Toward the Molecular Flashlight: Preparation, Properties, and Photophysics of a Hypericin–luciferin Tethered Molecule¶

Wen, Jin; Chowdhury, P. K.; Wills, Nick J.; Wannemuehler, Yvonne; Park, Jaehun; Kesavan, Sarathy; Carpenter, Susan; Kraus, George A.; Petrich, Jacob W.

doi:10.1562/0031-8655(2002)076<0153:ttmfpp>2.0.co;2

Cited by 10 publications

(7 citation statements)

References 24 publications

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“…The decay is well described by a single exponential with τ F = 5.5 ± 0.2 ns (based on the average of four measurements). For comparison, the fluorescence lifetime of hypericin in DMSO was found to be 5.6 ± 0.2 ns …”

Section: Resultsmentioning

confidence: 99%

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Maristentorin, a Novel Pigment from the Positively Phototactic Marine CiliateMaristentordinoferus, Is Structurally Related to Hypericin and Stentorin

et al. 2006

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The photoreceptor pigment of the heterotrich ciliate, Maristentor dinoferus, has been characterized. It is structurally similar to those of Stentor coeruleus and Blepharisma japonicum but differs significantly in that it bears no aromatic hydrogens. The structure of the pigment, maristentorin, is based upon the hypericin skeleton, and its spectra are nearly identical to those of hypericin but shifted toward the red. Within experimental error, its fluorescence lifetime is identical to that of hypericin, approximately 5.5 ns in dimethylsulfoxide. It is remarkable that while the pigments are structurally similar in S. coeruleus and M. dinoferus, in the former there is an abrupt photophobic response, whereas in the latter there is a slow response toward light. The roles of the hypericin-like pigments in the heterotrich ciliates are discussed as potentially analogous in Maristentor.

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Section: Resultsmentioning

confidence: 99%

“…For comparison, the fluorescence lifetime of hypericin in DMSO was found to be 5.6 ( 0.2 ns. 35 Figure 6. Electrospray mass spectra of maristentorin in the negative ion mode.…”

Section: Figurementioning

confidence: 99%

Maristentorin, a Novel Pigment from the Positively Phototactic Marine CiliateMaristentordinoferus, Is Structurally Related to Hypericin and Stentorin

et al. 2006

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“…Ultrafast femtosecond spectroscopy is a powerful tool to study the structural dynamics in molecular systems. 2 In the past decades, ultrafast femtosecond and other time-resolved techniques have been used to investigate the excited state behavior and the structural transitions of anticancer and antiviral drugs in solution [3][4][5][6] and in chemical and biological caging media, such as cyclodextrins and the human serum albumin protein. 5,[7][8][9][10][11][12][13] The latest developments in ultrafast spectroscopy techniques allow probing the structural dynamics of various chemical and biological systems at the atomic level.…”

Section: Introductionmentioning

confidence: 99%

“…5,[7][8][9][10][11][12][13] The latest developments in ultrafast spectroscopy techniques allow probing the structural dynamics of various chemical and biological systems at the atomic level. [14][15][16] Recently, we have reported on the ultrafast dynamics of the drugs (8E)-8-[hydroxy-(pyridin-2-ylamino)methylidene]-9-methyl-10,10-dioxo-10λ 6 thia-9-azabicyclo[4.4.0]deca-1,3,5-trien-7-one (piroxicam) and 1,6-dihydro-2-methyl-6-oxo-(3,4′-bipyridine)-5-carbonitrile (milrinone) in water solutions and in caging media. 7,17,18 The observed ultrafast dynamics was explained in terms of hydrogen bonding interactions with the medium, intramolecular chargetransfer and twisting motion in the excited drug, and the confinement effect of the nanocages in the above processes.…”

Section: Introductionmentioning

confidence: 99%

“…Ultrafast femtosecond spectroscopy is a powerful tool to study the structural dynamics in molecular systems . In the past decades, ultrafast femtosecond and other time-resolved techniques have been used to investigate the excited state behavior and the structural transitions of anticancer and antiviral drugs in solution − and in chemical and biological caging media, such as cyclodextrins and the human serum albumin protein. ,− The latest developments in ultrafast spectroscopy techniques allow probing the structural dynamics of various chemical and biological systems at the atomic level. − Recently, we have reported on the ultrafast dynamics of the drugs (8 E )-8-[hydroxy-(pyridin-2-ylamino)methylidene]-9-methyl-10,10-dioxo-10λ 6 -thia-9-azabicyclo[4.4.0]deca-1,3,5-trien-7-one (piroxicam) and 1,6-dihydro-2-methyl-6-oxo-(3,4′-bipyridine)-5-carbonitrile (milrinone) in water solutions and in caging media. ,, The observed ultrafast dynamics was explained in terms of hydrogen bonding interactions with the medium, intramolecular charge-transfer and twisting motion in the excited drug, and the confinement effect of the nanocages in the above processes.…”

