A new facile synthetic strategy was developed to prepare bifunctional monophosphinic acid Ln-DOTA derivatives, Gd-DO2AGAPNBn and Gd- DO2AGAPABn. The relaxivities of the Gd-complexes are enhanced compared to Gd-DOTA. Monophosphinic acid arm of these Gd-complexes affords enhancement of inner sphere water exchange rate due to its steric bulkiness. The different functionalities of DO2AGAPNBn were appended in trans positions and are designed to conjugate identical or different vectors according to the potential applications. The conjugation of Gd-DO2AGAPABn with E3 peptide known to target apoptosis was successfully performed and in vivo MRI allowed cell death detection in a mouse model.
- Klíčová slova
- Contrast agents, Gadolinium complex, Macrocyclic ligands, Peptide conjugation, Relaxivity,
- MeSH
- heterocyklické sloučeniny monocyklické chemická syntéza chemie MeSH
- kontrastní látky chemická syntéza chemie MeSH
- magnetická rezonanční tomografie MeSH
- molekulární struktura MeSH
- multimodální zobrazování * MeSH
- myši MeSH
- vztah mezi dávkou a účinkem léčiva MeSH
- vztahy mezi strukturou a aktivitou MeSH
- zvířata MeSH
- Check Tag
- myši MeSH
- ženské pohlaví MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- 1,4,7,10-tetraazacyclododecane- 1,4,7,10-tetraacetic acid MeSH Prohlížeč
- heterocyklické sloučeniny monocyklické MeSH
- kontrastní látky MeSH
Novel synthetic approaches for the development of multimodal imaging agents with high chemical stability are demonstrated. The magnetic cores are based on La0.63Sr0.37MnO3 manganite prepared as individual grains using a flux method followed by additional thermal treatment in a protective silica shell allowing to enhance their magnetic properties. The cores are then isolated and covered de novo with a hybrid silica layer formed through the hydrolysis and polycondensation of tetraethoxysilane and a fluorescent silane synthesized from rhodamine, piperazine spacer, and 3-iodopropyltrimethoxysilane. The aminoalkyltrialkoxysilanes are strictly avoided and the resulting particles are hydrolytically stable and do not release dye. The high colloidal stability of the material and the long durability of the fluorescence are reinforced by an additional silica layer on the surface of the particles. Structural and magnetic studies of the products using XRD, TEM, and SQUID magnetometry confirm the importance of the thermal treatment and demonstrate that no mechanical treatment is required for the flux-synthesized manganite. Detailed cell viability tests show negligible or very low toxicity at concentrations at which excellent labeling is achieved. Predominant localization of nanoparticles in lysosomes is confirmed by immunofluorescence staining. Relaxometric and biological studies suggest that the functionalized nanoparticles are suitable for imaging applications.
- Klíčová slova
- Cell labeling, Dual probes, MRI, Magnetic nanoparticles, Manganites, Molten salt synthesis, Silica coating,
- MeSH
- fibroblasty cytologie metabolismus MeSH
- fluorescence MeSH
- fluorescenční protilátková technika MeSH
- HeLa buňky MeSH
- Jurkat buňky MeSH
- kultivované buňky MeSH
- kůže cytologie metabolismus MeSH
- lanthan chemie MeSH
- lidé MeSH
- magnetická rezonanční tomografie MeSH
- magnetické nanočástice chemie MeSH
- membránové glykoproteiny asociované s lyzozomy imunologie metabolismus MeSH
- monoklonální protilátky imunologie MeSH
- oxid křemičitý chemie MeSH
- povrchové vlastnosti MeSH
- průtoková cytometrie MeSH
- silany chemie MeSH
- sloučeniny manganu chemie MeSH
- stroncium chemie MeSH
- transmisní elektronová mikroskopie MeSH
- velikost částic MeSH
- viabilita buněk MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- LAMP1 protein, human MeSH Prohlížeč
- lanthan MeSH
- magnetické nanočástice MeSH
- manganite MeSH Prohlížeč
- membránové glykoproteiny asociované s lyzozomy MeSH
- monoklonální protilátky MeSH
- oxid křemičitý MeSH
- silany MeSH
- sloučeniny manganu MeSH
- stroncium MeSH
- tetraethoxysilane MeSH Prohlížeč
Three magnetic resonance (MR)/fluorescence imaging probes were tested for visualization, cellular distribution, and survival of labeled pancreatic islets in vitro and following transplantation. As T(1) contrast agents (CAs), gadolinium(III) complexes linked to β-cyclodextrin (Gd-F-βCD) or bound to titanium dioxide (TiO2 @RhdGd) were tested. As a T(2) CA, perovskite manganite nanoparticles (LSMO@siF@si) were examined. Fluorescein or rhodamine was incorporated as a fluorescent marker in all probes. Islets labeled with gadolinium(III) CAs were visible as hyperintense spots on MR in vitro, but detection in vivo was inconclusive. Islets labeled with LSMO@siF@si CA were clearly visible as hypointense spots or areas on MR scans in vitro as well as in vivo. All CAs were detected inside the islet cells by fluorescence. Although the vitality and function of the labeled islets was not impaired by any of the tested CAs, results indicate that LSMO@siF@si CA is a superior marker for islet labeling, as it provides better contrast enhancement within a shorter scan time.
