A study of the stability of tri(glucosyloxyphenyl)chlorin, a sensitizer for photodynamic therapy, in human colon tumoural cells: a liquid chromatography and MALDI-TOF mass spectrometry analysis

Laville, Isabelle; Pigaglio, Sophie; Blais, Jean‐Claude; Loock, Bernard; Maillard, Ph.; Grierson, David S.

doi:10.1016/j.bmc.2004.04.022

Cited by 41 publications

(9 citation statements)

References 22 publications

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“…Cellular Metabolism. An important issue when considering an in vivo use of glycoconjugated drugs is the possible cleavage of glycoside bonds by endogenous glycosidases . This will result in the modification of the amphiphilic properties, biodistribution, blood clearance, and drug-cell interactions.…”

Section: Biologymentioning

confidence: 99%

Photodynamic Efficiency of Diethylene Glycol-Linked Glycoconjugated Porphyrins in Human Retinoblastoma Cells

et al. 2006

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Photodynamic therapy (PDT) is emerging as a new strategy for the conservative treatment of hereditary retinoblastoma. The glycoconjugated porphyrins TPP(p-Deg-O-alpha-GalOH)(3), TPP(p-Deg-O-beta-GalOH)(3), TPP(p-Deg-O-alpha-ManOH)(3), and their S-analogues were synthesized to obtain efficient photosensitizers with some retinoblastoma cell affinity. In these systems, a sugar motif and porphyrin core were linked by a diethylene glycol spacer (Deg). Cellular uptake, localization, and photoactivity have been examined in human retinoblastoma cells (Y79). After preincubation with corresponding glycosylated albumin, the uptake of TPP(p-Deg-O-beta-GalOH)(3) and TPP(p-Deg-O-alpha-ManOH)(3) was 40-45% inhibited, indicating a possible cell-sugar-receptor saturation. High photoactivity was observed for the two alpha-galacto/manno porphyrins 8 and 10 (LD(50) = 0.05 and 0.35 muM, respectively) at 514 nm and low fluence (1 J/cm(2)). Analysis by MALDI-TOF mass spectrometry only indicated a small metabolic cleavage of the O-glycoconjugates and a good stability of the S-glycoside porphyrins. On the basis of these in vitro data, TPP(p-Deg-O-alpha-GalOH)(3) and TPP(p-Deg-O-alpha-ManOH)(3) were selected for in vivo studies.

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Section: Biologymentioning

confidence: 99%

Photodynamic Efficiency of Diethylene Glycol-Linked Glycoconjugated Porphyrins in Human Retinoblastoma Cells

et al. 2006

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“…33 The number and position of functional groups on porphyrinoids has been discussed in terms of PDT effects. 16 O-glycoside attached sugars can be hydrolysed off of conjugates enzymatically, by lysosomal degradation, 34, 35 and the decreased pH surrounding cancer cells and tissues due to the Warburg effect. 36 Therefore, non-hydrolysable attachments may be more effective as therapeutics and for other applications.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and photophysics of an octathioglycosylated zinc(II) phthalocyanine

Aggarwal

Singh

Ya-zhou

et al. 2011

Tetrahedron Letters

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A water soluble zinc(II) phthalocyanine symmetrically appended with eight thioglucose units was synthesized from commercially available hexadecafluorophthalocyaninatozinc(II) by controlled nucleophilic substitution of the peripheral fluoro groups. The photophysical properties and cancer cell uptake studies of this nonhydrolyzable thioglycosylated phthalocyanine are reported. The new compound has amphiphilic character, is chemically stable, and can potentially be used as a photosensitizer in photodynamic therapy.

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“…In this two-step process, which involves sequential reaction with diimide (generated in situ from p -toluenesulfonhydrazide (TsNHNH 2 ) in the presence of pyridine and potassium carbonate) followed by o -chloranil, the regioisomeric chlorins 3a and 3b were obtained as a nonseparable 1/1 mixture. This situation has complicated the study of the stability and photoefficiency of these systems and, consequently, their preclinical assessment relative to the reference molecule FOSCAN 1 Preparation of Triglucosylated Chlorins …”

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confidence: 99%

Development of Strategies for the Regiocontrolled Synthesis of meso-5,10,20-Triaryl-2,3-chlorins

et al. 2007

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Triglycoconjugated photosensitizers show promise for use in the photodynamic therapy-based treatment of cancer. Two different routes have been studied for the regioselective preparation of 5,10,20-meso-triphenyl-2,3-chlorin, 9a, and 5,10,20-meso-tri(4-isopropyloxyphenyl)-2,3-chlorin, 9b. The main issue was to control the placement of the partially reduced pyrrole ring in the more hindered environment in the triarylchlorin products.

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A study of the stability of tri(glucosyloxyphenyl)chlorin, a sensitizer for photodynamic therapy, in human colon tumoural cells: a liquid chromatography and MALDI-TOF mass spectrometry analysis

Cited by 41 publications

References 22 publications

Photodynamic Efficiency of Diethylene Glycol-Linked Glycoconjugated Porphyrins in Human Retinoblastoma Cells

Photodynamic Efficiency of Diethylene Glycol-Linked Glycoconjugated Porphyrins in Human Retinoblastoma Cells

Synthesis and photophysics of an octathioglycosylated zinc(II) phthalocyanine

Development of Strategies for the Regiocontrolled Synthesis of meso-5,10,20-Triaryl-2,3-chlorins

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