Albert Gandioso

Chimie ParisTech

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Co-Authors

Vicente Marchán

Institut de Biomedicina de la Universitat de Barcelona

Gilles Gasser

Université Paris Sciences et Lettres

Anna Rovira

Institut de Biomedicina de la Universitat de Barcelona

Santi Nonell

Universitat Ramon Llull

Pierre Bürckel

Institut de physique du globe de Paris

Manel Bosch

Universitat de Barcelona

Anna Massaguer

University of Girona

Robin Vinck

Orano (France)

Bruno Saubaméa

Université Paris Cité

Laura Rodrı́guez

Universitat de Barcelona

Cooperative Institutions

Universitat de Barcelona

Centre National de la Recherche Scientifique

Université Paris Sciences et Lettres

Chimie ParisTech

Institute for Research in Biomedicine

FC Barcelona

Universitat Politècnica de Catalunya

Institut de Biomedicina de la Universitat de Barcelona

University of Warwick

Inserm

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A Photoactivatable Platinum(IV) Anticancer Complex Conjugated to the RNA Ligand Guanidinoneomycin

Chemistry - A European Journal (2015)

Evyenia Shaili Marta Fernández‐Giménez Savina Rodríguez‐Astor Albert Gandioso Lluís Sandín

Abstract A photoactivatable platinum(IV) complex, trans , trans , trans ‐[Pt(N 3 ) 2 (OH)(succ)(py) 2 ] (succ=succinylate, py=pyridine), has been conjugated to guanidinoneomycin to study the effect of this guanidinum‐rich compound on the photoactivation, intracellular accumulation and phototoxicity of the pro‐drug. Surprisingly, trifluoroacetic acid treatment causes the replacement of an azido ligand and the axial hydroxide ligand by trifluoroacetate, as shown by NMR spectroscopy, MS and X‐ray crystallography. Photoactivation of the platinum–guanidinoneomycin conjugate in the presence of 5′‐guanosine monophosphate (5′‐GMP) led to the formation of trans ‐[Pt(N 3 )(py) 2 (5′‐GMP)] + , as does the parent platinum(IV) complex. Binding of the platinum(II) photoproduct {PtN 3 (py) 2 } + to guanine nucleobases in a short single‐stranded oligonucleotide was also observed. Finally, cellular uptake studies showed that guanidinoneomycin conjugation improved the intracellular accumulation of the platinum(IV) pro‐drug in two cancer cell lines, particularly in SK‐MEL‐28 cells. Notably, the higher phototoxicity of the conjugate in SK‐MEL‐28 cells than in DU‐145 cells suggests a degree of selectivity towards the malignant melanoma cell line.

Conjugate

Ribonucleotide reductase

10.1002/chem.201502373

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Citations (27)

Frontispiece: Transformation of COUPY Fluorophores into a Novel Class of Visible‐Light‐Cleavable Photolabile Protecting Groups

Chemistry - A European Journal (2020)

Marta López‐Corrales Anna Rovira Albert Gandioso Manel Bosch Santi Nonell

A new class of visible-light-sensitive photolabile protecting groups based on low-molecular weight COUPY fluorophores, which expand the current photochemical toolbox, is described. Besides being efficiently photoactivated with yellow and red light under physiological-like conditions, COUPY photocages exhibit excellent cellular uptake and accumulate selectively in mitochondria, opening the door to the delivery of caged analogues of biologically active compounds into these organelles. For more details see the Communication by V. Marchán et al. on page 16222.

Organelle

Toolbox

Visible spectrum

10.1002/chem.202086964

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A ruthenium-oligonucleotide bioconjugated photosensitizing aptamer for cancer cell specific photodynamic therapy

Luke K. McKenzie Marie Flamme Patrick Felder Johannes Karges Frédéric Bonhomme

Ruthenium complexes have emerged as a promising class of compounds for use as photosensitizers (PSs) in photodynamic therapy (PDT) due to their attractive photophysical properties and relative ease of chemical alteration. While promising, they generally are not inherently targeting to disease sites and may therefore be prone to side effects and require higher doses. Aptamers are short oligonucleotides that bind specific targets with high affinity. One such aptamer is AS1411, a nucleolin targeting, G-quadruplex forming, DNA aptamer. Here we present the first example of direct conjugation of a Ru(II) polypyridyl complex-based PS to an aptamer and an assessment of its in vitro cancer cell specific photosensitization including discussion of the challenges faced.

