New bacteriochlorin derivatives with a fused N-aminoimide ring

Миронов, А. Ф.; Grin, M. A.; Tsiprovskiy, Alexander G.; Качала, В. В.; Karmakova, Tatyana; Plyutinskaya, A. D.; Yakubovskaya, Raisa I.

doi:10.1142/s1088424603000902

Cited by 26 publications

(22 citation statements)

References 9 publications

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“…N Aminobacteriopurpurinimide was synthesized by reacting bacteriopurpurin 2 with hydrazine hydrate in pyri dine according to a known procedure [34]. Bacteriopur purin was derived via allomerization of BChl a 1 accumu lated in purple nonsulfur bacterium Rhodobacter capsulatus strain B10 grown under chemoheterotrophic conditions following a procedure described in the literature [35 38].…”

Section: Resultsmentioning

confidence: 99%

Development of bacteriochlorophyll a-based near-infrared photosensitizers conjugated to gold nanoparticles for photodynamic therapy of cancer

Pantiushenko

Rudakovskaya

Starovoytova

et al. 2015

Biochemistry Moscow

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We report the synthesis and characterization of a new sulfur-containing derivative of bacteriochlorophyll a. The latter was isolated from biomass of the nonsulfur purple bacterium Rhodobacter capsulatus strain B10. The developed photosensitizer is N-aminobacteriopurpurinimide with an exocyclic amino group acylated with a lipoic acid moiety, which is a biogenic substance that acts as a cofactor of the pyruvate dehydrogenase and α-ketoglutarate dehydrogenase complexes in the body. The disulfide moiety of lipoic acid confers the compound aurophilicity, thus allowing its conjugation with gold nanoparticles (NP-Au) via S-Au bonds. The shape and the size of the resulting nanoconjugate with immobilized photosensitizer (PS-Au) were assessed by dynamic light scattering and transmission electron microscopy. The conjugated nanoparticles are spherical with hydrodynamic diameter of 100-110 nm. The PS-Au conjugate absorbs light at 824 nm and emits strong fluorescence at 830 nm, which allowed in vivo study of its dynamic biodistribution in rats bearing sarcoma M-1. Compared to the free photosensitizer, PS loaded on the gold nanoparticles (PS-Au) showed extended circulation time in the blood and enhanced tumor uptake due to nonspecific passive targeting when the drug accumulates in tumor sites through the leaky tumor neovasculature and does not return to the circulation.

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Section: Resultsmentioning

confidence: 99%

Development of bacteriochlorophyll a-based near-infrared photosensitizers conjugated to gold nanoparticles for photodynamic therapy of cancer

Pantiushenko

Rudakovskaya

Starovoytova

et al. 2015

Biochemistry Moscow

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“…Dioxane derivative 1 and bacteriochlorin p 6 methyl ester 13,15 (N aminocycloimide) 3 were prepared according to known procedures. 20, 21 The TLC analysis was carried out on silica gel plates.…”

Section: Methodsmentioning

confidence: 99%

New boron-containing bacteriochlorin p cycloimide conjugate

et al. 2008

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“…In this work we have performed an in vivo investigation of bacteriochlorin p N-methoxycycloimide oxyme methyl ester (BchlpOx-NOMe), synthesized by chemical modification of bacteriochlorophyll а, obtained from purpuric bacteria Rhodobacter capsulatus, as was described earlier in [9][10][11]. Structure of photosensitizer is shown on Fig.…”

Section: Methodsmentioning

confidence: 99%

New efficient near-IR photosensitizer based on bacteriochlorin p N-methoxycycloimide oxyme methyl ester

et al. 2007

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This work is devoted to investigation of new photosensitizer Bacteriochlorin p N-methoxycycloimide oxyme methyl ester (BchlpOx-NOMe). Investigations of photosensitizer in vivo and experimental PDT were performed on animals bearing intramuscularly inoculated Erlich tumor and B16 melanoma. Characteristic absorption maximum of BchlpOx-NOMe around 795 nm is within the range of minimum intrinsic absorption of biological tissue. Dynamics and selectivity of sensitizer accumulation in tumor and normal tissue were estimated from spectra of absorption of sensitized tissue in vivo. The investigation has shown that the optimum time range to start PDT irradiation of tumor is 10-30 min after administration. Photosensitizer has shown high photodynamic efficiency of relatively large tumors, including high PDT efficiency in preliminary experiments with BDF1 mice bearing B16 melanoma, causing tumor growth inhibition more than 90% and prolongation of lifespan of tumor-bearing animals more than 60%.

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New bacteriochlorin derivatives with a fused N-aminoimide ring

Cited by 26 publications

References 9 publications

Development of bacteriochlorophyll a-based near-infrared photosensitizers conjugated to gold nanoparticles for photodynamic therapy of cancer

Development of bacteriochlorophyll a-based near-infrared photosensitizers conjugated to gold nanoparticles for photodynamic therapy of cancer

New boron-containing bacteriochlorin p cycloimide conjugate

New efficient near-IR photosensitizer based on bacteriochlorin p N-methoxycycloimide oxyme methyl ester

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