Characterization of a NIR absorbing thienyl curcumin contrast agent for photoacoustic imaging

Bellinger, Stephanie; Hatamimoslehabadi, Maryam; Borg, Raymond E; La, Jeffrey; Catsoulis, Peter; Mithila, Farha; Yelleswarapu, Chandra S.; Rochford, Jonathan

doi:10.1039/c8cc03727b

Cited by 22 publications

(14 citation statements)

References 35 publications

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“…[ 16 ] To date, FDA‐approved indocyanine green (ICG) is widely studied as (off‐label) PA probe, despite its low PA‐signal and short blood half‐life. [ 17 ] Other small organic chromophores, e.g., azo‐dyes, [ 18 ] (na)phthalocyanines, [ 15b,19 ] IR‐dye fluorophores, [ 15a,20 ] (aza)BODIPYs, [ 21 ] porphyrins, [ 22 ] and other dyes [ 23 ] were also explored for PAI applications. Several of the above named probes could also be used in photothermal therapy (PTT), [ 24 ] as both applications share a similar underlying principle, optical absorption to thermal conversion via nonradiative process.…”

Section: Figurementioning

confidence: 99%

Tuning Optical Properties of BODIPY Dyes by Pyrrole Conjugation for Photoacoustic Imaging

Merkes

Lammers

Kancherla

et al. 2020

Advanced Optical Materials

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Photoacoustic imaging (PAI) is increasingly employed in (pre‐) clinical research, thus, development of suitable contrast agents, in particular fluorescence‐quenched chromophores, for PAI is of high importance. Small molecule dyes are appropriate due to favorable circulation, excretion properties, and ease of conjugation to targeting moieties. The BODIPY chromophores have been widely used in bioimaging, yet they are not ideal for PAI due to high fluorescence. Hence, here nonfluorescent BODIPY are designed by 1H‐pyrrole conjugation (PyBODIPY) to apply as probes for PAI. The PyBODIPYs exhibit absorption maxima up to 800 nm, and PA signal could be detected in concentrations of 1 nmol mL−1 and 35 pmol mm−3, by tube and tissue phantom, respectively. In addition to nonfluorescent, PyBODIPYs are non‐phototoxic, photostable, and show high molar extinction coefficients, as well as inertness toward nucleophilic addition. PyBODIPYs are modified with PEG‐400, to improve aqueous solubility and to enable in vivo imaging. Thus, PyBODIPY is an attractive small molecule to use as PA contrast agent, which could be coupled to targeting ligands for in vivo use. In addition, 1H‐pyrrole conjugation might be applied to the design of novel near‐infrared ranged quenchers suitable for PAI, and promote the development of probes for clinical translation.

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Section: Figurementioning

confidence: 99%

Tuning Optical Properties of BODIPY Dyes by Pyrrole Conjugation for Photoacoustic Imaging

Merkes

Lammers

Kancherla

et al. 2020

Advanced Optical Materials

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“…ACS reagent grade toluene, tetrahydrofuran, dichloromethane and hexane for synthesis were purchased from Pharmco Aaper. 1 , 2 , DMA‐2 , DMA‐3 , 4 and DMA‐4 have been previously reported . 3 , 5 and DMA‐5 were prepared using a previously reported standard procedure from the commercially available 5‐dimethylamino‐thiophene‐2‐carbaldehyde, and the prepared 5‐ald and DMA‐5‐ald , respectively.…”

Section: Methodsmentioning

confidence: 99%

“…As is discussed in detail below, DMA functionalization serves to destabilize the HOMO level of the curcuminoid dye thus decreasing their HOMO–LUMO band gap. This is responsible for shifting their absorbance toward the near NIR . In a prior study, we demonstrated that the naphth‐4‐yl substituted curcumin 4 exhibits the most impressive reverse saturable absorption and nonlinear PA emission of any curcumin dye studied to date .…”

Section: Introductionmentioning

confidence: 92%

Photophysical and Photoacoustic Properties of π‐Extended Curcumin Dyes. Effects of the Terminal Dimethylamino Electron‐donor and the Bridging Aryl Ring

Borg

Hatamimoslehabadi

Bellinger

et al. 2018

Photochem & Photobiology

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The synthesis, photophysical and photoacoustic characterization for a series of nine π-extended quadrupolar curcumin dyes is presented. A systematic evaluation of the π-bridging unit including the p-phenyl, naphth-4-yl, thien-2-yl and hybrid 4-naphthathien-2-yl groups is presented. Furthermore, evaluation of the strongly donating donor-π-acceptor-π-donor quadrupolar dimethylamino terminated derivatives is also included. Select dyes exhibit excited state absorption at increased laser fluence which translates to the production of a nonlinear enhanced photoacoustic response. In particular, the bis-4-dimethylaminonaphtha-2-thien-5-yl curcuminBF contrast agent DMA-5 exhibits an excellent molar photoacoustics (PA) emission at both low (9.4 × 10 V M ) and high (1.47 × 10 V M ) laser fluence which is confirmed by its strong contrast by photoacoustic tomography (PAT). In summary, the strong absorbance and enhanced photoacoustic properties of naphthyl and thienyl curcuminoids here presented provides great promise for future photoacoustic imaging applications as demonstrated by preliminary PAT studies.

