1,4-Diaminobutane dihydrochloride
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04484 |
| CAS | 333-93-7 |
| Molecular Weight | 161.07 |
| Molecular Formula | C4H12N2.2HCl |
| Purity | ≥ 98 % |
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Description
It is an NMDA receptor agonist produced by the breakdown of amino acids after the death of an organism. It is a polyamine plant growth regulator affecting the synthesis of macromolecules and the development of root systems in plants.
Specification
| Related CAS | 110-60-1 (free base) |
| Synonyms | 1,4-Butanediamine Dihydrochloride; Putrescine Dihydrochloride; Putrescine Hydrochloride; Tetramethylenediamine Dihydrochloride |
| Storage | Store at 2-8 ℃ under inert atmosphere |
| IUPAC Name | butane-1,4-diamine;dihydrochloride |
| Canonical SMILES | C(CCN)CN.Cl.Cl |
| InChI | InChI=1S/C4H12N2.2ClH/c5-3-1-2-4-6;;/h1-6H2;2*1H |
| InChI Key | XXWCODXIQWIHQN-UHFFFAOYSA-N |
Properties
| Appearance | White to off-white solid |
| Application | Used in biochemical research. |
| Boiling Point | 159 ℃ at 760 mmHg |
| Melting Point | >280 ℃ (dec.) |
| Density | 1.472 g/cm3 |
| Solubility | Slightly soluble in Water |
| LogP | 2.68860 |
Reference Reading
1. Spermidine endows macrophages anti-inflammatory properties by inducing mitochondrial superoxide-dependent AMPK activation, Hif-1α upregulation and autophagy
Zhiyuan Zheng, Yongjing Chen, Zhanhong Liu, Rui Liu, Gerry Melino, Peiqing Huang, Changshun Shao, Ying Wang, Jiankai Fang, Zheng Gong, Lin Song, Lijuan Cao, Yongsha Pan, Chao Feng, Qianwen Shang, Hui Ma, Xiaolei Li, Shengchao Zhang, Qian Yang, Yufang Shi, Yanan Li Free Radic Biol Med . 2020 Dec;161:339-350. doi: 10.1016/j.freeradbiomed.2020.10.029.
Distinct metabolic programs, either energy-consuming anabolism or energy-generating catabolism, were required for different biological functions. Macrophages can adopt different immune phenotypes in response to various cues and exhibit anti- or pro-inflammatory properties relying on catabolic pathways associated with oxidative phosphorylation (OXPHOS) or glycolysis. Spermidine, a natural polyamine, has been reported to regulate inflammation through inducing anti-inflammatory (M2) macrophages. However, the underlying mechanisms remain elusive. We show here that the M2-polarization induced by spermidine is mediated by mitochondrial reactive oxygen species (mtROS). The levels of mitochondrial superoxide and H2O2were markedly elevated by spermidine. Mechanistically, mtROS were found to activate AMP-activated protein kinase (AMPK), which in turn enhanced mitochondrial function. Furthermore, hypoxia-inducible factor-1α (Hif-1α) was upregulated by the AMPK activation and mtROS and was required for the expression of anti-inflammatory genes and induction of autophagy. Consistent with previous report that autophagy is required for the M2 polarization, we found that the M2 polarization induced by spermidine was also mediated by increased autophagy. The macrophages treated with spermidine in vitro were found to ameliorate Dextran Sulfate Sodium (DSS)-induced inflammatory bowel disease (IBD) in mice. Thus, spermidine can elicit an anti-inflammatory program driven by mtROS-dependent AMPK activation, Hif-1α stabilization and autophagy induction in macrophages. Our studies revealed a critical role of mtROS in shaping macrophages into M2-like phenotype and provided novel information for management of inflammatory disease by spermidine.
2. Biogenic amines profile and concentration in commercial milks for infants and young children
U Gianfranco Spizzirri, Francesco Puoci, Donatella Restuccia, Francesca Iemma Food Addit Contam Part A Chem Anal Control Expo Risk Assess . 2019 Mar;36(3):337-349. doi: 10.1080/19440049.2018.1563306.
