Porphyrin induced Z to B conversion of poly(dG-dC)2 in ethanol

McKinnie, Russell E.; Choi, Jonathan; Bell, James Washington; Pasternack, Robert F.; Gibbs, Esther J.

doi:10.1016/0162-0134(88)80028-x

Cited by 22 publications

(4 citation statements)

References 24 publications

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“…Interestingly, identical hypochromicity and bathochromic shift, similar negative ICD bands at 436 nm and fluorescence quenching also appear in the absorption, ICD and fluorescence spectra of TMPyP4 ( Figure 2 b, Figure 3 b and Figure S1b ) when B-DNA is replaced by Z-DNA. These spectroscopic results suggest that TMPyP4 also intercalates into Z-DNA, which is in good agreement with previous reports [ 10 , 11 ].…”

Section: Resultssupporting

confidence: 93%

“…Generally, recognition of Z-DNA is achieved by utilizing Z-DNA binding small molecules, which have particular binding modes to Z-DNA that are distinct from those to B-DNA, thus allowing the specific DNA form to be determined [ 8 , 9 ]. Although a large number of small molecules such as porphyrin molecules and its analogues, have been reported to bind with B-DNA and Z-DNA, only a few of them can recognize Z-DNA via detection of particular binding modes with Z-DNA [ 9 , 10 , 11 , 12 ]. This indicates that selecting an appropriate small molecule as a probe for Z-DNA requires a deep mechanistic understanding for the binding modes of small molecules to B-DNA and Z-DNA.…”

Section: Introductionmentioning

confidence: 99%

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Binding Interactions of Zinc Cationic Porphyrin with Duplex DNA: From B-DNA to Z-DNA

Qin

Liu

Song

et al. 2018

IJMS

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Recognition of unusual left-handed Z-DNA by specific binding of small molecules is crucial for understanding biological functions in which this particular structure participates. Recent investigations indicate that zinc cationic porphyrin (ZnTMPyP4) is promising as a probe for recognizing Z-DNA due to its characteristic chiroptical properties upon binding with Z-DNA. However, binding mechanisms of the ZnTMPyP4/Z-DNA complex remain unclear. By employing time-resolved UV-visible absorption spectroscopy in conjunction with induced circular dichroism (ICD), UV-vis, and fluorescence measurements, we examined the binding interactions of ZnTMPyP4 towards B-DNA and Z-DNA. For the ZnTMPyP4/Z-DNA complex, two coexisting binding modes were identified as the electrostatic interaction between pyridyl groups and phosphate backbones, and the major groove binding by zinc(II) coordinating with the exposed guanine N7. The respective contribution of each mode is assessed, allowing a complete scenario of binding modes revealed for the ZnTMPyP4/Z-DNA. These interaction modes are quite different from those (intercalation and partial intercalation modes) for the ZnTMPyP4/B-DNA complex, thereby resulting in explicit differentiation between B-DNA and Z-DNA. Additionally, the binding interactions of planar TMPyP4 to DNA were also investigated as a comparison. It is shown that without available virtual orbitals to coordinate, TMPyP4 binds with Z-DNA solely in the intercalation mode, as with B-DNA, and the intercalation results in a structural transition from Z-DNA to B-ZNA. These results provide mechanistic insights for understanding ZnTMPyP4 as a probe of recognizing Z-DNA and afford a possible strategy for designing new porphyrin derivatives with available virtual orbitals for the discrimination of B-DNA and Z-DNA.

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Section: Resultssupporting

confidence: 93%

Section: Introductionmentioning

confidence: 99%

Binding Interactions of Zinc Cationic Porphyrin with Duplex DNA: From B-DNA to Z-DNA

Qin

Liu

Song

et al. 2018

IJMS

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“…Because of their strong binding to DNA, MTMpyP(4) have been used in footprinting experiments to probe DNA structure (Bromley et al, 1986;Ward et al, 1986a,b). Upon binding, TMpyP(4), CuTMpyP(4), and TMpyP(2) have been shown to convert Z-form to B-form DNA (McKinnie et al, 1988;Pasternack et al, 1986b). Other porphyrins have been used in conjunction with a variety of techniques to detect and destroy DNA and neoplastic cells (Fiel et al, 1981(Fiel et al, , 1982Foster et al, 1985;Robinson et al, 1986; Van den Bergh, 1986;Vaum et al, 1982).…”

mentioning

confidence: 99%

Porphyrin and metalloporphyrin binding to DNA polymers: rate and equilibrium binding studies

