Guest Encapsulation in a Water-Soluble Molecular Capsule Based on Ionic Interactions

2003 ◽  
Vol 125 (33) ◽  
pp. 9946-9947 ◽  
Author(s):  
Francesca Corbellini ◽  
Luigi Di Costanzo ◽  
Mercedes Crego-Calama ◽  
Silvano Geremia ◽  
David N. Reinhoudt
Keyword(s):  
Water Soluble ◽  
Ionic Interactions ◽  
Molecular Capsule

Effect of aggregation of a cationic phthalocyanine in micelles and in the presence of human serum albumin

2006 ◽  
Vol 10 (01) ◽  
pp. 33-42 ◽  
Author(s):  
Myriam E. Rodriguez ◽  
Daniel A. Fernández ◽  
Josefina Awruch ◽  
Silvia E. Braslavsky ◽  
Lelia E. Dicelio
Keyword(s):  
Human Serum Albumin ◽  
Serum Albumin ◽  
Human Serum ◽  
Hydrophobic Interactions ◽  
Photophysical Properties ◽  
Sodium Dodecylsulfate ◽  
Water Soluble ◽  
Quantum Yields ◽  
Ionic Interactions ◽  
Triplet Quantum Yields

The photophysical properties of tetrakis(1,1-dimethyl-2-trimethylammonium)ethylphthalocyaninato zinc(II) tetraiodide (I) – a water-soluble cationic phthalocyanine – are presented in the presence of human serum albumin (HSA) and in micelles of sodium dodecylsulfate ( SDS ) and hexadecyltrimethylammonium chloride ( CTAC ). Spectrophotometric measurements showed that the surfactants SDS and CTAC induce monomerization of I, although the latter less efficiently than the former. This effect is less pronounced in the presence of HSA. The strength of this effect is evaluated through dimerization constants, which are Kd = (5 ± 1) × 105 m−1 in SDS , (1.5 ± 0.5) × 106 M −1 in CTAC , and (1.8 ± 0.9) × 106 M −1 in HSA. Fluorescence experiments confirm that aggregation of I drops as the concentration of surfactant is raised. Triplet quantum yields also decreased upon aggregation and were Φ T = 0.59, 0.16, and < 0.01 in SDS , CTAC , and HSA, respectively. These results indicate that the affinity of I for the environment is not just due to ionic interactions; hydrophobic interactions play an equally important role.

scholarly journals Polarisable Hydrogen Bond Formation and Ionic Interactions in Model Phospholipid Polar Head Molecules

1973 ◽  
Vol 28 (5-6) ◽  
pp. 323-330 ◽  
Author(s):  
Georg Papakostidis ◽  
Georg Zundel
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Phosphoric Acid ◽  
Bond Formation ◽  
Ion Pairs ◽  
Water Soluble ◽  
Ionic Interactions ◽  
Hydrogen Bond Formation ◽  
Continuous Absorption ◽  
Phosphate Groups

The serine phosphoric acid P-methylester (SPM) and the ethanol-amine phosphoric acid P-methylester (EPM) were synthesized as water soluble models for the functional groups of the corresponding phospholipids. Investigations were made of the aqueous solutions of these molecules as a function of deprotonation and protonation. An intramolecular, easily polarisable hydrogen bond occurs in the zwitterion of the SPM. The solutions of different salts of SPM were studied as well as the influence of counter ion pairs. Counterion pairs hardly influence these bonds. At about 50% deprotonation extremely easily polarisable intermolecular bonds form. At about 100% deprotonation of the zwitterion the hydrogen bonds observed are affected by the presence of CO2. The above is indicated by changes of the bands of the carboxylic and phosphate groups, and in particular by a continuous absorption in the infrared spectrum. During protonation of the EPM easily polarisable intermolecular POH+ ... OP hydrogen bonds form at first, but as protonation increases the solutions become acidic, that is, H5O2+ groupings form.

