Photophysical properties and in vitro and in vivo photoinduced antitumor activity of cationic salts of meso-tetrakis(N-alkyl-3-pyridyl)bacteriochlorins

Yakubovskaya, Raisa I.; Plotnikova, Еkaterina А.; Plyutinskaya, A. D.; Морозова, Наталья Борисовна; Чиссов, В И; Макарова, Е. А.; Dudkin, Semyon V.; Luk’yanets, E. A.; Vorozhtsov, Georgy N.

doi:10.1016/j.jphotobiol.2013.10.017

Cited by 17 publications

(12 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Cationic amphiphilic porphyrin-based PSs obtained completely by synthesis are mostly meso-substituted porphyrins with different symmetry patterns, free or in complex with metal (Caminos et al 2006;Lazzeri and Durantini 2003). There are somewhat fewer examples of different cationic amphiphilic phthalocyanines, mostly metalated with zinc(II) (Dummin et al 1997;Kussovski et al 2009), but also with other metals such as silicon (Allen et al 2001;Mantareva et al 2013), then synthetic chlorins (Costa et al 2012a), bacteriochlorins (Sharma et al 2013;Yakubovskaya et al 2014) and isobacteriochlorins (Mesquita et al 2014). The great advantage of phthalocyanines, chlorins and (iso)bacteriochlorins as PSs is better absorption of red light, which facilitates treatments of deeper infections and deep-seated tumours, but some of the frequent drawbacks often associated with these compounds include a propensity for aggregation and insufficient solubility in water (Mantareva et al 2013;Sharma et al 2013).…”

Section: Types Of Porphyrin-based Cationic Amphiphilic Pssmentioning

confidence: 99%

Porphyrin-based cationic amphiphilic photosensitisers as potential anticancer, antimicrobial and immunosuppressive agents

2017

View full text Add to dashboard Cite

Photodynamic therapy (PDT) combines a photosensitiser, light and molecular oxygen to induce oxidative stress that can be used to kill pathogens, cancer cells and other highly proliferative cells. There is a growing number of clinically approved photosensitisers and applications of PDT, whose main advantages include the possibility of selective targeting, localised action and stimulation of the immune responses. Further improvements and broader use of PDT could be accomplished by designing new photosensitisers with increased selectivity and bioavailability. Porphyrin-based photosensitisers with amphiphilic properties, bearing one or more positive charges, are an effective tool in PDT against cancers, microbial infections and, most recently, autoimmune skin disorders. The aim of the review is to present some of the recent examples of the applications and research that employ this specific group of photosensitisers. Furthermore, we will highlight the link between their structural characteristics and PDT efficiency, which will be helpful as guidelines for rational design and evaluation of new PSs.

show abstract

Section: Types Of Porphyrin-based Cationic Amphiphilic Pssmentioning

confidence: 99%

Porphyrin-based cationic amphiphilic photosensitisers as potential anticancer, antimicrobial and immunosuppressive agents

2017

View full text Add to dashboard Cite

show abstract

“…Very low amounts were seen at 48–72 h . Cationic salts of bacteriochlorin such as meso‐tetrakis (N‐alkyl‐3‐pyridyl)bacteriochlorin 31 showed accumulation peaks in tumors as early as after 15‐30 min after administration, followed by progressive clearance, with only 7.3–26.3% remaining 96 h after injection . Tumor specificity was confirmed by the tumor/skin and tumor/muscle ratios .…”

Section: Pharmacokinetics and Biodistributionmentioning

confidence: 92%

“…Cationic salts of bacteriochlorin such as meso‐tetrakis (N‐alkyl‐3‐pyridyl)bacteriochlorin 31 showed accumulation peaks in tumors as early as after 15‐30 min after administration, followed by progressive clearance, with only 7.3–26.3% remaining 96 h after injection . Tumor specificity was confirmed by the tumor/skin and tumor/muscle ratios . Studies with Radachlorin (chlorin e6 derivative) 27 in 2014 showed gradual accumulation in tissues (tumor sites among these) 3–6 h postadministration.…”

