New conjugates of cobalt bis(dicarbollide) with chlorophyll a derivatives

Grin, Mikhail A.; Titeev, Rustam A.; Brittal, Dmitry I.; Ulybina, Olga V.; Tsiprovskiy, Alexander G.; Berzina, Мaria Ya.; Lobanova, I. A.; Sivaev, Igor B.; Bregadze, V. I.; Mironov, A. F.

doi:10.1016/j.mencom.2011.03.008

Cited by 33 publications

(15 citation statements)

References 35 publications

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“…Another scheme for the preparation of the boron-containing chlorin included the interaction of the previously described chlorin–cyclen 1 with a dioxonium derivative of bis(1,2-dicarbollide) cobalt. Earlier, our research group studied the reaction of the nucleophilic opening of the dioxonium ring with aminoamides of natural chlorins [ 8 ]. This approach was extended to the cyclic chlorin derivative ( Scheme 2 ), while the question of the number of attached clusters remained open.…”

Section: Resultsmentioning

confidence: 99%

“…The effectiveness of BNCT is ensured by a high concentration of 10B atoms in a cancer cell; however, boron clusters themselves do not possess targeting properties. For targeted delivery and the tracking of tumor accumulation, it is promising to use conjugates of boron clusters with photosensitizers (PS), which can be derivatives of natural chlorins [ 8 , 9 , 10 ]. Due to their ability to absorb light in the near infrared region of the spectrum (650–700 nm), chlorin derivatives are widely used in photodynamic therapy (PDT) and fluorescence diagnostics (FD) [ 11 , 12 ].…”

Section: Introductionmentioning

confidence: 99%

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Highly Purified Conjugates of Natural Chlorin with Cobalt Bis(dicarbollide) Nanoclusters for PDT and BNCT Therapy of Cancer

et al. 2021

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To combine the neutron-capturing and photodynamic properties of boron nanoclusters and derivatives of natural chlorins, respectively, in one molecule, conjugate of chlorin e6 methyl ester with cyclen and dioxane and nitrile derivatives of cobalt bis(dicarbollide) were synthesized. The conditions for the purification of compounds by HPLC were selected since the work with natural compounds is complicated by the production of closely related impurities.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Highly Purified Conjugates of Natural Chlorin with Cobalt Bis(dicarbollide) Nanoclusters for PDT and BNCT Therapy of Cancer

et al. 2021

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“…The biodistribution of CCDC containing 18 boron atoms per molecule ( Figure 1 ) was studied. The CCDC was synthesized as described earlier [ 54 ]. The purity of the CCDC was 96–98% according to HPLC analysis.…”

Section: Methodsmentioning

confidence: 99%

Pharmacokinetics of Chlorin e6-Cobalt Bis(Dicarbollide) Conjugate in Balb/c Mice with Engrafted Carcinoma

Volovetsky

Sukhov

Balalaeva

et al. 2017

IJMS

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The necessary precondition for efficient boron neutron capture therapy (BNCT) is control over the content of isotope 10B in the tumor and normal tissues. In the case of boron-containing porphyrins, the fluorescent part of molecule can be used for quantitative assessment of the boron content. Study Objective: We performed a study of the biodistribution of the chlorin e6-Cobalt bis(dicarbollide) conjugate in carcinoma-bearing Balb/c mice using ex vivo fluorescence imaging, and developed a mathematical model describing boron accumulation and release based on the obtained experimental data. Materials and Methods: The study was performed on Balb/c tumor-bearing mice (CT-26 tumor model). A solution of the chlorin e6-Cobalt bis(dicarbollide) conjugate (CCDC) was injected into the blood at a dose of 10 mg/kg of the animal’s weight. Analysis of the fluorescence signal intensity was performed at several time points by spectrofluorimetry in blood and by laser scanning microscopy in muscle, liver, and tumor tissues. The boron content in the same samples was determined by mass spectroscopy with inductively coupled plasma. Results: Analysis of a linear approximation between the fluorescence intensity and boron content in the tissues demonstrated a satisfactory value of approximation reliability with a Spearman’s rank correlation coefficient of r = 0.938, p < 0.01. The dynamics of the boron concentration change in various organs, calculated on the basis of the fluorescence intensity, enabled the development of a model describing the accumulation of the studied compound and its distribution in tissues. The obtained results reveal a high level of correspondence between the model and experimental data.

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“…为了扩展叶绿素降解产物的研究范围, 对具有六元外接环的红紫素-18 进行了相应的亲电取代反应, 结果表明, 象溴正离子或硝酰正离子等较大体积的亲电质点难于在 20-meso-位上完成取代反应 [3] . 为此, 我们由 MPa (1)开始, 经酸性条件下的空气氧化和 20-meso-位的硝化反应, 一步法制得 46%的 20-硝基和 13 2 [4～6] . 对于吸电子取代基团而言, 其π-反键轨道的微扰作用在一定程度上降低了共轭体系的最低空轨道(LUMO)的能级, 缩小了与最高占有轨道(HOMO)以及非键轨道之间的能级差, 因此, 相应的 n-π*和 π-π*跃迁需要较少的能量即可完成 [13a] .…”

Section: -位乙烯基的亲电加成往往使得 20-位溴代反应变unclassified

Synthesis of 20-meso-Substituted Chlorins with the Basic Skeleton of Chlorophyll-a

王鲁敏¹,

王振²,

杨泽³

et al. 2012

Chin. J. Org. Chem.

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Methyl pheophorbide-a (MPa) was used as starting material. The coupling reaction of MPa with diazobenzene hydrochloride, hydrobromide and sulfate was carried out to give traces of expected product, while major products were 20-halogenated and nitroso-substituted chlorins. Zinc methyl pyropheophorbide-a reacted with 3-N,N-dimethylacrolein to give Vilsmeier product. The bromination of pyropheophorbide-d with N-bromosuccinimide (NBS) formed single 20-brominated product, the vinyl group of which was resumed by Wittig reaction to give 20-bromopyropheophorbide-a. The electrophilic substitution of other chlorphyllous degradation products afforded corresponding 20-meso-substituted chlorin derivatives in better yields, respectively. The structures of all the new chlorins with basic skeleton of chlorophyll were characterized by UV, IR, 1 H NMR spectra and elemental analysis.

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New conjugates of cobalt bis(dicarbollide) with chlorophyll a derivatives

Cited by 33 publications

References 35 publications

Highly Purified Conjugates of Natural Chlorin with Cobalt Bis(dicarbollide) Nanoclusters for PDT and BNCT Therapy of Cancer

Highly Purified Conjugates of Natural Chlorin with Cobalt Bis(dicarbollide) Nanoclusters for PDT and BNCT Therapy of Cancer

Pharmacokinetics of Chlorin e6-Cobalt Bis(Dicarbollide) Conjugate in Balb/c Mice with Engrafted Carcinoma

Synthesis of 20-meso-Substituted Chlorins with the Basic Skeleton of Chlorophyll-a

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