Porphyrin Analogues That Consist of Indole, Benzofuran, and Benzothiophene Subunits

2013 ◽  
Vol 2 (4) ◽  
pp. 312-319 ◽  
Author(s):  
Shoichi Nakamura ◽  
Takeshi Kondo ◽  
Satoru Hiroto ◽  
Hiroshi Shinokubo
Keyword(s):  
Porphyrin Analogues

A Brief Introduction to Porphyrin Compounds Used in Tumor Imaging and Therapies

2020 ◽  
Vol 20 ◽  
Author(s):  
Lili Pan ◽  
Yu Ma ◽  
Xiaoai Wu ◽  
Huawei Cai ◽  
Feng Qin ◽  
...  
Keyword(s):  
Tumor Imaging ◽  
Photoacoustic Imaging ◽  
Therapeutic Agents ◽  
Biochemical Properties ◽  
Therapeutic Effects ◽  
Future Prospects ◽  
Animal Tissues ◽  
Sonodynamic Therapy ◽  
Porphyrin Derivatives ◽  
Porphyrin Analogues

Abstract:: As a group of heterocyclic macrocycle organic natural compounds occurring universally in animal tissues and plants, porphyrins are composed of four modified pyrrole subunits. Porphyrin analogues/derivatives possess multiple biochemical properties because of their unique structures and have been extensively investigated in cancer treatment. Studies have shown that porphyrins and their derivatives have the ability to locate in tumor cells in a variety of human cancers, and these compounds not only exhibit potent therapeutic effects as photodynamic agents but also show promising properties in medicinal imaging, such as MRI, photoacoustic imaging, fluorescence imaging and PET/SPECT imaging. This paper reviews the recent reports of porphyrin derivatives as therapeutic agents used in tumor therapies, such as sonodynamic therapy, photodynamic therapy and radiotherapy, as well as imaging agents for multimodality tumor imaging. The limitations of porphyrin-based compounds in tumor treatments and future prospects are also summarized.

Photophysical Analysis of 1,10-Phenanthroline-Embedded Porphyrin Analogues and Their Magnesium(II) Complexes

2012 ◽  
Vol 18 (45) ◽  
pp. 14329-14341 ◽  
Author(s):  
Masatoshi Ishida ◽  
Jong Min Lim ◽  
Byung Sun Lee ◽  
Fumito Tani ◽  
Jonathan L. Sessler ◽  
...  
Keyword(s):  
Porphyrin Analogues

Heteroatom-Containing Porphyrin Analogues

2016 ◽  
Vol 117 (4) ◽  
pp. 3254-3328 ◽  
Author(s):  
Tamal Chatterjee ◽  
Vijayendra S. Shetti ◽  
Ritambhara Sharma ◽  
Mangalampalli Ravikanth
Keyword(s):  
Porphyrin Analogues

Synthesis and structural properties of porphyrin analogues of bacteriochlorophyll c

Tetrahedron ◽  
2007 ◽  
Vol 63 (51) ◽  
pp. 12629-12638 ◽  
Author(s):  
Marcin Ptaszek ◽  
Zhen Yao ◽  
Dhanalekshmi Savithri ◽  
Paul D. Boyle ◽  
Jonathan S. Lindsey
Keyword(s):  
Structural Properties ◽  
Bacteriochlorophyll C ◽  
Porphyrin Analogues

Synthetic and structural studies on metal complexes of tripyrrin

2003 ◽  
Vol 07 (01) ◽  
pp. 17-24 ◽  
Author(s):  
Martin Bröring ◽  
Carsten D. Brandt ◽  
Serguei Prikhodovski
Keyword(s):  
Transition Metal ◽  
Metal Complexes ◽  
Metal Ion ◽  
Coordination Geometry ◽  
Structural Studies ◽  
Structural Investigations ◽  
Coordination Polyhedra ◽  
X Ray ◽  
Step Procedure ◽  
Porphyrin Analogues

A general two-step procedure for the synthesis of metallotripyrrinates TrpyMOAc f with M = Co(II) , Cu(II) , Zn(II) and Pd(II) , and OAc f = trifluoroacetate, is described, starting from well-known monopyrrolic precursors and simple transition metal acetates. X-ray structural investigations were undertaken on four different complexes, and the results reveal, that the nature of the metal ion, rather than the ligand, determines the coordination geometry of these porphyrin fragment complexes. The finding of pseudotetrahedral and strained pseudoplanar coordination polyhedra at the metal centres makes a clear distinction between metalloporphyrins and metallotripyrrins and shows the latter to be related to some recently discovered metal chelates of macrocyclic porphyrin analogues.