Section: Pharmacokinetics and Biodistributionmentioning

confidence: 99%

Design features for optimization of tetrapyrrole macrocycles as antimicrobial and anticancer photosensitizers

et al. 2017

View full text Add to dashboard Cite

Photodynamic therapy (PDT) uses non-toxic dyes called photosensitizers (PS) and harmless visible light that combine to form highly-toxic reactive oxygen species that kill cells. Originally a cancer therapy, PDT now includes applications for infections. The most widely studied PS are tetrapyrrole macrocycles including porphyrins, chlorins, bacteriochlorins and phthalocyanines. The present review covers the design features in PS that can work together to maximize the PDT activity for various disease targets. Photophysical and photochemical properties include the wavelength and size of the long-wavelength absorption peak (for good light penetration into tissue), the triplet quantum yield and lifetime, and the propensity to undergo Type I (electron-transfer) or Type II (energy-transfer) photochemical mechanisms. The central metal in the tetrapyrrole macrocycle has a strong influence on the PDT activity. Hydrophobicity and charge are important factors that govern interactions with various types of cells (cancer and microbial) in vitro, and the pharmacokinetics and biodistribution in vivo. Hydrophobic structures tend to be water-insoluble and require a drug delivery vehicle for maximal activity. Molecular asymmetry and amphiphilicity are also important for high activity. In vivo some structures possess the ability to selectively accumulate in tumors, and to localize in the tumor microvasculature producing vascular shutdown after illumination.

show abstract

“…Эти флуорохромы существенно превосходят препараты 1-го поколения -фотофрин (Канада), фотогем (Россия), но все же обладают определенными недостатками. Так, в частности, при внутривенном введении производных хлорина е 6 уровень их накопления в опухолевых клетках остается достаточно низким, преимущественно это происходит в сосудах стромы опухоли [2].…”

Section: Introductionunclassified

Specific properties of chlorin e<sub>6</sub> trimethyl ester and its glycolized derivative as photosensitizers in vitro and in vivo

Plotnikova

Morozova

Plyutinskaya

et al. 2016

Rossijskij bioterapevtičeskij žurnal

View full text Add to dashboard Cite

Цель исследования-сравнение эффективности фотодинамического действия триметилового эфира хлорина е6 (3МеChl) и его производного с остатком галактозы в пирроле А (3MeChl_gal_NoAc), а также сравнительная характеристика накопления этих соединений в опухоли и их биораспределения в нормальных органах и тканях животных. Материалы и методы. Исследования в системе in vitro проводили на опухолевых клетках мышиной карциномы легкого Льюиса (LLC) в мультипараметрической системе. Фотоиндуцированную противоопухолевую активность и биораспределение 3МеChl и 3MeChl_gal_NoAc изучали на мышах BDF 1 с LLC. Биораспределение и фармакокинетику оценивали методом локальной флуоресцентной спектроскопии. Облучение проводили на 7-й день роста опухоли светодиодным источником с длиной волны 661 ± 16 нм при варьировании дозы фотосенсибилизаторов от 0,5 до 7,5 мг/кг и интервале времени между введением и облучением от 5 до 120 мин и при плотности энергии 90 Дж/см 2 .

show abstract

Photophysical properties and in vitro and in vivo photoinduced antitumor activity of cationic salts of meso-tetrakis(N-alkyl-3-pyridyl)bacteriochlorins

Cited by 17 publications

References 11 publications

Porphyrin-based cationic amphiphilic photosensitisers as potential anticancer, antimicrobial and immunosuppressive agents

Porphyrin-based cationic amphiphilic photosensitisers as potential anticancer, antimicrobial and immunosuppressive agents

Design features for optimization of tetrapyrrole macrocycles as antimicrobial and anticancer photosensitizers

Specific properties of chlorin e<sub>6</sub> trimethyl ester and its glycolized derivative as photosensitizers in vitro and in vivo

Contact Info

Product

Resources

About