5‘-Porphyrin−Oligonucleotide Conjugates:  Neutral Porphyrin−DNA Interactions

Baláž, Milan; Steinkruger, Jay D.; Ellestad, George A.; Berova, Nina

doi:10.1021/ol0522992

Cited by 42 publications

(31 citation statements)

References 29 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[4] Various artificial photoelectronic systems based on chiral porphyrin supramolecular assemblies are anticipated to be potentially useful for practical applications in the fields of nonlinear optics, material and polymer sciences, catalysis, biochemistry, and molecular devices. [3a-d, 4, 5] Driven by these factors, supramolecular chirality generation/induction (termed supramolecular chirogenesis), amplification, and memory derived from porphyrin derivatives have currently become some of the hottest topics in the interdisciplinary area of supramolecular chemistry/chirality.…”

Section: Introductionmentioning

confidence: 99%

“…Keywords: porphyrinoids · supramolecular assemblies · symmetry breaking · thin films assemblies: i) from intrinsically chiral porphyrin molecules bearing chiral substituents that have assembled through covalent bonds or noncovalent intermolecular interactions; [4,6] ii) from achiral porphyrin components that have assembled in a chiral circumstance, or were induced by chiral inducers or chiral templates; [3,7] iii) entirely from achiral porphyrin molecules through the asymmetric outer-vortex motion, or directional spin coating. [8,9] The third case is thought to be very important, because it relates to the origin of supramolecular chirality and the symmetry breaking of a system.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

A General Method for Constructing Optically Active Supramolecular Assemblies from Intrinsically Achiral Water‐Insoluble Free‐Base Porphyrins

Zhang

Chen

Liu

2008

Chemistry A European J

View full text Add to dashboard Cite

We have developed a general method to construct optically active porphyrin supramolecular assemblies by using a simple air-water interfacial assembly process. The method involved the in situ diprotonation of the free-base porphyrins at the air-water interface and subsequent assembly under compression. We showed that two intrinsically achiral water-insoluble free-base porphyrin derivatives, 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphine (H(2)OEP) and 5,10,15,20-tetra-p-tolyl-21H,23H-porphine (H(2)TPPMe), could be diprotonated when spread onto a 2.4 M hydrochloric acid solution surface, and the Langmuir-Schaefer (LS) films fabricated from the subphase exhibited strong circular dichroism (CD) absorption, whereas those fabricated from pure Milli-Q water subphase did not. The experimental data suggested that the helical stacking of the achiral porphyrin building blocks was responsible for the supramolecular chirality of the assemblies. Interestingly, such a method was successfully applied to a series of other intrinsically achiral free-base porphyrins such as 5,10,15,20-tetrakis(4-methoxyphenyl)-21H,23H-porphine (H(2)TPPOMe), 5,10,15,20-tetraphenyl-21H,23H-porphine (H(2)TPP), 5,10,15,20-tetrakis(4-(allyloxy)phenyl)-21H,23H-porphine (H(2)TPPOA), and 5,10,15,20-tetrakis(3,5-dimethoxyphenyl)-21H,23H-porphine (H(2)TPPDOMe). A possible mechanism has been proposed. The method provides a facile way to obtain optically active porphyrin supramolecular assemblies by using intrinsically achiral water-insoluble free-base porphyrin derivatives.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

A General Method for Constructing Optically Active Supramolecular Assemblies from Intrinsically Achiral Water‐Insoluble Free‐Base Porphyrins

Zhang

Chen

Liu

2008

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…Other metal cations do not exhibit binding affinity towards thymine or pyridine, so they are not expected to promote structural or spectroscopic changes of porphyrin–DNA conjugates. The synthesis of porphyrin–oligodeoxynucleotide (Por‐ODN) conjugates ZnPorT8 , 2HPorT8 , and ZnPorA8 has been reported previously 31–33. Porphyrin–deoxythymidine ( ZnPorT1 ) was synthesized by following the standard phosphoramidite synthesis method.…”

Section: Resultsmentioning

confidence: 99%

Highly Sensitive and Selective Spectroscopic Detection of Mercury(II) in Water by Using Pyridylporphyrin–DNA Conjugates

Choi

Sargsyan

Olive

et al. 2012

Chemistry A European J

Self Cite

View full text Add to dashboard Cite

Single-labeled pyridylporphyrin-DNA conjugates are reported as highly sensitive and selective spectroscopic sensors for mercury(II) ions in water. The effects of chemical structure (thymine versus adenine), number of nucleotides (monomer versus octamer), and porphyrin metalation (Zn versus free base) on the sensitivity and selectivity of mercury(II) detection are explored. The results indicated that pyridylporphyrin rather than the nucleobase plays a crucial role in mercury(II) sensing, because porphyrin conjugates with both adenosine and thymidine exhibited excellent mercury(II) detection. Mercury(II) recognition was shown in emission quenching, as well as in a redshift of the porphyrin Soret band absorption. The limit of detection (LOD, 3σ/slope) of zinc(II) pyridylporphyrin-5'-oligodeoxythymidine (ZnPorT8) obtained by fluorescence quenching was calculated to be 21.14 nM. Other metal cations (Zn(2+), Cd(2+), Pb(2+), Mn(2+), Ca(2+), Ni(2+), Mg(2+), Fe(2+), Cu(2+), and Na(+)) did not interfere with the emission and absorption sensing of mercury(II). Free-base porphyrin-oligothymine conjugate 2HPorT8 displayed similar sensitivity to ZnPorT8 but different selectivity. The results also implied that the sensing properties of porphyrin-deoxythymidine conjugates could potentially be tuned by porphyrin metalation.

show abstract

“…Another interesting family of metal-binding artificial DNA is porphyrin-modified DNA, where porphyrins can coordinate to a variety of metals and display unique electronic and photophysical properties [68][69][70].…”

Section: Dna Modified With Porphyrinmentioning

confidence: 99%

DNA modified with metal complexes: Applications in the construction of higher order metal–DNA nanostructures

Yang

Metera

Sleiman

2010

Coordination Chemistry Reviews

View full text Add to dashboard Cite

5‘-Porphyrin−Oligonucleotide Conjugates: Neutral Porphyrin−DNA Interactions

Cited by 42 publications

References 29 publications

A General Method for Constructing Optically Active Supramolecular Assemblies from Intrinsically Achiral Water‐Insoluble Free‐Base Porphyrins

A General Method for Constructing Optically Active Supramolecular Assemblies from Intrinsically Achiral Water‐Insoluble Free‐Base Porphyrins

Highly Sensitive and Selective Spectroscopic Detection of Mercury(II) in Water by Using Pyridylporphyrin–DNA Conjugates

DNA modified with metal complexes: Applications in the construction of higher order metal–DNA nanostructures

Contact Info

Product

Resources

About