Photoinduced Intramolecular Electron-Transfer Reactions of Reconstituted Met- and Zinc-Myoglobins Appending Acridine and Methylacridinium Ion as DNA-Binders

Takashima, Hiroshi; Tara, Chisako; Namikawa, Sachiko; Kato, Tomoko; Araki, Yasuyuki; Ito, Osamu; Tsukahara, Keiichi

doi:10.1021/jp0655571

Cited by 10 publications

(16 citation statements)

References 85 publications

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“…Thus, the conformational changes of [Pt(bpy)(en)] 2 þ at the surface of ZnMb, where the donor -acceptor distance was probably elongated by CT-DNA, may affect the intramolecular ENT efficiency and also change the heme environment. Further studies are necessary to investigate interactions between [Pt(bpy)(en)] 2 þ and DNA in detail, including determination of the lifetimes of the photo-excited states of 1 (ZnMb)* and 3 (ZnMb)* by means of fluorescence lifetime [40] and T -T absorption spectral measurements, as we previously reported for ZnMb appending an ethidium ion as a DNA intercalator [46]. However, our DNAregulated system based on the ZnMb scaffold is one of the new interesting biomimetic models for the photoinduced ET reactions within a protein -DNA complex [47] [48].…”

Section: Preparation Ofmentioning

confidence: 99%

“…Previously reported Mbs, utilized for the complexation with DNA, are covalently conjugated with the designed peptide or the complementary polynucleotide at the heme propanoates [38] [39]. We recently developed Zn-and met-Mb modified with acridine derivatives as DNA-binding small molecules to form Mb -DNA complexes using noncovalent interactions by hydrophobic and p -p interactions [40]. [31 -33].…”

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confidence: 99%

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Synthesis and Spectroscopic Properties of Reconstituted ZincMyoglobin Appending a DNA‐Binding Platinum(II) Complex

Takashima

Fujimoto

Hirai

et al. 2008

Chemistry & Biodiversity

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A reconstituted zinc-myoglobin (ZnMb) dyad, ZnMb-[Pt(bpy)(en)]2+, has been prepared by incorporating chemically-modified zinc-porphyrin, being capable of DNA-binding of the Pt complex, [Pt(bpy)(en)]2+, where bpy and en are 2,2'-bipyridine and ethylenediamine, respectively. The steady-state fluorescence of the cofactor, [Pt(bpy)(mu-enPP)Zn]Cl2, in MeOH indicates that the excited singlet state of zinc--porphyrin was almost quenched, probably because of the strong hydrophobic and pi-pi stacking interactions between the [Pt(bpy)(mu-enPP)Zn]2+ ions. In the reconstituted ZnMb-[Pt(bpy)(en)]2+, the quenching reaction of 1(ZnMb)* with the [Pt(bpy)(en)]2+ moiety does not occur, indicating apo-Mb matrix is essential. On the other hand, when the [Pt(bpy)(en)]2+ moiety was excited, the enhancement of the fluorescence from ZnMb unit was observed. It is suggested that the energy transfer from (1)([Pt(bpy)(en)]2+)* to ZnMb occurs. The spectroscopic changes of ZnMb-[Pt(bpy)(en)]2+ in the presence of calf-thymus DNA were also provided. Soret band at 428 nm gradually decreased, and isosbestic points at 321, 414, and 432 nm were observed with increasing the DNA concentration. When the Pt(II) moiety was excited at lambda(ex) 321 nm, the fluorescence signal around 600 nm similarly decreased. The synthetic manipulation of ZnMb by using a DNA-binding Pt(II) complex demonstrates sensitive fluorescent signal for DNA and valuable information to study photoinduced electron transfer within a Mb-DNA complex.

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Section: Preparation Ofmentioning

confidence: 99%

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confidence: 99%

Synthesis and Spectroscopic Properties of Reconstituted ZincMyoglobin Appending a DNA‐Binding Platinum(II) Complex

Takashima

Fujimoto

Hirai

et al. 2008

Chemistry & Biodiversity

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“…Conjugates have also been formed by linkers containing a modified heme propionate and a DNA-binding moiety such as the DNA binding peptide GCN4, [Pt(bpy)(en)] 2+ , or the DNA intercalators acridine and ethidium. − …”

Section: Historymentioning

confidence: 99%

Site-Selective Conjugation of Native Proteins with DNA

2017

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Conjugation of DNA to proteins is increasingly used in academia and industry to provide proteins with tags for identification or handles for hybridization to other DNA strands. Assay technologies such as immuno-PCR and proximity ligation and the imaging technology DNA-PAINT require DNA-protein conjugates. In DNA nanotechnology, the DNA handle is exploited to precisely position proteins by self-assembly. For these applications, site-selective conjugation is almost always desired because fully functional proteins are required to maintain the specificity of antibodies and the activity of enzymes. The introduction of a bioorthogonal handle at a specific position of a protein by recombinant techniques provides an excellent approach to site-specific conjugation, but for many laboratories and for applications where several proteins are to be labeled, the expression of recombinant proteins may be cumbersome. In recent years, a number of chemical methods that target conjugation to specific sites at native proteins have become available, and an overview of these methods is provided in this Account. Our laboratory has investigated DNA-templated protein conjugation (DTPC), which offers an alternative approach to site-selective conjugation of DNA to proteins. The method is inspired by the concept of DNA-templated synthesis where functional groups conjugated to DNA strands are preorganized by DNA hybridization to dramatically increase the reaction rate. In DPTC, we target metal binding sites in proteins to template selective covalent conjugation reactions. By chelation of a DNA-metal complex with a metal binding site of the protein, an electrophile on a second DNA strand is aligned for reaction with a lysine side chain on the protein in the proximity of the metal binding site. The method is quite general because approximately one-third of all wild-type proteins contain metal-binding sites, including many IgG antibodies, and it is also applicable to His-tagged proteins. This emerging field provides direct access to site-selective conjugates of DNA to commercially available proteins. In this Account, we introduce these methods to the reader and describe current developments and future aspects.

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“…The zinc‐substituted heme into apo‐myoglobin (Mb) and direct chemical modification of the heme propionate with a redox‐active compound connected by a methylene “wire” spacer have been topics of some interests . These artificial models realize intramolecular photoinduced reaction within a protein scaffold and generate charge separated state in order to elucidate the complicated mechanisms of photoinduced ET …”

Section: Introductionmentioning

confidence: 99%

Photoinduced electron‐transfer reactions of tris(2,2′‐bipyridine)ruthenium(II)‐based carbonic anhydrase inhibitors tethering plural binding sites

Suwa

Imamura

Awano

et al. 2018

J of Physical Organic Chem

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Photoinduced Intramolecular Electron-Transfer Reactions of Reconstituted Met- and Zinc-Myoglobins Appending Acridine and Methylacridinium Ion as DNA-Binders

Cited by 10 publications

References 85 publications

Synthesis and Spectroscopic Properties of Reconstituted ZincMyoglobin Appending a DNA‐Binding Platinum(II) Complex

Synthesis and Spectroscopic Properties of Reconstituted ZincMyoglobin Appending a DNA‐Binding Platinum(II) Complex

Site-Selective Conjugation of Native Proteins with DNA

Photoinduced electron‐transfer reactions of tris(2,2′‐bipyridine)ruthenium(II)‐based carbonic anhydrase inhibitors tethering plural binding sites

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