| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| 25mg |
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| 50mg |
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| 100mg |
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| 500mg |
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| Other Sizes |
| Targets |
Polyamine oxidase (PAO)
N1-Acetylspermidine targets polyamine oxidase (PAO), a key enzyme in the polyamine catabolic pathway. It also binds to nicotinic acetylcholine receptors and activates them, leading to the release of calcium ions and the activation of various intracellular signaling pathways. It also binds to metal ions. |
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| ln Vitro |
The cleavage efficiency of spermidine and its acetyl derivatives (N1-acetylspermidine and N8-acetylspermidine) at apurinic sites in DNA were examined by PAGE-urea analysis. The three polyamines induced different rates of cleavage when compared at 1 mM concentrations. The order of effectiveness were: spermidine greater than N8-acetylspermidine greater than N1-acetylspermidine. Thus a decrease in efficiency was observed when the first order amino-groups of spermidine were blocked. The N-8amino-group of spermidine was less effective in inducing cleavage at AP-sites than the N1-amino-group. Among several proposed models of polyamine-DNA interactions, our results can best be explained by the model postulated by Liquori et al[3].
In vitro, N1-acetylspermidine acts as a substrate for polyamine oxidase (PAO). It is used in assays to measure PAO activity. It selectively increases the levels of N1-acetylspermidine in human colorectal cancer cells. It can promote apoptosis in combination with Procyanidins. |
| ln Vivo |
The association of N1-acetylspermidine with human colorectal adenocarcinomas has been evaluated in this study. Free polyamines and their monoacetylated forms in adenocarcinomas, adenomas, and apparently healthy mucosae were determined using high-performance ion-exchange chromatography. The N1-acetylspermidine levels in well- and moderately differentiated adenocarcinomas were 27.30 +/- 3.13 (S.E.) (n = 99) and 22.86 +/- 3.60 (n = 22) nmol/g, wet weight, respectively. These values were significantly higher than those of benign adenomas (5.38 +/- 0.85 nmol/g, n = 31) and of control mucosae. The N1-acetylspermidine levels in control mucosae on the oral and anal side of adenocarcinomas were 5.84 +/- 1.44 (n = 57) and 7.92 +/- 2.89 (n = 50) nmol/g, respectively; no significant difference was observed between control mucosae and adenomas. The mean levels of three polyamines, putrescine, spermidine, and spermine in both adenomas and adenocarcinomas were about twice as high as those of control mucosae. The molar ratios of spermidine to spermine were significantly greater in both adenomas and adenocarcinomas than in control tissues. There was no obvious correlation between the free polyamine concentrations and the degree of malignancy of the colorectal tumors. These results suggest that the metabolism of N1-acetylspermidine in colorectal adenocarcinomas is quite different from that in adenomas and in nonneoplastic mucosae and that N1-acetylspermidine can be a promising biochemical marker of cancer in the human large intestine[2].
In vivo, N1-acetylspermidine is an endogenous metabolite and plays a role in polyamine metabolism. Its levels are regulated by the balance between its synthesis (by spermidine/spermine N1-acetyltransferase, SSAT) and its degradation (by PAO). It is used as a biomarker for polyamine metabolism. |
| Enzyme Assay |
Non-cellular assays for N1-acetylspermidine are primarily analytical. It is measured in biological samples (urine, plasma, tissues) using liquid chromatography-mass spectrometry (LC-MS) to study polyamine metabolism. It can also be used as a substrate in in vitro assays to measure polyamine oxidase (PAO) activity.
