Gennaro Piccialli

Gennaro Piccialli
University of Naples Federico II | UNINA · Department of Pharmacy

PhD, full Professor Org. Chem.

About

226
Publications
17,892
Reads
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3,203
Citations
Introduction
Scientific interest and research area: - Synthesis of modified and/or conjugated oligonucleotides. -Synthesis of nucleoside analogues with potential anticancer/antiviral activity. -Studies of DNA/proteins interactions by spectroscopic and molecular modelling techniques. - Structural studies of uncommon secondary structures of DNA. - Modified oligonucleotides and peptide nucleic acids (PNA) as regulator of the gene expression
Additional affiliations
March 2013 - present
University of Naples Federico II
Position
  • Teaching Coordinator of Degree Courses in Biotecnology
September 2010 - February 2013
University of Naples Federico II
Position
  • Dean of Faculty of Biotechnology
January 2009 - September 2010
University of Naples Federico II
Position
  • President of the Degree Course in Biotecnologie per la Salute (“Biotechnologies for Health”)
Education
January 1975 - May 1980
Università di Napoli Federico II
Field of study
  • Organic Chemistry, Bioorganic Chemistry

Publications

Publications (226)
Article
1,3-diaryl-2-propanone derivatives are synthetic compounds used as building blocks for the realization not only of antimicrobial drugs but also of new nanomaterials thanks to their ability to self-assemble in solution and interact with nucleopeptides. However, their ability to interact with proteins is a scarcely investigated theme considering the...
Article
i-Motifs, also known as i-tetraplexes, are secondary structures of DNA occurring in cytosine-rich oligonucleotides (CROs) that recall increasing interest in the scientific community for their relevance in various biological processes and DNA nanotechnology. This study reports the design of new structurally modified CROs, named Double-Ended-Linker-C...
Article
Full-text available
We herein report an innovative antisense approach based on Peptide Nucleic Acids (PNAs) to down-modulate CD5 expression levels in chronic lymphocytic leukemia (CLL). Using bioinformatics tools, we selected a 12-mer tract of the CD5 mRNA as the molecular target and synthesized the complementary and control PNA strands bearing a serine phosphate dipe...
Article
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Coronaviruses (CoVs) are positive-sense RNA enveloped viruses, members of the family Coronaviridae, that cause infections in a broad range of mammals including humans. Several CoV species lead to mild upper respiratory infections typically associated with common colds. However, three human CoV (HCoV) species: Severe Acute Respiratory Syndrome (SARS...
Conference Paper
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Cyclic ADP-ribose (cADPR, 1, Figure 1) is a naturally occurring metabolite of NAD+capable of mobilizing Ca2+ ions from intracellular stores. [...]
Article
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Peptide nucleic acid (PNA) is a synthetic DNA mimic that outperforms the properties of traditional oligonucleotides (ONs). On account of its outstanding features, such as remarkable binding affinity towards complementary DNA or RNA as well as high thermal and chemical stability, PNA has been proposed as a valuable alternative to the ON probe in gen...
Preprint
Peptide nucleic acid (PNA) is a synthetic DNA mimic that outperforms the properties of traditional oligonucleotides (ONs). On account of its outstanding features, such as remarkable binding affinity towards complementary DNA or RNA as well as high thermal and chemical stability, PNA has been proposed as a valuable alternative to the ON probe in gen...
Article
The interest in DNA based nanostructures arises from their potential applications in diagnostics and drug delivery and in the development of new hybrid and conducting materials. Guanine-rich oligonucleotides can multimerize forming long and stable supramolecular structures, known as G-wires, based on the G-quadruplex (G4) motif. Herein, we report a...
Article
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Herein, we reported on the synthesis of a novel Pt(II) neutral complex having as ligand the nucleoside tubercidin, a potent anti-tumor agent extracted from the bacterium Streptomyces Tubercidicus. In detail, the chelation of the metal by a diamine linker installed at C6 purine position of tubercidin assured the introduction of a cisplatin-like unit...
