Metal-containing peptide nucleic acid conjugates

Gasser, Gilles; Sosniak, Anna M.; Metzler‐Nolte, Nils

doi:10.1039/c0dt01706j

Cited by 63 publications

(58 citation statements)

References 176 publications

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“…[28] PNAs have high binding affinity towards DNA/RNA, are resistant to nucleases, and are strongly sequence-selective. Hence, labeling PNAs would be an important step towards understanding the functional and mechanistic details of DNAs and RNAs by means of electrochemical biosensing.…”

Section: Bioconjugatesmentioning

confidence: 99%

10 Years of Click Chemistry: Synthesis and Applications of Ferrocene‐Derived Triazoles

Ganesh

Sudhir

Kundu

et al. 2011

Chemistry An Asian Journal

123

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Click chemistry has played a significant role as a rapid and versatile strategy for conjugating two molecular fragments under very mild reaction conditions. Introduction of ferrocene-derived triazole systems using click chemistry has attracted enormous interest in various fields due to its potential applications in electrochemical techniques for detection and sensing. The present discussion focuses on the synthesis of ferrocene-triazole and the importance of using a CuAAC reaction for such conjugation. Applications of ferrocene-based click reactions in conjugate chemistry, asymmetric catalysis, medicinal chemistry, host-guest interactions, and materials chemistry have been highlighted.

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Section: Bioconjugatesmentioning

confidence: 99%

10 Years of Click Chemistry: Synthesis and Applications of Ferrocene‐Derived Triazoles

Ganesh

Sudhir

Kundu

et al. 2011

Chemistry An Asian Journal

123

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“…[6][7][8] The covalent attachment of metal complexes to PNA oligomers is currently being intensively investigated all around the world. 9 These metal conjugates have found applications in various research fields such as radioactive probes, as in the sequence-specific detection of nucleic acids, in the hydrolysis of nucleic acids and peptides, or as modulators of PNA•DNA hybrid stability. 9 However, to the best of our knowledge, there has been no report, to date, of the utilization of metal-PNAs for gene silencing.…”

Section: Introductionmentioning

confidence: 99%

“…9 These metal conjugates have found applications in various research fields such as radioactive probes, as in the sequence-specific detection of nucleic acids, in the hydrolysis of nucleic acids and peptides, or as modulators of PNA•DNA hybrid stability. 9 However, to the best of our knowledge, there has been no report, to date, of the utilization of metal-PNAs for gene silencing. This is rather surprising as the addition of a specific metal complex to a PNA oligomer can be of significant interest.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterisation and bioimaging of a fluorescent rhenium-containing PNA bioconjugate

et al. 2012

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A new rhenium tricarbonyl complex of a bis(quinoline)-derived ligand (2-azido-N,N-bis((quinolin-2-yl)methyl)ethanamine, L-N(3)), namely [Re(CO)(3)(L-N(3))]Br was synthesized and characterized indepth, including by X-ray crystallography. [Re(CO)(3)(L-N(3))]Br exhibits a strong UV absorbance in the range 300-400 nm with a maximum at 322 nm, and upon photoexcitation, shows two distinct emission bands at about 430 and 560 nm in various solvents (water, ethylene glycol). [Re(CO)(3)(L-N(3))]Br could be conjugated, on a solid phase, to a peptide nucleic acid (PNA) oligomer using the copper(I)-catalyzed azide-alkyne cycloaddition reaction (Cu-AAC, "click" chemistry) and an alkyne-containing PNA building block to give Re-PNA. It was demonstrated that upon hybridisation with a complementary DNA strand (DNA), the position of the maxima and emission intensity for the hybrid Re-PNA·DNA remained mainly unchanged compared to those of the single strand Re-PNA. The rhenium-containing PNA oligomer Re-PNA could be then mediated in living cells where they have been shown to be non-toxic contrary to the general notion that organometallic compounds are usually unstable under physiological conditions and/or cytotoxic. Furthermore, Re-PNA could be detected in living cells using fluorescent microscopy.

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“…Sodium chloride, potassium phosphate monobasic 5 and potassium phosphate dibasic, cholesterol, chloroform (≥99.8%) and methanol (≥99.9%) were purchased from SigmaAldrich. Synthetic phospholipids derivatives, 1,2-dimyristoyl-snglycero-3-phosphocholine (DMPC) and 1,2-dimyristoyl-snglycero-3-phospho-rac-(1-glycerol) (sodium salt) (DMPG), were 10 purchased from Avanti Polar Lipids (Alabaster, USA).…”

Section: Methodsmentioning

confidence: 99%

“…2 However, poor cellular uptake and limited in vivo bioavailability have to date restricted their 20 application in this field. [3][4][5][6][7][8][9] Despite possessing a neutral pseudopeptide backbone, PNAs are large and hydrophilic molecules. This implies that cellular administration in an unmodified form cannot be readily achieved.…”

Section: Introductionmentioning

confidence: 99%

Specific uptake and interactions of peptide nucleic acid derivatives with biomimetic membranes

et al. 2012

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There is a growing interest in understanding the uptake mechanism of metal-containing peptide nucleic acid (PNA) bioconjugates into living cells. In this study, quartz crystal microbalance with dissipation monitoring (QCM-D) has been used to explore the membrane specific uptake and interactions of PNA/peptide/Ru(II) conjugates. For all lipid compositions, the unmodified PNA oligomer and its Ru(II) conjugate were found to traverse freely across the membrane in a trans-membrane manner, causing no significant changes in the membrane structure. The nuclear localised signal peptide (NLS) conjugated sequences showed membrane specific activities. In model mammalian and bacterial-mimetic membranes, rapid trans-membrane insertion was observed followed by a concentration dependent disruption and irreversible structural changes to the membrane system. The variations in the magnitude of the structural changes and in their tendency to facilitate disruption are ascribed to hydrophobicity, the cationic charge introduced on modification of the original PNA backbone as well as the physical state of the model membrane used. There is a growing interest in understanding the uptake mechanism of metal-containing peptide nucleic acid (PNA) bioconjugates into living cells. In this study, Quartz Crystal Microbalance with Dissipation monitoring (QCM-D) has been used to explore the membrane specific uptake and interactions of PNA/peptide/Ru(II) conjugates. For all lipid compositions, the unmodified PNA oligomer and its Ru(II) conjugate were found to traverse freely across the membrane in a trans-membrane manner, causing no significant changes in 10 membrane structure. The Nuclear Localised Signal Peptide (NLS) conjugated sequences showed membrane specific activities. In model mammalian and bacterial-mimetic membranes, rapid trans-membrane insertion was observed followed by a concentration dependent disruption and irreversible structural changes to the membrane system. The variations in the magnitude of the structural changes and in their tendency to facilitate disruption are ascribed to hydrophobicity, the cationic charge introduced on modification of the original PNA 15 backbone as well as the physical state of the model membrane used.

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Metal-containing peptide nucleic acid conjugates

Cited by 63 publications

References 176 publications

10 Years of Click Chemistry: Synthesis and Applications of Ferrocene‐Derived Triazoles

10 Years of Click Chemistry: Synthesis and Applications of Ferrocene‐Derived Triazoles

Synthesis, characterisation and bioimaging of a fluorescent rhenium-containing PNA bioconjugate

Specific uptake and interactions of peptide nucleic acid derivatives with biomimetic membranes

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