Sugar-dependent aggregation of glycoconjugated chlorins and its effect on photocytotoxicity in HeLa cells

Hirohara, Shiho; Obata, Makoto; Ogata, Shinichi; Kajiwara, Kouichi; Ohtsuki, Chikara; Tanihara, Masao; Yano, Shigenobu

doi:10.1016/j.jphotobiol.2006.01.011

Cited by 42 publications

(53 citation statements)

References 30 publications

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“…The first step towards nano-sized PS formulations were made through the preparation of dendritic [80,81], glyco [82,83], amino acid [84] and peptide [85] functionalized porphyrins. Initially, many of these studies were just aimed at increasing the water solubility, formulation properties and targeting of the PS [86].…”

Section: Ps Linkermentioning

confidence: 99%

Nanodrug applications in photodynamic therapy

Paszko

Ehrhardt

Senge

et al. 2011

Photodiagnosis and Photodynamic Therapy

326

215

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SummaryPhotodynamic therapy (PDT) has developed over last century and is now becoming a more widely used medical tool having gained regulatory approval for the treatment of various diseases such as cancer and macular degeneration. It is a two-step technique in which delivery of a photosensitizing drug is followed by irradiation of light. Activated photosensitizers transfer energy to molecular oxygen which results in generation of reactive oxygen species which in turn cause cells apoptosis or necrosis. Although this modality has significantly improved quality of life and survival time for many cancer patients it still offers significant potential for further improvement. In addition to the development of new PDT drugs, the use of nanosized carriers for photosensitizers is a promising approach which might improve the efficiency of photodynamic activity and which can overcome many side effects associated with classic photodynamic therapy. This review aims at highlighting the different types of nanomedical approaches currently used in PDT and outlines future trends and limitations of nanodelivery of photosensitizers. PDT -photodynamic therapy; PGA -poly(glycolic acid); PGLA -poly(D,L-lactide-coglycolide); PLA -poly(lactic acid); PS -photosensitizer; PEG -polyethylene glycol; ALA  aminolevulinic acid; m-THPC  5,10,15,20-tetra-(m-hydroxyphenyl)chlorine; m-THPP  meso-tetra(p-hydroxyphenyl); PpIX  protoporphyrin; Hp  hematoporphyrin; Pc4  silicon phthalocyanine; Ig  immunoglobulin; Tf  transferrin; TfR  transferrin receptor; VEGF  vascular endothelial growth factor; EPR  enhanced permeability and retention effect; FRET  fluorescence resonance energy transfer; MRI  magnetic resonance imaging; RES  reticuloendothelial system; ROS  reactive oxygen species; NP  nanoparticle; ND -nanodiamonds; SNP  silica nanoparticle; AMD  age-related macular degeneration; CNV  choroidal neovascularization; PTT  photothermal therapy;

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Section: Ps Linkermentioning

confidence: 99%

Nanodrug applications in photodynamic therapy

Paszko

Ehrhardt

Senge

et al. 2011

Photodiagnosis and Photodynamic Therapy

326

215

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“…However, reduction of the trisubstituted porphyrin yielded two inseparable isomers 2,3-and 7,8-meta-triglucosylated chlorins (516, 517) while the metasubstituted tetraglucosylated chlorin 514f was formed as a mixture of four atropisomers at r.t. [260] . By now, many other glycochlorins have been prepared using the Whitlock method, including a series of 5,10,15,20-tetrakis[3-or 4-(β-D-glycopyranosyloxy)phenyl]chlorins with glucopyranosyl, galactopyranosyl, xylopyranosyl and arabinopyranosyl groups (514a,b,d-i) [261,262] . Note, that reduction can afford a mixture of chlorins and bacteriochlorins which was the case in this study.…”

Section: Reductionmentioning

confidence: 99%

“…No significant difference in Log P was observed, but chlorins 540a and 540c were only slightly more hydrophilic than 540b,d [271] . Similar methods were used by Hirohara et al to study a range of O-glycosylated tetraarylporphyrins and -chlorins, which showed several advantages including reduced dark cytotoxicity, improved water-solubility, better cellular uptake, and sugar-dependent photocytotoxicity [165,261,262,272,273] . The O-glycosylated chlorins had promising photocytotoxicity in HeLa cells but were difficult to purify.…”

Section: 3-dipolar Cycloadditionsmentioning

confidence: 99%

“…Here, porphyrins 205 and 114 were identified as good PDT PS [210] . Similarly, the photochemical properties and the in vitro photocytotoxicity in HeLa cells of the four chlorin derivatives 514d-g were investigated [262] . Fluorescence intensities in phosphate-buffered saline of 514f and 514g (hexose groups) were ~ 2-times greater than 514d and 514e (pentose groups) proving a sugar-dependent difference of aggregation behavior.…”

Section: Hydroporphyrinsmentioning

confidence: 99%

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Chemical Synthesis and Medicinal Applications of Glycoporphyrins

