Understanding binding interactions of cationic porphyrins with B-form DNA

McMillin, David R.; Shelton, Alexander H.; Bejune, Stephanie A.; Fanwick, Phillip E.; Wall, Rebecca K.

doi:10.1016/j.ccr.2004.11.016

Cited by 86 publications

(121 citation statements)

References 53 publications

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“…Zinc porphyrins are five coordinate in aqueous solutions and have been shown not to lose the axial water ligand easily. [8] On the other hand, nickel porphyrins have been shown to easily lose axial ligands to form four-coordinate species. [10] We hypothesized that the axial ligand on the zinc atom sterically prevented the efficient p-stacking and hampered formation of ZnPor- Figure 1.…”

Section: Assembly Of Right-handed 2 Hpor-dap:dtx and Nipor-dap:dtx Namentioning

confidence: 99%

“…Zinc porphyrins are five-coordinate, while nickel porphyrins are four-and six-coordinate in aqueous solutions with water as (an) axial ligand(s). [8] The DNA templated multiporphyrin nanoassemblies exhibited modular structural and chiroptical properties and high thermal stability. We have constructed molecular models for the 2 HPor-DAP nanoassemblies and employed time-dependent density functional theory (TDDFT) simulations of UV/Vis and CD spectra for direct comparison with experimental data.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Supramolecular ssDNA Templated Porphyrin and Metalloporphyrin Nanoassemblies with Tunable Helicity

Sargsyan

Leonard

Kubelka

et al. 2014

Chemistry A European J

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Free-base and nickel porphyrin-diaminopurine conjugates were formed by hydrogen-bond directed assembly on single-stranded oligothymidine templates of different lengths into helical multiporphyrin nanoassemblies with highly modular structural and chiroptical properties. Large red-shifts of the Soret band in the UV/Vis spectroscopy confirmed strong electronic coupling among assembled porphyrin-diaminopurine units. Slow annealing rates yielded preferentially right-handed nanostructures, whereas fast annealing yielded left-handed nanostructures. Time-dependent DFT simulations of UV/Vis and CD spectra for model porphyrin clusters templated on the canonical B-DNA and its enantiomeric form, were employed to confirm the origin of observed chiroptical properties and to assign the helicity of porphyrin nanoassemblies. Molar CD and CD anisotropy g factors of dialyzed templated porphyrin nanoassemblies showed very high chiroptical anisotropy. The DNA-templated porphyrin nanoassemblies displayed high thermal and pH stability. The structure and handedness of all assemblies was preserved at temperatures up to +85 °C and pH between 3 and 12. High-resolution transition electron microscopy confirmed formation of DNA-templated nickel(II) porphyrin nanoassemblies and their self-assembly into helical fibrils with micrometer lengths.

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Section: Assembly Of Right-handed 2 Hpor-dap:dtx and Nipor-dap:dtx Namentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Supramolecular ssDNA Templated Porphyrin and Metalloporphyrin Nanoassemblies with Tunable Helicity

Sargsyan

Leonard

Kubelka

et al. 2014

Chemistry A European J

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“…4 Cationic porphyrins, especially meso-tetrakis (N-methylpyridinium-4-yl) porphyrin (H 2 TMPyP) and its metal complexes, possess significant and wide research value for the reason that they possess good water solubility, which makes DNA-binding possible under physiological conditions and interact with DNA strongly. 5,6 Meanwhile, tris-, tetra-and multiple charge cationic porphyrins are also known as good photosensitizers for DNA photocleavage.…”

Section: 3mentioning

confidence: 99%

Synthesis, DNA Photocleavage and Singlet Oxygen Measurement of Cationic Bisporphyrins

Wang¹,

Jin²,

Zhang³

et al. 2013

Journal of the Korean Chemical Society

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ABSTRACT. With −OCH2CO− as a linker, a non β-substituted cationic bisporphyrin (4a) and a β-substituted cationic bisporphyrin (4b) were prepared through methylation of the intermediate which was obtained from β-amino-5,10,15,20-tetra (4-cyanophenyl) porphyrin or 5-hydroxylphenyl-10,15,20-tris(4-cyanophenyl) reacting with 5-hydroxy-10,15,20-trispyridinylporphyrin. Their structures were confirmed by 1 H NMR, IR, UV-vis, MS and elemental analysis. DNA photocleavage ability and the singlet oxygen ability of those cationic bisporphyrins were investigated. DNA photocleavage activity of β-substituted cationic bisporphyrin was significantly weaker than that of H2TMPyP, but similar to that of non β-substituted cationic bisporphyrin. While 4a and 4b showed substantial photocleavage activities toward DNA, with 68% and 66% observed at 10 µM. The assessment of indirectly measured 1 O2 production rates against H2TMPyP were described and the relative singlet oxygen production yields were: free cationic bisporphyrins > H2TMPyP. The results showed the cationic bisporphyrins with β-substitution and non β-substitution could be developed as potential photodynamic agents.

