The synthesis of 64Cu-chelated porphyrin photosensitizers and their tumor-targeting peptide conjugates for the evaluation of target cell uptake and PET image-based pharmacokinetics of targeted photodynamic therapy agents

Mukai, Hidefumi; Wada, Yasuhiro; Watanabe, Yasuyoshi

doi:10.1007/s12149-013-0728-2

Cited by 32 publications

(27 citation statements)

References 38 publications

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“…These include coupling various BnR-ligands(primarily agonists) to cytotoxic-radioisotopes( 90 Y, 177 Lu)[16•,82,83]; the coupling of BnR-ligands to phthalocyanine or to porphyrin-photosensitizers[84] to allow photodynamic therapy[85]; the coupling to various siRNA which can affect tumor proliferation/growth/viability[35,86]; coupling to various cytotoxic-chemotherapeutic agents including paclitaxel[87], camptothecin[88,89], and doxorubicin[32,90], as well as to various cytotoxic-marine toxins[hemiasterlin,dolastatin][91]; coupling BnR-agonists to the antimicrobial peptide, magainin 11[92] markedly increase the cytotoxiticity of magainin 11 both in vitro in a number of GRPR-containing tumor cells and in vivo in MCF-7- breast-cancer-cells; and coupling BnR-agonists coupled to antimicrobial cytotoxic-peptides showed enhanced cytotoxicity for breast-cancer-cells[93]. A doxorubicin-containing Bn-conjugated-analogue, AN-215,has been studied in a number of different cancers and shown to have antitumor activity in cancers of the pancreas, lung, prostate, colon, ovary, endometrium, breast,stomach,and CNS(glioblastomas)[16•,32].…”

Section: Imaging and Targeted-delivery Of Cytotoxic-agents To Neopmentioning

confidence: 99%

Bombesin related peptides/receptors and their promising therapeutic roles in cancer imaging, targeting and treatment

Moreno

Ramos-Álvarez

Moody

et al. 2016

Expert Opinion on Therapeutic Targets

102

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Introduction Despite remarkable advances in tumor treatment, many patients still die from common tumors (breast, prostate, lung, CNS, colon, and pancreas), and thus, new approaches are needed. Many of these tumors synthesize bombesin (Bn)-related peptides and over-express their receptors (BnRs), hence functioning as autocrine-growth-factors. Recent studies support the conclusion that Bn-peptides/BnRs are well-positioned for numerous novel antitumor treatments, including interrupting autocrine-growth via the use of over-expressed receptors for imaging and targeting cytotoxic-compounds, either by direct-coupling or combined with nanoparticle-technology. Areas covered The unique ability of common neoplasms to synthesize, secrete, and show a growth/proliferative/differentiating response due to BnR over-expression, is reviewed, both in general and with regard to the most frequently investigated neoplasms (breast, prostate, lung, and CNS). Particular attention is paid to advances in the recent years. Also considered are the possible therapeutic approaches to the growth/differentiation effect of Bn-peptides, as well as the therapeutic implication of the frequent BnR over-expression for tumor-imaging and/or targeted-delivery. Expert opinion Given that Bn-related-peptides/BnRs are so frequently ectopically-expressed by common tumors, which are often malignant and become refractory to conventional treatments, therapeutic interventions using novel approaches to Bn-peptides and receptors are being explored. Of particular interest is the potential of reproducing BnRs in common tumors, such as the recent success of utilizing overexpression of somatostatin-receptors by neuroendocrine-tumors to provide the most sensitive imaging methods and targeted delivery of cytotoxic-compounds.

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Section: Imaging and Targeted-delivery Of Cytotoxic-agents To Neopmentioning

confidence: 99%

Bombesin related peptides/receptors and their promising therapeutic roles in cancer imaging, targeting and treatment

