N,N'-Bis(2-hydroxyethyl)ethylenediamine

Manipulating selectivity of covalently-bonded hyperbranched anion exchangers toward organic acids. Part III: Effect of diamine structure in the external part of the functional layer.[Pubmed:31182306]

J Chromatogr A. 2019 Sep 27;1602:310-316.

The chromatographic properties of three hyperbranched anion exchangers having various diamines in the external part of the functional layer are studied in order to reveal diamine influence on selectivity toward mono- and divalent organic acids. The obtained stationary phases have the same structure of the internal part of the functional layer formed by repeating 4 modification cycles including alkylation with 1,4-butanediol diglycidyl ether (1,4-BDDGE) and amination with methylamine (MA) and differ by the structure of diamine used in the 5(th) modification cycle. For the first time several diamines (ethylenediamine, (2-aminoethyl)aminoethanol, and N,N'-bis(2-hydroxyethyl)ethylenediamine) are used for completing the last modification cycle in hyperbranching. The performance of three prepared anion exchangers is investigated using KOH and NaHCO3 as eluents and discussed with respect to the differences in hydrophilicity of the external part of the functional layer showing its effect on the separation of organic acids.

Hydrogen-bonding network of N,N'-bis[2-(tert-butyldimethylsiloxy)ethyl]ethylenediammonium dichloride.[Pubmed:23832044]

Acta Crystallogr C. 2013 Jul;69(Pt 7):787-9.

The title salt, C18H46N2O2Si2(2+).2Cl(-), has been synthesized by reaction of N,N'-bis(2-hydroxyethyl)ethylenediamine with tert-butyldimethylsilyl chloride. The zigzag backbone dication is located across an inversion centre and the two chloride anions are related by inversion symmetry. The ionic components form a supramolecular two-dimensional network via N-H...Cl hydrogen bonding, which is responsible for the high melting point compared with the oily compound N,N'-bis[2-(tert-butyldimethylsiloxy)ethyl]ethylenediamine.

Biodegradable nitric oxide-releasing poly(diol citrate) elastomers.[Pubmed:19569216]

J Biomed Mater Res A. 2010 Apr;93(1):356-63.

We have developed novel poly(diol citrate) elastomers, which are capable of providing localized and sustained release of nitric oxide (NO). The elastomer prepolymer was obtained by condensation of citric acid, 1,8-octanediol, and N,N'-bis(2-hydroxyethyl)ethylenediamine at 130 degrees C for 40 min. Films were prepared by solvent casting followed by crosslinking at 80 degrees C for 4 days. Mechanical properties were tested. NO-releasing expanded poly(tetrafluoroethylene) (ePTFE) vascular grafts were fabricated by coating the graft's lumen with the prepolymer and crosslinking it at 80 degrees C for 4 days prior to diazeniumdiolation. Samples were diazeniumdiolated via exposure to pressurized NO. Cell compatibility was assessed by monitoring the proliferation of porcine aortic smooth muscle cells (PASMC) on the elastomers. Degradation in phosphate buffer saline (PBS) (pH = 7) at 37 degrees C was evaluated for up to 6 weeks. The secondary amine-containing poly(diol citrate) films had a Young's modulus that ranged from 5.91 to 32.64 MPa, an ultimate tensile stress that ranged from 1.47 to 10.71 MPa, and an elongation at break from 200 to 260%, depending on the content of secondary amine in the feed monomer. These elastomers were degradable and compatible with PASMC. Furthermore, degradation rate was found to be independent of the content of secondary amines in the prepolymer. The NO release from diazeniumdiolated films and ePTFE grafts was sustained for two days. In conclusion, these novel diazeniumdiolated polyester elastomers may be useful in medical devices that require blood contact or control of cell proliferation.

(Aminoethanol)dichloroplatinum(II) complexes: influence of the hydroxyethyl moiety on 5'-GMP and DNA binding, intramolecular stability, the partition coefficient and anticancer activity.[Pubmed:11897338]

J Inorg Biochem. 2002 Feb;88(3-4):254-9.

The influence of tethered hydroxyl groups on the binding behavior of the three (aminoethanol)dichloroplatinum complexes, dichloro(N,N'-bis(2-hydroxyethyl)ethylenediamine)-platinum(II) (1), dichloro(N-(2-hydroxyethyl)ethylenediamine)platinum(II) (2) and cis-dichlorobis(2-hydroxyethylamine)platinum(II) (3) towards 5'-GMP and DNA was investigated by 1H NMR and r(b) measurements, respectively. At pH 7.2, the sequence of reactivity with 5'-GMP is 1>2>>3. Complex 3 reacts very slowly with 5'-GMP and DNA and the amount and lifetime of the intermediate 5'-GMP monoadduct are much larger than for 1 and 2. At pH 5.5, the reaction of 3 with 5'-GMP is markedly accelerated and very small amounts of monoadduct are observed, indicating a pH-dependent ability of the pendant hydroxyl group to interact with the platinum moiety. In addition, the effect of the hydroxyethyl functionality on octanol/water partitioning and in vitro anticancer activity was studied. No correlation between lipophilicity and anticancer activity was detected. Furthermore, the lipophilicity and anticancer activity could not be directly correlated to 5'-GMP or DNA binding activity.

Poly(amidoamine)s with potential as drug carriers: degradation and cellular toxicity.[Pubmed:1772834]

J Biomater Sci Polym Ed. 1991;2(4):303-15.

Poly(amidoamine)s were synthesized by polyaddition reaction: to bis-acryloylpiperazine of piperazine (1), or N,N'-bis(2-hydroxyethyl)ethylenediamine (2), and to 2,2-bis(acrylamido)acetic acid of piperazine (3). Compound 2 was also end-capped with 4-hydroxythiophenol, thus introducing a terminal moiety suitable for radio-iodination using the chloramine T method (4). Such polymers behave as bases in aqueous solution, and their net average charge alters considerably as the pH changes from 7.4 to 5.5. This results in a change in polymer conformation which may prove useful in the design of polymeric drug delivery systems. However, their suitability for use in the organism will depend on polymer toxicity and also on their rate of biodegradation. Here we studied the biological properties of the above poly(amidoamine)s with a view to optimizing the synthesis of novel drug carriers. The general cytotoxicity of compounds 1, 2, 3, and 4 was examined in vitro using two human cell lines, hepatoma (HepG2) and a lymphoblastoid leukaemia (CCRF). Several different methods [the tetrazolium (MTT) test, [3H]leucine or [3H]thymidine incorporation, or counting cell numbers] were used to measure cell viability. Compounds 1, 2, and 4 were much less toxic to both cell lines than equivalent concentrations of the polycationic poly-L-lysine, and in no case did viability fall below 50% (concentrations up to 2 mg/ml). Although compound 2 was not markedly toxic to HepG2 cells, concentration-dependent toxicity was observed against CCRF cells. In this case, the polymer concentration decreasing viability by 59% (ID50) was approximately 50 micrograms/ml for compound 2 compared with an ID50 of approximately 10 micrograms/ml for poly-L-lysine. The rate of hydrolytic degradation of compound 2 was examined using viscometric measurements and gel permeation chromatography (GPC). After incubation at pH 7.5 and 8.0 for 24 h, polymer intrinsic viscosity was decreased by approximately 50% and GPC elution profiles showed a simultaneous increase in polymer retention time, indicating a fall in molecular weight. Hydrolytic degradation progressed much more slowly at pH 5.5. Compound 4 was also incubated with a mixture of isolated rat liver lysosomal enzymes (tritosomes) at pH 5.5, but no increase in the rate of degradation was observed.