Aptamer

Nucleolin

10.33774/chemrxiv-2021-5n9xv

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A Novel Near‐IR Absorbing Ruthenium(II) Complex as Photosensitizer for Photodynamic Therapy and its Cetuximab Bioconjugates

ChemBioChem (2023)

Marta Martínez‐Alonso Albert Gandioso Chloé Thibaudeau Xue Qin Philippe Arnoux

Abstract A novel Ru(II) cyclometalated photosensitizer (PS), Ru‐NH 2 , for photodynamic therapy (PDT) of formula [Ru(appy)(bphen) 2 ]PF 6 (where appy=4‐amino‐2‐phenylpyridine and bphen=bathophenanthroline) and its cetuximab (CTX) bioconjugates, Ru‐Mal‐CTX and Ru‐BAA‐CTX (where Mal=maleimide and BAA=benzoylacrylic acid) were synthesised and characterised. The photophysical properties of Ru‐NH 2 revealed absorption maxima around 580 nm with an absorption up to 725 nm. The generation of singlet oxygen ( 1 O 2 ) upon light irradiation was confirmed with a 1 O 2 quantum yield of 0.19 in acetonitrile. Preliminary in vitro experiments revealed the Ru‐NH 2 was nontoxic in the dark in CT‐26 and SQ20B cell lines but showed outstanding phototoxicity when irradiated, reaching interesting phototoxicity indexes (PI) >370 at 670 nm, and >150 at 740 nm for CT‐26 cells and >50 with NIR light in SQ20B cells. The antibody CTX was successfully attached to the complexes in view of the selective delivery of the PS to cancer cells. Up to four ruthenium fragments were anchored to the antibody (Ab), as confirmed by MALDI‐TOF mass spectrometry. Nonetheless, the bioconjugates were not as photoactive as the Ru‐NH 2 complex.

Phototoxicity

Bioconjugation

10.1002/cbic.202300203

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Citations (11)

Unexpected photoactivation pathways in a folate-receptor-targeted trans-diazido Pt(iv) anticancer pro-drug

Dalton Transactions (2020)

Albert Gandioso Anna Rovira Huayun Shi Peter J. Sadler Vicente Marchán

Photoactivation of a conjugate between a photoactive trans-diazido Pt(iv) pro-drug and folic acid generates different cytotoxic species, including Pt(ii) photoproducts and pterin derivatives.

Pterin

Conjugate

Folate receptor

10.1039/d0dt02577a

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Citations (8)

Structurally Simple Osmium(II) Polypyridyl Complexes as Photosensitizers for Photodynamic Therapy in the Near Infrared

A. Mani Tao Feng Albert Gandioso Robin Vinck Anna Notaro

Five osmium(II) polypyridyl complexes of the general formula [Os(4,7-diphenyl-1,10-phenanthroline)2L]2+ were synthesized as photosensitizers for photodynamic therapy by varying the nature of the ligand L. Thanks to the pronounced π-extended structure of the ligands and the heavy atom effect provided by the osmium center, these complexes exhibit a high absorption in the near infrared (NIR) region (up to 740 nm), unlike related ruthenium complexes. This led to promising phototoxicity in vitro against cancer cells cultured as 2D cell layers but also in multicellular tumor spheroids upon irradiation at 740 nm. The complex [Os(4,7-diphenyl-1,10-phenanthroline)2(2,2’-bipyridine)]2+ was found to be the most efficient against various cancer cell lines, with high phototoxicity indexes. Experiments on CT26 tumor-bearing BALB/c mice also indicate that the Os(II) complexes could significantly reduce tumor growth under 740 nm laser irradiation. The high phototoxicity in the biological window of this structurally simple complex makes it a promising photosensitizer for cancer treatment.

