Quadrol
(Synonyms: N,N,N',N'-四(2-羟基丙基)乙二胺,N,N,N′,N′-Tetrakis(2-hydroxypropyl)ethylenediamine; EDTP) 目录号 : GC31784Quadrol 是一种免疫刺激剂,被认为是加速伤口愈合的潜在有用剂。
Cas No.:102-60-3
Sample solution is provided at 25 µL, 10mM.
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- Purity: >98.00%
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Cell experiment: | The standard trypan blue exclusion test is performed to measure cell viability (10). Cells are exposed to increasing concentrations of Quadrol (0.5 mM to 32 mM) and incubated at 37°C for varying lengths of time before treatment with trypan blue[1]. |
Animal experiment: | At the time of polytetrafluoroethylene (PTFE) tubing implantation, six test groups (3 streptozotocin-induced (STZ) diabetic and 3 non-diabetic) consisting of 5 to 7 animals per sampling time receive either diluent (control group) or Quadrol (10 mM) injected approximately 1 cm from the implantation site. The PTFE implants recovered from the mice after 2 to 14 days are stored frozen until processed and then analyzed by the HPLC method[2]. |
References: [1]. Bhide MV, et al. In vitro stimulation of macrophages by quadrol [N,N,N',N'-tetrakis(2-hydroxypropyl)ethylenediamine]. J Immunopharmacol. 1985;7(3):303-12. |
Quadrol is an immunostimulant and has been implicated as a potentially useful agent in accelerated wound healing.
Results show that viability of macrophages incubated with Quadrol at concentrations of 0.5 mM, 1 mM and 4mM are identical to that for controls. Viability, however, is reduced to 50% of control at concentrations of 16 mM to 32 mM. After four hours, at concentrations of 1 mM and 4 mM, Quadrol produces enhanced spreading of 88% and 80%, respectively, as compared to the control of 28%. Quadrol, at a concentration of 16 mM, shows reduced percentage of spreading of macrophages after four hours. Exposure of macrophages to 1.0 mM or 4.0 mM Quadrol concentrations enhances phagocytic activity, 41% and 57%, respectively, over that of the cells exposed to media alone (34%)[1].
On day eight after the implantation, the amount of collagen in the implants of normal mice injected with Quadrol exceeds controls by more than 200% (p<0.025). By day 11, the collagen content increases to over 300% higher than controls (p<0.01) and by the end of two weeks after wounding, the time interval typically required for normal and complete wound healing, the collagen accumulated in the implants of the Quadrol-treated mice is about 50% above control (p<0.1). The accumulation of collagen in the implants of Quadrol treated STZ-diabetic mice about 100% above the untreated diabetic control on days 8 to 11. By day 14, the collagen deposition has increased to 200% above the controls (p<0.0 5)[2].
[1]. Bhide MV, et al. In vitro stimulation of macrophages by quadrol [N,N,N',N'-tetrakis(2-hydroxypropyl)ethylenediamine]. J Immunopharmacol. 1985;7(3):303-12. [2]. Bhide MV, et al. Promotion of wound collagen formation in normal and diabetic mice by quadrol. Immunopharmacol Immunotoxicol. 1988;10(4):513-22.
Cas No. | 102-60-3 | SDF | |
别名 | N,N,N',N'-四(2-羟基丙基)乙二胺,N,N,N′,N′-Tetrakis(2-hydroxypropyl)ethylenediamine; EDTP | ||
Canonical SMILES | CC(O)CN(CC(O)C)CCN(CC(O)C)CC(O)C | ||
分子式 | C14H32N2O4 | 分子量 | 292.41 |
溶解度 | DMSO : ≥ 83.3 mg/mL (284.87 mM) | 储存条件 | Store at -20°C |
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制备储备液 | |||
1 mg | 5 mg | 10 mg | |
1 mM | 3.4199 mL | 17.0993 mL | 34.1986 mL |
5 mM | 0.684 mL | 3.4199 mL | 6.8397 mL |
10 mM | 0.342 mL | 1.7099 mL | 3.4199 mL |
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1. 首先保证母液是澄清的;
2.