- MeSH
- beta-cyklodextriny chemie MeSH
- fluorescenční barviva chemie MeSH
- fluorescenční mikroskopie MeSH
- gadolinium chemie MeSH
- kontrastní látky chemie MeSH
- kovové nanočástice chemie MeSH
- krysa rodu Rattus MeSH
- kultivované buňky MeSH
- Langerhansovy ostrůvky cytologie diagnostické zobrazování metabolismus MeSH
- magnetická rezonanční tomografie MeSH
- potkani inbrední LEW MeSH
- rentgendiagnostika MeSH
- sloučeniny manganu chemie MeSH
- titan chemie MeSH
- zvířata MeSH
- Check Tag
- krysa rodu Rattus MeSH
- mužské pohlaví MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- srovnávací studie MeSH
- Názvy látek
- beta-cyklodextriny MeSH
- betadex MeSH Prohlížeč
- fluorescenční barviva MeSH
- gadolinium MeSH
- kontrastní látky MeSH
- manganite MeSH Prohlížeč
- sloučeniny manganu MeSH
- titan MeSH
- titanium dioxide MeSH Prohlížeč
Three symmetrical methylene-bis[(aminomethyl)phosphinic acids] bearing different substituents on the central carbon atom, (NH(2)CH(2))PO(2)H-C(R(1))(R(2))-PO(2)H(CH(2)NH(2)) where R(1) = OH, R(2) = Me (H(2)L(1)), R(1) = OH, R(2) = Ph (H(2)L(2)) and R(1),R(2) = H (H(2)L(3)), were synthesized. Acid-base and complexing properties of the ligands were studied in solution as well as in the solid state. The ligands show unusually high basicity of the nitrogen atoms (log K(1) = 9.5-10, log K(2) = 8.5-9) if compared with simple (aminomethyl)phosphinic acids and, consequently, high stability constants of the complexes with studied divalent metal ions. The study showed the important role of the hydroxo group attached to the central carbon atom of the geminal bis(phosphinate) moiety. Deprotonation of the hydroxo group yields the alcoholate anion which tends to play the role of a bridging ligand and induces formation of polynuclear complexes. Solid-state structures of complexes [H(2)N=C(NH(2))(2)][Cu(2)(H(-1)L(2))(2)]CO(3)·10H(2)O and Li(2)[Co(4)(H(-1)L(1))(3)(OH)]·17.5H(2)O were determined by X-ray diffraction. The complexes show unexpected geometries forming dinuclear and cubane-like structures, respectively. The dinuclear copper(II) complex contains a bridging μ(2)-alcoholate group with the (-)O-P(=O)-CH(2)-NH(2) fragments of each ligand molecule chelated to the different central ion. In the cubane cobalt(II) complex, one μ(3)-hydroxide and three μ(3)-alcoholate anions are located in the cube vertices and both phosphinate groups of one ligand molecule are chelating the same cobalt(II) ion while each of its amino groups are bound to different neighbouring metal ions. All such three metal ions are bridged by the alcoholate group of a given ligand.
