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Chemical Structure| 71-44-3 Chemical Structure| 71-44-3

Structure of Spermine
CAS No.: 71-44-3

Chemical Structure| 71-44-3

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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

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Product Citations

Product Citations

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.

Keywords: Covalent organic framework ; Rheumatoid arthritis ; Kynurenine ; Metabolites ; Drug delivery

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Product Details of Spermine

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

Safety of Spermine

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P280-P305+P351+P338-P310
Class:8
UN#:3259
Packing Group:

Isoform Comparison

Biological Activity

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 <<

Protocol

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

References

 

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