Linker chemistry dictates the delivery of a phototoxic organometallic rhenium(<scp>i</scp>) complex to human cervical cancer cells from core crosslinked star polymer nanoparticles

Yu, Sul Hwa; Ferrari, Stefano; Garcia, Paulina Ramirez; Veldhuis, Nicholas A.; Kaminskas, Lisa M.; Graham, Bim; Quinn, John F.; Whittaker, Michael R.; Gasser, Gilles; Davis, Thomas P.

doi:10.1039/c8tb02464b

Cited by 11 publications

(14 citation statements)

References 45 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…No-carrier-added fluorine-18 ( 18 F) was produced via an 18 O(p,n) 18 F nuclear reaction by bombarding enriched H 2 [ 18 O]O with 16.5-MeV protons using a GE PETtrace 880 cyclotron at MSKCC (New York, USA). Zirconium-89 ( 89 Zr) was produced via proton beam bombardment of yttrium foil and isolated as high purity [ 89 Zr]Zr-oxalate [34].…”

Section: Methodsmentioning

confidence: 99%

“…Radiochemical yields were calculated based on the decay-corrected radioactivity balance from the addition of the radioactivity to the reaction vial until completion of the synthesis. Radioactive samples were counted using a 2480 Wizard 2 automatic gamma counter (1 minute per measurement; 350-1300 keV for 18 F, 800-1000 keV for 89 Zr).…”

Section: Characterizationsmentioning

confidence: 99%

“…[ 18 F]F-Tz-PEG 11 -NODA and [ 18 F]F-Tz-NODA were produced and characterized according to protocols described previously [28]. Briefly, no-carrier-added 18 F was trapped on a preconditioned anion exchange cartridge (QMA sep-pak, Waters) and eluted with 0.4 M KHCO 3 . Metal-free glacial acetic acid was used to adjust the pH to 3.5-4, before adding a 2 mM AlCl 3 solution in 0.1 M NaOAc buffer (pH 4).…”

Section: Radiolabeling Of Tetrazines With 18 Fmentioning

confidence: 99%

“…Total image volumes were cropped into individual image volumes using the Inveon Research Workspace software (Siemens Medical Solutions, Knoxville, USA). Counting rates in the reconstructed images were converted into activity concentrations (%ID/g) using a system calibration factor, derived from a mouse-sized waterequivalent phantom containing 18 F. Open source 3D Slicer software (v4.8.1) was used for further image processing. Three-dimensional volumes of interest (VOIs) were defined through semi-automatic segmentation techniques and activity concentrations were quantified by selecting the maximal uptake value per VOI.…”

Section: Small-animal Positron Emission Tomography (Pet) Imagingmentioning

confidence: 99%

“…We have recently demonstrated that polymeric nanostars can be used for effective passive delivery of cytotoxic compounds to cancer cells [17,18]. Nanostars, or star polymers, consist of linear polymer arms that are cross-linked at one end to form the core of the macromolecule.…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

Design and preclinical evaluation of nanostars for the passive pretargeting of tumor tissue

Goos

Davydova

Dilling

et al. 2020

Nuclear Medicine and Biology

Self Cite

View full text Add to dashboard Cite

show abstract

Section: Methodsmentioning

confidence: 99%

Section: Characterizationsmentioning

confidence: 99%

Section: Radiolabeling Of Tetrazines With 18 Fmentioning

confidence: 99%

Section: Small-animal Positron Emission Tomography (Pet) Imagingmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Design and preclinical evaluation of nanostars for the passive pretargeting of tumor tissue

