024 Sep 4;27(10):110883 |
| Mice | BAPN-induced thoracic aortic dissection model | Drinking water | 0.25% BAPN (wt/vol) | 4 weeks | To investigate the role of NE in BAPN-induced thoracic aortic dissection, results showed that NE gene deficiency prevents BAPN-induced TAD formation and development. | Arterioscler Thromb Vasc Biol. 2023 Oct;43(10):1900-1920 |
| Mice | BAPN-induced TAA model | Oral | 0.25% BAPN in water | Once daily for 4 weeks | BAPN successfully induced TAA and thoracic aortic dissection in mice. | Nat Commun. 2023 Apr 20;14(1):2265 |
| Mice (ApoE−/−/MMP8−/−) | BAPN-induced thoracic aortic dissection model | Drinking water | 0.25% wt/vol BAPN | Continuous for 4 weeks | To investigate the role of MMP8 in BAPN-induced thoracic aortic dissection, results showed MMP8 deficiency significantly reduced TAD incidence and aortic elastin fragmentation | Cells. 2022 Oct 14;11(20):3218 |
| C57BL/6J mice | BAPN-induced aortic dissection model | Oral administration via drinking water | 0.3% BAPN | Continuous for 4 weeks | The BAPN-induced aortic dissection model was used to study the pathological mechanisms of aortic dissection. Results showed that BAPN-induced mice exhibited significant aortic dilation and dissection, accompanied by abnormal expression of ferroptosis markers (HMOX1, ACSL4, and 4-HNE), as well as elevated levels of ferrous iron and lipid peroxidation. | Cell Death Dis. 2024 Dec 18;15(12):900 |
| C57BL/6 mice | Abdominal aortic aneurysm model | Oral | 0.4% BAPN drinking water | For 2 weeks | Induce abdominal aortic aneurysm formation | Clin Sci (Lond). 2023 Oct 11;137(19):1533-1545 |
| C57BL/10 mice | BAPN-induced TAAD model | Drinking water | 0.5 g/kg | Daily administration for 28 days | To study the pathogenesis and progression of TAAD, identifying the critical role of macrophages in TAAD development | Cell Discov. 2022 Feb 8;8(1):11 |
| Mice (C57BL/6J) | Β-Aminopropionitrile monofumarate (BAPN)-induced TAD model | Drinking water | 0.5 g/kg/day | Once daily for 28 days | Investigate the effect of KLF15 deficiency on BAPN-induced TAD. Results showed that KLF15-deficient mice had a significantly higher incidence of TAD (70%) compared to wild-type mice (35%), accompanied by aggravated aortic dilation and vascular inflammation. | J Biol Chem. 2024 May;300(5):107260 |
| C57BL/6J mice | Β-Aminopropionitrile-induced thoracic aortopathy model | Drinking water | 0.5% wt/vol | Continuous for 4 weeks | To investigate whether β-aminopropionitrile-induced thoracic aortopathies can be attenuated by inhibition of the renin-angiotensin system. Results showed that inhibition of either angiotensin II action or production did not attenuate β-aminopropionitrile-induced thoracic aortopathies. | Arterioscler Thromb Vasc Biol. 2022 Oct;42(10):1254-1261 |
| Sprague-Dawley rats | TAAD model with BAPN pre-treatment and METH exposure | Intragastric administration | 1 g/kg | Every 24 hours for 4 weeks | To establish a TAAD model with BAPN pre-treatment and METH exposure. Results showed that the combination of BAPN and METH caused thoracic aortic aneurysm/dissection in 60% of rats. | Biochim Biophys Acta Mol Basis Dis. 2022 Sep 1;1868(9):166447 |
| Mice | BAPN-induced TAD mouse model | Drinking water | 1 g/kg per day | Daily for 4 weeks | SGK1 deficiency or pharmacological blockade inhibits vascular degeneration and TAD progression, suppressing VSMC phenotypic transformation. | Arterioscler Thromb Vasc Biol. 2025 Feb;45(2):238-259 |
| C57BL/6J mice | BAPN-induced thoracic aortic dissection model | Oral | 1 g/kg/day | Once daily for 4 weeks | To study BAPN-induced thoracic aortic dissection formation, results showed BAPN promoted thoracic aortic dilation and dissection. | Mol Med. 2024 Sep 19;30(1):154 |
| C57BL/6 mice | BAPN-induced aortic aneurysm and dissection (AAD) model | Oral administration via drinking water | 1 g/kg/day | Once daily for four weeks | To evaluate the effect of miR-1204 inhibition on BAPN-induced AAD formation. Results showed that inhibition of miR-1204 reduced the incidence and mortality of AAD and attenuated vascular cell senescence. | Nat Commun. 2024 Jul 16;15(1):5985 |
| C57BL/6 mice | Streptozotocin-induced diabetic model | Intraperitoneal injection | 100 mg/kg/day | Every two days for 14 weeks | Inhibit Lox expression, alleviate cardiac dysfunction and fibrosis in diabetic mice | J Adv Res. 2023 Dec;54:223-237 |
| BALB/c female mice | CCl4-induced liver fibrosis model | Tail vein injection | 125 mg/kg | Once daily for 4 weeks | To evaluate the inhibitory effect of BAPN on LOXL2 expression and collagen crosslinking in CCl4-induced liver fibrosis model. Results showed that BAPN significantly reduced serum LOXL2 levels and LOXL2 and Col1A2 expression in the liver, and partially decreased collagen deposition. | J Nanobiotechnology. 2023 Jun 16;21(1):195 |
| C57BL/6J mice | BAPN-induced TAD model | Oral administration via drinking water | 1g/kg/day | Consecutive 4 weeks | Establish TAD model for studying the role of NINJ1 in TAD formation. | BMC Med. 2023 Oct 20;21(1):396 |
| Mice | Fbn1C1041G/+ mice and wild-type (WT) mice | Intraperitoneal injection | 300 mg/kg | Daily for 8 weeks | To test the effects of BAPN on optic nerve and elastic fibers in Fbn1C1041G/+ and WT mice. Results showed that BAPN treatment exacerbated optic nerve and axon expansion in Fbn1C1041G/+ mice and altered the ultrastructure of elastic fibers in the optic nerve pia mater. | Am J Pathol. 2024 Jul;194(7):1317-1328 |
| C57BL/6J mice | Acute aortic dissection model | Drinking water | 5 g/L (drinking water) | Continuous administration | Induce acute aortic dissection and observe immune response | Sci Rep. 2024 Jun 28;14(1):14893 |
| C57BL/6J mice | KA-induced seizure mouse model | Intraperitoneal injection | 50 or 100 mg/kg | Once daily for seven days | Significantly blocked seizure-induced ferroptosis and alleviated neuronal damage. | Acta Pharm Sin B. 2022 Sep;12(9):3513-3528 |
| Bio Calculators | ||||
| Preparing Stock Solutions | ![]() |
1mg | 5mg | 10mg |
|
1 mM 5 mM 10 mM |
14.27mL 2.85mL 1.43mL |
71.34mL 14.27mL 7.13mL |
142.67mL 28.53mL 14.27mL |
|
| Dissolving Methods |
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.
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Tags: β-Aminopropionitrile | BAPN | Monoamine Oxidase | Endogenous Metabolite | MAO | thoracic aortic dissection | GLUT4 | insulin | cervical carcinoma cells | SiHa | obesity | lysyl oxidase | 151-18-8 |
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| P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
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| 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. |
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| H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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