- MeSH
- acidobazická rovnováha MeSH
- koncentrace vodíkových iontů MeSH
- kyseliny fosfinové chemická syntéza chemie MeSH
- magnetická rezonanční spektroskopie MeSH
- molekulární modely MeSH
- molekulární struktura MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- kyseliny fosfinové MeSH
Middle-molecular-weight MRI contrast agents based on conjugates of a phosphinic acid DOTA analogue, 1,4,7,10-tetraazacyclododecane-4,7,10-triacetic-1-{methyl[(4-aminophenyl)methyl]phosphinic acid} (DO3AP(ABn)), with amino-substituted cyclodextrins were prepared and studied by a variety of physico-chemical methods. The conjugates were formed by reaction of the corresponding isothiocyanate with per-6-amino-α/β-cyclodextrin and were complexed with the Ln(III) ion to get the final complexes, (LnL)(6)-α-CD and (LnL)(7)-β-CD. Solution structure of the complexes was estimated by investigation of the Eu(III) complexes. The Gd(III) conjugate complexes are endowed with a short water residence time (τ(M) ∼ 10-15 ns at 298 K) and a high abundance of the twisted-square antiprismatic diastereoisomer. They show a high (1)H relaxivity at high fields due to a convenient combination of the fast water exchange rate and the slow rate of the molecular tumbling given by their macromolecular nature. The (1)H relaxation enhancements per molecule of a contrast agent (CA) are very high reaching for a larger (GdL)(7)-β-CD conjugate ∼140 s(-1) mM(-1) and ∼100 s(-1) mM(-1) at 25 °C and magnetic fields 1.5 T and 3 T, respectively, which is the highest reported longitudinal relaxivity for kinetically stable contrast agents of an intermediate molecular mass (<10 kDa) with one water molecule in the first coordination sphere.
- MeSH
- cyklodextriny chemie MeSH
- gadolinium chemie MeSH
- heterocyklické sloučeniny monocyklické chemie MeSH
- komplexní sloučeniny chemická syntéza chemie MeSH
- kontrastní látky chemická syntéza chemie MeSH
- lanthanoidy chemie MeSH
- magnetická rezonanční tomografie MeSH
- magnetické pole MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- 1,4,7,10-tetraazacyclododecane- 1,4,7,10-tetraacetic acid MeSH Prohlížeč
- cyklodextriny MeSH
- gadolinium MeSH
- heterocyklické sloučeniny monocyklické MeSH
- komplexní sloučeniny MeSH
- kontrastní látky MeSH
- lanthanoidy MeSH
Mn(2+) complexes represent an alternative to Gd(3+) chelates which are widely used contrast agents in magnetic resonance imaging. In this perspective, we investigated the Mn(2+) complexes of two 12-membered, pyridine-containing macrocyclic ligands bearing one pendant arm with a carboxylic acid (HL(1), 6-carboxymethyl-3,6,9,15-tetraazabicyclo[9.3.1] pentadeca-1(15),11,13-triene) or a phosphonic acid function (H(2)L(2), 6-dihydroxyphosphorylmethyl-3,6,9,15-tetraazabicyclo[9.3.1]pentadeca-1(15),11,13-triene). Both ligands were synthesized using nosyl or tosyl amino-protecting groups (starting from diethylenetriamine or tosylaziridine). The X-ray crystal structures confirmed a coordination number of 6 for Mn(2+) in their complexes. In aqueous solution, these pentadentate ligands allow one free coordination site for a water molecule. Potentiometric titration data indicated a higher basicity for H(2)L(2) than that for HL(1), related to the electron-donating effect of the negatively charged phosphonate group. According to the protonation sequence determined by (1)H and (31)P pH-NMR titrations, the first two protons are attached to macrocyclic amino groups whereas the subsequent protonation steps occur on the pendant arm. Both ligands form thermodynamically stable complexes with Mn(2+), with full complexation at physiological pH and 1:1 metal to ligand ratio. The kinetic inertness was studied via reaction with excess of Zn(2+) under various pHs. The dissociation of MnL(2) is instantaneous (at pH 6). For MnL(1), the dissociation is very fast (k(obs) = 1-12 × 10(3) s(-1)), much faster than that for MnDOTA, MnNOTA, or the Mn(2+) complex of the 15-membered analogue. It proceeds exclusively via the dissociation of the monoprotonated complex, without any influence of Zn(2+). In aqueous solution, both complexes are air-sensitive leading to Mn(3+) species, as evidenced by UV-vis and (1)H NMRD measurements and X-ray crystallography. Cyclic voltammetry gave low oxidation peak potentials (E(ox) = 0.73 V for MnL(1) and E(ox) = 0.68 V for MnL(2)), in accordance with air-oxidation. The parameters governing the relaxivity of the Mn(2+) complexes were determined from variable-temperature (17)O NMR and (1)H NMRD data. The water exchange is extremely fast, k(ex) = 3.03 and 1.77 × 10(9) s(-1) for MnL(1) and MnL(2), respectively. Variable-pressure (17)O NMR measurements have been performed to assess the water exchange mechanism on MnL(1) and MnL(2) as well as on other Mn(2+) complexes. The negative activation volumes for both MnL(1) and MnL(2) complexes confirmed an associative mechanism of the water exchange as expected for a hexacoordinated Mn(2+) ion. The hydration number of q = 1 was confirmed for both complexes by (17)O chemical shifts. A relaxometric titration with phosphate, carbonate or citrate excluded the replacement of the coordinated water molecule by these small endogenous anions.
