Luminescent lanthanide complexes with a pyridine-bis(carboxamide)-bithiophene sensitizer showing wavelength-dependent singlet oxygen generation

Johnson, Katie N.; Vittardi, Sebastian B.; Gracia-Nava, Manuel A.; Rack, Jeffrey J.; Bettencourt‐Dias, Ana de

doi:10.1039/d0dt01034k

Cited by 10 publications

(5 citation statements)

References 72 publications

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“…Again, the Er III emission efficiency was not quantifiable. The emission efficiencies obtained for the Nd III and Yb III complexes are of the same order of magnitude as values reported for other complexes of these ions …”

Section: Resultssupporting

confidence: 82%

“…The φ 1O2 values are 11 % for [Yb(3Tcbx) 2 ] 3+ and [Nd(3Tcbx) 2 ] 3+ and 13 % for [Er(3Tcbx) 2 ] 3+ (Table ). The largest φ 1O2 is 62 % for the Gd III complex, indicating that coordinating luminescent Ln III (Nd III , Yb III , or Er III ) to 3Tcbx decreases φ 1O2 owing to sensitization of Ln III luminescence, as expected, and as observed in other Ln III complexes that display both properties . Nonetheless, the values of φ 1O2 are comparable to values for known photosensitizers such as the ones indicated above.…”

Section: Resultssupporting

confidence: 74%

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Wavelength‐Dependent Singlet Oxygen Generation in Luminescent Lanthanide Complexes with a Pyridine‐Bis(Carboxamide)‐Terthiophene Sensitizer

Johnson

Vittardi

Gracia-Nava

et al. 2020

Chemistry A European J

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Lanthanide ion (LnIII) complexes, [Ln(3Tcbx)2]3+ (LnIII=YbIII, NdIII, ErIII) are isolated with a new pyridine‐bis(carboxamide)‐based ligand with a 2,2′:5′,2′′‐terthiophene pendant (3TCbx), and their resulting photophysical properties are explored. Upon excitation of the complexes at 490 nm, only LnIII emission is observed with efficiencies of 0.29 % at 976 nm for LnIII=YbIII and 0.16 % at 1053 nm for LnIII=NdIII. ErIII emission is observed but weak. Upon excitation at 400 nm, concurrent 1O2 formation is seen, with efficiencies of 11 % for the YbIII and NdIII complexes and 13 % for the ErIII complex. Owing to the concurrent generation of 1O2, as expected, the efficiency of metal‐centered emission decreases to 0.02 % for YbIII and 0.05 % for NdIII. The ability to control 1O2 generation through the excitation wavelength indicates that the incorporation of 2,2′:5′,2′′‐terthiophene results in access to multiple sensitization pathways. These energy pathways are unraveled through transient absorption spectroscopy.

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Section: Resultssupporting

confidence: 82%

Section: Resultssupporting

confidence: 74%

Wavelength‐Dependent Singlet Oxygen Generation in Luminescent Lanthanide Complexes with a Pyridine‐Bis(Carboxamide)‐Terthiophene Sensitizer

Johnson

Vittardi

Gracia-Nava

et al. 2020

Chemistry A European J

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“…These complexes are not water-soluble and are thus not viable for imaging and therapy applications in biological systems. More recently, we described a family of oligothiophene-based sensitizers of Ln III emission, which show wavelength-dependent 1 O 2 generation , but are also not water-soluble. Another series of oligothiophene-based ligands that were water-soluble were studied for their cytotoxicity toward HeLa cells .…”

Section: Introductionmentioning

confidence: 99%

“…Oligothiophenes are naturally occurring plant pigments known for their ability to generate 1 O 2 with high . Because of this property, oligothiophenes and thienyl-derivatized compounds are reported to have applications as antiviral, anticancer, and antifungal agents. − Thus, thiophene-based functional groups are promising because of their ability to enhance ISC , and efficiently generate 1 O 2 and of their interesting photophysical properties. ,,− …”

