Phthalocyanines and related compounds: XLIV. Synthesis of conjugates of phthalocyanines with rhodamines

Derkacheva, V. M.; Mikhalenko, S. A.; Solov'eva, L. I.; Alekseeva, V. I.; Marinina, L. E.; Savina, L. P.; Butenin, A. V.; Luk’yanets, E. A.

doi:10.1134/s1070363207060291

Cited by 9 publications

(6 citation statements)

References 3 publications

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“…Similar conjugates of sulfono- and carboxy-substituted phthalocyanines with rhodamines have also been synthesized and their efficient intramolecular energy transfer (from Rh to Pc ) studied as well . In our design, Rh B, instead of connecting to the macrocyclic ring as peripheral substituents as in previous works, − is axially connected to SiPc via a polyether linkage to form two SiPc-Rh B conjugates, 3 and 2 , possessing one and two Rh B moieties, respectively. This axial ligation design can reduce Pc aggregation, thereby increasing its excited state lifetimes and improving its cellular uptake and imaging properties.…”

Section: Introductionmentioning

confidence: 98%

“…17 Enhanced (>5-fold) photocytotoxicity, relative to its components (i.e., TPP-OH and Rh B), and preferential accumulation at mitochondria were observed for this conjugate. Similar conjugates of sulfono-and carboxy-substituted phthalocyanines with rhodamines have also been synthesized 18 and their efficient intramolecular energy transfer (from Rh to Pc) studied as well. 19 In our design, Rh B, instead of connecting to the macrocyclic ring as peripheral substituents as in previous works, 17−19 is axially connected to SiPc via a polyether linkage to form two SiPc-Rh B conjugates, 3 and 2, possessing one and two Rh B moieties, respectively.…”

Section: ■ Introductionmentioning

confidence: 99%

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Highly Selective Mitochondria-Targeting Amphiphilic Silicon(IV) Phthalocyanines with Axially Ligated Rhodamine B for Photodynamic Therapy

Zhao

Chan

et al. 2011

Inorg. Chem.

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Two axially ligated rhodamine-Si(IV)-phthalocyanine (Rh-SiPc) conjugates, bearing one and two rhodamine B, were synthesized and their linear and two-photon photophysical, subcellular localization and photocytotoxic properties were studied. These Rh-SiPc conjugates exhibited an almost exclusive mitochondrial localizing property in human nasopharyngeal carcinoma (HK-1) cells and human cervical carcinoma (HeLa) cells. Strong photocytotoxic but low dark cytotoxic properties were also observed for the two Rh-SiPc conjugates toward the HK-1 cells. Using nuclei staining method and flow cytometric DNA content analysis, apoptotic cell death was induced by these conjugates upon photoactivation. This observation is consistent with their mitochondrial localization property. The observed properties of these conjugates qualify them as promising PDT agents.

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Section: Introductionmentioning

confidence: 98%

Section: ■ Introductionmentioning

confidence: 99%

Highly Selective Mitochondria-Targeting Amphiphilic Silicon(IV) Phthalocyanines with Axially Ligated Rhodamine B for Photodynamic Therapy

Zhao

Chan

et al. 2011

Inorg. Chem.

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“…23 However, polymethine cyanine dyes are not so easy to synthesize and to modify, their photo-stabilities are relatively low and their Stokes shift is usually less than 25 nm, which may cause self-quenching as well as the increase of measurement error due to detection of scattered excitation, thus decreasing the detection sensitivity to a great extent as it is in the case of using simple porphyrin sensitizers. Some examples of BODIPY-phthalocyanine 24,25 and rhodamine-phthalocyanine 26,27 conjugates have also been described in the literature. Despite the higher photostability of BODIPY and rhodamine derivatives as compared with cyanine dyes, these types of fluorophores also demonstrate a small difference between absorption and emission maxima.…”

Section: Introductionmentioning

confidence: 99%

A novel bacteriochlorin–styrylnaphthalimide conjugate for simultaneous photodynamic therapy and fluorescence imaging

Panchenko

Grin

Федорова

et al. 2017

Phys. Chem. Chem. Phys.

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Propargyl-15,17-dimethoxy-13-amide of bacteriochlorin e (BChl) and a 4-(4-N,N-dimethylaminostyryl)-N-alkyl-1,8-naphthalimide bearing azide group in the N-alkyl fragment were conjugated by the copper(i)-catalyzed 1,3-dipolar cycloaddition to produce a novel dyad compound BChl-NI for anticancer photodynamic therapy (PDT) combining the modalities of a photosensitizer (PS) and a fluorescence imaging agent. A precise photophysical investigation of the conjugate in solution using steady-state and time-resolved optical spectroscopy revealed that the presence of the naphthalimide (NI) fragment does not decrease the photosensitizing ability of the bacteriochlorin (BChl) core as compared with BChl; however, the fluorescence of naphthalimide is completely quenched due to resonance energy transfer (RET) to BChl. It has been shown that the BChl-NI conjugate penetrates into human lung adenocarcinoma A549 cells, and accumulates in the cytoplasm where it has a mixed granular-diffuse distribution. Both NI and BChl fluorescence in vitro provides registration of bright images showing perfectly intracellular distribution of BChl-NI. The ability of NI to emit light upon excitation in imaging experiments has been found to be due to hampering of RET as a result of photodestruction of the energy acceptor BChl unit. Phototoxicity studies have shown that the BChl-NI conjugate is not toxic for A549 cells at tested concentrations (<8 μM) without light-induced activation. At the same time, the concentration-dependent killing of cells is observed upon the excitation of the bacteriochlorin moiety with red light that occurs due to reactive oxygen species formation. The presented data demonstrate that the BChl-NI conjugate is a promissing dual function agent for cancer diagnostics and therapy.

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“…20,21 Some sulfonated phthalocyanines show potential application as catalysts, 4,22 sensors, 20,23 while others are being studied as photosensitizers for photodynamic therapy. 24,25 In this Letter we describe a new method to synthesize symmetrically substituted phthalocyanines bearing eight sulfonamide groups. It involves the chlorosulfonation of a diphenoxyphthalonitrile, followed by the reaction of the chlorosulfonyl groups with alkyl or aryl amines and then the macrocyclization of the resulting sulfonamide-substituted phthalonitriles.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of sulfonamide-substituted phthalocyanines

Carvalho

Calvete

Tomé

et al. 2009

Tetrahedron Letters

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Phthalocyanines and related compounds: XLIV. Synthesis of conjugates of phthalocyanines with rhodamines

Cited by 9 publications

References 3 publications

Highly Selective Mitochondria-Targeting Amphiphilic Silicon(IV) Phthalocyanines with Axially Ligated Rhodamine B for Photodynamic Therapy

Highly Selective Mitochondria-Targeting Amphiphilic Silicon(IV) Phthalocyanines with Axially Ligated Rhodamine B for Photodynamic Therapy

A novel bacteriochlorin–styrylnaphthalimide conjugate for simultaneous photodynamic therapy and fluorescence imaging

Synthesis of sulfonamide-substituted phthalocyanines

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