- MeSH
- chelátory chemická syntéza MeSH
- heterocyklické sloučeniny bicyklické chemická syntéza MeSH
- kinetika MeSH
- komplexní sloučeniny chemická syntéza MeSH
- koncentrace vodíkových iontů MeSH
- kontrastní látky chemická syntéza MeSH
- krystalografie rentgenová MeSH
- kyseliny karboxylové chemie MeSH
- magnetická rezonanční spektroskopie MeSH
- magnetická rezonanční tomografie metody MeSH
- mangan chemie MeSH
- molekulární modely MeSH
- molekulární struktura MeSH
- organofosfonáty chemie MeSH
- oxidace-redukce MeSH
- potenciometrie MeSH
- pyridiny chemie MeSH
- teplota MeSH
- termodynamika MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- chelátory MeSH
- heterocyklické sloučeniny bicyklické MeSH
- komplexní sloučeniny MeSH
- kontrastní látky MeSH
- kyseliny karboxylové MeSH
- mangan MeSH
- organofosfonáty MeSH
- pyridiny MeSH
A new class of macrocyclic ligands based on 1-oxa-4,7-diazacyclononane was synthesized and their Mn(2+) complexes were investigated with respect to stability and relaxation properties. Each ligand has two pendant arms involving carboxylic (H(2)L(1)--1-oxa-4,7-diazacyclononane-4,7-diacetic acid), phosphonic (H(4)L(2)--1-oxa-4,7-diazacyclononane-4,7-bis(methylenephosphonic acid)), phosphinic (H(2)L(3)--1-oxa-4,7-diazacyclononane-4,7-bis(methylenephosphinic acid)) or phenylphosphinic (H(2)L(4)--1-oxa-4,7-diazacyclononane-4,7-bis[methylene(phenyl)phosphinic acid]) acid moieties. H(2)L(3) and H(2)L(4) were synthesized for the first time. The crystal structure of the Mn(2+) complex with H(2)L(4) confirmed a coordination number of 6 for Mn(2+). The protonation constants of all ligands and the stability constants of their complexes with Mn(2+) and some biologically or biomedically relevant metal ions were determined by potentiometry. The protonation sequence of H(2)L(3) was followed by (1)H and (31)P NMR titration and the second protonation step was attributed to the second macrocyclic nitrogen atom. The potentiometric data revealed a relatively low thermodynamic stability of the Mn(2+) complexes with all ligands investigated. For H(2)L(3) and H(2)L(4), full Mn(2+) complexation cannot be achieved even with 100% ligand excess. The transmetallation of MnL(1) and MnL(2) with Zn(2+) was too fast to be followed at pH 6. Variable temperature (1)H NMRD and (17)O NMR measurements have been performed on MnL(1) and MnL(2) to provide information on water exchange and rotational dynamics. The (17)O chemical shifts indicate hydration equilibrium between mono- and bishydrated species for MnL(1), while MnL(2) is monohydrated. The water exchange is considerably faster on MnL(1) (k(ex)(298) = 1.2 × 10(9) s(-1)) than on MnL(2) (k(ex)(298) = 1.2 × 10(7) s(-1)). Small endogenous anions (phosphate, carbonate, citrate) do not replace the coordinated water in either of the complexes, but they induce their slow decomposition. All Mn(2+) complexes are stable toward air-oxidation.