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“…Ìîжëè-âî, äîäàòêîâîю ì³шåííю ä³ї пîðф³ðèí³â âèñòóпàє ДНК бàêòåð³îфàгà. Дîñë³äжåííÿ McMillin et al ñâ³ä÷àòü пðî òå, щî пîðф³ðèíè ìîжóòü зâ'ÿзóâàòèñÿ ззîâí³ àбî ³íòåðêàëюâàòè ó ДНК ó зàëåжíîñò³ â³ä пðèðî-äè ДНК ñóбñòðàòó [10]. Пðèì³òêà: â³ñü îðäèíàò -àíòèфàгîâà àêòèâí³ñòü ñпîëóê, %; * -ð³зíèöÿ äîñòîâ³ðíà ó пîð³âíÿíí³ з êîíòðîëåì êîíöåíòðàö³ÿ пîðф³ðèíó, ìêÌ…”

Section: нс водзIнська ов кондратюк то фIлiповаunclassified

Influence of Quinolinilporphyrin Bismut and Tin Complexes on Lactococcus Lactis Phages Activity

Водзінська¹,

Kondratiuk²,

Філіпова³

2011

Microbiology&Biotechnology

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ВПËИВ ВIСÌУÒÎВÎÃÎ ÒА ÎËÎВ'ßÍÎÃÎ ÊÎÌПËÅÊСIВ ХIНОЛIНIЛПОРФIРИНУ НА АКТИВНIСТЬ ФАГIВ LACTOCOCCUS LACTISФàгè ìîëî÷íîêèñëèх бàêòåð³é âèêëèêàюòü пîñò³éíèé ³íòåðåñ, пåðåäó-ñ³ì, ÷åðåз åêîíîì³÷í³ âòðàòè, ÿê³ íåñóòü п³äпðèєìñòâà ìîëî÷íîї пðîìèñëî-âîñò³ âíàñë³äîê фàгîâîї ³íфåêö³ї. Îñê³ëüêè ó âèðîбíèöòâ³ фåðìåíòîâàíèх ìîëî÷íèх пðîäóêò³â íàé÷àñò³шå âèêîðèñòîâóюòü ìîëî÷íîêèñë³ бàêòåð³ї ðîäó Lactococcus, ñàìå ëàêòîêîêîâ³ фàгè íàéб³ëüш ðîзпîâñюäжåíí³ íà ìîëî÷íèх êîìб³íàòàх òà є пðè÷èíîю б³ëüшîñò³ íååфåêòèâíèх òåхíîëîг³÷íèх пðîöåñ³â [7]. Лàêòîфàгè âèêëèêàюòü зàгèбåëü зàêâàñî÷íèх ì³êðîîðгàí³з-ì³â, щî пðèзâîäèòü äî óпîâ³ëüíåííÿ âèðîбíèöòâà пðîäóêö³ї, пîг³ðшåííÿ її ÿêîñò³. Пîðóшåííÿ пðîöåñ³â êèñëîìîëî÷íîгî бðîä³ííÿ ìîжå пðèзâåñòè íå ò³ëüêè äî зíèжåííÿ ÿêîñò³ òà âòðàò ñèðîâèíè, àëå é äî âèíèêíåííÿ хàð÷î-âèх îòðóєíü, àäжå ó íîðì³ зàêâàñî÷íà ì³êðîб³îòà ³íг³бóє óìîâíîпàòîгåíí³ ì³êðîîðгàí³зìè, пðèñóòí³ ó ìîëîö³ [1,3]. Нà ñüîгîäí³ ³ñíóюòü ð³зí³ п³äхîäè, зàâäÿêè ÿêèì ìîжíà зìåíшèòè ðèзèê фàгîâîї ³íфåêö³ї: ðîòàö³ÿ ñòàðòåð-íèх êóëüòóð, âèêîðèñòàííÿ гåíåòè÷íèх ìåòîä³â äëÿ зб³ëüшåííÿ фàгîðå-зèñòåíòíîñò³ ñòàðòåðíèх êóëüòóð, пðÿìà ³íîêóëÿö³ÿ ñòàðòåð³â ó зàêðèò³ фåðìåíòåðè òà âèêîðèñòàííÿ ñåðåäîâèщ з àíòèфàгîâèìè âëàñòèâîñòÿìè äëÿ збåð³гàííÿ ³ ðîзìíîжåííÿ ñòàðòåðíèх êóëüòóð [7].

show abstract

Understanding binding interactions of cationic porphyrins with B-form DNA

Cited by 86 publications

References 53 publications

Supramolecular ssDNA Templated Porphyrin and Metalloporphyrin Nanoassemblies with Tunable Helicity

Supramolecular ssDNA Templated Porphyrin and Metalloporphyrin Nanoassemblies with Tunable Helicity

Synthesis, DNA Photocleavage and Singlet Oxygen Measurement of Cationic Bisporphyrins

Influence of Quinolinilporphyrin Bismut and Tin Complexes on Lactococcus Lactis Phages Activity

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