Goos

Davydova

Dilling

et al. 2020

Nuclear Medicine and Biology

Self Cite

View full text Add to dashboard Cite

show abstract

Photodynamic therapy applications of Re(I)‐BODIPY functionalized nanoparticles

Tyagi

Kaur

Sahoo³

et al. 2021

Applied Organom Chemis

View full text Add to dashboard Cite

Organometallic Re(I)‐BODIPY compounds have recently received attention as metal‐based photosensitizers for photodynamic therapy (PDT) applications owing to their strong absorption in the visible region. We synthesized and characterized an organometallic [ReI(L)2(CO)3Br] (ReL) complex containing a BODIPY ligand (L) and prepared nanoparticles of the ligand (NPL) as well as the complex (NPReL). The formation of nanoparticles was confirmed by dynamic light scattering (DLS), atomic force microscopy (AFM), transmission electron microscopy (TEM), and energy dispersive X‐ray (EDX) analyses. Single‐crystal structure of ReL showed octahedral environment around Re center, and the BODIPY chromophore was placed at distances of around 12 Å. Detailed photophysical properties of ReL were investigated which showed strong visible absorption at 551 nm (ε = 1.46 × 105 M−1 cm−1) owing to π‐conjugation of BODIPY with the metal center Re(I). Efficient intersystem crossing (ISC) and formation of triplet‐excited states with lifetimes of 0.80 and 0.65 μs for L and ReL, respectively, were confirmed through nanosecond‐laser flash photolysis and density functional theory (DFT) calculations. The photosensitization efficiency of ReL was observed to be ϕΔ = 0.77. In vitro biological studies of NPReL showed negligible toxicity and reactive oxygen species (ROS) generation in the dark as compared with NPL despite the good photosensitization ability of NPL. Therefore, NPReL showed coordination‐enhanced cytotoxicity under irradiation conditions and interestingly found to be nontoxic to normal NIH3T3 cell lines in comparison with L. Flow cytometry studies further indicated that the major cause of cell death by NPReL was via apoptotic pathways (54%), which authenticates its potential as a PDT agent.

show abstract

Photostimulated Anticancer Activity of Mitochondria Localized Rhenium(I) Tricarbonyl Complexes Bearing 1H‐imidazo[4,5‐f][1,10]phenanthroline Ligands Against MDA‐MB‐231 Cancer Cells

Kar,

Paira

2024

Chemistry A European J

View full text Add to dashboard Cite

We have introduced Re(I) tricarbonyl complexes (ReL1 ‐ ReL6) [Re(CO)3(N^N)Cl] where N^N = extensive π conjugated imidazo‐[4,5‐f]1,10‐phenanthroline derivatives that helps in strong DNA intercalation, enhanced photophysical behavior, increase the 3π‐π* character of T1 state for PDT and high value of lipophilicity for cell membrane penetration. These complexes exhibited prominent intraligand/ligand‐centered (π ‐ π*/ 1LC) absorption bands at λ 260 ‐ 350 nm and relatively weak metal‐to‐ligand charge‐transfer (1MLCT) bands within the λ 350 ‐ 550 nm range. Among the six synthesized complexes, [(CO)3ReICl(K2‐N,N‐2‐(4‐(1‐benzyl‐1H‐tetrazol‐5‐yl)phenyl)‐1H‐imidazo[4,5‐f][1,10]phenanthroline] (ReL6) exhibited outstanding potency (IC50 ~ 6 µM, PI > 9) under yellow light irradiation compared to dark conditions. Importantly, extremely lipophilic complex ReL6 showed effective penetration through the cell membrane and localized primarily in mitochondria (Pearson’s correlation coefficient, PCC = 0.918) of MDA‐MB‐231 cells. Complex ReL6 exhibited more than 9 times higher photo‐toxicity in normoxic and hypoxic environment of tumor by inducing 1O2 generation (type II PDT), radical generation triggered by NADH oxidation (type I PDT). This complex is a promising candidate for TNBC treatment in hypoxic tumors, with efficacy comparable to photofrin and have demonstrated CO release ability under UV light irradiation.

show abstract

Linker chemistry dictates the delivery of a phototoxic organometallic rhenium(i) complex to human cervical cancer cells from core crosslinked star polymer nanoparticles

Abstract: Release of a photoactive Re(i) complex from a polymer star via ketimine linkages gives improved phototoxicity.

Cited by 11 publications

References 45 publications

Design and preclinical evaluation of nanostars for the passive pretargeting of tumor tissue

Design and preclinical evaluation of nanostars for the passive pretargeting of tumor tissue

Photodynamic therapy applications of Re(I)‐BODIPY functionalized nanoparticles

Photostimulated Anticancer Activity of Mitochondria Localized Rhenium(I) Tricarbonyl Complexes Bearing 1H‐imidazo[4,5‐f][1,10]phenanthroline Ligands Against MDA‐MB‐231 Cancer Cells

Contact Info

Product

Resources

About