- MeSH
- kinetika MeSH
- komplexní sloučeniny chemie MeSH
- krystalografie rentgenová MeSH
- kyselina octová chemie MeSH
- kyseliny fosfinové chemie MeSH
- ligandy MeSH
- magnetická rezonanční spektroskopie MeSH
- mangan chemie MeSH
- molekulární konformace MeSH
- organofosfonáty chemie MeSH
- organokovové sloučeniny chemie MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- komplexní sloučeniny MeSH
- kyselina octová MeSH
- kyseliny fosfinové MeSH
- ligandy MeSH
- mangan MeSH
- manganese(II)-1-oxa-4,7-diazacyclononane MeSH Prohlížeč
- organofosfonáty MeSH
- organokovové sloučeniny MeSH
Multimodal imaging-therapeutic nanoprobe TiO(2)@RhdGd was prepared and successfully used for in vitro and in vivo cell tracking as well as for killing of cancer cells in vitro. TiO(2) nanoparticles were used as a core for phosphonic acid modified functionalities, responsible for contrast in MRI and optical imaging. The probe shows high (1)H relaxivity and relaxivity density values. Presence of fluorescent dye allows for visualization by means of fluorescence microscopy. The applicability of the probe was studied, using mesenchymal stem cells, cancer HeLa cells, and T-lymphocytes. The probe did not exhibit toxicity in any of these systems. Labeled cells were successfully visualized in vitro by means of fluorescence microscopy and MRI. Furthermore, it was shown that the probe TiO(2)@RhdGd can be changed into a cancer cell killer upon UV light irradiation. The above stated results represent a valuable proof of a principle showing applicability of the probe design for diagnosis and therapy.
- MeSH
- afinitní značky chemická syntéza chemie farmakologie MeSH
- antitumorózní látky chemická syntéza chemie farmakologie MeSH
- fluorescenční barviva chemická syntéza chemie farmakologie MeSH
- fluorescenční mikroskopie MeSH
- gadolinium MeSH
- HeLa buňky MeSH
- komplexní sloučeniny chemická syntéza chemie farmakologie MeSH
- léky antitumorózní - screeningové testy MeSH
- lidé MeSH
- magnetická rezonanční tomografie MeSH
- mezenchymální kmenové buňky metabolismus MeSH
- myši MeSH
- nanočástice * MeSH
- organofosfonáty chemická syntéza chemie farmakologie MeSH
- T-lymfocyty metabolismus MeSH
- titan chemie farmakologie MeSH
- ultrafialové záření MeSH
- viabilita buněk účinky léků MeSH
- vztahy mezi strukturou a aktivitou MeSH
- zvířata MeSH
- Check Tag
- lidé MeSH
- myši MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- afinitní značky MeSH
- antitumorózní látky MeSH
- fluorescenční barviva MeSH
- gadolinium MeSH
- komplexní sloučeniny MeSH
- organofosfonáty MeSH
- titan MeSH
- titanium dioxide MeSH Prohlížeč
The kinetics of transmetallation of [Mn(nota)](-) and [Mn(dota)](2-) was investigated in the presence of Zn(2+) (5-50-fold excess) at variable pH (3.5-5.6) by (1)H relaxometry. The dissociation is much faster for [Mn(nota)](-) than for [Mn(dota)](2-) under both experimental and physiologically relevant conditions (t(½) = 74 h and 1037 h for [Mn(nota)](-) and [Mn(dota)](2-), respectively, at pH 7.4, c(Zn(2+)) = 10(-5) M, 25 °C). The dissociation of the complexes proceeds mainly via spontaneous ([Mn(nota)](-)k(0) = (2.6 ± 0.5) × 10(-6) s(-1); [Mn(dota)](2-)k(0) = (1.8 ± 0.6) × 10(-7) s(-1)) and proton-assisted pathways ([Mn(nota)](-)k(1) = (7.8 ± 0.1) × 10(-1) M(-1) s(-1); [Mn(dota)](2-)k(1) = (4.0 ± 0.6) × 10(-2) M(-1) s(-1), k(2) = (1.6 ± 0.1) × 10(3) M(-2) s(-1)). The observed suppression of the reaction rates with increasing Zn(2+) concentration is explained by the formation of a dinuclear Mn(2+)-L-Zn(2+) complex which is about 20-times more stable for [Mn(dota)](2-) than for [Mn(nota)](-) (K(MnLZn) = 68 and 3.6, respectively), and which dissociates very slowly (k(3)∼10(-5) M(-1) s(-1)). These data provide the first experimental proof that not all Mn(2+) complexes are kinetically labile. The absence of coordinated water makes both [Mn(nota)](-) and [Mn(dota)](2-) complexes inefficient for MRI applications. Nevertheless, the higher kinetic inertness of [Mn(dota)](2-) indicates a promising direction in designing ligands for Mn(2+) complexation.
