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Structure of Spermine
CAS No.: 71-44-3
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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.
Spermine is a polyamine derived from spermidine by spermine synthase, functions as a free radical scavenger and forms a variety of adducts that prevent oxidative damage to DNA. Spermine is also implicated in the regulation of gene expression, the stabilization of chromatin and the prevention of endonuclease-mediated DNA fragmentation. Also used for nutritional supplementation and treatment of dietary shortage or imbalance.
Synonyms: NSC 268508; Neuridine; 1,5,10,14-Tetraazatetradecane
4.5
*For Research Use Only !
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Madhan Mohan Chandra Sekhar Jaggarapu ; Abhirami Thumsi ; Richard Nile ; Brian D Ridenour ; Taravat Khodaei ; Abhirami P Suresh , et al.
Abstract: Covalent organic framework (COF) crystalline biomaterials have great potential for drug delivery since they can load large amounts of small molecules (e.g. metabolites) and release them in a controlled manner, as compared to their amorphous counterparts. Herein, we screened different metabolites for their ability to modulate T cell responses in vitro and identified Kynurenine (KyH) as a key metabolite that not only decreases frequency of pro-inflammatory RORgt + T cells but also supports frequency of anti-inflammatory GATA3+ T cells. Moreover, we developed a methodology to generate imine-based TAPB-PDA COF at room temperature and loaded these COFs with KyH. KyH loaded COFs (COF-KyH) were able to then release KyH in a controlled manner for 5 days in vitro. Notably, COF-KyH when delivered orally in mice induced with collagen-induced rheumatoid arthritis (CIA) were able to increase frequency of anti-inflammatory GATA3+CD8+ T cells in the lymph nodes and decrease antibody titers in the serum as compared to the controls. Overall, these data demonstrate that COFs can be an excellent drug delivery vehicle for delivering immune modulating small molecule metabolites.
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Keywords: Covalent organic framework ; Rheumatoid arthritis ; Kynurenine ; Metabolites ; Drug delivery
Show More >
CAS No. : | 71-44-3 |
Formula : | C10H26N4 |
M.W : | 202.34 |
SMILES Code : | NCCCNCCCCNCCCN |
Synonyms : |
NSC 268508; Neuridine; 1,5,10,14-Tetraazatetradecane
|
MDL No. : | MFCD00008215 |
InChI Key : | PFNFFQXMRSDOHW-UHFFFAOYSA-N |
Pubchem ID : | 1103 |
GHS Pictogram: |
![]() |
Signal Word: | Danger |
Hazard Statements: | H314 |
Precautionary Statements: | P280-P305+P351+P338-P310 |
Class: | 8 |
UN#: | 3259 |
Packing Group: | Ⅱ |
In Vitro:
Cell Line
|
Concentration | Treated Time | Description | References |
Primary CD4+ T cells | 0.6 mM | 1 hour | Inhibited X4-HIV-1 infection but not R5-HIV-1 infection | PMC10321752 |
TZM-bl cells | 0.66 ± 0.14 mM (IC50) | 1 hour | Inhibited X4-HIV-1 infection but not R5-HIV-1 infection | PMC10321752 |
Human normal liver cells (WRL-68) | 2 μg/mL | 14 days | Increased SA-β-gal positive cells, decreased EdU positive cells, upregulated P21, IL-8, and IL-1A gene expression | PMC11538647 |
Human primary fibroblasts (GM00038) | 1 μg/mL | 14 days | Induced cellular senescence phenotype, increased SA-β-gal positive cells, decreased EdU positive cells, upregulated P21, IL-8, and IL-1A gene expression, downregulated LMNB1 | PMC11538647 |
BEAS-2B cells | 10–100 µM | 24 hours | To investigate the effect of spermine on BEAS-2B cell apoptosis, it was found that spermine was the most effective polyamine in inducing BEAS-2B cell apoptosis, which was associated with mitochondrial dysfunction. | PMC6461714 |
MDA-MB-231/R (R) | 10.6 μM (IC50) | 48 hours | Investigation of Pd2Spm's metabolic impact on resistant cells, showing stronger amino acid depletion, enhanced TCA cycle activity, and significant increases in GSH and GABA, indicating higher cytotoxicity | PMC11056979 |