Commercial milks for infants and young children (CMIYC) received much attention during last years for their impact on the nutritional status, health and development of the new-born and babies. Among possible contaminants contained in these foods, biogenic amines (BAs) have rarely been determined although they can exert toxic effects in humans if ingested at high concentrations. Spermine, spermidine, putrescine, histamine, tyramine, β-phenylethylamine and cadaverine have been quantified in CMIYC samples by LC-UV after derivatisation with dansyl-chloride. Once optimised in terms of linearity (R2≥ 0.989), recovery percentages (92.9-97.3), LOD (0.2-0.4 μg g-1or 0.03-0.05 μg mL-1depending on the samples), LOQ (0.5-1.0 μg g-1and 0.08-0.13 μg mL-1depending on the samples) and repeatability (0.1-0.2 intra-day; 0.2-0.4 inter-day), the method has been applied to real samples. Very low total BAs concentrations have been found in reconstituted (1.18-3.12 mg L-1) and liquid milks (0.33-2.30 mg L-1), with different biogenic amine profiles and distributions. A risk assessment based on the available information regarding Acute Reference Doses of histamine and tyramine, as well as the application of common Biogenic Amine Indexes, showed that none of the analysed samples represented a possible risk for babies, also considering a worst case evaluation. These findings confirmed the strict safety and quality protocols adopted during the production of CMIYC. Chemical compounds studied in this article: Ammonium chloride (PubChem CID: 25517); Cadaverine hydrochloride (PubChem CID: 5351467); Hydrochloridric acid (PubChem CID: 313); Histamine dihydrochloride (PubChem CID: 5818); Phenylethylamine hydrochloride (PubChem CID: 9075); Putrescine dihydrochloride (PubChem CID: 9532); Sodium hydroxide (PubChem CID: 14798); Spermine tetrahydrochloride (PubChem CID: 1103); Spermidine trihydrochloride (PubChem CID: 1102); Tyramine hydrochloride (PubChem CID: 66449).
3. Preventive and Therapeutic Spermidine Treatment Attenuates Acute Colitis in Mice
Xin Huang, Luting Hu, Liyang Ni, Tianqi Yang, Yufeng Zhao, Yeqin Luo, Yinhua Ni, Zhiyuan Jiang, Pei Mao, Lingyan Ma, Zhengwei Fu J Agric Food Chem . 2021 Feb 17;69(6):1864-1876. doi: 10.1021/acs.jafc.0c07095.
Inflammatory bowel disease (IBD) is associated with acute and chronic inflammation of the gastrointestinal tract and has emerged to be a global disease. Spermidine, a natural polyamine, plays a critical role in maintaining cellular homeostasis. Herein, we investigated the impact and mechanism of spermidine on both dextran sulfate sodium (DSS)- and 2,4,6-trinitrobenzenesulfonic acid solution (TNBS)-induced colitis in mice. We found that spermidine exerted protective effects against acute colitis, evidenced by reduced disease activity index (DAI) and colonic inflammation, increased colonic length, and upregulated tight junction proteins in these two colitis models. Importantly, spermidine exerted significant therapeutic and preventive effects against DSS-induced colitis. Pre- and post-treatment with spermidine reduced the expression of proinflammatory cytokines, phosphorylation of (nuclear factor-κB) NF-κB and (mitogen-activated protein kinase) MAPK, and the activation of F4/80 macrophages and T cells in the colon. Furthermore, spermidine upregulated M2 macrophage markers, whereas it downregulated M1 markers in the inflamed colons. In parallel, spermidine reduced M1 pro-inflammatory markers and enhanced M2 anti-inflammatory genes in RAW264.7 cells. These results revealed that spermidine-ameliorated colitis might be through the regulation of M1/M2 macrophage polarization. In addition, spermidine treatment also alleviated LPS/TNF-α-induced inflammation in Caco-2 cells. Taken together, spermidine prevented and reversed colonic inflammation in colitis mice and might be a promising candidate for IBD intervention.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
