Spectroscopic Studies on Photoinduced Reactions of the Anticancer Prodrug, trans,trans,trans‐[Pt(N3)2(OH)2(py)2]

Vernooij, Robbin R.; Joshi, Tanmaya; Horbury, Michael D.; Graham, Bim; Izgorodina, Ekaterina I.; Stavros, Vasilios G.; Sadler, Peter J.; Spiccia, Leone; Wood, Bayden R.

doi:10.1002/chem.201705349

Cited by 32 publications

(20 citation statements)

References 57 publications

(38 reference statements)

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“…was detected as an intermediate, implying release of at least one hydroxyl radical and one azidyl radical or two hydroxyl radicals during the photoreduction. 98 No pyridine release was detected by 1 H NMR, in contrast to NH 3 complexes, and might contribute to its higher potency. 81…”

Section: Photodecomposition Pathwaysmentioning

confidence: 95%

“…97 Both mono-and bis-GMP adducts (trans-[Pt(N 3 ) (Py) 2 (5′-GMP)] + and trans-[Pt(Py) 2 (5′-GMP) 2 ] 2+ ) were detected as photoproducts of 13 and 5′-GMP by NMR, LC-MS and ATR-FTIR spectra. 81,98 DNA platination photoinduced by 1 with r b = 0.01 (r b = Pt coordinated per nucleotide residue) gave a preference for GG sequences, forming bifunctional GG adducts, which is similar to cisplatin. 101 Intriguingly, photoactivated 1 and 2 formed GG adducts more rapidly than cisplatin.…”

Section: Photoreactions With Important Biomoleculesmentioning

confidence: 97%

“…97 Comprehensive spectroscopic studies of the photodecomposition of the most promising diazido Pt(IV) complex 13 have been performed by Attenuated Total Reflection Fourier Transform Infrared (ATR-FTIR) and NMR. 81,98 ATR-FTIR revealed the binding of water to platinum in the final product, which was assigned as trans-…”

Section: Photodecomposition Pathwaysmentioning

confidence: 99%

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Diazido platinum(iv) complexes for photoactivated anticancer chemotherapy

Shi

Imberti

Sadler

2019

Inorg. Chem. Front.

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103

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Section: Photodecomposition Pathwaysmentioning

confidence: 95%

Section: Photoreactions With Important Biomoleculesmentioning

confidence: 97%

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Diazido platinum(iv) complexes for photoactivated anticancer chemotherapy

Shi

Imberti

Sadler

2019

Inorg. Chem. Front.

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103

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“…The complexes [Pt (dppf)(N 3 ) 2 ] (dppf = 1,10‐bis (diphenylphosphino)ferrocene), [Pt (bpy)(N 3 ) 2 ] (bpy = 2,2′‐bipyridine), and [Pt (phen)(N 3 ) 2 ] (phen = 1,10‐phenanthroline) are examples for this category. So far, there are a few reports on the photophysical properties of Pt (IV) or Pt (II) azido complexes in the literature . In this regard, we have very recently reported the first C^N cycloplatinated (II) complex containing azide and triphenyl phosphine (PPh 3 ) ligands in which C^N is a double rollover orthometalated bpy ligand .…”

Section: Introductionmentioning

confidence: 99%

Luminescent mononuclear and dinuclear cycloplatinated (II) complexes comprising azide and phosphine ancillary ligands

Nikahd

Aghakhanpour

Nabavizadeh

et al. 2019

Applied Organom Chemis

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A new series of cycloplatinated (II) complexes with general formulas of [Pt (bhq)(N 3 )(P)] [bhq = deprotonated 7,8-benzo[h]quinoline, P = triphenyl phosphine (PPh 3 ) and methyldiphenyl phosphine], [Pt (bhq)(P^P)]N 3 [P^P = 1,1-bis (diphenylphosphino)methane (dppm) and 1,2-bis (diphenylphosphino)ethane] and [Pt 2 (bhq) 2 (μ-P^P)(N 3 ) 2 ] [P^P = dppm and 1,2-bis (diphenylphosphino) acetylene] is reported in this investigation. A combination of azide (N 3 − ) and phosphine (monodentate and bidentate) was used as ancillary ligands to study their influences on the chromophoric cyclometalated ligand. All complexes were characterized by nuclear magnetic resonance spectroscopy. To confirm the presence of the N 3 − ligand directly connected to the platinum center, complex [Pt (bhq)(N 3 )(PPh 3 )] was further characterized by single-crystal X-ray crystallography. The photophysical properties of the new products were studied by UV-Vis spectroscopy in CH 2 Cl 2 and photoluminescence spectroscopy in solid state (298 or 77 K) and in solution (77 K). Using density functional theory calculations, it was proved that, in addition to intraligand chargetransfer (ILCT) and metal-to-ligand charge-transfer (MLCT) transitions, the L ′LCT (L′ = N 3 , L = C^N) electronic transition has a remarkable contribution in low energy bands of the absorption spectra (for complexes [Pt (bhq)(N 3 ) (P)] and [Pt 2 (bhq) 2 (μ-P^P)(N 3 ) 2 ]). It is indicative of the determining role of the N 3 − ligand in electronic transitions of these complexes, specifically in the low energy region. In this regard, the photoluminescence studies indicated that the emissions in such complexes originate from a mixed 3 ILCT/ 3 MLCT (intramolecular) and also from aggregations (intermolecular). /journal/aoc 1 of 12 3 J PtH ≈ 50 Hz, 2 J PH = 21 Hz, 2H, CH 2 of dppm]; aromatic protons: 8.55 [d, 3 J HH = 8.0 Hz, 1H, H 9 of bhq]; 8.67 [t, 3 J HH ≈ 4 J PH = 3.7 Hz, 3 J PtH ≈ 23 Hz, 1 H, H 2 of bhq]; other aromatic protons: 6.8-8.4 ppm; δ ( 31 P) = 35.59 [d, 2 J PP = 42 Hz, 1 J PtP = 3364 Hz, P of dppm]; 21.78 [d, 2 J PP = 42 Hz, 3 J PtP = 1446 Hz, P of dppm].[Pt (bhq)(dppe)]N 3 , 5bDppe (40 mg, 0.1 mmol) was added to a solution of 3 (48 mg, 0.1 mmol) in acetone (20 mL). The mixture was NIKAHD ET AL. 9 of 12

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“…These results were similar to those obtained for 1, suggesting a negligible effect of axial substituents on the photoreaction with guanine. 38 DNA melting experiments monitored by UV-vis were carried out in phosphate buffer (1 mM, pH = 7.9) to investigate DNA binding with a drug/base pair ratio of 0.2 (Table S1, ESI †). Similar to parent complex 1, 2a and 2b interact with ct-DNA only weakly (DT m o 2 K) in the dark, while upon irradiation with blue light (420 nm) an apparent interaction was observed (DT m ca.…”

mentioning

confidence: 99%