一定要按照顺序依次将溶剂加入,进行下一步操作之前必须保证上一步操作得到的是澄清的溶液,可采用涡旋、超声或水浴加热等物理方法助溶。
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Resolution of diastereomers of N,N,N',N'-tetrakis(2-hydroxypropyl)ethylenediamine (quadrol) by reversed-phase high-performance liquid chromatography
Quadrol, N,N,N',N'-tetrakis(2-hydroxypropyl)ethylenediamine, has been recently observed to display biological activity. It is an immunostimulant and has been implicated as a potentially useful agent in accelerated wound healing. Quadrol exists as a mixture of four unique diastereomers, each of which may, upon further investigation, display differences in biological activity. This paper describes an high-performance liquid chromatographic procedure (both analytical and prep) for the separation of the Quadrol diastereomers. Gas-liquid chromatography and NMR data are presented which corroborate the high-performance liquid chromatographic results. This procedure may be used to obtain pure Quadrol diastereomers, to monitor the progress of Quadrol synthesis from propylene oxide and ethylenediamine or to develop a quantitative assay for Quadrol diastereomers.
Quadrol-Pd(II) complexes: phosphine-free precatalysts for the room-temperature Suzuki-Miyaura synthesis of nucleoside analogues in aqueous media
Commercially available Quadrol, N,N,N',N'-tetrakis(2-hydroxypropyl)ethylenediamine (THPEN), has been used for the first time as a N^N-donor neutral hydrophilic ligand in the synthesis and characterization of new water soluble palladium(II) complexes containing chloride, phthalimidate or saccharinate as co-ligands. [PdCl2(THPEN)] (1) [Pd(phthal)2(THPEN)] (2), [Pd(sacc)2(THPEN)] (3) and the analogous complex with the closely related N,N,N',N'-tetrakis(2-hydroxyethyl)ethylenediamine (THEEN) [Pd(sacc)2(THEEN)] (4) were efficiently prepared in a one-pot reaction from [PdCl2(CH3CN)2] or Pd(OAc)2. Structural characterization of 1 and 3 by single crystal X-ray diffraction produced the first structures reported to date of palladium complexes with Quadrol. The resultant palladium complexes are highly soluble in water and were found to be effective as phosphine-free catalysts for the synthesis of functionalized nucleoside analogues under room-temperature Suzuki-Miyaura cross-coupling conditions between 5-iodo-2'-deoxyuridine (& 5-iodo-2'-deoxycytidine) with different aryl boronic acids in neat water. This is the first report of the coupling process performed on nucleosides in water at room temperature.
In vitro stimulation of macrophages by quadrol [N,N,N',N'-tetrakis(2-hydroxypropyl)ethylenediamine]
Mouse peritoneal macrophages, when exposed to Quadrol [N,N,N',N'-tetrakis(2-hydroxypropyl)ethylenediamine] in vitro, show a dose dependent enhanced spreading over a four-hour period. In vitro Quadrol induced phagocytosis of polystyrene beads was found to be time and concentration dependent. The rate and extent of the enhancement of phagocytosis was comparable to that observed for lipopolysaccharide and tuftsin.
Quantitation of N,N,N',N'-tetrakis (2-hydroxypropyl)-ethylenediamine in plasma by gas chromatography
A wide-bore capillary gas chromatographic method with nitrogen-selective thermionic detection is described for the quantitative analysis of N,N,N',N'-tetrakis (2-hydroxypropyl)ethylenediamine (Quadrol) in plasma. N,N,N',N'-tetrakis (2-hydroxybutyl)ethylenediamine is used as an internal standard. Rat or human plasma samples (0.5 ml) are mixed with internal standard, adjusted to alkaline pH and subjected to a single extraction with dichloromethane. Quadrol recovery from plasma typically exceeds 90%. The method is linear over the range 1.0-50 micrograms/ml. The working detection limit is 0.5 microgram/ml and the analysis time is under 7 min. The procedure has been used to obtain plasma concentration versus time data for the evaluation of Quadrol pharmacokinetics in rats.
Investigation into the mechanism of stimulation of macrophages by Quadrol
Enhanced glucose utilization was observed in continuous cultures of macrophages in medium containing 4mM Quadrol, [N,N,N',N',Tetrakis(2-hydroxypropyl)ethylenediamine]. This enhancement was both time and concentration dependent. Radiolabeled 4mM Quadrol, after incubation with macrophages for 60 minutes, was shown to be associated with the cells at a level of 4 nmoles/10(6) cells. This association increased linearly with time, reaching a maximum at 60 minutes with no observable difference after 24 hours. Trypsin-EDTA treatment of these macrophages for 15 minutes reduced the amount of Quadrol associated with cells by about 50%. Quadrol, unlike Ca Ionophore A23187, did not induce influx of 45Ca into the cells within the incubation period of 60 minutes. Quadrol methacrylate and Poly(Quadrol methacrylate) stimulated macrophages to exhibit increased phagocytosis of polystyrene beads. This stimulation was comparable to that observed for Quadrol.