Article
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Mature microRNAs are short non-coding RNA sequences which upon incorporation into the RISC ribonucleoprotein complex, play a crucial role in regulation of gene expression. However, miRNAs can exist within the cell also as free molecules fulfilling their biological activity. Therefore, it is emerging that in addition to sequence even the structure a...
Article
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ε-poly-l-Lysine (ε-PLL) peptide is a product of the marine bacterium Bacillus subtilis with antibacterial and anticancer activity largely used worldwide as a food preservative. ε-PLL and its synthetic analogue α,ε-poly-l-lysine (α,ε-PLL) are also employed in the biomedical field as enhancers of anticancer drugs and for drug and gene delivery applic...
Article
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Herein, we report on the synthesis of a small set of linear precursors of an inosine analogue of cyclic ADP-ribose (cADPR), a second messenger involved in Ca2+ mobilization from ryanodine receptor stores firstly isolated from sea urchin eggs extracts. The synthesized compounds were obtained starting from inosine and are characterized by an N1-alkyl...
Article
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Aptamers are artificial nucleic acid ligands identified and obtained from combinatorial libraries of synthetic nucleic acids through the in vitro process SELEX (systematic evolution of ligands by exponential enrichment). Aptamers are able to bind an ample range of non-nucleic acid targets with great specificity and affinity. Devices based on aptame...
Article
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G-quadruplexes (G4s) are unusual secondary structures of DNA occurring in guanosine-rich oligodeoxynucleotide (ODN) strands that are extensively studied for their relevance to the biological processes in which they are involved. In this study, we report the synthesis of a new kind of G4-forming molecule named double-ended-linker ODN (DEL-ODN), in w...
Article
The B-cell lymphoma 2 (Bcl-2) gene encodes for an antiapoptotic protein associated with the onset of many human tumors. Several oligonucleotides (ONs) and ON analogues are under study as potential tools to counteract the Bcl-2 expression. Among these are Peptide Nucleic Acids (PNAs). The absence of charges on PNA backbones allows the formation of P...
Article
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The development of new strategies for enhancing drug delivery to the brain represents a major challenge in treating cerebral diseases. In this paper, we report on the synthesis and structural characterization of a biocompatible nanoparticle (NP) made up of poly(lactic-co-glycolic acid) (PLGA)-polyethylene glycol (PEG) co-polymer (namely PELGA) func...
Article
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Herein, we reported on the synthesis of cpIPP, which is a new structurally-reduced analogue of cyclic ADP-ribose (cADPR), a potent Ca2+-releasing secondary messenger that was firstly isolated from sea urchin eggs extracts. To obtain cpIPP the "northern" ribose of cADPR was replaced by a pentyl chain and the pyrophosphate moiety by a phophono-phosph...
Article
By combining the ability of short G-rich oligodeoxynucleotides (ODNs) containing the sequence 5'CGGA3' to form higher-order G-quadruplex (G4) complexes with the tetra-end-linked (TEL) concept to produce aptamers targeting the HIV envelope glycoprotein 120 (gp120), three new TEL-ODNs (1–3) having the sequence 5'CGGAGG3' were synthesized with the aim...
Article
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This article describes the synthesis of Thy-(Phe-Phe) and Thy-(Tyr-Tyr), two thymine-bearing dipeptides based on L-phenylalanine and L-tyrosine, the circular dichroism (CD), UV and dynamic light scattering (DLS) characterization of their self-assemblies, and a CD study of their interaction with nucleic acids (using homoadenine DNA and RNA) and seru...
Article
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Pseudomans anguilliseptica-A1 strain, isolated in an urban area, improved the efficiency of a microbial consortium, composed of Bacillaceae, Staphylococcacea, Xantomonadaceae and Enterbacteriaceae, whose ability to degrade five Polycyclic Aromatic Hydrocarbons (PAHs) among the priority pollutants was previously ascertained. Six soil microcosms were...
Article
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Cystic Fibrosis (CF) is one of the most common life shortening conditions in Caucasians. CF is caused by mutations in the CF Transmembrane Conductance Regulator (CFTR) gene which result in reduced or altered CFTR functionality. Several microRNAs (miRNAs) downregulate the expression of CFTR, thus causing or exacerbating the symptoms of CF. In this c...