Modification of the porphyrin chromophore by ring fusion: identifying trends due to annelation of the porphyrin nucleus

2001 ◽  
Vol 05 (03) ◽  
pp. 267-288 ◽  
Author(s):  
TIMOTHY D. LASH
Keyword(s):  
Soret Band ◽  
Spectral Shift ◽  
Aromatic Rings ◽  
Ring Fusion ◽  
Spectral Shifts ◽  
Hyper Spectral ◽  
Two Factors ◽  
Porphyrin Analogues ◽  
Soret Absorption ◽  
Soret Region

The effects exerted by fused aromatic rings on the UV-vis spectra of porphyrins are surveyed. Modified porphyrin chromophores with fused benzene, 1,2-naphthalene, 9,10-phenanthrene or phenanthroline rings are surprisingly little affected even when a maximum number of ring fusions are incorporated. Linearly annealed naphtho- or anthraporphyrins show large red shifts to the Q bands but the Soret absorptions are weakened and undergo only minor bathochromic shifts. Fluoranthoporphyrins give multiple bands in the Soret region, but the Q band region is virtually unaffected by this tetracyclic ring system. On the other hand, metal chelates of fluoranthoporphyrins show surprisingly strong bands near 600 nm. Benzothiadiazole rings split and weaken the Soret band, but the Q bands region is unexceptional. However, metal coordination again produces relatively intense bands near 600 nm. The most significant results were obtained for porphyrins with fused acenaphthylene rings. Monoacenaphthoporphyrins (41) have three Soret bands at 387, 431 and 454 nm, and the longest wavelength Q band is shifted to 658 nm. opp-Diacenaphthoporphyrin (43) further shifts these bands with two Soret absorbances at 443 and 470 nm, and an additional strong peak is observed at 692 nm. The metal complexes of these systems also show strong bands between 602 and 656 nm. Still larger effects are produced by tetraacenaphthoporphyrin (47), the dication for which in trifluoroacetic acid (TFA)–chloroform has a Soret absorption at 528 nm. Tetraaryltetraacenaphthoporphyrins (48) are even more red shifted, showing Soret bands between 556 and 570 nm for the free bases and 565 to 588 nm for the related dications. The lead(II) chelate for tetraphenylporphyrin (48a) shows an additional 'hyper' spectral shift that brings the Soret band to 604 nm, and this effect can also be achieved by introducing four meso-phenylethynyl substituents onto the tetraacenaphthoporphyrin nucleus (49). In addition, by combining these two factors for the lead(II) chelate of 49, a record-breaking value for the Soret band of 642 nm can be achieved. Spectral shifts due to ring annelation in porphyrin analogues are also discussed, including those for oxybenziporphyrins, oxypyriporphyrins, carbaporphyrins and sapphyrins.

Development of Ion Chemosensors Based on Porphyrin Analogues

2016 ◽  
Vol 117 (4) ◽  
pp. 2203-2256 ◽  
Author(s):  
Yubin Ding ◽  
Wei-Hong Zhu ◽  
Yongshu Xie
Keyword(s):  
Porphyrin Analogues

Molecular “Texas Longhorn”: An expanded Schiff base oligopyrrolic macrocycle

2021 ◽  
pp. A-G
Author(s):  
Chenxing Guo ◽  
Vincent M. Lynch ◽  
Jonathan L. Sessler
Keyword(s):  
Schiff Base ◽  
Solid State ◽  
Structural Characterization ◽  
Building Blocks ◽  
State Structure ◽  
Architectural Form ◽  
Molecular Building Blocks ◽  
Texas Longhorn ◽  
Porphyrin Analogues

We report here the synthesis and structural characterization of a novel expanded Schiff base oligopyrrolic macrocycle TxLH (i.e. compound 2) along with its smaller congener hemi-TxLH (i.e. compound 1). The solid-state structure of TxLH is reminiscent of the shape of a Texas Longhorn[Formula: see text]. It thus defines a new architectural form for porphyrin analogues. The present study thus underscores the potential of using functionalized oligopyrroles as readily accessible molecular building blocks for the construction of structurally non-trivial molecules.

Molecular orbitals and electronic spectra of benzo-fused and related porphyrin analogues

2001 ◽  
Vol 05 (03) ◽  
pp. 233-255 ◽  
Author(s):  
NAGAO KOBAYASHI ◽  
HIDEO KONAMI
Keyword(s):  
Molecular Structure ◽  
Molecular Orbital ◽  
Electronic Spectra ◽  
Molecular Orbitals ◽  
Systematic Change ◽  
Mo Calculations ◽  
Porphyrin Analogues

Molecular orbital (MO) calculations of more than 60 porphyrinic π conjugated structures have been performed within the framework of the Pariser–Parr–Pople approximation. The results of a series of compounds are introduced and summarized in order to show how they vary depending on the systematic change in molecular structure. These are shown schematically or itemized. Our results are compared with the spectra of the corresponding known compounds and with the MO results reported by previous workers, if available. In addition, the results have continually been compared, where possible, with those of tetraazaporphyrin or phthalocyanine systems. In naphthalene- or anthracene-fused compounds, these molecule-centered orbitals often appear, and these are indicated using either triangles or circles in figures if they appear between HOMO – 3 and LUMO + 3 orbitals.

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