Pharmaceutical development and medical applications of porphyrin-type macrocycles

Mody, Tarak D.

doi:10.1002/(sici)1099-1409(200006/07)4:4<362::aid-jpp250>3.0.co;2-z

Cited by 80 publications

(19 citation statements)

References 57 publications

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“…Porphyrins and their derivatives are a group of conjugated planar molecules that possess broad applications in the field of biomedical science, materials chemistry, and electrochemistry due to their unique spectroscopic properties and electrochemical performance (11)(12)(13)(14). Of particular interest for biomedical science is their significant role in therapies that are associated with microbial infection and tumor therapies (15)(16).…”

Section: Introductionmentioning

confidence: 99%

Broad-spectrum antivirals of protoporphyrins inhibit the entry of highly pathogenic emerging viruses

Pan

Chen

et al. 2020

Preprint

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Severe emerging and re-emerging viral infections such as Lassa fever, Avian influenza (AI), and COVID-19 caused by SARS-CoV-2 urgently call for new strategies for the development of broad-spectrum antivirals targeting conserved components in the virus life cycle. Viral lipids are essential components, and viral-cell membrane fusion is the required entry step for most unrelated enveloped viruses. In this paper, we identified a porphyrin derivative of protoporphyrin IX (PPIX) that showed broad antiviral activities in vitro against a panel of enveloped pathogenic viruses including Lassa virus (LASV), Machupo virus (MACV), and SARS-CoV-2 as well as various subtypes of influenza A viral strains with IC 50 values ranging from 0.91±0.25 μ M to 1.88±0.34μ M. A mechanistic study using influenza A/Puerto Rico/8/34 (H1N1) as a testing strain showed that PPIX inhibits the infection in the early stage of virus entry through biophysically interacting with the hydrophobic lipids of enveloped virions, thereby inhibiting the formation of the negative curvature required for fusion and blocking the entry of enveloped viruses into host cells. In addition, the preliminary antiviral activities of PPIX were further assessed by testing mice infected with the influenza A/Puerto Rico/8/34 (H1N1) virus. The results showed that compared with the control group without drug treatment, the survival rate and mean survival time of the mice treated with PPIX were apparently prolonged. : bioRxiv preprint 3 encourage us to conduct further investigations using PPIX as a lead compound for the rational design of lipid-targeting antivirals for the treatment of infection with enveloped viruses.

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Section: Introductionmentioning

confidence: 99%

Broad-spectrum antivirals of protoporphyrins inhibit the entry of highly pathogenic emerging viruses

Pan

Chen

et al. 2020

Preprint

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“…The conjugation of the carboxylic group of porphyrin 5 or 6 with methyl esters of aliphatic and aromatic amino acids was performed with the use of Boc 2 O in pyridine to afford serine- (7,9), valine-(8), tryptophan-(10) and tyrosine- (11) substituted derivatives in 40-80% yields.…”

Section: Resultsmentioning

confidence: 99%

“…We also obtained amino acid conjugates of boronated protohemin 11 (12) containing anionic closo-monocarbon carborane as substituent. At concentrations that caused no dark toxicity, 12 was highly efficient in photodynamic treatment of transplanted rat M-1 sarcoma 11 .…”

Section: Resultsmentioning

confidence: 99%

“…At concentrations that caused no dark toxicity, 12 was highly efficient in photodynamic treatment of transplanted rat M-1 sarcoma 11 .…”

Section: Resultsmentioning

confidence: 99%

“…The solvents were purified according to standard procedures. Cell culture, drug treatment and cytotoxicity assays were performed as described 11 . Cytotoxicity of novel compounds was tested in MTT-test as described 14 Di-tert-butyl dicarbonate (22 mg, 0.1 mmol) was added to a solution of porphyrin 12 (0.07 mmol) in CH 2 Cl 2 (4 ml) and Py (4 ml) at 0°C followed by stirring for 15 min.…”

Section: Methodsmentioning

confidence: 99%

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Boronated Conjugates of Protohemin IX with L-Amino Acids: Synthesis and Antitumor Activity

Ol’shevskaya

Savchenko

Gorshkov

et al. 2007

Collect. Czech. Chem. Commun.

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We report the synthesis of novel conjugates of protohemin IX with neutral and anionic boron polyhedra and L-amino acids. The amino acids are linked to the porphyrin macrocycle via the amide or ester bond. The serine containing boronated protohemin was the most cytotoxic for K562 human leukemia cell line. This compound interacted with doublestranded DNA in vitro and caused apoptosis of tumor cells including those that are resistant to several chemotherapeutic drugs.Porphyrins accumulate predominantly in tumor cells. This valuable feature makes natural and synthetic porphyrins attractive for conjugation with boron compounds and useful for boron neutron capture therapy of cancer (BNTC) 1,2 . Boronated porphyrins have been recently proposed to be employed for delivery of boron to tumors in BNTC and as photosensitizers in photodynamic therapy (PDT) 3,4 . Furthermore, boronated porphyrins can be visualized in cells and tissues by fluorescent microscopy. In the cells boronated porphyrins can interact with DNA due to their planar structure 5,6 . These characteristics together with physical treatments (thermal

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Supramolecular Chemistry

Cragg¹

2006

Kirk-Othmer Encyclopedia of Chemical Technology

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Supramolecular chemistry has its origins in the supermolecule, a term used by Nobel Laureate Jean‐Marie Lehn from the early 1970s when referring to a well‐defined chemical species comprising several components. The realization that supermolecules could in turn form larger molecular assemblies led to the shift in emphasis from super‐ to supramolecular in the literature to more accurately describe the complexity of systems involved. Supramolecular chemistry has since advanced to include complexes between molecules with complementary binding sites (molecular recognition), multicomponent complexes (supramolecular assemblies), the programmed interactions between large molecular assemblies (molecular tectonics), and even the directed assembly of three‐dimensional solids (crystal engineering). This article sets out the concepts and aims of supramolecular chemistry, illustrates some of the early development in the field, considers the synthesis and structures of individual supramolecular synthons as well as supramolecular assemblies, and concludes with an assessment of current and anticipated applications in materials science, medicine, the interface with biology, molecular computing, nanomaterials, and nanomachines.

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Pharmaceutical development and medical applications of porphyrin-type macrocycles

Cited by 80 publications

References 57 publications

Broad-spectrum antivirals of protoporphyrins inhibit the entry of highly pathogenic emerging viruses

Broad-spectrum antivirals of protoporphyrins inhibit the entry of highly pathogenic emerging viruses

Boronated Conjugates of Protohemin IX with L-Amino Acids: Synthesis and Antitumor Activity

Supramolecular Chemistry

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