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“…[19] Other groups also reported interesting photophysical ande lectronic properties of curcuminoids-BF 2 , [20] including charge transport in nanojunctions [21] and enhanced photoacousticr esponses. [22] Single-crystal X-ray diffraction studies have shown that curcuminoid backbones interact strongly in p-stacks. [5] The monochromophoric compound R-Me ( Figure 1) provides at ypical example of such tightly packed dye molecules in the crystal.…”

Section: Quadrupolar-like D-p-a-p-d (Or A-p-d-p-a) Chromophoresmentioning

confidence: 99%

“…Depending on the nature of the terminal electron‐donor groups, they display a broad range of optical and electronic properties in the solid state, such as near‐infrared fluorescence emission, thermally assisted delayed fluorescence, two‐photon excited fluorescence, amplified spontaneous emission, and charge separation in bulk heterojunction organic solar cells . Other groups also reported interesting photophysical and electronic properties of curcuminoids‐BF 2 , including charge transport in nanojunctions and enhanced photoacoustic responses . Single‐crystal X‐ray diffraction studies have shown that curcuminoid backbones interact strongly in π‐stacks .…”

Section: Introductionmentioning

confidence: 99%

Exciton Interactions, Excimer Formation, and [2π+2π] Photodimerization in Nonconjugated Curcuminoid‐BF₂ Dimers

Catherin

Uranga-Barandiaran

Brosseau

et al. 2020

Chemistry A European J

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We describe the synthesis of a series of covalently linked dimers of quadrupolar curcuminoid‐BF2 dyes and the detailed investigation of their solvent‐dependent spectroscopic and photophysical properties. In solvents of low polarity, intramolecular folding induces the formation of aggregated chromophores, the UV/Vis absorption spectra of which display the optical signature characteristic of weakly‐coupled H‐aggregates. The extent of folding and, in turn, of ground‐state aggregation is strongly dependent on the nature of the flexible linker. Steady‐state and time‐resolved fluorescence emission spectroscopies show that the Frenkel exciton relaxes into a fluorescent symmetrical excimer state with a long lifetime. Furthermore, our in‐depth studies show that a weakly emitting excimer lies on the pathway toward a photocyclomer. Two‐dimensional 1H NMR spectroscopy and density functional theory (DFT) allowed the structure of the photoproduct to be established. To our knowledge, this represents the first example of a [2π+2π] photodimerization of the curcuminoid chromophore.

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Characterization of a NIR absorbing thienyl curcumin contrast agent for photoacoustic imaging

Cited by 22 publications

References 35 publications

Tuning Optical Properties of BODIPY Dyes by Pyrrole Conjugation for Photoacoustic Imaging

Tuning Optical Properties of BODIPY Dyes by Pyrrole Conjugation for Photoacoustic Imaging

Photophysical and Photoacoustic Properties of π‐Extended Curcumin Dyes. Effects of the Terminal Dimethylamino Electron‐donor and the Bridging Aryl Ring

Exciton Interactions, Excimer Formation, and [2π+2π] Photodimerization in Nonconjugated Curcuminoid‐BF₂ Dimers

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Characterization of a NIR absorbing thienyl curcumin contrast agent for photoacoustic imaging

Cited by 22 publications

References 35 publications

Tuning Optical Properties of BODIPY Dyes by Pyrrole Conjugation for Photoacoustic Imaging

Tuning Optical Properties of BODIPY Dyes by Pyrrole Conjugation for Photoacoustic Imaging

Photophysical and Photoacoustic Properties of π‐Extended Curcumin Dyes. Effects of the Terminal Dimethylamino Electron‐donor and the Bridging Aryl Ring

Exciton Interactions, Excimer Formation, and [2π+2π] Photodimerization in Nonconjugated Curcuminoid‐BF2 Dimers

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Exciton Interactions, Excimer Formation, and [2π+2π] Photodimerization in Nonconjugated Curcuminoid‐BF₂ Dimers