Water Soluble Molecular Capsules via Multiple Ionic Interactions

2013 ◽  
Vol 10 (2) ◽  
pp. 147-149
Author(s):  
Reza Zadmard ◽  
Hajar Entezari ◽  
Parinaz Ataeian ◽  
Maryam Mirza-Aghayan
Keyword(s):  
Water Soluble ◽  
Ionic Interactions ◽  
Molecular Capsules

scholarly journals Co-Amorphous Screening for the Solubility Enhancement of Poorly Water-Soluble Mirabegron and Investigation of Their Intermolecular Interactions and Dissolution Behaviors

Pharmaceutics ◽  
2018 ◽  
Vol 10 (3) ◽  
pp. 149 ◽  
Author(s):  
Ji-Hun An ◽  
Changjin Lim ◽  
Alice Kiyonga ◽  
In Chung ◽  
In Lee ◽  
...  
Keyword(s):  
Phase Transformation ◽  
Amorphous State ◽  
Magic Angle Spinning ◽  
Water Soluble ◽  
Crystalline Solid ◽  
Ionic Interactions ◽  
Magic Angle ◽  
Solid Materials ◽  
Produce Water ◽  
Monitoring Result

In the present study, the screening of Mirabegron (MBR) co-amorphous was performed to produce water-soluble and thermodynamically stable MBR co-amorphous with the purpose of overcoming the water solubility problem of MBR. MBR is Biopharmaceutics Classification System (BCS) class II drug used for the treatment of an overreactive bladder. The co-amorphous screening was carried out by means of the vacuum evaporation crystallization technique in methanol solvent using three water-soluble carboxylic acids, characterized by a pKa difference greater than 3 with MBR such as fumaric acid (FA), l-pyroglutamic acid (PG), and citric acid (CA). Powder X-ray diffraction (PXRD) results suggested that all solid materials produced at MBR-FA (1 equivalent (eq.)/1 equivalent (eq.)), MBR-PG (1 eq./1 eq.), and MBR-CA (1 eq./1 eq.) conditions were amorphous state solid materials. Furthermore, by means of solution-state nuclear magnetic resonance (NMR) (1H, 13C, and 2D) and attenuated total reflection Fourier transform infrared (ATR-FTIR) spectroscopy, we could assess that MBR and carboxylic acid molecules were linked via ionic interactions to produce MBR co-amorphous. Besides, solid-state cross polarization (CP)/magic angle spinning (MAS) 13C-NMR analysis was conducted for additional assessment of MBR co-amorphous. Afterwards, dissolution tests of MBR co-amorphouses, MBR crystalline solid, and MBR amorphous were carried out for 12 h to evaluate and to compare their solubilities, dissolution rates, and phase transformation phenomenon. Here, the results suggested that MBR co-amorphouses displayed more than 57-fold higher aqueous solubility compared to MBR crystalline solid, and PXRD monitoring result suggested that MBR co-amorphouses were able to maintain their amorphous state for more than 12 h. The same results revealed that MBR amorphous exhibited increased solubility of approximatively 6.7-fold higher compared to MBR crystalline solid. However, the PXRD monitoring result suggested that MBR amorphous undergo rapid phase transformation to crystalline form in just 35 min and that within an hour all MBR amorphous are completely converted to crystalline solid. Accordingly, the increase in MBR co-amorphous’ solubility was attributed to the presence of ionic interactions in MBR co-amorphous molecules. Moreover, from the differential scanning calorimetry (DSC) monitoring results, we predicted that the high glass transition temperature (Tg) of MBR co-amorphous compared to MBR amorphous was the main factor influencing the phase stability of MBR co-amorphous.

