Synthetic meroterpenoids based on terpene alcohols: synthesis, self-assembly, and membranotropic properties

2020 ◽  
Vol 63 (7) ◽  
pp. 11-18
Author(s):  
Alan A. Akhmedov ◽  
◽  
Dmitriy N. Shurpik ◽  
Zainab R. Latypova ◽  
Rustem R. Gamirov ◽  
...  
Keyword(s):  
Drug Delivery ◽  
Aqueous Solutions ◽  
Self Assembly ◽  
Lipid Membrane ◽  
Bilayer Membrane ◽  
Water Soluble ◽  
Polar Component ◽  
Terpene Alcohols ◽  
Archaeal Lipids ◽  
Pharmacologically Active

Currently, targeted drug delivery is of great interest in the field of medicine. The study of compounds capable of permeating cell membranes is a major problem in this area. The synthesis of pharmacologically active compounds includes the formation of structures with various combinations of pharmacophore fragments and properties. Amphiphilic compounds tend to exhibit membranotropic activity. From this point of view, the modification of natural products, especially terpenoids, is of particular interest. Terpenoid structures are used as membrane anchors in the development of modulators for membrane-integrated proteins or structures for creating nanocontainers. In this paper we synthesized a number of water-soluble amphiphilic meroterpenoids containing a charged pyridinium fragment on the basis of acyclic terpene alcohols. Residue of terpene alcohols – geraniol (monoterpenol), farnesol (sesquiterpenol), and phytol (diterpenol) – were used as the hydrophobic part of the amphiphilic structure. Linear acyclic alcohols are commercially available reagents and have a structure similar to that of polyprenols in archaeal lipids, which made it possible to obtain synthetic lipid-like meroterpenoids capable of self-assembly in aqueous solutions. The charged pyridinium fragment, which is included in numerous natural compounds, was of interest as a polar component. This meroterpenoids are synthetic analogs of archaeal lipids. It was shown that the studied meroterpenoids form nanosized aggregates in aqueous solutions by the method of dynamic light scattering and the Doppler microelectrophoresis method. Turbidimetric titration on model dipalmitoylphosphatidylcholine vesicles revealed that the synthesized compounds are embedded into the bilayer membrane without destroying it. Self-assembled aggregates of synthesized compounds in water can find application for drug delivery – in the creation of nanocontainers containing membrane anchors capable of interacting with the outer surface of the cell (lipid membrane).

Development of Solid-Self Micron Emulsifying Drug Delivery Systems

2013 ◽  
Vol 6 (2) ◽  
pp. 2014-2021
Author(s):  
Preethi Sudheer ◽  
Koushik Y ◽  
Satish P ◽  
Uma Shankar M S ◽  
R S Thakur
Keyword(s):  
Drug Delivery ◽  
Systemic Circulation ◽  
Water Soluble ◽  
Future Research ◽  
Steady Increase ◽  
Liquid Form ◽  
Lipophilic Compounds ◽  
Modern Drug ◽  
Pharmaceutical Scientist ◽  
Pharmacologically Active

As a consequence of modern drug discovery techniques, there has been a steady increase in the number of new pharmacologically active lipophilic compounds that are poorly water soluble and solubility is one of the most important parameter to achieve desired concentration of drug in systemic circulation for therapeutic response. It is a great challenge for pharmaceutical scientist to convert those molecules into orally administered formulation with sufficient bioavailability.  Among the several approaches to improve oral bioavailability of these molecules, Self-micron emulsifying drug delivery system (SMEDDS) is one of the approaches usually used to improve the bioavailability of hydrophobic drugs. However, conventional SMEDDS are mostly prepared in a liquid form, which can have several disadvantages. Accordingly, solid SMEDDS (S-SMEDDS) prepared by solidification of liquid/semisolid self-micron emulsifying (SME) ingredients into powders have gained popularity. This article provides an overview of the recent advancements in S-SMEDDS such as methodology, techniques and future research directions.

