Interactions of Dihydrochloride Fluphenazine with DPPC Liposomes: ATR-IR and <sup>31</sup>P NMR Studies

Cieślik-Boczula, Katarzyna; Szwed, Joanna; Jaszczyszyn, Agata; Gąsiorowski, Kazimierz; Koll, A.

doi:10.1021/jp904805t

Cited by 44 publications

(28 citation statements)

References 40 publications

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“…Such effect is indicative of a higher degree of hydration of the headgroups and can be readily interpreted in terms of hydrogen bonding to the PO 2 − group, either LG or water molecules, influenced by the presence of the LG in the system. The band in the region between 1094 and 1085 cm −1 is associated with the symmetric stretching vibrations of the phosphate group ν s (PO 2 − ) (Cieślik-Boczula et al 2009 ). The shift to lower frequencies is also visible on the absorption spectra confirming the hydrogen bond connection between LG and the phosphate lipid part.…”

Section: Resultsmentioning

confidence: 99%

Properties of Artificial Phospholipid Membranes Containing Lauryl Gallate or Cholesterol

2018

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Lauryl gallate (LG) is an antioxidant agent. However, it exhibits poor solubility in water. Its interactions with the membrane result in structure evolution thus affecting the membrane functionality. In this paper the Brewster angle microscope coupled with the Langmuir trough was applied to determine the morphology, phase behaviour, thickness and miscibility of ternary Langmuir monolayers with equal mole fractions of 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC); 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC) and an increasing mole fraction of LG. The results were discussed as regards analogous systems where cholesterol (Chol) was the third component. Moreover, the phosphatidylcholine–lauryl gallate (PC–LG) interactions were monitored by the attenuated total reflectance Fourier transform infrared spectroscopy and time-of-flight secondary ion mass spectrometry. Besides lipid composition, the addition of LG was found to be a significant factor to modulate the model membrane properties. The LG molecules adjust themselves to the PC monolayer structure. The hydrophobic fragment is dipped into the membrane interior while the hydroxyl groups of phenolic gallate moiety associate with the polar groups of PC mainly through hydrogen bonding inducing the compacting effect. LG is found to be deeply submerged within DOPC, closer to the double bonds, and its insertion practically does not affect the DPPC/DOPC membrane fluidity. This is crucial for getting more profound insight into the role of LG in stabilizing the non-raft domains, mostly exposed to oxidation in which LG can co-localize and serve its antioxidant function.

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Section: Resultsmentioning

confidence: 99%

Properties of Artificial Phospholipid Membranes Containing Lauryl Gallate or Cholesterol

2018

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“…These drugs exert their activity by the blockade of dopaminergic receptors in the brain; they also inhibit alpha adrenoreceptors and muscarinic, cholinergic, histamine, serotonin, and opioid receptors in the central nervous system [e.g., 4,5]. Fluphenazine is one of the piperazine class of phenothiazines and is extremely potent; more potent than haloperidol and around 50-70 times the potency of chlorpromazine [6].…”

