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22 M.-C. Jones
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Fig. 2.5 Structure, loading and activity of a gemini SLP. (a) Structure formula and (b) molecular
model for gemini APK and linear A6K (A ¼ Ala; K ¼ Lys); (c) Model for APK self-assembly and
hypothesised loading in spherical and cylindrical micelles; (d) TEM of pyrene-loaded A6K (right)
and APK (left) showing that a higher loading and more regular shape for APK. Scale bar ¼ 100 nm;
(e) Toxicity of paclitaxel-loaded APK micelles compared to Taxol
ovarian cancer cells SKOV-3. (Adapted from Peng et al. (
2021) with permission)
®
and empty APK micelles in
short sequence of alternating hydrophilic and hydrophobic amino acids between the
head and the tail can induce β-sheet formation and prevent the formation of spherical
micelles; while alternating hydrophobic and anionic amino acids could produce
one-dimensional structures, so-called nanobel ts or nanotapes (Cui et al.
Paramonov et al. conducted a comprehensive study of the structure–activity relationship of PAs and discovered that switching hydrogen bonds on or off could help
shift the morphology of their self-assemblies from spherical micelles to nanofibers
(Paramonov et al.
nanocarriers for
hydrogel which can help sustain drug release (Eskandari et al.
2.5 Conclusions
In many ways, low-molecular weight amphiphiles form the basis of pharmaceutical
nanoscience. The simple core-shell structure achieved allowed major improvements
in the formulation of poorly soluble drugs which we are still trying to mimic through
2009).
2006). The resulting supramolecular structures can then be used as
drug delivery and for the formulation of shear-thinning, self-healing
2017).
2 Low-Molecular Weight Amphiphiles 23
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more complex macromolecular materials. Unfortunately, many properties that make
small amphiphiles exceptional drug carriers also lead to severe adverse reactions.
Nowadays, questions of sustainability, large-scale production and cost, along with
an increased awareness of the biological activity of ‘inert excipients’ mean that new
amphiphiles must be designed carefully and go through extensive biocompatibility
testing to avoid the many pitfalls of the existi
ng agents.
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Chapter 3
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Niosomes
Maria Gioia Fabiano, Jacopo Forte, Patrizia Nadia Hanieh,
Federica Rinaldi, Carlotta Marianecci, and Maria Carafa
3.1 Introduction
The increasing interest in designing new drug delivery vehicles stems from the
necessity to overcome the barriers to drug action, such as limited circulation halflife, reduced solubility, and undesirable side effects associated with a given therapeutic agent. Some candidate drugs are not bioavailable in parenteral formulations,
making the drug formulation insufficiently active, regardless of its therapeutic
potential. The use of pharmaceutical carriers to enhance the in vivo efficiency of
many drugs is well established in pharmaceutical research and in the clinical setting
(Alonso 2004; Gregoriadis 1988; Müller 1991; Rolland 1993), and thousands of
scientists have been involved in the study of liposomes and other colloidal structures
as carriers for drug delivery. Liposomes, described by Bangham in 1965 (Bangham
1965), have been prepared with a variety of phospholipids and have been
et al.
extensively studied as drug carriers (Alberts and Garcia 1997; Bandak et al. 1999;
Berry et al. 1998; Boswell et al. 1998; Gabizon et al. 1998; Manosroi and Manosroi
1997; Tsuchihashi et al. 1999). However, problems arise with the general application
of liposomes; problems include their low physical and chemical stability. One
alternative to the use of phospholipids is the use of non-ionic surfactants (Horiuchi
and Tajima 2000; Uchegbu and Florence 1995; Saman et al. 2022). Vesicles formed
by surfactants are known as niosomes or non-ionic surfactant vesicles (NSVs).
Niosomes are similar in terms of structure and certain physical properties to liposomes (Uchegbu and Florence
into vesicles was first reported in the 1970s by researchers in the cosmetic industry
(Handjani-Vila et al.
1979), and the research interest in surfactant-based vesicular
1995). The self-assembly of non-ionic surfactants
M. G. Fabiano · J. Forte · P. N. Hanieh · F. Rinaldi · C. Marianecci · M. Carafa (*)
Department of Chimica e Tecnologie del Farmaco, University “Sapienza” of Rome, Rome, Italy
e-mail: maria.carafa@uniroma1.it
© The Editor(s) (if applicable) and The Author(s), under exclusive license to
Springer Nature Switzerland AG 2024
I. F. Uchegbu et al. (eds.), Fundamentals of Pharmaceutical Nanoscience,
https://doi.org/10.1007/978-3-031-59478-6_3
29
30 M. G. Fabiano et al.
https://t.me/med1917
carriers is still high (keyword-niosomes: 1827 articles published in the last 10 years;
data retrieved from Scopus).