Article
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Obtaining DNA nanostructures with potential applications in drug discovery, diagnostics, and electronics in a simple and affordable way represents one of the hottest topics in nanotechnological and medical sciences. Herein, we report a novel strategy to obtain structurally homogeneous DNA G-wire nanostructures of known length, starting from the sho...
Article
The interaction of the porphyrin derivative H2TCPPSpm4, having spermine pendants in the four meso positions, with the G-quadruplex (GQ) structure formed by the DNA aptamer TGGGAG has been investigated by means of UV, electronic circular dichroism and PAGE studies. The results here reported demonstrate that porphyrin derivative is capable of stabili...
Article
A chiral pool protocol toward the synthesis of the smenamide family of natural products is described. Two stereoisomers of smenamide A, namely, ent-smenamide A and 16-epi-smenamide A were synthesized with a 2.6 and 2.5% overall yield, respectively. Their carboxylic acid moieties were assembled starting from S-citronellene via two Wittig reactions a...
Article
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The title compound, C 12 H 20 N 4 O 5 , crystallizes in the monoclinic space group P 2 1 , with four crystallographically independent molecules in the asymmetric unit. The four molecules have a very similar conformation that is basically determined by the formation of two intramolecular hydrogen bonds between the amino NH 2 donors and the carbonyl...
Article
Background: G-quadruplex DNA is involved in many physiological and pathological processes. Both clinical and experimental studies on DNA G-quadruplexes are slowed down by their enzymatic instability. In this frame, more stable chemically modified analogs are needed. Methods: The bis-end-linked-(gggt)2 PNA molecule (BEL-PNA) was synthesized using...
Article
Human α-thrombin (TB) is a serine protease with a crucial role in coagulation and hemostasis. The monitoring of TB level in blood serum could be of great importance in order to prevent serious damages to human health. In this work, an aptasensor is realized by in situ synthesis of a 17-mer Thrombin Binding Aptamer analogue (TBATT) on silanized macr...
Article
By using a new rapid screening platform set on molecular docking simulations and fluorescence quenching techniques, three new anti-HIV aptamers targeting the viral surface glycoprotein 120 (gp120) were selected, synthesized and assayed. The use of the short synthetic fluorescent peptide V35-Fluo mimicking the V3 loop of gp120, as the molecular targ...
Article
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Efficient biorecognition of thrombin (TB), a serine protease with crucial role in physiological and pathological blood coagulation, is a hot topic in medical diagnostics. In this work, we investigate the ability of synthetic thrombin aptamer (TBA), immobilized on a gold substrate, to bind thrombin by two different label-free techniques: the quartz...
Article
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Cyclic N (1)-pentylinosine monophosphate (cpIMP), a novel simplified inosine derivative of cyclic ADP-ribose (cADPR) in which the N (1)-pentyl chain and the monophosphate group replace the northern ribose and the pyrophosphate moieties, respectively, was synthesized. The role played by the position of the phosphate group in the key cyclization step...
Article
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This unit contains four basic protocols describing the synthesis of 5-aminoimidazole-4-carboxamide riboside (AICAR), 5-aminoimidazole-4-carboxamide riboside (ZPM), their 4-N functionalized derivatives, and two sugar-modified analogs of AICAR. The first and second basic protocols reveal the importance of solid-phase synthesis to obtain novel AICAR a...
Article
Herein, the synthesis of a nucleoside platinum(II) complex in which a cisplatin-like unit is joined to 7-deazaadenosine through an amino alkyl chain installed at the C6 position of purine was explored. The capability of the new complex to react with DNA purine bases was confirmed by a model reaction with deoxyguanosine monophosphate, whereas its an...
Article
Full-text available
5-Aminoimidazole-4-carboxamide riboside (AICAR) has an important role in the regulation of the cellular metabolism showing a broad spectrum of therapeutic activities against different metabolic processes. Due to these proven AICAR properties, we have designed, synthesized and tested the biological activity of two ribose-modified AICAR derivatives,...
Article
A general synthesis of C6-pyridylpurine nucleosides is described. The reported synthetic procedure exploits the regioselective addition of pyridinyl Grignard reagents, obtained by bromine/magnesium exchange between mono- or dihalopyridines and iPrMgCl, to the C6–N1–O– moiety of nebularine N1-oxide. The regioselective transmetallation of unsymmetric...
