Development of a novel carboplatin like cytoplasmic trackable near infrared fluorophore conjugate via strain-promoted azide alkyne cycloaddition

Kitteringham, Eolann; Wu, Dan; Cheung, Shane; Twamley, Brendan; O’Shea, Donal F.; Griffith, Darren M.

doi:10.1016/j.jinorgbio.2018.02.010

Cited by 11 publications

(6 citation statements)

References 31 publications

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“…(2-(4-(estradiol)-1H-1,2,3-triazol-1-yl)propane-1,3-diamine) dihydrochloride 2 was synthesised in two steps, Scheme 1, in line with previous reports [21][22][23].…”

Section: Synthesis Of 2-(4-(estradiol)-1h-123-triazol-1-yl)propane-mentioning

confidence: 82%

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Synthesis, characterisation and in vitro antitumour potential of novel Pt(II) estrogen linked complexes

Kitteringham

Andriollo

Gandin

et al. 2019

Inorganica Chimica Acta

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The Cu(I) alkyne azide click reaction of 17α-ethynylestradiol and di-tert-butyl (2-azidopropane-1,3-diyl)dicarbamate afforded the novel 1,4 disubstituted 1,2,3 triazole and estrogen-based ligand 2-(4-(estradiol)-1H-1,2,3-triazol-1-yl)propane-1,3-diamine, EDiolDap. Reaction of EDiolDap with Pt(II) DMSO precursors, cis-[PtCl 2 (DMSO) 2 ] and cis-[Pt(CBDCA)(DMSO) 2 ] gave the corresponding Pt(II) estrogen linked complexes [PtCl 2 (EDiolDap)] and [Pt(CBDCA)(EDiolDap)] respectively in good yield. Both Pt(II) estrogen linked complexes exhibited superior activity as compared to cisplatin and carboplatin in 2D culture and exhibited ca. 30 fold higher activity, in terms of IC 50 values, against ER+ cancer cells (cervical, breast and ovarian) as compared to the reference ER− colon cancer line. [PtCl 2 (EDiolDap)] and [Pt(CBDCA)(EDiolDap)] retained their anti-tumour activity in an ovarian 3D spheroid culture model and reduced the viability of ovarian cancer cell spheroids ca. 9fold and 5-fold better, respectively, as compared to cisplatin.

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“…(2-(4-(estradiol)-1H-1,2,3-triazol-1-yl)propane-1,3-diamine) dihydrochloride 2 was synthesised in two steps, Scheme 1, in line with previous reports [21][22][23].…”

Section: Synthesis Of 2-(4-(estradiol)-1h-123-triazol-1-yl)propane-mentioning

confidence: 82%

“…We are interested in the functionalisation of Pt based complexes [19,20] and more recently in the development of click-based conjugation strategies [21,22]. The Cu(I) catalysed azide-alkyne cycloaddition (CuAAC), Fig.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterisation and in vitro antitumour potential of novel Pt(II) estrogen linked complexes

Kitteringham

Andriollo

Gandin

et al. 2019

Inorganica Chimica Acta

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“…Selected bond lengths and bond angles around the Pt(II) center can be seen in Tables and , respectively. The metal-centered Pt–N (2.033 and 2.027 Å) and Pt–O (2.020 and 2.024 Å) bond lengths are similar and comparable to the few literature examples of N-donor Pt(CBDCA) (CBDCA = 1,1-cyclobutanedicarboxylic acid) complexes. − In 4 , the chelate amino groups form intramolecular hydrogen bonds with the N atoms of the NMe 2 groups, N15···N23 [ d (D···A) = 2.925(5) Å], as seen in complexes 2 and 3 .…”

Section: Resultsmentioning

confidence: 99%

Ni(II), Pd(II), and Pt(II) Complexes of the Hedgehog Pathway Inhibitor GANT61-D

et al. 2019

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GANT61-D is an important hedgehog pathway inhibitor and an interesting ligand candidate for metal coordination. The first examples of metal complexes of the potent hedgehog pathway inhibitor GANT61-D are described. The reaction of Ni(II), Pd(II), and Pt(II) precursors with the hedgehog pathway inhibitor GANT61-D gave [NiII(GANT61-D)(OH2)3(μ2-SO4)(μ3-SO4)] (1), [PdII(Cl)(GANT61-D)]Cl (2), [PtII(Cl)(GANT61-D)]Cl, and [PtII(CBDCA–2H)(GANT61-D)]. X-ray crystal structure analysis revealed that GANT61-D is a versatile N-donor ligand that can act as a bidentate ligand via the diaminopropane (DAP) N atoms or a tridentate ligand via the DAP N atoms and one dimethylaniline N atom. Protonation constants of the GANT61-D ligand in water and in a 60:40 (w/w) dimethyl sulfoxide–water solvent mixture were determined. Potentiometric and spectroscopic data on the NiII(GANT61-D) system indicate the formation of octahedral 1:1 species with medium stability in solution. 1 and 2 exhibited noteworthy in vitro cytotoxicity against medulloblastoma cancer cells.

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“…Eolann Kitteringham and colleagues synthesized non-toxic carboplatin-like NIR-fluorophore conjugate 13 from cis-[Pt(2-azidopropane-1,3-diamine)(cbdca)] and bicyclo[6.1.0]non-4-yne BF 2 -azadipyrromethene fluorophore (Scheme 8) [13]. The band maxima positions in the absorption and fluorescence spectra of compound 13 are at 695 nm (ε = 64,000 M −1 cm −1 ) and 720 nm (Φ F 0.11) in H 2 O/1% SDS.…”

Section: Bodipy Conjugates With Platinum Drugsmentioning

confidence: 99%

BODIPY Conjugates as Functional Compounds for Medical Diagnostics and Treatment

et al. 2022

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Fluorescent dyes absorbing and emitting in the visible and near-IR regions are promising for the development of fluorescent probes for labeling and bio-visualization of body cells. The ability to absorb and emit in the long-wavelength region increases the efficiency of recording the spectral signals of the probes due to the higher permeability of the skin layers. Compared to other fluorescent dyes, BODIPYs are attractive due to their excellent photophysical properties–narrow absorption and emission, intense fluorescence, simple signal modulation for the practical applications. As part of conjugates with biomolecules, BODIPY could act as a biomarker, but as therapeutic agent, which allows solving several problems at once-labeling or bioimaging and treatment based on the suppression of pathogenic microflora and cancer cells, which provides a huge potential for practical application of BODIPY conjugates in medicine. The review is devoted to the discussion of the recent, promising directions of BODIPY application in the field of conjugation with biomolecules. The first direction is associated with the development of BODIPY conjugates with drugs, including compounds of platinum, paclitaxel, chlorambucil, isoxazole, capsaicin, etc. The second direction is devoted to the labeling of vitamins, hormones, lipids, and other biomolecules to control the processes of their transport, localization in target cells, and metabolism. Within the framework of the third direction, the problem of obtaining functional optically active materials by conjugating BODIPY with other colored and fluorescent particles, in particular, phthalocyanines, is being solved.

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Development of a novel carboplatin like cytoplasmic trackable near infrared fluorophore conjugate via strain-promoted azide alkyne cycloaddition

Cited by 11 publications

References 31 publications

Synthesis, characterisation and in vitro antitumour potential of novel Pt(II) estrogen linked complexes

Synthesis, characterisation and in vitro antitumour potential of novel Pt(II) estrogen linked complexes

Ni(II), Pd(II), and Pt(II) Complexes of the Hedgehog Pathway Inhibitor GANT61-D

BODIPY Conjugates as Functional Compounds for Medical Diagnostics and Treatment

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