Section: Introductionmentioning

confidence: 99%

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Exploring the Ground and Excited States Structural Diversity of Levosimendan, a Cardiovascular Calcium Sensitizer

et al. 2010

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Exploring the relationship between the structure and dynamics of a molecular system is fundamental to a better understanding of its function. Here, we report on studies of femtosecond dynamics of the most stable molecular structures of a cardiovascular drug, levosimendan (LSM), in water at three different pHs, in chemical (β-cyclodextrin, β-CD) and biological (human serum albumin protein, HSA) nanocavities, and in two organic solvents with different viscosities. In the used organic solvents, the structural dynamics, ranging from 50 fs to 3 ps, depends on the viscosity of the solvent, reflecting the involvement of a twisting motion in the excited molecule. In water solutions at pH 3 and 5, the excited neutral form is decaying in a time of ∼0.4 ps, undergoing an ultrafast (<50 fs) intramolecular charge transfer (ICT) to generate charge transfer species decaying in ∼1 ps. In neutral (pH 7) and alkaline water (pH 12), the LSM is present in its anion structure at the ground state. In these media, the experiments reveal, in addition to the ultrafast decay of the anionic structure (1.3 ps), the formation of an ICT state having (n, π*) character, produced in ∼0.3 ps and decaying in ∼0.5 ps. Encapsulation by β-CD and HSA protein leads to a 1:1 stoichiometry complex, which shows longer decaying times (4 and 7 ps, respectively) of the caged anionic forms due to the nanoconfinement. Our results show a structural diversity of the LSM dynamics, reflecting its intimate interaction with its surrounding. We believe that the reported findings and the related discussion and conclusions bring new knowledge for a better understanding of the molecular activity of this drug, taking into account its rich structural dynamics. Furthermore, the results might be relevant for a better drug design and nanodelivery involving CDs and proteins.

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Plasmid DNA‐Based Bioluminescence‐Activated System for Photodynamic Therapy in Cancer Treatment

Fan

Wang

et al. 2021

ChemMedChem

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The low depth of tissue penetration by therapeutic light sources severely restricts photodynamic therapy (PDT) in treating deep‐seated tumors. Using a luciferase/d‐luciferin bioluminescence system to artificially create internal light sources in cells instead of external light sources is an effective means of solving the above problems. However, high‐efficiency bioluminescence requires a higher concentration of luciferase in the cell, which poses a considerable challenge to the existing system of enzyme loading, delivery, activity and retention of drugs, and dramatically increases the cost of treatment. We loaded the substrate D‐luciferin, and the photosensitizer hypericin into a polyethyleneimine (PEI)‐modified nano‐calcium phosphate (CaP) to solve this problem. Subsequently, the plasmid DNA containing the luciferase gene was loaded onto it using the high‐density positive charge characteristic of PEI from the nanodrug (denoted DHDC). After the DHDC enters the tumor cell, it collapses and releases the plasmid DNA, which uses the intracellular protein synthesis system to continuously and massively express luciferase. Using endogenous ATP, Mg2+, and O2 in cells, luciferase oxidizes d‐luciferin and produces luminescence. The luminescence triggers hypericin excitation to generate ROS and kill cancer cells. This study provides a new strategy for the application of bioluminescence in PDT treatment.

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Toward the Molecular Flashlight: Preparation, Properties, and Photophysics of a Hypericin–luciferin Tethered Molecule¶

Cited by 10 publications

References 24 publications

Maristentorin, a Novel Pigment from the Positively Phototactic Marine CiliateMaristentordinoferus, Is Structurally Related to Hypericin and Stentorin

Maristentorin, a Novel Pigment from the Positively Phototactic Marine CiliateMaristentordinoferus, Is Structurally Related to Hypericin and Stentorin

Exploring the Ground and Excited States Structural Diversity of Levosimendan, a Cardiovascular Calcium Sensitizer

Plasmid DNA‐Based Bioluminescence‐Activated System for Photodynamic Therapy in Cancer Treatment

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