MDA-MB-231 (S) | 7.9 μM (IC50) | 48 hours | Investigation of Pd2Spm's metabolic impact on sensitive cells, showing amino acid depletion, enhanced TCA cycle activity, and significant increases in GSH and GABA | PMC11056979 |
Human Umbilical Vein Endothelial Cells (HUVECs) | 2 μg/mL | 5 days | Induced typical senescence characteristics, increased SA-β-gal positive cells, decreased EdU positive cells, upregulated IL-6, IL-8, P16, P21, and IL-1A gene expression | PMC11538647 |
Monocyte-derived macrophages | 0.6 mM | 6 or 24 hours | Inhibited X4-HIV-1 cell-to-cell transfer but not R5-HIV-1 | PMC10321752 |
Mycobacterium tuberculosis H37Rv | 90 µM | 7 days | To evaluate the antibacterial activity of Spermine in combination with bedaquiline (BDQ). Results showed that Spermine significantly enhanced the antituberculosis activity of BDQ, demonstrating a synergistic effect. | PMC10782994 |
CAD22L cells | 5 μM | 72 hours | Spermine treatment significantly reduced PrPSc aggregates in CAD22L neuronal cells and decreased intracellular reactive oxygen species (ROS) levels. | PMC6030104 |
SMB.s15 cells | 5 μM | 72 hours | Spermine treatment significantly reduced PrPSc aggregates in SMB.s15 cells and cleared these aggregates by enhancing autolysosomal flux. | PMC6030104 |
Arabidopsis leaf discs | 50-400 µM | To study the effect of different concentrations of spermine on flg22-induced ROS burst, results showed that spermine at 100 µM and higher concentrations significantly inhibited ROS production. | PMC9786854 |
In Vivo:
Species
|
Animal Model
|
Administration | Dosage | Frequency | Description | References |
ApoE−/− mice | High-fat diet-induced atherosclerosis model | Intraperitoneal injection | 2.5 mg/kg | Once daily for 16 weeks | Evaluate the therapeutic efficacy and safety of CD16/32-ZIF90@Sp on atherosclerosis. Results showed that CD16/32-ZIF90@Sp significantly reduced plaque area and lipid deposition, increased plaque collagen deposition, and had no significant side effects. | PMC11877808 |
Arabidopsis thaliana | Wild-type Arabidopsis | Leaf infiltration | 100 µM | 24 hours | To investigate the effect of spermine on flg22-induced disease resistance against Pseudomonas syringae in Arabidopsis, results showed that spermine treatment reduced flg22-induced disease resistance. | PMC9786854 |
C57BL/6J mice | High-fat diet-induced obese Mice model | Oral | 0.1% | 12 weeks | To evaluate the effect of oral spermine on body weight and fat accumulation in high-fat diet-fed mice, results showed that spermine significantly reduced body weight, blood triglycerides, and visceral fat. | PMC9569936 |
Mice | SAMP8 mice | Oral | 2 mM | 8 weeks | Spermine delays brain aging and improves cognitive dysfunction by inducing autophagy and ameliorating mitochondrial dysfunction. | PMC7185103 |
Clinical Trial:
NCT Number | Conditions | Phases | Recruitment | Completion Date | Locations |
NCT02915757 | Depression Diagnosis | Not Applicable | Unknown | March 2017 | France ... More >> Montpellier University Hospital Montpellier, France, 34295 Less << |
NCT02855918 | Major Depression | Not Applicable | Not yet recruiting | July 2019 | France ... More >> University Hospital Not yet recruiting Montpêllier, France, 34295 Contact: Catherine GENTY, MD +33 4 67 99 61 45 75 c-genty@chu-montpellier.fr Contact: Aurélie CAZALS, MD +33 4 67 33 63 76 a-cazals@chu-montpelier.fr Less << |
NCT01095731 | Aneurysmal Subarachnoid Hemorr... More >>hage Less << | Phase 2 | Completed | - | United States, Florida ... More >> University of Florida Gainesville, Florida, United States, 32611 United States, New York Columbia University Medical Center New York, New York, United States, 10032 United States, Washington University of Washington Seattle, Washington, United States, 96104 Less << |
NCT00641147 | Familial Adenomatous Polyposis | Phase 2 | Completed | - | United States, Maryland ... More >> Johns Hopkins University/Sidney Kimmel Cancer Center Baltimore, Maryland, United States, 21287 Puerto Rico University of Puerto Rico San Juan, Puerto Rico, 00936 Less << |
