Research at the Interface between Chemistry and Virology:  Development of a Molecular Flashlight

Kraus, George A.; Zhang, Weijiang; Fehr, Michael J.; Petrich, Jacob W.; Wannemuehler, Yvonne; Carpenter, Susan

doi:10.1021/cr9500139

Cited by 141 publications

(89 citation statements)

References 94 publications

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“…[1][2][3][4][5] We have argued that they also present a fascinating system with which to study excited-state intramolecular H-atom transfer. [6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] Hypericin executes an intramolecular excited-state H-atom transfer in ∼10 ps.…”

Section: Introductionmentioning

confidence: 99%

Coupling of Large-Amplitude Side Chain Motions to the Excited-State H-Atom Transfer of Perylene Quinones: Application of Theory and Experiment to Calphostin C

et al. 2001

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The excited-state intramolecular H-atom transfer reactions of hypocrellins B and A are compared with those of calphostin C. On the basis of the results of transient absorption measurements and ab initio quantum mechanical calculations, it is concluded that large-amplitude conformational changes are coupled to the Hatom transfer in calphostin C, just as they are in hypocrellins A and B. The calculations on this very large molecule with a very complex ground electronic state potential energy surface were made possible by the use of highly scalable electronic structure theory codes on large parallel computers. Disciplines Chemistry CommentsReprinted (adapted) The excited-state intramolecular H-atom transfer reactions of hypocrellins B and A are compared with those of calphostin C. On the basis of the results of transient absorption measurements and ab initio quantum mechanical calculations, it is concluded that large-amplitude conformational changes are coupled to the H-atom transfer in calphostin C, just as they are in hypocrellins A and B. The calculations on this very large molecule with a very complex ground electronic state potential energy surface were made possible by the use of highly scalable electronic structure theory codes on large parallel computers.

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Section: Introductionmentioning

confidence: 99%

Coupling of Large-Amplitude Side Chain Motions to the Excited-State H-Atom Transfer of Perylene Quinones: Application of Theory and Experiment to Calphostin C

et al. 2001

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“…These have been the subject of several reviews [1][2][3][4][5] and have been referred to in detail in our previous work. One of the most interesting photophysical processes that these molecules execute is excited-state proton or H atom transfer, both intramolecular [6][7][8][9][10][11][12][13][14][15][16][17][18][19] and intermolecular.…”

Section: Introductionmentioning

confidence: 99%

Excited-State Intramolecular H Atom Transfer of Hypericin and Hypocrellin A Investigated by Fluorescence Upconversion

et al. 1999

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The excited-state intramolecular H atom transfer reaction occurring in hypericin and hypocrellin A is investigated by means of the fluorescence upconversion technique in a variety of solvents. Rising components of ∼10 ps, attributable to intramolecular H atom transfer, are clearly observed in the fluorescence upconversion traces of both hypericin and hypocrellin A. The amplitude of the rising component is emission wavelength dependent and occurs on the blue edge of the emission spectra. Neither in hypericin nor in hypocrellin A does this fluorescent component exhibit a deuterium isotope effect. This result identifies it with the ∼10 ps component, also lacking a deuterium isotope effect, observed in hypericin in transient absorption measurements monitoring stimulated emission. The clear and complementary observation in fluorescence of the ∼10 ps component in both hypericin and hypocrellin A is a crucial link in refining a unified model of the hypericin and hypocrellin photophysics that we first proposed in J. Phys The excited-state intramolecular H atom transfer reaction occurring in hypericin and hypocrellin A is investigated by means of the fluorescence upconversion technique in a variety of solvents. Rising components of ∼10 ps, attributable to intramolecular H atom transfer, are clearly observed in the fluorescence upconversion traces of both hypericin and hypocrellin A. The amplitude of the rising component is emission wavelength dependent and occurs on the blue edge of the emission spectra. Neither in hypericin nor in hypocrellin A does this fluorescent component exhibit a deuterium isotope effect. This result identifies it with the ∼10 ps component, also lacking a deuterium isotope effect, observed in hypericin in transient absorption measurements monitoring stimulated emission. The clear and complementary observation in fluorescence of the ∼10 ps component in both hypericin and hypocrellin A is a crucial link in refining a unified model of the hypericin and hypocrellin photophysics that we first proposed in

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“…4,5 Although the requirement of light for this activity in hypericin and hypocrellin is absolute, these two molecules possess very different modes of reactivity. 6 Consequently, we have undertaken the task [6][7][8][9][10][11][12][13][14][15] of unraveling the excited-state primary photophysical processes of hypericin and hypocrellin.…”

Section: Introductionmentioning

confidence: 99%

Hypericin, Hypocrellin, and Model Compounds: Primary Photoprocesses of Light-Induced Antiviral Agents

et al. 1997

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The excited-state photophysics of the light-induced antiviral agents hypericin and hypocrellin are compared with those of the hexa-and tetramethoxy analogues of hypericin. The results are consistent with the interpretation of the primary photoprocess in hypericin and hypocrellin as that of excited-state intramolecular proton or atom transfer. DisciplinesChemistry | Organic Chemistry | Other Chemistry | Polymer Chemistry CommentsReprinted (adapted) October 3, 1996; In Final Form: February 3, 1997 X The excited-state photophysics of the light-induced antiviral agents hypericin and hypocrellin are compared with those of the hexa-and tetramethoxy analogues of hypericin. The results are consistent with the interpretation of the primary photoprocess in hypericin and hypocrellin as that of excited-state intramolecular proton or atom transfer.

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Research at the Interface between Chemistry and Virology: Development of a Molecular Flashlight

Cited by 141 publications

References 94 publications

Coupling of Large-Amplitude Side Chain Motions to the Excited-State H-Atom Transfer of Perylene Quinones: Application of Theory and Experiment to Calphostin C

Coupling of Large-Amplitude Side Chain Motions to the Excited-State H-Atom Transfer of Perylene Quinones: Application of Theory and Experiment to Calphostin C

Excited-State Intramolecular H Atom Transfer of Hypericin and Hypocrellin A Investigated by Fluorescence Upconversion

Hypericin, Hypocrellin, and Model Compounds: Primary Photoprocesses of Light-Induced Antiviral Agents

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