Strickland

Marzillï²,

Wilson³

1988

Biochemistry

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Interactions of meso-tetrakis(4-N-methylpyridiniumyl)porphyrin [TMpyP(4)] with poly[d(G-C)].poly[d(G-C)] [poly[d(G-C)2] and poly[d(A-T)].poly[d(A-T)] [poly[d(A-T)2] were studied by equilibrium dialysis and stopped-flow dissociation kinetics as a function of [Na+]. Metalloderivatives of TMpyP(4), NiTMpyP(4), and ZnTMpyP(4) were also investigated. The apparent equilibrium binding constants (Kobs) were approximately the same for TMpyP(4) binding to either poly[d(G-C)2] or poly[d(A-T)2] and decreased with increasing [Na+]. The slopes of the plots of log Kobs vs log [Na+] were similar, with values close to -2.7. Contrary to implications in previously reported studies, these data do not indicate that TMpyP(4) prefers to bind to GC sites at low ionic strength and to AT sites at high ionic strength. In contrast, binding of ZnTMpyP(4) to these two polymers is very different. Comparisons of Kobs values at 0.065 M [Na+] indicate that ZnTMpyP(4) binding to AT sites is approximately 200 times more favorable than binding to GC sites, a finding in agreement with previous qualitative observations. Although the binding of the Zn species to the GC polymer was too weak for us to assess the salt effect, the plot of log Kobs vs log [Na+] gave a slope of -2.0 for ZnTMpyP(4) binding to poly[d(A-T)2]. Application of condensation theory for polyelectrolytes suggests similar charge interactions for ZnTMpyP(4) and for TMpyP(4) binding to poly[d(A-T)2]. Likewise, the rates of dissociation from poly[d(A-T)2] were similar for TMpyP(4) and ZnTMpyP(4) [and also NiTMpyP(4)]. However, whereas TMpyP(4) [and NiTMpyP(4)] dissociation from poly[d(G-C)2] was measurable, that for ZnTMpyP(4) was too fast to measure.(ABSTRACT TRUNCATED AT 250 WORDS)

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“…如果卟啉配有金属离子时, 不同的金属与卟啉结合的空间结构不同、轴向有无配体等也将导致它们与 DNA 的作用方式及位置的不同 [23] . Ni(II)-TMPyP 可以选择性地插入 DNA 中富 G-C 碱基对区域 [8a,24] , 而 TMPyP 则自身诱导 DNA 的构型从 Z 型转化为 E 型 [25] . [4,26] .…”

Section: 的作用方式各不相同 Meso-四(4-n-甲基吡啶基)卟啉unclassified

Development of Study on Water-Soluble Porphyrins and Metalloporphyrins in DNA

Zhang¹,

Chen²

2012

Acta Chim. Sinica

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The research of the interaction between porphyrins or metalloporphyrins and DNA becomes one focal point in recent years. The research conduces to realize the structure and the function of DNA more deeply, and profits porphyrins or metalloporphyrins to use in the medicine, and also be very important for understanding the treatment mechanism and the drug design of many diseases. The mode and influencing factors of interaction between porphyrins or metalloporphyrins and DNA are elucidated, and the water-soluble porphyrins and metalloporphyrins are classified into three types: the cationic porphyrins and metalloporphyrins which have pyridyl group or ammonium group, the anionic porphyrins and metalloporphyrins which have sulfonic group or carboxyl group, and the neutral porphyrins and metalloporphyrins. The interaction and the recent exploratory development in the study of the three types of the water-soluble porphyrins and metalloporphyrins in DNA are emphatically reviewed.

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Porphyrin induced Z to B conversion of poly(dG-dC)2 in ethanol

Cited by 22 publications

References 24 publications

Binding Interactions of Zinc Cationic Porphyrin with Duplex DNA: From B-DNA to Z-DNA

Binding Interactions of Zinc Cationic Porphyrin with Duplex DNA: From B-DNA to Z-DNA

Porphyrin and metalloporphyrin binding to DNA polymers: rate and equilibrium binding studies

Development of Study on Water-Soluble Porphyrins and Metalloporphyrins in DNA

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