Moreno

Ramos-Álvarez

Moody

et al. 2016

Expert Opinion on Therapeutic Targets

102

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“…The former include coupling Bn analogues to iron oxide nanoparticles for enhancing sensitivity of magnetic resonance imaging [125,204], to various fluorescent molecules which can be used for in vivo imaging [41,173,187,222] or to nanorods containing a photoacoustic imaging moieties [108]. Potentially cytotoxic compounds include coupling Bn analogues to chemotherapeutic agents [camptothecin [88,227,232], doxorubicin [240,241,258], paclitaxel [303,304]]; marine toxins [230]; to diphtheria toxin [360]; to mitochondria-disruptive peptides [40]; to agents that activate polyclonal T lymphocytes [398]; coupled to other immunotherapeutic agents that lead to cell death [48,49]; to photosensitizers [73,73,236,282] and to siRNA or adenoviral delivery vectors[116,242,308,374,375,375]. In addition BnR agonists have been one of the main targeting agents coupled to various nanoparticle carriers to assess delivery [44,342] or for targeted delivery of various cytotoxic agents including chemotherapeutic agents [docataxel [157], doxorubicin [1,3]]; radiolabeled analogues [140]; or gold nanoparticles [45].…”

Section: Bnr Function In Disease and A Therapeutic Target (Table 3)mentioning

confidence: 99%

Insights into bombesin receptors and ligands: Highlighting recent advances

et al. 2015

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This following article is written for Prof. Abba Kastin’s Festschrift, to add to the tribute to his important role in the advancement of the role of peptides in physiological, as well as pathophysiological processes. There have been many advances during the 35 years of his prominent role in the Peptide field, not only as editor of the journal Peptides, but also as a scientific investigator and editor of two volumes of the Handbook of Biological Active Peptides [146,147]. Similar to the advances with many different peptides, during this 35 year period, there have been much progress made in the understanding of the pharmacology, cell biology and the role of (Bombesin) Bn receptors and their ligands in various disease states, since the original isolation of bombesin from skin of the European frog Bombina bombina in 1970 [76]. This paper will briefly review some of these advances over the time period of Prof Kastin 35 years in the peptide field concentrating on the advances since 2007 when many of the results from earlier studies were summarized [128,129]. It is appropriate to do this because there have been 280 articles published in Peptides during this time on Bombesin-related peptides and it accounts for almost 5% of all publications. Furthermore, 22 Bn publications we have been involved in have been published in either Peptides [14,39,55,58,81,92,93,119,152,216,225,226,231,280,302,309,355,361,362] or in the Prof Kastin’s Handbook of Biological Active Peptides [137,138,331].

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“…The resulting conjugate proved to be selective and upon light irradiation cytotoxic on integrin over‐expressing cells, showing the possibility of using the same conjugate as both PDT and PET agent . This conjugate represents an improvement of the strategy previously reported by Mukai et al in which the conjugate between a tumor targeting peptide (a bombesin analogue, Table , entry 26) and a 64 Cu radiolabelled porphyrin was prepared as PET agent to evaluate in vivo the pharmacokinetics of the PS prior of the PDT treatment. Porphyrin chelation with paramagnetic isotopes, such 64 Cu, quenches the therapeutic action of the PS, requiring use of the unmetallated porphyrin as the treatment agent.…”

Section: Tumor Photodynamic Therapymentioning

confidence: 79%

Porphyrin–peptide conjugates in biomedical applications

Biscaglia

Gobbo

2018

Peptide Science

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The conjugation of peptides to porphyrins and related tetrapyrrole based macrocycles have extended their applications in biological systems, where the photophysical properties of these molecules and their ability to coordinate metals can be exploited for detecting and opposing to the onset of important diseases. This review presents a survey of the published literature over last years on biomedical applications of these hybrid compounds, mostly in the field of photodynamic therapy (PDT), but also in sensing key metabolites and peculiar structures of biomolecules in living systems. Peptides based strategies to improve the efficacy of the photosensitizer (PS) in PDT will be discussed, as well as solutions to overcome some limitations recently emerged in the use of peptides as delivery vehicles. An overview on possible application of porphyrin–peptide conjugates in detection of biomarkers of physiological and pathological states will be also presented.

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The synthesis of 64Cu-chelated porphyrin photosensitizers and their tumor-targeting peptide conjugates for the evaluation of target cell uptake and PET image-based pharmacokinetics of targeted photodynamic therapy agents

Cited by 32 publications

References 38 publications

Bombesin related peptides/receptors and their promising therapeutic roles in cancer imaging, targeting and treatment

Bombesin related peptides/receptors and their promising therapeutic roles in cancer imaging, targeting and treatment

Insights into bombesin receptors and ligands: Highlighting recent advances

Porphyrin–peptide conjugates in biomedical applications

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