Recent Advances in Novasome Formulation Technology

2014 ◽  
Vol 7 (2) ◽  
pp. 2407-2411
Author(s):  
J M Shah ◽  
N.H Shah ◽  
Hadiya P D
Keyword(s):  
Drug Delivery ◽  
Effective Means ◽  
Entrapment Efficiency ◽  
Bilayer Membrane ◽  
Water Soluble ◽  
Delivery Methods ◽  
Liposomal Drug ◽  
Pharmaceutical Technology ◽  
Insoluble Drugs ◽  
Novel Drug

Pharmaceutical technology has developed various newer modes of novel drug delivery aspects. Modifications in the previously existing drug delivery methods have led to various newly innovated technologies serving as a safe and effective means of improvement over the existing ones. Novasome technology is one of the new innovations of liposomes which have solved many of the problems related to liposomal drug delivery system. It offers a seven bilayer membrane which has the ability to incorporate both water soluble and insoluble drugs. It has an excellent entrapment efficiency which provides better medication. Formulation of novasomes is achieved in a high shear device. Due to its numerous advantages, novasomes have been used extensively in various fields like cosmetics, chemical, personal care, foods, pharmaceuticals and agrochemicals.

scholarly journals A Literature Review on Self Nanoemulsifying Drug Delivery System (SNEDDS)

2021 ◽  
Vol 70 (1) ◽  
Author(s):  
Saikumar D ◽  
Leela Prasanna J
Keyword(s):  
Drug Delivery ◽  
Drug Delivery System ◽  
Delivery System ◽  
Water Solubility ◽  
Solvent Molecule ◽  
Water Soluble ◽  
Statistical Experimental Design ◽  
Characterization Methods ◽  
Nano Emulsion ◽  
Pharmacologically Active

The Lipid-based drug delivery system is extensively reported within the literature for the enhancing drug solubility, permeability, and bioavailability. A considerable majority of novel pharmacologically active constituents produced in recent drug discovery programs are lipophilic and poorly soluble, posing a significant problem for pharmaceutical researchers enhancing the oral bioavailability of such drug molecules. Self-nano emulsifying drug delivery systems (SNEDDS), are the viable oil-based approaches for drugs that exhibit low dissolution rate and inadequate absorption. Ever since the progress of SNEDDS, researchers have been focusing on the challenges of BCS Class II and Class IV Drugs for enhancing water Solubility of poorly water-soluble drugs. SNEDDS is a Validate method for enhancing the solubility and bioavailability of lipophilic compounds. It’s the isotropic mixture of oil, surfactant, co-surfactant molecules and it also containing co-solvent molecule. which spontaneously form oil-in-water nano emulsion of approximately 200 nm or less in size upon dilution with water under gentle stirring. It’s Drug delivery system Which possess thermodynamically and kinetically stability. The physicochemical properties, drug solubilization capacity considerably regulates the selection of the SNEDDS components. The compositions of the SNEDDS are often optimized with the assistance of phase diagrams. Further to optimize SNEDDS can be done with the help of statistical experimental design. It’s a Novel drug delivery system which is applicable for the parenteral, Ophthalmic, intranasal and cosmetic drug delivery system. And therefore, the present review describes Preparation, components, mechanism of self-Nano emulsification, biopharmaceutical aspects, characterization methods and applications of Selfnanoemulsifying drug delivery system (SNEDDS).

scholarly journals pH Responsive Self-Assembly of Cucurbit[7]urils and Polystyrene-Block-Polyvinylpyridine Micelles for Hydrophobic Drug Delivery

2013 ◽  
Vol 2013 ◽  
pp. 1-6 ◽  
Author(s):  
Basem A. Moosa ◽  
Afnan Mashat ◽  
Wengang Li ◽  
Karim Fhayli ◽  
Niveen M. Khashab
Keyword(s):  
Drug Delivery ◽  
Aqueous Solution ◽  
Self Assembly ◽  
Room Temperature ◽  
Water Soluble ◽  
Hydrophobic Drug ◽  
Ph Responsive ◽  
Ph Values ◽  
Neutral Ph ◽  
Release Study