Section: Introductionmentioning

confidence: 99%

Photocytotoxicity of Thiophene- and Bithiophene-Dipicolinato Luminescent Lanthanide Complexes

et al. 2021

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New thiophene-dipicolinato-based compounds, K 2 nTdpa (n = 1, 2), were isolated. Their anions are sensitizers of lanthanide ion (Ln III ) luminescence and singlet oxygen generation ( 1 O 2 ). Emission in the visible and near-infrared regions was observed for the Ln III complexes with efficiencies (ϕ Ln ) ϕ Eu = 33% and ϕ Yb = 0.31% for 1Tdpa 2− and ϕ Yb = 0.07% for 2Tdpa 2− . The latter does not sensitize Eu III emission. Fluorescence imaging of HeLa live cells incubated with K 3 [Eu(1Tdpa) 3 ] indicates that the complex permeates the cell membrane and localizes in the mitochondria. All complexes generate 1 O 2 in solution with efficiencies (ϕ O 1 2 ) as high as 13 and 23% for the Gd III complexes of 1Tdpa 2− and 2Tdpa 2− , respectively. [Ln(nTdpa) 3 ] 3− (n = 1, 2) are phototoxic to HeLa cells when irradiated with UV light with IC 50 values as low as 4.2 μM for [Gd(2Tdpa) 3 ] 3− and 91.8 μM for [Eu(1Tdpa) 3 ] 3− . Flow cytometric analyses indicate both apoptotic and necrotic cell death pathways.

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“…While pursuing luminescent lanthanide complexes, which are also able to generate SO for theranostics applications, − we isolated a naphthalimide-based molecule, Nap-cbx, and its gadolinium complex, [Gd(Nap-cbx) 3 ](NO 3 ) 3 (Scheme ). The insolubility of these two compounds in water precluded their screening as imaging and therapy agents.…”

Section: Introductionmentioning

confidence: 99%

Degradation of Model Compounds by ¹O₂-Generating Photosensitizer–Doped Membranes

Fredericks

Bettencourt‐Dias

2023

ACS EST Water

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We report the synthesis, performance, and stability of photosensitizer-doped membranes and their ability to generate singlet oxygen and degrade a model pharmaceutical. Specifically, we doped Clear Flex 50, a polyurethane rubber, with either terthiophene (3T) or one of two 1,8-naphthalimide-based (Napcbx and its gadolinium complex [Gd(Nap-cbx) 3 (NO 3 ) 3 )] photosensitizers and photodegraded propranolol. After irradiating for 24 h with visible light in the presence of the 3T-doped membrane, the decreased emission intensity of propranolol was consistent with 42% degradation, while irradiation with UV light in the presence of a membrane doped with either Nap-cbx or [Gd(Nap-cbx) 3 ]-(NO 3 ) 3 led to 36 and 41% degradation, respectively. Additionally, the three doped membranes successfully degraded several organic pollutants present in the standard MegaMix. Our findings show that the singlet oxygen-generating membranes experience minimal loss in performance after three 24-hour irradiation cycles.

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Luminescent lanthanide complexes with a pyridine-bis(carboxamide)-bithiophene sensitizer showing wavelength-dependent singlet oxygen generation

Abstract: A new pyridine-bis(carboxamide)-based ligand with a bithiophene pendant, 2Tcbx, was synthesized.

Cited by 10 publications

References 72 publications

Wavelength‐Dependent Singlet Oxygen Generation in Luminescent Lanthanide Complexes with a Pyridine‐Bis(Carboxamide)‐Terthiophene Sensitizer

Wavelength‐Dependent Singlet Oxygen Generation in Luminescent Lanthanide Complexes with a Pyridine‐Bis(Carboxamide)‐Terthiophene Sensitizer

Photocytotoxicity of Thiophene- and Bithiophene-Dipicolinato Luminescent Lanthanide Complexes

Degradation of Model Compounds by ¹O₂-Generating Photosensitizer–Doped Membranes

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Luminescent lanthanide complexes with a pyridine-bis(carboxamide)-bithiophene sensitizer showing wavelength-dependent singlet oxygen generation

Abstract: A new pyridine-bis(carboxamide)-based ligand with a bithiophene pendant, 2Tcbx, was synthesized.

Cited by 10 publications

References 72 publications

Wavelength‐Dependent Singlet Oxygen Generation in Luminescent Lanthanide Complexes with a Pyridine‐Bis(Carboxamide)‐Terthiophene Sensitizer

Wavelength‐Dependent Singlet Oxygen Generation in Luminescent Lanthanide Complexes with a Pyridine‐Bis(Carboxamide)‐Terthiophene Sensitizer

Photocytotoxicity of Thiophene- and Bithiophene-Dipicolinato Luminescent Lanthanide Complexes

Degradation of Model Compounds by 1O2-Generating Photosensitizer–Doped Membranes

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Degradation of Model Compounds by ¹O₂-Generating Photosensitizer–Doped Membranes