Article
In a previous work we have demonstrated that the DNA sequence CGGTGGT folds into a higher order G-quadruplex structure (2Q), obtained by the 5'-5' stacking of two unusual G(:C):G(:C):G(:C):G(:C) planar octads belonging to two identical tetra-stranded parallel quadruplexes, when annealed in the presence of ammonium or potassium ions. In the present...
Article
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The synthesis of four novel platinum complexes, bearing N6-(6-amino-hexyl)adenosine or a 1,6-di(adenosin-N6-yl)-hexane respectively, as ligands of mono-functional cisplatin or monochloro(ethylendiamine)platinum(II), is reported. The chemistry exploits the high affinity of the charged platinum centres towards the N7 position of the adenosine base sy...
Article
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Rapid screening tests in medical diagnostic and environmental analysis are often based on oligonucleotide biochips. In this paper, we studied the stability of functionalized mesoporous silicon supports in the solid-phase synthesis of oligonucleotides, exploiting several chemical procedures. A 19-mer mixed sequence has been successfully synthesized...
Article
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Herein, we report optically pure modified acyclic nucleosides as ideal probes for aptamer modification. These new monomers offer unique advantages in exploring the role played in thrombin inhibition by a single residue modification at key positions of the TBA structure.
Article
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In recent years considerable attention has been given to the use of natural substances as anticancer drugs. The natural antioxidant dipeptide L-carnosine belongs to this class of molecules because it has been proved to have a significant anticancer activity both in vitro and in vivo. Previous studies have shown that L-carnosine inhibits the prolife...
Conference Paper
Full-text available
Direct solid phase of oligonucleotides (ONs) requires high chemical stability of the support material. in this work, we investigate the passivation ability of porous oxidized silicon multilayered structures by two aminosilane compounds, APTES and APDMES, for the realization of a label-free ON optical biosensor.
Article
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Computational techniques, and in particular molecular dynamics (MD) simulations, have been successfully used as a complementary technique to predict and analyse the structural behaviour of nucleic acids, including peptide nucleic acid- (PNA-) RNA hybrids. This study shows that a 7-base long PNA complementary to the seed region of miR-509-3p, one of...
Article
Recently, microRNAs (miRNAs) were identified as being able to inhibit the expression of the Cystic Fibrosis Transmembrane Regulator (CFTR) disease-gene of Cystic Fibrosis (CF) and CFTR-Related Disorders (CFTRRD). This study shows the use of peptide nucleic acids (PNAs) as inhibitors of miR-509-3p, one of the CFTR regulating miRNAs, by reverting the...
Article
Full-text available
Recently, microRNAs (miRNAs) were identified as being able to inhibit the expression of the Cystic Fibrosis Transmembrane Regulator (CFTR) disease-gene of Cystic Fibrosis (CF) and CFTR-Related Disorders (CFTR-RD). This study shows the use of peptide nucleic acids (PNAs) as inhibitors of miR-509-3p, one of the CFTR regulating miRNAs, by reverting th...
Article
Full-text available
Dominant diseases are single gene disorders occurring in the heterozygous state. The mutated allele exerts a dominant effect because it produces an abnormal polypeptide that interferes with the function of the normal allele product. Peptide Nucleic Acids (PNAs) offer a route for a potential therapy for dominant diseases by selectively silencing the...
Article
The synthesis of 2,6-dialkyl(aryl)purine nucleosides by application of a double addition of Grignard reagents to N1-oxide purine nucleosides is described. The synthetic protocol exploits the reactivity of both the C6–N1–O– and C2–N1–O– moieties of the purine base. The overall process consists of initial Grignard reagent addition to the C6 of nebula...
Article
Full-text available
The antiviral activity of certain acyclic nucleosides drew our attention to the fact that the replacement of the furanose ring by an alkyl group bearing hydroxyl(s) could be a useful structural modification to modulate the biological properties of those nucleosides. Herein, we report on the synthesis of some novel acadesine analogues, where the rib...