Polystyrene-block-polyvinylpyridine (PS-b-P4VP) polypseudorotaxanes with cucurbit[7]urils (CB[7]) were prepared from water soluble PS-b-P4VPH+polymer and CB[7] in aqueous solution at room temperature. At acidic and neutral pH, the pyridinium block of PS-b-P4VP is protonated (PS-b-P4VPH+) pushing CB[7] to preferably host the P4VP block. At basic pH (pH 8), P4VP is not charged and thus is not able to strongly complex CB[7]. This phenomenon was verified further by monitoring the release of pyrene, a hydrophobic cargo model, from a PS-b-P4VPH+/CB[7] micellar membrane. Release study of UV active pyrene from the membrane at different pH values revealed that the system is only operational under basic conditions and that the host-guest interaction of CB[7] with P4VPH+significantly slows down cargo release.

scholarly journals Supramolecular Amphiphiles Based on Pillar[5]arene and Meroterpenoids: Synthesis, Self-Association and Interaction with Floxuridine

2021 ◽  
Vol 22 (15) ◽  
pp. 7950
Author(s):  
Alan A. Akhmedov ◽  
Dmitriy N. Shurpik ◽  
Pavel L. Padnya ◽  
Alena I. Khadieva ◽  
Rustem R. Gamirov ◽  
...  
Keyword(s):  
Drug Delivery ◽  
Self Assembly ◽  
Drug Delivery Systems ◽  
Biomedical Application ◽  
Delivery Systems ◽  
Water Soluble ◽  
Vis Spectroscopy ◽  
Wide Range ◽  
Self Association ◽  
Supramolecular Amphiphiles

In recent years, meroterpenoids have found wide biomedical application due to their synthetic availability, low toxicity, and biocompatibility. However, these compounds are not used in targeted drug delivery systems due to their high affinity for cell membranes, both healthy and in cancer cells. Using the approach of creating supramolecular amphiphiles, we have developed self-assembling systems based on water-soluble pillar[5]arene and synthetic meroterpenoids containing geraniol, myrtenol, farnesol, and phytol fragments. The resulting systems can be used as universal drug delivery systems. It was shown by turbidimetry that the obtained pillar[5]arene/synthetic meroterpenoid systems do not interact with the model cell membrane at pH = 7.4, but the associates are destroyed at pH = 4.1. In this case, the synthetic meroterpenoid is incorporated into the lipid bilayer of the model membrane. The characteristics of supramolecular self-assembly, association constants and stoichiometry of the most stable pillar[5]arene/synthetic meroterpenoid complexes were established by UV-vis spectroscopy and dynamic light scattering (DLS). It was shown that supramolecular amphiphiles based on pillar[5]arene/synthetic meroterpenoid systems form monodisperse associates in a wide range of concentrations. The inclusion of the antitumor drug 5-fluoro-2′-deoxyuridine (floxuridine) into the structure of the supramolecular associate was demonstrated by DLS, 19F, 2D DOSY NMR spectroscopy.

scholarly journals UTILIZATION OF POLYMER AND LIPID-BASED DRUG DELIVERY SYSTEMS IN TREATMENT OF NEUROLOGICAL DISORDERS- A MINI REVIEW

2020 ◽  
Vol 4 (11) ◽  
Author(s):  
Arsalan Sarmad
Keyword(s):  
Drug Delivery ◽  
Neurological Disorders ◽  
Neurological Disorder ◽  
Drug Delivery Systems ◽  
Delivery Systems ◽  
Water Soluble ◽  
Medical Practitioners ◽  
Modern Drug ◽  
Lipid Compounds ◽  
Pharmacologically Active

In modern drug discovery techniques consistently increasing in the number of new pharmacologically active lipid compounds these compounds are poorly water-soluble. A great challenge of making this medication for oral administration with the desired bioavailability. Epilepsy is a severe neurological disorder that needs rapid treatment. To enhancement of its bioavailability, we need to make lipid-based drugs. On other hand, the surface tension reducing agents will give poor water-soluble formulation. Treatment of Neurological disorder is still a challenge for medical practitioners because of restricted moments and barriers. The solid lipid nanoparticles (SLN) and nanoemulsions are easily avoided the blood-brain barrier. Therefore, there is a maximum therapeutic efficacy achieved by using the lipid and polymer-based drug delivery system in the treatment of neurological disorders. Keywords: Neurological disorder, Lipid, Polymer, Lipid Based Drug delivery systems, Epilepsy, Treatment.