- MeSH
- chloridy chemie MeSH
- heterocyklické sloučeniny monocyklické MeSH
- heterocyklické sloučeniny chemie MeSH
- kinetika MeSH
- komplexní sloučeniny chemická syntéza MeSH
- koncentrace vodíkových iontů MeSH
- krystalografie rentgenová metody MeSH
- ligandy MeSH
- magnetická rezonanční spektroskopie MeSH
- molekulární modely * MeSH
- relaxace MeSH
- sloučeniny manganu chemie MeSH
- sloučeniny zinku chemie MeSH
- voda chemie MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- 1,4,7-triazacyclononane-N,N',N''-triacetic acid MeSH Prohlížeč
- chloridy MeSH
- heterocyklické sloučeniny monocyklické MeSH
- heterocyklické sloučeniny MeSH
- komplexní sloučeniny MeSH
- ligandy MeSH
- sloučeniny manganu MeSH
- sloučeniny zinku MeSH
- voda MeSH
- zinc chloride MeSH Prohlížeč
Given the practical advantages of the (68)Ga isotope in positron emission tomography applications, gallium complexes are gaining increasing importance in biomedical imaging. However, the strong tendency of Ga(3+) to hydrolyze and the slow formation and very high stability of macrocyclic complexes altogether render Ga(3+) coordination chemistry difficult and explain why stability and kinetic data on Ga(3+) complexes are rather scarce. Here we report solution and solid-state studies of Ga(3+) complexes formed with the macrocyclic ligand 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid, (DOTA)(4-), and its mono(n-butylamide) derivative, (DO3AM(Bu))(3-). Thermodynamic stability constants, log K(GaDOTA) = 26.05 and log K(GaDO3AM(Bu)) = 24.64, were determined by out-of-cell pH-potentiometric titrations. Due to the very slow formation and dissociation of the complexes, equilibration times of up to ∼4 weeks were necessary. The kinetics of complex dissociation were followed by (71)Ga NMR under both acidic and alkaline conditions. The GaDOTA complex is significantly more inert (τ(1/2) ∼12.2 d at pH = 0 and τ(1/2) ∼6.2 h at pH = 10) than the GaDO3AM(Bu) analogue (τ(1/2) ∼2.7 d at pH = 0 and τ(1/2) ∼0.7 h at pH = 10). Nevertheless, the kinetic inertness of both chelates is extremely high and approves the application of Ga(3+) complexes of such DOTA-like ligands in molecular imaging. The solid-state structure of the GaDOTA complex, crystallized from a strongly acidic solution (pH < 1), evidenced a diprotonated form with protons localized on the free carboxylate pendants.
- MeSH
- amidy chemie MeSH
- galium chemie MeSH
- heterocyklické sloučeniny monocyklické chemie MeSH
- kinetika MeSH
- koncentrace vodíkových iontů MeSH
- krystalografie rentgenová MeSH
- molekulární modely MeSH
- organokovové sloučeniny chemie MeSH
- termodynamika MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- 1,4,7,10-tetraazacyclododecane- 1,4,7,10-tetraacetic acid MeSH Prohlížeč
- amidy MeSH
- galium MeSH
- heterocyklické sloučeniny monocyklické MeSH
- organokovové sloučeniny MeSH