Section: Resultsmentioning

confidence: 99%

The Crystal Structure of Fluphenazinium Dipicrate Dimethylsulphoxide Solvate

Dutkiewicz

Siddaraju²,

Yathirajan

et al. 2010

J Chem Crystallogr

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The title compound, C 22 H 28 F 3 N 3 OS 2? 9 2(C 6 H 2 N 3 O 7 -) 9 (CH 3 ) 2 SO-the picrate salt of the potent antipsychotic drug, fluphenazine-crystallizes in the triclinic P-1 space group with unit cell parameters a = 10.6333(12) Å , b = 11.9696(12) Å , c = 17.7036 (15) Å , a = 103.265(9)°, b = 98.414(9)°, c = 102.702 (10)°. The ionic fragments: the fluphenazinium dictation, and two picrate anions, are joined by means of strong N-HÁÁÁO and weak C-HÁÁÁO hydrogen bonds into the chains of alternating cations and anions, expanding along [010] direction. Within the chain, the picrates interact by means of short pÁÁÁp interactions: the mean distance between the planes is 3.366 Å ; additional interaction of the same type between one of the picrates and the phenyl ring of the phenothiazine ring system additionally strengthen the pattern. The phenothiazine ring exists in a typical, ''butterflylike'' conformation, with two terminal rings planar and the central ring in a slightly flattened boat form. This conformation results in the dihedral angle between the terminal rings of 41.76(5)°. The aliphatic chain which substitutes phenothiazine at N-position is not in an extended conformation, the torsion angles along this chain are 75.95(14)°a nd -163.96(10)°. The structure contains also the solvent-dimethylsulphoxide molecules, which are connected with the cation-anion structure by means of strong O-HÁÁÁO hydrogen bonds.Keywords Fluphenazine Á Phenothiazines Á Picrates Á Hydrogen bonds Á Crystal packing Experimental PreparationFluphenazine dihydrochloride (5.6 g, 0.01 mol) was dissolved in 25 mL of methanol and picric acid (2.4 g, 0.01 mol) was dissolved in 25 mL of methanol. Both the solutions were mixed and the mixture was stirred in a beaker at 333 K for 1 h and was kept aside for 3 days at room temperature. The formed salt was filtered and dried in vaccum desiccator over phosphorous pentoxide. It was observed that, regardless of the proportions in which the donor and acceptor were mixed, only the 1:2 complex was formed. X-ray quality crystals were obtained from a solution of dimethylsulphoxide after slow evaporation (m.p.: 501-503 K). CrystallographyYellow transparent prism-like crystal (0.2, 0.2, 0.08 mm) was used for data collection. Diffraction data were collected at 120(1) K by the x-scan technique up to 2h = 56.5°, on an Xcalibur Eos diffractometer [1] with graphite-monochromatized MoK a radiation (k = 0.71073 Å ). The temperature

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“…For instance, the strongest bands in the IR are the C-H stretching modes that are not seen in the RRS spectrum. The C=O stretching band at 1743 cm −1 (ester carbonyl group phospholipid [23]) is not present in the RRS spectrum, instead we see the ring stretching of fluorescein at 1646 and 1335 cm −1 as the most intense bands in the RRS spectrum. None of the strong Raman vibrational bands seen in Figure 11.1 are prominent in the RRS spectrum of OG488 ® -DHPE.…”

Section: Characteristic Vibrational Modes Of the Tagged Phospholipidmentioning

confidence: 73%

Plasmon‐Enhanced Scattering and Fluorescence Used for Ultrasensitive Detection in Langmuir–Blodgett Monolayers

Volpati

Alsaleh

Constantino

et al. 2014

Frontiers of Surface‐Enhanced Raman Scattering

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Interactions of Dihydrochloride Fluphenazine with DPPC Liposomes: ATR-IR and ³¹P NMR Studies

Cited by 44 publications

References 40 publications

Properties of Artificial Phospholipid Membranes Containing Lauryl Gallate or Cholesterol

Properties of Artificial Phospholipid Membranes Containing Lauryl Gallate or Cholesterol

The Crystal Structure of Fluphenazinium Dipicrate Dimethylsulphoxide Solvate

Plasmon‐Enhanced Scattering and Fluorescence Used for Ultrasensitive Detection in Langmuir–Blodgett Monolayers

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Interactions of Dihydrochloride Fluphenazine with DPPC Liposomes: ATR-IR and 31P NMR Studies

Cited by 44 publications

References 40 publications

Properties of Artificial Phospholipid Membranes Containing Lauryl Gallate or Cholesterol

Properties of Artificial Phospholipid Membranes Containing Lauryl Gallate or Cholesterol

The Crystal Structure of Fluphenazinium Dipicrate Dimethylsulphoxide Solvate

Plasmon‐Enhanced Scattering and Fluorescence Used for Ultrasensitive Detection in Langmuir–Blodgett Monolayers

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Interactions of Dihydrochloride Fluphenazine with DPPC Liposomes: ATR-IR and ³¹P NMR Studies