scholarly journals NOVASOME: A PIONEERING ADVANCEMENTIN VESICULAR DRUG DELIVERY

2021 ◽  
pp. 59-64
Author(s):  
ASLAM ABDUL RAHIMAN C.A. ◽  
KARTHIK KRISHNAN ◽  
SREELEKSHMI A.S. ◽  
ARJUN K.K. ◽  
SREEJA C. NAIR
Keyword(s):  
Drug Delivery ◽  
Pharmaceutical Research ◽  
Bilayer Membrane ◽  
Water Soluble ◽  
Depth Of Penetration ◽  
Delivery Methods ◽  
Liposomal Drug ◽  
Insoluble Drugs ◽  
Shear System ◽  
Liposomal Drug Delivery

Pharmaceutical research has developed various new types of innovative forms of drug delivery. Advancement in current drug delivery methods has led to the development of numerous new revolutionary technologies that support safe and efficient formulations over existing ones. Novasome technology is one of the latest liposome developments that have overcome many of the liposomal drug delivery system-related problems. This provides a seven bilayer membrane which is capable of absorbing water-soluble as well as insoluble drugs. The improved efficiency of entrapping drugs with good encapsulation features enables better frequency of dosing, which can be accomplished through the high shear system. These find their applications in diverse fields such as cosmetics, chemicals, personal care, food, pharmacy, and agrochemicals. Several products have already been launched into the market using this technology with an additional launch plan. Due to its depth of penetration, novasomes have been one of the most popular derma cosmetics. It is being studied continuously to obtain improved release characteristics. The prospect of drug delivery and targeting using novasomes is an important area of research and development. This review pinpoints the various aspect of the novasome and will be a milestone for the researchers in the area of drug delivery.

scholarly journals Self-Assembly of Amphiphilic Compounds as a Versatile Tool for Construction of Nanoscale Drug Carriers

2020 ◽  
Vol 21 (18) ◽  
pp. 6961
Author(s):  
Ruslan Kashapov ◽  
Gulnara Gaynanova ◽  
Dinar Gabdrakhmanov ◽  
Denis Kuznetsov ◽  
Rais Pavlov ◽  
...  
Keyword(s):  
Drug Delivery ◽  
Self Assembly ◽  
Lipid Membrane ◽  
Synergetic Effect ◽  
Drug Carriers ◽  
Biological Species ◽  
Endosomal Escape ◽  
Macrocyclic Compounds ◽  
Intracellular Drug Delivery ◽  
Lipid Formulations

This review focuses on synthetic and natural amphiphilic systems prepared from straight-chain and macrocyclic compounds capable of self-assembly with the formation of nanoscale aggregates of different morphology and their application as drug carriers. Since numerous biological species (lipid membrane, bacterial cell wall, mucous membrane, corneal epithelium, biopolymers, e.g., proteins, nucleic acids) bear negatively charged fragments, much attention is paid to cationic carriers providing high affinity for encapsulated drugs to targeted cells. First part of the review is devoted to self-assembling and functional properties of surfactant systems, with special attention focusing on cationic amphiphiles, including those bearing natural or cleavable fragments. Further, lipid formulations, especially liposomes, are discussed in terms of their fabrication and application for intracellular drug delivery. This section highlights several features of these carriers, including noncovalent modification of lipid formulations by cationic surfactants, pH-responsive properties, endosomal escape, etc. Third part of the review deals with nanocarriers based on macrocyclic compounds, with such important characteristics as mucoadhesive properties emphasized. In this section, different combinations of cyclodextrin platform conjugated with polymers is considered as drug delivery systems with synergetic effect that improves solubility, targeting and biocompatibility of formulations.

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