NCT03431363 | - | Recruiting | June 2020 | United States, New York ... More >> Montefiore Medical Center Recruiting Bronx, New York, United States, 10467 Contact: Alyssa Asaro, BA 718-920-5636 aasaro@montefiore.org Less << | |
NCT00641147 | - | Completed | - | - | |
NCT03536728 | Cancer Solid ... More >>Tumor Solid Carcinoma Advanced Cancer Less << | Phase 1 | Recruiting | October 2020 | United States, Texas ... More >> Mays Cancer Center at UT Health San Antonio Not yet recruiting San Antonio, Texas, United States, 78229 Contact: Rachel Ortiz-Wong 210-450-5055 wongro@uthscsa.edu Principal Investigator: John Sarantopoulos, MD Next Oncology Recruiting San Antonio, Texas, United States, 78240 Contact: Research Coordinator 210-595-5300 crosas@nextsat.com Principal Investigator: Anthony Tolcher, MD Less << |
NCT00118365 | Precancerous Condition | Phase 3 | Completed | - | United States, California ... More >> University of California Medical Center At Irvine-Orange Campus Orange, California, United States, 92868 Less << |
NCT00304850 | Breast Cancer ... More >> Surgery Less << | Phase 2 | Completed | - | France ... More >> CLCC-Institut Bergonie, service d'anesthésie réanimation, 229 cours de l'Argonne Bordeaux, France, 33000 département d'anesthésie-réanimation 3, hôpital Pellegrin Bordeaux, France, 33076 CLCC Alexis Vautrin Nancy, France, 54511 APHParis Hôpital Pitié Salpétrière - Dépt. d'anesthésie réanimation Paris, France, 75013 CLCC Réné Huguenin de Saint Cloud Saint Cloud, France, 92210 Less << |
NCT00118365 | - | Completed | - | - | |
NCT01467258 | Healthy Metabolism | Not Applicable | Completed | - | Canada, Manitoba ... More >> St. Boniface General Hospital Winnipeg, Manitoba, Canada, R2H 2A6 Less << |
NCT00755898 | Cancer | Phase 2 | Completed | - | Canada, Manitoba ... More >> University of Manitoba Winnipeg, Manitoba, Canada, R3E 0W3 Less << |
NCT00484042 | - | Completed | - | - | |
NCT00086736 | Prostate Cancer | Phase 2 | Completed | - | United States, Alabama ... More >> University of Alabama at Birmingham Comprehensive Cancer Center Birmingham, Alabama, United States, 35294-3300 Less << |
NCT02755246 | Subjective Cognitive Decline | Phase 2 | Completed | - | Germany ... More >> Charité Universitätsmedizin Berlin Berlin, Germany, 10117 Less << |
Bio Calculators | ||||
Preparing Stock Solutions | ![]() |
1mg | 5mg | 10mg |
1 mM 5 mM 10 mM |
4.94mL 0.99mL 0.49mL |
24.71mL 4.94mL 2.47mL |
49.42mL 9.88mL 4.94mL |
Tags: Spermine | Neuridine | Amines | Aliphatic Chain Hydrocarbons | Organic Building Blocks | 71-44-3
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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. |
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P285 | In case of inadequate ventilation wear respiratory protection. |
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Code | Phrase |
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P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
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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. |
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P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
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H242 | Heating may cause a fire |
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H260 | In contact with water releases flammable gases which may ignite spontaneously |
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H316 | Causes mild skin irritation |
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H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
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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 |
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H351 | Suspected of causing cancer |
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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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