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| Cell Assay |
In mammalian cells, the flavoprotein polyamine oxidase catalyzes a key step in the catabolism of polyamines, the oxidation of N1-acetylspermine and N1-acetylspermidine to spermidine and putrescine, respectively. The mechanism of the mouse enzyme has been studied with N1,N12-bisethylspermine (BESPM) as a substrate. At pH 10, the pH optimum, the limiting rate of reduction of the flavin in the absence of oxygen is comparable to the k(cat) value for turnover, establishing reduction as rate-limiting. Oxidation of the reduced enzyme is a simple second-order reaction. No intermediates are seen in the reductive or oxidative half-reactions. The k(cat) value decreases below a pK(a) of 9.0. The k(cat)/K(m) value for BESPM exhibits a bell-shaped pH profile, with pK(a) values of 9.8 and 10.8. These pK(a) values are assigned to the substrate nitrogens. The rate constant for the reaction of the reduced enzyme with oxygen is not affected by a pH between 7.5 and 10. Active site residue Tyr430 is conserved in the homologous protein monoamine oxidase. Mutation of this residue to phenylalanine results in a 6-fold decrease in the k(cat) value and the k(cat)/K(m) value for oxygen due to a comparable decrease in the rate constant for flavin reduction. This moderate change is not consistent with this residue forming a tyrosyl radical during catalysis[1].
In vitro cellular assays for N1-acetylspermidine are conducted to study its effects on polyamine metabolism and apoptosis. Cells are treated with the compound, and PAO activity is measured. Its effects on cell viability and apoptosis can be assessed. Its ability to bind and activate nicotinic acetylcholine receptors can be studied in cells expressing these receptors. |
| Animal Protocol |
In vivo animal experiments with N1-acetylspermidine are conducted to study polyamine metabolism and its role in diseases such as cancer. Animal models of colorectal cancer can be used to study the effects of modulating N1-acetylspermidine levels on tumor growth.
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| ADME/Pharmacokinetics |
N1-Acetylspermidine is an endogenous metabolite. It is acetylated by SSAT and oxidized by PAO. It has a relatively short half-life. The compound is soluble in water and is typically stored as a powder at -20°C.
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| Toxicity/Toxicokinetics |
N1-Acetylspermidine is considered to have low toxicity as an endogenous metabolite. However, its role in polyamine metabolism is complex and dysregulation can be associated with disease. It is not used as a therapeutic agent.
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| References |
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| Additional Infomation |
N1-Acetylspermidine hydrochloride is an acetyl derivative of spermidine and a substrate for polyamine oxidase (PAO). It plays a role in polyamine metabolism and can promote apoptosis. It binds to nicotinic acetylcholine receptors and is used as a research tool in cancer and metabolic studies.
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| Molecular Formula |
C₉H₂₃CL₂N₃O
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|---|---|
| Molecular Weight |
260.20
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| Exact Mass |
223.145
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| CAS # |
34450-16-3
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| PubChem CID |
214848
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| Appearance |
White to light brown solid powder
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| LogP |
2.125
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| Hydrogen Bond Donor Count |
5
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
8
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| Heavy Atom Count |
15
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| Complexity |
128
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC(NCCCNCCCCN)=O.[H]Cl.[H]Cl
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| InChi Key |
IVLOLMVLUOGVCZ-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C9H21N3O.2ClH/c1-9(13)12-8-4-7-11-6-3-2-5-10;;/h11H,2-8,10H2,1H3,(H,12,13);2*1H
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| Chemical Name |
N-[3-(4-aminobutylamino)propyl]acetamide;dihydrochloride
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| Synonyms |
N1Acetylspermidine HCl; 34450-16-3; N-(3-((4-Aminobutyl)amino)propyl)acetamide dihydrochloride; N1-Acetylspermidine Dihydrochloride; N-[3-(4-aminobutylamino)propyl]acetamide;dihydrochloride; N1-Acetylspermidine (hydrochloride); N8-ACETYLSPERMIDINEDIHYDROCHLORIDE; Acetamide, N-(3-((4-aminobutyl)amino)propyl)-, dihydrochloride; Acetamide, N-[3-[(4-aminobutyl)amino]propyl]-, dihydrochloride; N1 Acetylspermidine HCl
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
H2O : ~25 mg/mL (~96.08 mM)
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.8432 mL | 19.2160 mL | 38.4320 mL | |
| 5 mM | 0.7686 mL | 3.8432 mL | 7.6864 mL | |
| 10 mM | 0.3843 mL | 1.9216 mL | 3.8432 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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