Phototoxicity

Osmium

10.26434/chemrxiv-2022-8gxvj

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Citations (1)

Mitochondria-Targeted COUPY Photocages: Synthesis and Visible-Light Photoactivation in Living Cells

The Journal of Organic Chemistry (2023)

Marta López‐Corrales Anna Rovira Albert Gandioso Santi Nonell Manel Bosch

Releasing bioactive molecules in specific subcellular locations from the corresponding caged precursors offers great potential in photopharmacology, especially when using biologically compatible visible light. By taking advantage of the intrinsic preference of COUPY coumarins for mitochondria and their long wavelength absorption in the visible region, we have synthesized and fully characterized a series of COUPY-caged model compounds to investigate how the structure of the coumarin caging group affects the rate and efficiency of the photolysis process. Uncaging studies using yellow (560 nm) and red light (620 nm) in phosphate-buffered saline medium have demonstrated that the incorporation of a methyl group in a position adjacent to the photocleavable bond is particularly important to fine-tune the photochemical properties of the caging group. Additionally, the use of a COUPY-caged version of the protonophore 2,4-dinitrophenol allowed us to confirm by confocal microscopy that photoactivation can occur within mitochondria of living HeLa cells upon irradiation with low doses of yellow light. The new photolabile protecting groups presented here complement the photochemical toolbox in therapeutic applications since they will facilitate the delivery of photocages of biologically active compounds into mitochondria.

Protonophore

Visible spectrum

10.1021/acs.joc.3c00387

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Citations (6)

Towards Novel Photodynamic Anticancer Agents Generating Superoxide Anion Radicals: A Cyclometalated Ir^IIIComplex Conjugated to a Far‐Red Emitting Coumarin

Angewandte Chemie International Edition (2019)

Vojtěch Novohradský Anna Rovira Cormac Hally Alex Galindo Gloria Vigueras

Abstract Although cyclometalated Ir III complexes have emerged as promising photosensitizers for photodynamic therapy, some key drawbacks still hamper clinical translation, such as operability in the phototherapeutic window and reactive oxygen species (ROS) production efficiency and selectivity. In this work, a cyclometalated Ir III complex conjugated to a far‐red‐emitting coumarin, Ir III –COUPY, is reported with highly favourable properties for cancer phototherapy. Ir III –COUPY was efficiently taken up by HeLa cells and showed no dark cytotoxicity and impressive photocytotoxicity indexes after irradiation with green and blue light, even under hypoxia. Importantly, a clear correlation between cell death and intracellular generation of superoxide anion radicals after visible light irradiation was demonstrated. This strategy opens the door to novel fluorescent photodynamic therapy agents with promising applications in theragnosis.

HeLa

10.1002/anie.201901268

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Citations (165)

A Green Light-Triggerable RGD Peptide for Photocontrolled Targeted Drug Delivery: Synthesis and Photolysis Studies

The Journal of Organic Chemistry (2016)

Albert Gandioso Marc Cano Anna Massaguer Vicente Marchán

We describe for the first time the synthesis and photochemical properties of a coumarin-caged cyclic RGD peptide and demonstrate that uncaging can be efficiently performed with biologically compatible green light. This was accomplished by using a new dicyanocoumarin derivative (DEAdcCE) for the protection of the carboxyl function at the side chain of the aspartic acid residue, which was selected on the basis of Fmoc-tBu SPPS compatibility and photolysis efficiency. The shielding effect of a methyl group incorporated in the coumarin derivative near the ester bond linking both moieties in combination with the use of acidic additives such as HOBt or Oxyma during the basic Fmoc-removal treatment were found to be very effective for minimizing aspartimide-related side reactions. In addition, a conjugate between the dicyanocoumarin-caged cyclic RGD peptide and ruthenocene, which was selected as a metallodrug model cargo, has been synthesized and characterized. The fact that green-light triggered photoactivation can be efficiently performed both with the caged peptide and with its ruthenocenoyl bioconjugate reveals great potential for DEAdcCE-caged peptide sequences as selective drug carriers in the context of photocontrolled targeted anticancer strategies.

Bioconjugation

Conjugate

Derivative (finance)

10.1021/acs.joc.6b02415

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Citations (48)

A ruthenium-oligonucleotide bioconjugated photosensitizing aptamer for cancer cell specific photodynamic therapy

Luke K. McKenzie Marie Flamme Patrick Felder Johannes Karges Frédéric Bonhomme

Aptamer

Nucleolin

10.26434/chemrxiv-2021-5n9xv

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Citations (0)