Moylan¹,

Scanlan²,

Senge

2015

CMC

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Abstract:This review presents an in-depth overview of the modification of porphyrins with bioconjugates and their applications in medicine today. Porphyrin bioconjugates ranging from nucleotides to steroids are under active scrutiny. However, carbohydrates have been at the forefront of such research in recent years and offer significant potential. This is attributed to their own selectivity to lectins on the surface of cancer cells and their influence on the amphiphilicity of the porphyrin macrocycle. These characteristics and the tendency of porphyrin photosensitizers to accumulate in tumor tissues make glycoporphyrins promising candidates for use as photosensitizers. Thus, a detailed overview of the synthesis and biological evaluation of glycoporphyrins is given with a particular focus on their applications in photodynamic therapy and their future prospects as drug candidates have been reported.

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“…Since the discovery of the glycoconjugated porphyrin derivatives by Fülling et al, 7) many glycoconjugates have been reported. [7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][27][28][29][30][31][32]34) Momenteau and Mailard et al synthesized a number of O-glycosylated tetraphenylporphyrins (TPPs) and chlorins (TPCs) having various substituents (phenyl, alkyl and so on) and examined 1 O 2 generation, partition coefficients and photocytotoxicity in KB cells. 17) They reported that the photocytotoxicity varies with the sugar unit attached, and concluded that planar structure and amphiphilic character were the keys to a potent photocytotoxic effect on KB cells.…”

mentioning

confidence: 99%

Structure-Photodynamic Effect Relationships of 24 Glycoconjugated Photosensitizers in HeLa Cells

Hirohara

Obata

Alitomo³

et al. 2008

Biological & Pharmaceutical Bulletin

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Photodynamic therapy (PDT) with a photosensitizing dye and light irradiation is used to treat cancer; the photosensitizer accumulated in malignant cells photochemically generates highly cytotoxic reactive oxygen species (ROS), such as singlet oxygen ( 1 O 2 ) and hydroxyl radical (OH · ). 1-6) These ROSs damage the microorganella, such as mitochondria, lysosomes, plasma membrane, Golgi apparatus and endoplasmic reticulum, leading to necrotic and/or apoptotic cell death. Because the efficacy of PDT treatment crucially depends on the photosensitizer used, development of an efficient photosensitizer is very important. Porphyrin derivatives, including reduced porphyrins such as chlorins and bacteriochlorins, are the most studied photosensitizing dyes in PDT applications owing to their large molar absorption coefficient in the longer wavelength region, sufficient photochemical stability, and inherent "enhanced permeability and retention (EPR) effect" in tumor tissue. However, the tetrapyrrolic macrocycle of porphyrin derivatives is quite hydrophobic, and so chemical modification is usually required for physiological application. Modification with saccharide is a wellknown approach for improving the water-solubility of a compound. Since the discovery of the glycoconjugated porphyrin derivatives by Fülling et al.,7) many glycoconjugates have been reported. [7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][27][28][29][30][31][32]34) Momenteau and Mailard et al. synthesized a number of O-glycosylated tetraphenylporphyrins (TPPs) and chlorins (TPCs) having various substituents (phenyl, alkyl and so on) and examined 1 O 2 generation, partition coefficients and photocytotoxicity in KB cells. 17) They reported that the photocytotoxicity varies with the sugar unit attached, and concluded that planar structure and amphiphilic character were the keys to a potent photocytotoxic effect on KB cells. Sol and Krausz et al. reported many O-glycosylated TPPs having unique structures, such as strapped porphyrin, 18) charged porphyrin, 19,20) peptide-conjugated porphyrin 21,22) and porphyrin dimer.23) The photocytotoxicity of these O-glycosylated TPP derivatives can usually be interpreted in terms of the hydrophilicity and the molecular asymmetry. Saccharide also plays an important role in cellular recognition. Aoyama et al. reported that hydrophobicity masking is important for saccharide-directed cell recognition of glycoconjugated porphyrin derivatives by rat hepatoma cells (RLC-16).24) Focusing on PDT application, Pandey et al. synthesized of benzochlorins bearing galactosamine, glucosamine and lactosamine, and examined their photocytotoxicity in radiation-induced fibrosarcoma (RIF). 25) They found that preincubation with lactose inhibited the photocytotoxicity of benzochlorins bearing galactosamine and lactosamine, suggesting an interaction with galectin-mediated photocytotoxicity. Zheng et al. prepared pyropheophorbide bearing 2-deoxyglucosamine and showed that these compounds are taken up via the glucose tr...

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Sugar-dependent aggregation of glycoconjugated chlorins and its effect on photocytotoxicity in HeLa cells

Cited by 42 publications

References 30 publications

Nanodrug applications in photodynamic therapy

Nanodrug applications in photodynamic therapy

Chemical Synthesis and Medicinal Applications of Glycoporphyrins

Structure-Photodynamic Effect Relationships of 24 Glycoconjugated Photosensitizers in HeLa Cells

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