3.2 Niosomal Components
3.2.1 Surfactants
It is well known that the surfactant structure clearly affects the size, stability,
entrapment efficiency, pharmacokinetics, pharmacodynamics, and targeting properties of vesicular systems. A large selection of surfactants displaying favourable
properties for specific drug delivery applications is readily available.
Several non-ionic surfactants are known to form vesicles. These amphiphiles
have two portions: a hydrophilic head group and a hydrophobic tail. Ether, amide, or
ester bonds may link the two portions of the molecule. Surfactant vesicles may be
prepared from amino acids (Mohanty and Dey
(Morigaki and Walde 2007; Namani et al. 2007), amides (Wieprecht et al. 2002),
alkyl esters (van Hal et al. 1996), and alkyl ether surfactants (Harvey et al. 2005).
Alkyl ether surfactants may be broadly divided into two classes based on the nature
of the hydrophilic head group: alkyl ethers in which the hydrophilic head group
consists of repeat glycerol subunits, related isomers or larger sugar molecules, and
those in which the hydrophilic head group consists of repeat ethylene oxide subunits.
The synthesis and characterization of new surfactants with specific physical and
chemical properties have been reported in which the surfactants are useful to
pharmacy and colloid science (Dipti and Tyagi
Muzzalupo et al. 2008; Renouf et al. 1998, 1999; Zana 1997).
New non-ionic surfactant molecules, in which the hydrophilic region consists of
azacrown ether units, have been synthesized by Muzzalupo and co-workers (2005).
One such compound is a bolaamphiphile and is composed of two identical azacrown
ether units, as polar heads, linked by a long alkyl chain (Muzzalupo et al. 1996).
It has been demonstrated that the bolaamphiphile is able to assemble into
colloidal structures, if associated with cholesterol or other amphiphilic molecules
(Muzzalupo et al. 2005
friendly alternative to synthetic surfactants led to a class of new-age surfactants
derived from microorganism, referred to as ‘biosurfactants’. They attracted attention
because of their biodegradability and eco-friendly attributes. Biosurfactants exhibit
several advantages over their chemical counterparts in terms of lower toxicity,
biocompatibility, and digestibility which makes them excellent candidates for use
in nanotechnology, including for use to fabricate niosomes (Haque et al.
application in other fields. Surfactin is one of the most powerful biosurfactants; it is a
lipopeptide type that is generated by the gram-posi tive, endospore-producing, microorganism. Surfactin is composed of seven amino acids that are bonded to the
carboxyl and hydroxy groups on long fatty acid chains (C
2015; Sarubbo et al. 2022).
). The necessity to discover an efficient but environmentally
2006; Roy and Dey 2007), fatty acids
2006; Menger and Littau 1993;
2017) and
) (Chen et al.
13-C15
3 Niosomes 31
https://t.me/med1917
This wide selection of potential molecules offers the possibility of selecting the
more suitable surfactants to achieve tailor-made niosomes for the desired therapeutic
response.
3.2.2 Cholesterol
Cholesterol provides rigidity, fluidity, and permeability to cell membranes and
vesicle membranes, which is not provided by the surfactants alone (they are relatively brittle otherwise) (Simons and Ikonen
into the artificial vesicle bilayers in order to increase their ordered state.
Some non-ionic surfactants only form vesicles when cholesterol is included in the
bilayer to the level of 30–50 mole % and so cholesterol is usually included at a 1:1
molar ratio in most vesicular formulations. In fact, the water-soluble detergent
polysorbate 20 [Hydrophobic Lipophilic Balance (HLB) value ¼ 16.7] is not able
to form niosomes in the absence of cholesterol, whereas it forms stable non-ionic
surfactant vesicles in the presence of equimolar cholesterol concentrations (Carafa
et al. 1998; Saettone et al. 1996; Santucci et al. 1996). It has been suggested (Nasseri
2005) that an interaction occurs between the ester bond of the amphiphilic molecule
(phospholipid/surfactant) and the 3-OH group of cholesterol in vesicular systems
3.1).
(Fig.
Furthermore, cholesterol stabilizes niosomes against the destabilizing effects of
plasma and serum proteins and decreases the permeability of vesicles to entrapped
solute, preventing leakage (Baillie et al.
2000). Cholesterol is thus incorporated
1985; Rogerson et al. 1988).
Fig. 3.1 Possible hydrogen bonding interaction between the 3-OH group of the cholesterol and the
carbonyl oxygen and also weaker interaction at oxygen of the ester bond
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