New polyethyleneglycol-functionalized texaphyrins: synthesis and in vitro biological studies

Wei, W.; Wang, Zhong; Mizuno, Toshihisa; Cortez, Cecilia; Fu, Lei; Sirisawad, Mint; Naumovski, Louie; Magda, Darren; Sessler, Jonathan L.

doi:10.1039/b515636j

Cited by 52 publications

(35 citation statements)

References 22 publications

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“…The electrochemistry of MGd in DMF has been described previously in the literature. [14] Therefore, we decided to carry out initial studies in DMF. An aqueous medium (PBS, pH = 7, 0.1 M KCl) was also used so as to allow comparisons with the RP-HPLC experiments described above.…”

Section: Resultsmentioning

confidence: 99%

Activation of Platinum(IV) Prodrugs By Motexafin Gadolinium as a Redox Mediator

Thiabaud

McCall

et al. 2016

Angew Chem Int Ed

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Water soluble platinum(IV) prodrugs, which proved kinetically stable to reduction in the presence of physiological concentration of ascorbate, were quickly reduced to their active form, oxaliplatin, when co-incubated with a macrocycle metallotexaphyrin (i.e., Motexafin Gadolinium (MGd)). The reduction of Pt(IV) to Pt(II) promoted by MGd occurs in cell culture as well, leading to an increase in the antiproliferative activity of the Pt(IV) species in question. The mediated effect is proportional to the concentration of MGd and gives rise to an enhancement when the prodrug is relatively hydrophilic. MGd is known to localize/accumulate preferentially in tumor tissues. Thus, the present “activation by reduction” approach may allow for the cancer-selective enhancement in the cytotoxicity of Pt(IV) prodrugs.

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Section: Resultsmentioning

confidence: 99%

Activation of Platinum(IV) Prodrugs By Motexafin Gadolinium as a Redox Mediator

Thiabaud

McCall

et al. 2016

Angew Chem Int Ed

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“…Also analogously to its all-pyrrole analogues, VilsmeierHaack-type bisformylation of 6 c is possible, generating 5 c in good yields (88 %). [21] Introduction of the formyl groups greatly stabilizes the compound, and 5 c can be kept for extended periods of time without decomposition. Among other things, the replacement of the a-pyrrole signals in the 1 H NMR spectrum of 6 c by aldehyde signals (at d = 9.45 ppm) and the characteristic n C=O signal at 1608 cm À1 in the IR spectrum of 5 c define the identity of this product.…”

Section: Wwwchemeurjorgmentioning

confidence: 99%

Schiff Base Macrocycles Containing Pyrroles and Pyrazoles

Katsiaouni¹,

Dechert²,

Briñas³

et al. 2008

Chemistry A European J

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A double nucleophilic substitution reaction of 3,5-bis(chloromethyl)pyrazole with pyrroles generates a novel pyrrole-pyrazole hybrid building block, the pyrazole analogue to tripyrrane. Vilsmeier-Haack formylation produces the corresponding dialdehyde, which was used in the formation of a series of nonaromatic Schiff base macrocycles. NMR and UV/Vis spectroscopy and single-crystal diffractometry were used to characterize the novel macrocycles. The solid-state structures of select free bases and protonated members of this class of macrocycles display a range of intra- and intermolecular hydrogen-bonding patterns that suggest their use in molecular-recognition systems. They also contain an acid-sensitive chromophore. Their acid-base and anion-recognition properties were ascertained; alas, only modest anion-selective spectroscopic signatures could be detected by using UV/Vis and (1)H NMR spectroscopy. The macrocycles proved resistant toward oxidation to their aromatic congeners. The pyrrole-pyrazole building blocks presented are potentially useful for the synthesis of a range of pyrazole analogues of all-pyrrole macrocycles.

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“…[17][18][19][20][21] The concept of using metal-based photocytotoxic agents originates from the medicinal use of organic dyes like Photofrin ® as photodynamic therapy (PDT) agents that selectively damage cancer cells in red light leaving the unexposed healthy cells unaffected. [22][23][24][25][26] PDT presents a non-invasive treatment modality of cancer as a viable alternative to chemotherapy. The metal-based PDT agents could alleviate problems associated with the porphyrin-based PDT agents that show prolonged skin toxicity and hepatotoxicity.…”

Section: Introductionmentioning

confidence: 99%

Terpyridine Oxovanadium(IV) Complexes of Phenanthroline Bases for Cellular Imaging and Photocytotoxicity in HeLa Cells

et al. 2011

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Oxovanadium(IV) complexes [VO(N‐N‐N)(N‐N)](NO3)2 (1–4) of (4′‐phenyl)‐2,2′:6′,2″‐terpyridine (ph‐tpy in 1 and 2) or (4′‐pyrenyl)‐2,2′:6′,2″‐terpyridine (py‐tpy in 3 and 4) having N‐N as 1,10‐phenanthroline (phen in 1 and 3) or dipyrido[3,2‐a:2′,3′‐c]phenazine (dppz in 2 and 4) are prepared and characterized. The crystal structure of 1 has VO2+ group in VN5O coordination geometry. The terpyridine ligand coordinates in a meridional binding mode. The phen ligand displays a chelating mode of binding with an N‐donor site trans to the vanadyl oxo group. The complexes show a d‐d band in the range of 710–770 nm in aqueous DMF (4:1 v/v). The complexes exhibit an irreversible VIV/VIII redox response near –1.0 V vs. SCE in aqueous DMF/0.1 M KCl. The complexes bind to CT DNA giving Kb values within 3.5 × 105 to 1.2 × 106 M–1. The complexes show poor chemical nuclease activity in dark. Complexes 2–4 show photonuclease activity in UV‐A light of 365 nm forming 1O2 and ·OH. Complex 4 shows DNA photocleavage activity at near‐IR light of 785 nm forming ·OH radicals. Complexes 2 and 4 show significant photocytotoxicity in HeLa cancer cells. Uptake of the complexes in HeLa cells, studied by fluorescence imaging, show predominantly cytosolic localization inside the cells.

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New polyethyleneglycol-functionalized texaphyrins: synthesis and in vitro biological studies

Cited by 52 publications

References 22 publications

Activation of Platinum(IV) Prodrugs By Motexafin Gadolinium as a Redox Mediator

Activation of Platinum(IV) Prodrugs By Motexafin Gadolinium as a Redox Mediator

Schiff Base Macrocycles Containing Pyrroles and Pyrazoles

Terpyridine Oxovanadium(IV) Complexes of Phenanthroline Bases for Cellular Imaging and Photocytotoxicity in HeLa Cells

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