Formation and characterization of water-soluble hetero capsules derived from multiple ionic interactions

Tetrahedron ◽  
2012 ◽  
Vol 68 (5) ◽  
pp. 1492-1501 ◽  
Author(s):  
Takahiro Kusukawa ◽  
Chikako Katano ◽  
Chizuru Kim
Keyword(s):  
Water Soluble ◽  
Ionic Interactions

scholarly journals Synthesis and Coordination Properties of a Water-Soluble Material by Cross-Linking Low Molecular Weight Polyethyleneimine with Armed Cyclotriveratrilene

Polymers ◽  
2021 ◽  
Vol 13 (23) ◽  
pp. 4133
Author(s):  
Yoke Mooi Ng ◽  
Paolo Coghi ◽  
Jerome P. L. Ng ◽  
Fayaz Ali ◽  
Vincent Kam Wai Wong ◽  
...  
Keyword(s):  
Molecular Weight ◽  
Hydrophobic Interactions ◽  
Water Soluble ◽  
Ionic Interactions ◽  
Cross Linking ◽  
Low Molecular Weight ◽  
Hydrophilic Drugs ◽  
Drug Molecules ◽  
Soluble Material ◽  
High Coordination

In this study, a full organic and water-soluble material was synthesized by coupling low molecular weight polyethylenimine (PEI-800) with cyclotriveratrilene (CTV). The water-soluble cross-linked polymer contains hydrophobic holes with a high coordination capability towards different organic drug molecules. The coordinating capability towards hydrophilic drugs (doxorubicin, gatifloxacin and sinomenine) and hydrophobic drugs (camptothecin and celastrol) was analyzed in an aqueous medium by using NMR, UV-Vis and emission spectroscopies. The coordination of drug molecules with the armed CTV unit through hydrophobic interactions was observed. In particular, celastrol exhibited more ionic interactions with the PEI moiety of the hosting system. In the case of doxorubicin, the host–guest detachment was induced by the addition of ammonium chloride, suggesting that the intracellular environment can facilitate the release of the drug molecules.

Water-Soluble Molecular Capsule for the Complexation of Cesium and Thallium Cations

2012 ◽  
Vol 116 (35) ◽  
pp. 10905-10914 ◽  
Author(s):  
Thierry Brotin ◽  
Dominique Cavagnat ◽  
Patrick Berthault ◽  
Roland Montserret ◽  
Thierry Buffeteau
Keyword(s):  
Water Soluble ◽  
Molecular Capsule

A Resorcinol-Formaldehyde Resin as an Embedding Material for Electron Microscopy of Membranes

1969 ◽  
Vol 27 ◽  
pp. 328-329 ◽  
Author(s):  
J. G. Robertson ◽  
D. F. Parsons
Keyword(s):  
Electron Microscopy ◽  
Osmium Tetroxide ◽  
Neutral Lipids ◽  
Lipid Extraction ◽  
Water Soluble ◽  
Formaldehyde Resin ◽  
Electron Microscope Autoradiography ◽  
Resorcinol Formaldehyde ◽  
Major Disadvantage ◽  
Cell Organization

The extraction of lipids from tissues during fixation and embedding for electron microscopy is widely recognized as a source of possible artifact, especially at the membrane level of cell organization. Lipid extraction is also a major disadvantage in electron microscope autoradiography of radioactive lipids, as in studies of the uptake of radioactive fatty acids by intestinal slices. Retention of lipids by fixation with osmium tetroxide is generally limited to glycolipids, phospholipids and highly unsaturated neutral lipids. Saturated neutral lipids and sterols tend to be easily extracted by organic dehydrating reagents prior to embedding. Retention of the more saturated lipids in embedded tissue might be achieved by developing new cross-linking reagents, by the use of highly water soluble embedding materials or by working at very low temperatures.

Ferritin Labeled Antibody Staining of Thin Sections

1969 ◽  
Vol 27 ◽  
pp. 420-421
Author(s):  
J. D. McLean ◽  
S. J. Singer
Keyword(s):  
Biological Material ◽  
Water Soluble ◽  
Thin Sections ◽  
Antibody Staining ◽  
Thin Sectioning ◽  
Ultrathin Sections

The successful application of ferritin labeled antibodies (F-A) to ultrathin sections of biological material has been hampered by two main difficulties. Firstly the normally used procedures for the preparation of material for thin sectioning often result in a loss of antigenicity. Secondly the polymers employed for embedding may non-specifically absorb the F-A. Our earlier use of cross-linked polyampholytes as embedding media partially overcame these problems. However the water-soluble monomers used for this method still extract many lipids from the material.

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