Danièle Carrez
Curie Institute
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Featured researches published by Danièle Carrez.
Bioorganic & Medicinal Chemistry | 2003
I Laville; T Figueiredo; B Loock; S Pigaglio; Ph. Maillard; David S. Grierson; Danièle Carrez; Alain Croisy; Jean-Claude Blais
Glucoconjugated tri and tetra(meta-hydroxyphenyl)chlorins have been synthesized in order to explore how glucoconjugation of the macrocycle affects the photoactivity of the molecule. Internalization processes, photosensitizing efficacy of TPC(m-O-GluOH)(3) and TPC(m-O-GluOH)(4), in HT29 human adenocarcinoma cells have been compared to those of tetra(meta-hydroxyphenyl) chlorin (m-THPC, Foscan). The tetra glucoconjugated chlorin, TPC(m-O-GluOH)(4), was found to be poorly internalized and weakly photoactive. In contrast, the asymmetric and more amphiphilic compound TPC(m-O-GluOH)(3), exhibited superior phototoxicity compared to m-THPC. Drug concentration, temperature and sodium azide effects indicated that TPC(m-O-GluOH)(3) internalization partly proceeds via an active receptor-mediated endocytosis mechanism. Cellular uptake appeared as a saturable process and remained 30% lower than for mTHPC. However, a maximum phototoxicity in HT29 cells (survival fraction of 2+/-0.6%) were observed for concentration as low as 2 microM. A 4-fold higher concentration of m-THPC was necessary to observe the same level of photoactivity. This higher phototoxicity has been correlated to a greater mitochondrial affinity. On the basis of these results, work is in progress to further evaluate the potential of glycosylated chlorins in photodynamic therapy (PDT).
Bioorganic & Medicinal Chemistry | 2000
Martine Croisy-Delcey; Alain Croisy; Danièle Carrez; Christiane Huel; Angèle Chiaroni; Pierre Ducrot; Emile Bisagni; Lu Jin; Guy Leclercq
The synthesis of a series of 35 substituted 3,4-diphenyl quinolines and isoquinolines is described. The majority of these molecules differ from all other triphenylethylene based antiestrogens by a different spatial location of the aminoalkyl side chain. The binding affinity of the most representative molecules (8, 9, 19, 20, 21, 23 and 25), including analogues 8 and 21 without the side chain, for the estrogen receptor alpha (ER) was determined. The ability of these molecules to induce the progesterone receptor was also studied. Antiproliferative activity was evaluated on MCF-7 human breast cancer cells, while intrinsic cytotoxic/cytostatic properties resulting from interaction with other targets than ER were assayed on L1210 murine leukemia cells. Introduction of an aminoalkylamino side chain at carbon 2 confers strong cytotoxic properties to diphenylquinolines 9 and 10 as well as pure antiestrogenic activities. However, cytotoxicity is so high with respect to antiestrogenicity that the latter was clearly observable only in one case (9b). The structure of compound 9b was determined by X-ray crystallography. Molecular modeling of its docking within the hormone-binding domain of the receptor was subsequently undertaken. According to our results, the design of molecules with the side chain bound to the ethylene part of the triphenyl ethylene skeleton might generate compounds of potential pharmacological interest.
Journal of Biomedical Optics | 1999
Michel Momenteau; Philiippe Maillard; Marie-Anne De Belinay; Danièle Carrez; Alain Croisy
The synthesis and characterization of amphiphilic glycoconjugated porphyrins, benzochlorin, and azaporphyrins were reported. Among these molecules, several were found to be efficient photosensitizers in an in vitro assay using the human tumoral cell line HT29. Moreover, glycosylated benzochlorin and azaporphyrins, whose absorption bands in the red region of the visible spectrum are substantially increased as compared to porphyrins, display a good photocytotoxicity on tumor cells after irradiation with wavelength above 590 nm.
