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Mini-Reviews
in Organic Chemistry
ISSN: 1570-193X
Mini-Reviews
in Organic Chemistry
Volume 5, Number 3, August 2008
Contents
Recent Advances in Positron Emission Tomography (PET)
Imaging of Biomolecules: From Chemical Labeling to Cancer
Diagnostics Pp. 153-162
Katsunori Tanaka and Koichi Fukase
[Abstract]
Molecularly Imprinted Polymers as Nucleotide Receptors
Pp. 163-170
L. Longo and G. Vasapollo
[Abstract]
Antagonists Against Anti-Apoptotic Bcl-2 Family Proteins
for Cancer Treatment Pp. 171-178
Jignesh M. Doshi and Chengguo Xing
[Abstract]
Recent Developments in 5'-Terminal Cap Analogs: Synthesis
and Biological Ramifications Pp. 179-192
Anilkumar R. Kore, Irudaya Charles, Muthian
Shanmugasundaram, Zejun Xiao and Richard C. Conrad
[Abstract]
A Convenient Access to the Piperidine Ring by Cyclization
of Allylsilyl Substituted N-Acyliminium and Iminium
Ions: Application to the Synthesis of Piperidine Alkaloids
Pp. 193-208
R. Remuson and Y. Gelas-Mialhe
[Abstract]
Potential of Amino Acid-Derived a-Amino Nitriles for
Generating Molecular Diversity Pp. 209-221
Juan A. González-Vera, M. Teresa
García-López and Rosario Herranz
[Abstract]
N-Hydroxyphthalimide (NHPI)/Lead
Tetraacetate, a Peculiar System for the Phthalimide-N-Oxyl
(PINO) Radical Generation Pp. 222-227
Sergiu Coseri
[Abstract]
Chiral Macrocyclic Schiff Bases: An Overview Pp.
228-242
Sankareswaran Srimurugan, Paulsamy Suresh,
Balaji Babu and Hari N. Pati
[Abstract]
Fine Chemicals and New Hybrid Materials From Cardanol
Pp. 243-253
Giuseppe Mele and Giuseppe Vasapollo
[Abstract]
The Reactions Between HOCl and Differently Saturated
Phospholipids: Physiological Relevance, Products and Methods
of Evaluation Pp. 254-261
Beate Fuchs, Celestina Schober, Grit Richter,
Ariane Nimptsch, Rosmarie Süβ
and Jürgen Schiller
[Abstract]
Abstracts
[Back to top]
Recent Advances in Positron Emission Tomography
(PET) Imaging of Biomolecules: From Chemical Labeling to Cancer
Diagnostics
Katsunori Tanaka and Koichi Fukase
The recent advances of PET using biomolecules, such as peptides,
monoclonal antibodies, oligonucleotides, and glycoproteins
will be described. So far, PET of biomolecules has been used
mainly for diagnosis of cancers. The biomolecules have been
conjugated with DOTA ligand, labeled with radiometals as the
β+
emitter, and targeted to specific tumors, where they have
enabled visualization of even small metastatic lesions, due
to the high sensitivity of the PET scanners.
[Back to top]
Molecularly Imprinted Polymers as Nucleotide Receptors
L. Longo and G. Vasapollo
Molecularly imprinted polymers (MIPs) are highly cross-linked
porous polymers with a predetermined selectivity for a given
analyte or structurally related compounds, that make them
ideal materials to be used in a wide range of areas including
chemical sensing, separation, drug delivery and catalysis.
The aim of this short review is to outline the molecular imprinting
technology with particular reference to the development of
MIPs as artificial receptors for the recognition of nucleotide
bases and their derivatives.
[Back to top]
Antagonists Against Anti-Apoptotic Bcl-2 Family Proteins
for Cancer Treatment
Jignesh M. Doshi and Chengguo Xing
Apoptosis is a programmed cell death process, critical for
normal cellular development and tissue homeostasis. B-cell
lymphocyte/leukemia 2 (Bcl-2) family proteins are important
regulators of apoptosis. Numerous studies have demonstrated
that over-expressing anti-apoptotic Bcl-2 proteins is one
mechanism for cancer cells to acquire resistance against cancer
chemotherapies, suggesting antagonizing these proteins would
be a potential approach to overcoming such drug resistance.
This review briefly discusses the principle and the recent
advances in the development of such antagonists, with some
highlights about several promising antagonists.
[Back to top]
Recent Developments in 5'-Terminal Cap Analogs: Synthesis
and Biological Ramifications
Anilkumar R. Kore, Irudaya Charles, Muthian
Shanmugasundaram, Zejun Xiao and Richard C. Conrad
The 5'-terminus of eukaryotic messenger RNA (mRNA) molecules
contains a unique ‘cap’ structure: 7-methylguanosine
(m7G) linked by a 5'-5'-triphosphate
bridge to the first nucleoside in the standard polymer chain.
This 5'-cap is recognized by numerous enzymes involved in
the transport and translation of mRNA, as well as its processing,
both in terms of generating mature mRNA from the initial transcript
and its natural degradation. In vitro generation
of capped RNAs uses a cap analog in which two nucleosides
are joined in a 5'-5' triphosphate linkage, allowing incorporation
of the cap along with the first nucleotide in the polymer
chain. The conventional cap analog, m7G[5']ppp[5']G,
has a 3'-OH on both nucleoside moieties, resulting in the
incorporation of the dinucleotide in either orientation. This
results in one-third to one-half of the mRNAs containing a
non-methylated cap and a methylated initial nucleotide. These
‘reverse cap’ structures bind poorly to elF4E
and other cap binding proteins, greatly reducing the overall
translational efficiency in vitro and biological
activity in vivo. This drawback of the conventional
cap analog has been addressed by creating an "anti-reverse
cap analog" (ARCA), m2 7,
3'-OG[5']ppp[5']G, in which the 3'-OH
of the ribose connected to the m7Guo
moiety is replaced with a 3'-O-methyl group, allowing
incorporation only in the forward orientation due to the presence
of the single extendable 3'-OH group. In addition to the chemical
modification at the 3'-OH group of the ribose connected to
the m7 G moiety, modifications
at the 2'-OH group also preclude attachment of a second nucleotide
by polymerase, again forcing the forward orientation. This
mini-review focuses on recent developments in the synthesis
of novel cap analogs, highlighting modifications at several
positions including; the heterocyclic bases, the sugars, and
the α-,
β-,
and γ-phosphates
in the triphosphate chain, and assessing their impact on biological
activity.
[Back to top]
A Convenient Access to the Piperidine Ring by Cyclization
of Allylsilyl Substituted N-Acyliminium and Iminium
Ions: Application to the Synthesis of Piperidine Alkaloids
R. Remuson and Y. Gelas-Mialhe
This review relates a new access to the piperidine ring by
intramolecular cyclization of acyl iminium and iminium ions
substituted by an allylsilyl side chain as an internal
∏-nucleophile.
This methodology was applied to the synthesis of piperidine
alkaloids.
[Back to top]
Potential of Amino Acid-Derived a-Amino Nitriles for
Generating Molecular Diversity
Juan A. González-Vera, M. Teresa
García-López and Rosario Herranz
This review covers some of the contributions of the authors
to the peptidomimetic field. These contributions explore the
potential of amino acid-derived α-amino
nitriles for generating molecular diversity. Cyanomethyleneamino
pseudopeptide analogues of several bioactive peptides and
α-quaternary
amino nitriles were obtained via a modified three component
Strecker synthesis. Taking advantage of the reactivity of
the cyano group and the diverse functionality of amino acid
derivatives, cyanomethyleneamino pseudopeptides were transformed
into carbamoylmethyleneamino and branched pseudopeptides or
privileged heterocyclic scaffolds, such as: piperazine, pyrazino[1,2-c]pyrimidine,
1,4-benzodiazepine, and novel indole derivatives, including
some spirocyclic compounds.
[Back to top]
N-Hydroxyphthalimide (NHPI)/Lead
Tetraacetate, a Peculiar System for the Phthalimide-N-Oxyl
(PINO) Radical Generation
Sergiu Coseri
The development of efficient catalytic system for selective
organic transformation is currently one of the challenging
tasks in synthetic organic chemistry. In recent years, N-hydroxyphthalimide
(NHPI) has been recognized as a valuable catalyst for the
aerobic oxidation of various organic compounds under mild
conditions. The generation of the phthalimide-N-oxyl
(PINO) radicals from its precursor NHPI, can be achieved by
using different ways including electrochemical, enzymatic
and chemical methods. Among all of these methods, the use
of lead tetraacetate for the PINO radicals’ generation
seems to be the most peculiar, several kinetic and mechanistic
“anomalies” for this catalytic system being reported.
[Back to top]
Chiral Macrocyclic Schiff Bases: An Overview
Sankareswaran Srimurugan, Paulsamy Suresh,
Balaji Babu and Hari N. Pati
Macrocyclic Schiff bases form an important class of macrocyclic
host systems, which are formed by self condensation of a diamine
with a diformyl compound. Chiral modification of macrocyclic
Schiff bases with different central cavity sizes were recently
developed and explored. This mini-review will discuss some
of the synthetic strategies, solid state crystal structures,
and recent applications of different [n+n] chiral macrocyclic
Schiff bases.
[Back to top]
Fine Chemicals and New Hybrid Materials From Cardanol
Giuseppe Mele and Giuseppe Vasapollo
Cardanol, a low-cost largely available renewable material
obtained from distillation of CNSL (Cashew Nut Shell Liquid),
has been used for the preparation of fine chemicals and hybrid
materials. The long chain attached to the meta position of
the phenolic ring of cardanol makes this compound a unique
natural source because it confers to all derivatives, particular
properties (good solubility, good processability, interesting
physical properties and so on). New fine chemicals as well
as new cardanol hybrid materials combined with porphyrins,
phthalocyanines and fullerenes have been synthesized recently,
developing at the same time new synthetic strategies for the
preparation of new eco-friendly fine chemicals, composites
and functional organic materials. The aim of this review is
also to show that the chemistry of cardanol is becoming a
stimulating area in academic and industrial research.
[Back to top]
The Reactions Between HOCl and Differently Saturated
Phospholipids: Physiological Relevance, Products and Methods
of Evaluation
Beate Fuchs, Celestina Schober, Grit Richter,
Ariane Nimptsch, Rosmarie Süβ
and Jürgen Schiller
Phospholipids (PLs) are important constituents of cellular
membranes. HOCl is a reactive oxygen species (ROS) generated
under inflammatory conditions and capable of reacting with
(a) the head group of PLs and (b) the olefinic groups of their
fatty acyl residues under the preferred generation of chloramines
and chlorohydrines, respectively.
This review discusses these products, their stabilities and
in vivo relevance. Additionally, important methods
(spectroscopic as well as mass spectrometric techniques) to
analyze these products are compared.
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