Bioconjugate Chemistry | 2008
Mohamed Amessou; Danièle Carrez; Delphine Patin; Marianne Sarr; David S. Grierson; Alain Croisy; Antonio C. Tedesco; Philippe Maillard; Ludger Johannes
Photodynamic therapy involves administration of a photosensitizing drug and its subsequent activation by visible light of the appropriate wavelength. Several approaches to increasing the specificity of photosensitizers for cancerous tissues and, in particular, through their conjugation to ligands that are directed against tumor-associated antigens have been investigated. Here, we have studied the delivery of the photocytotoxic porphyrin compound TPP(p-O-beta-D-GluOH)3 into tumor cells that overexpress the glycosphingolipid Gb3, using the Gb3-binding nontoxic B-subunit of Shiga toxin (STxB) as a vector. To allow for site-directed chemical coupling, an STxB variant carrying a free sulfhydryl moiety at its C-terminal end has been used. Binding affinity, cellular uptake, singlet oxygen quantum yield, and phototoxicity of the conjugate have been examined. Despite some effect of coupling on both the photophysical properties of TPP(p-O-beta-D-GluOH)3 and the affinity of STxB for its receptor, the conjugate exhibited a higher photocytotoxic activity than the photosensitizer alone and was exquisitely selective for Gb3-expressing tumor cells. Furthermore, our data strongly suggest that STxB-mediated retrograde delivery of the photosensitizer to the biosynthetic/secretory pathway is critical for optimal cytotoxic activity. In conclusion, a strong rationale for using retrograde delivery tools such as STxB in combination with photosensitizing agents for the photodynamic therapy of tumors is presented.
ChemBioChem | 2005
Marguerite Pitié; Alain Croisy; Danièle Carrez; Christophe Boldron; Bernard Meunier
The cytostatic activities of a series of twelve 1,10‐phenanthroline (Phen) derivatives and of their copper complexes were studied on L1210 murine leukemia cells. Large increases in the biological activity were observed for compounds of the 3‐Clip‐Phen series, in which two Phen moieties were bridged at their C3 positions by an alkoxy linker, the 3‐pentyl‐Clip‐Phen derivative showing an IC50 value of 130 nM while Phen shows an IC50 value of 2500 nM under the same conditions. IC50 values seemed to be modulated not only by the position, the nature, and the length of the linker of Clip‐Phen but also by hydrophobicity. Since copper complexes of Phen are chemical nucleases and nucleic acids are thus a potential target for these compounds, the corresponding copper complexes were also studied. Copper complexation of the 3‐Clip‐Phen ligands did not increase their biological activities. Attempts to vectorize 3‐Clip‐Phen derivatives with a DNA binder such as spermine or with a cell‐penetration peptide failed to increase their biological activity relative to the original 3‐Clip‐Phen series.
NMR in Biomedicine | 2000
Jean-Luc Guerquin-Kern; Andreas Volk; Evelyne Chenu; Rachel Lougerstay‐Madec; Claude Monneret; Jean-Claude Florent; Danièle Carrez; Alain Croisy
A glucuro‐conjugated carbamate derivative of 5‐fluorouracil (5‐FU), originally designed as a prodrug for antibody‐directed enzyme prodrug therapy (ADEPT) application, has been used for direct in vivo observation of in situ 5‐FU generation in two human colon tumors heterotransplanted in nude mice. Because of the very fast elimination of glucuro‐conjugated drugs, this observation required intratumoral injection. These tumors, when becoming necrotic, are rich enough in β‐glucuronidase to allow 19F magnetic resonance spectroscopy monitoring, at the tumor level, of both prodrug elimination and 5‐FU liberation without preliminary treatment by a specifically targeted enzyme conjugate. Convenient tumors have been selected by magnetic resonance imaging (MRI) on the basis of a correlative study between MRI and conventional histology. This contribution is the first report evidencing such a direct intra‐tumoral conversion of a glucuro‐conjugated prodrug into the expected active drug. This method, which should allow overall estimation of the β‐glucuronidase content of tumors, might also be helpful for selecting tumors as specific targets for non‐toxic glucuro‐conjugated prodrugs without prior treatment with a fusion protein. Copyright
Photodiagnosis and Photodynamic Therapy | 2012
Florent Poyer; Carole D. Thomas; Guillaume Garcia; Alain Croisy; Danièle Carrez; Philippe Maillard; Mihaela Lupu; Joël Mispelter
BACKGROUND Previous in vivo studies on photodynamic therapy (PDT)-treated, high cellular density tumors showed evidences of a bystander effect accompanying the therapy, cellular death continuing beyond the limits of the photochemical reactions in time and space. This process is generated by the initially damaged cells on the light pathway. The aim of this study was to determine if the bystander effect may be induced as well in colorectal xenografted tumors (less compact structure) and if the cellular signaling depends primarily on cellular proximity or not. METHODS The photosensitizer was a glycoconjugated, meso substituted porphyrin derivative synthesized at Institut Curie. The longitudinal follow-up of the tumors was carried out by (23)Na/(1)H MRI, ideal imaging modality for mapping the extracellular compartment. Two regimens were followed in order to target either blood vessels alone or blood vessels and cancer cells simultaneously. RESULTS The antivascular PDT did not succeed to arrest the tumors growth at the end of the follow-up. For double targeting PDT, we managed to stop the tumoral evolution. Sodium MRI evidenced a bystander effect. CONCLUSION The results obtained showed that the bystander effect is more difficult to induce for the type of colorectal tumors used in this work. It needs a double treatment, 4 days apart, in order to be promoted.
Microscopy Research and Technique | 1997
Jean-Luc Guerquin-Kern; Maïté Coppey; Danièle Carrez; Anne-Christine Brunet; Chi Hung Nguyen; Christian Rivalle; Georges Slodzian; Alain Croisy
Low light level fluorescence microscopy studies have been carried out on MCF7‐P human mammary tumor cells to localize the intracellular distribtion of two new anticancer drugs, Pazelliptine and Intoplicine, which are currently under clinical evaluation. These two molecules are thought to act at the nuclear level, through DNA topoisomerase interactions. Because fluorescence of these compounds appears strongly quenched by intercalation in double strand DNA, secondary ion mass spectrometry (SIMS) imaging was used to check the presence of the drugs in the nuclear compartment. In spite of chemical structure similitudes, pazelliptine and intoplicine appear to be distributed in quite different ways within the cells. Incubation for 1 and 24 hours also allowed us to bring to light strong differences in the distribution kinetics. Pazelliptine quickly enters into the nucleoli but is no longer present in the nucleus after 24 hours incubation. Intoplicine was not detected by fluorescence in the nucleus, however SIMS microscopy allowed us to show its accumulation within this cellular compartment as a function of time of exposure. This study shows the complementarity of fluorescence and SIMS microscopies. Microsc. Res. Tech. 36:287–295, 1997.
European Journal of Medicinal Chemistry | 2009
Paul Peixoto; Walid Zeghida; Danièle Carrez; Ting Di Wu; Nicole Wattez; Alain Croisy; Martine Demeunynck; Jean Luc Guerquin-Kern; Amélie Lansiaux
Aminoacridine derivatives display interesting chemical and biological properties in the field of antitumor agents. The synthesis of 4-hydroxymethyl-3-aminoacridine and its iodo labelled analogue allows the study of cell distribution using two innovative, complementary and powerful techniques, real time fluorescence microscopy and dynamic secondary ion mass spectrometry (SIMS). All the data point to lysosomal localization of the active molecule.
NMR in Biomedicine | 1996
Valerie Collet; Danièle Carrez; Alain Croisy; Jean-Luc Dimicoli
Inhibition of glycolysis by methionine is a phenomenon previously shown in transformed cells growing in culture. In a recent paper, [Collet V. et al., Q. Magn. Res. Biol. Med. 11, 127–134 (1995)] we investigated this effect in vivo by 13C nuclear magnetic resonance spectroscopy, but the results did not clearly support this hypothesis. In this work, in vivo 13C NMR spectroscopy has been performed on tumors developing in nude mice following the injection of two types of cells established in culture: (1) rat kidney cells transformed by Kirsten murine sarcoma virus, (NRK‐K), i.e. the same tumor cell line as that used in the original paper; and (2) a well dedifferentiated human prostate adenocarcinoma cell line (PC3). Furthermore, in vitro experiments were performed with the same tumor cell lines. The effect of methionine on glycolysis was assayed by biochemical monitoring of lactate production in the supernatant of these cells grown in vitro. Lastly, 1H in vitro NMR spectroscopy of the PC3 line performed on perchloric extracts of both supernatants and cells growing in the presence of (1‐13C) glucose, allowed simultaneous detection of glucose and lactate as well as estimation of the lactate‐specific enrichment. The in vitro experiments confirmed the inhibiting effect of methionine on glycolysis and demonstrated the absence of a significant modification of the pentose phosphate pathway activity by this aminoacid. In contrast, none of the in vivo experimental results were compatible with this phenomenon, which is probably affected by more general physiological events.