Dual activity of amphiphilic Zn(II) nitroporphyrin derivatives as HIV-1 entry inhibitors and in cancer photodynamic therapy

Sengupta, Devashish; Timilsina, Uddhav; Mazumder, Zeaul Hoque; Mukherjee, Avinaba; Ghimire, Dibya; Markandey, Manasvini; Upadhyaya, Kalpana; Sharma, Debdulal; Mishra, Nawneet; Jha, Tarun; Basu, Samita; Gaur, Ritu

doi:10.1016/j.ejmech.2019.04.051

Cited by 37 publications

(31 citation statements)

References 37 publications

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“…and their chemical and thermal stability [16][17][18][19][20][21][22][23][24]. Natural porphyrins and their synthetic analogues are widely used as photosensitizers for the photodynamic therapy (PDT) of neoplasms [25][26][27][28][29] and the photodynamic inactivation (PDI) of microorganisms, such as viruses [30][31][32][33][34], bacteria [35][36][37][38] and fungi [39,40].…”

Section: Introductionmentioning

confidence: 99%

“…Synthetic porphyrins with positive-charged groups have shown antiviral and antibacterial effects directly depending on their structure [31,33,35]. The cationic charge of the molecule promotes the electrostatic binding of porphyrin to the outer surface of the bacterial cell.…”

Section: Introductionmentioning

confidence: 99%

“…Porphyrins with pyridinium residues are especially interesting in this regard. The use of cationic 5,10,15,20tetrakis (4-methylpyridine-4-yl)porphyrin (TMePyP) and its derivatives against HIV [33,43], bacteriophage MS2 [44], T7 [45] and hepatitis A virus [46] is also known. Elsewhere [31,32], the photoinduced activity of TMePyP derivatives against HSV-1 and HSV-2 have also been shown.…”

Section: Introductionmentioning

confidence: 99%

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Novel Cationic Meso-Arylporphyrins and Their Antiviral Activity against HSV-1

et al. 2021

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This work is devoted to the search for new antiherpes simplex virus type 1 (HSV-1) drugs among synthetic tetrapyrroles and to an investigation of their antiviral properties under nonphotodynamic conditions. In this study, novel amphiphilic 5,10,15,20-tetrakis(4-(3-pyridyl-n-propanoyl)oxyphenyl)porphyrin tetrabromide (3a), 5,10,15,20-tetrakis(4-(6-pyridyl-n-hexanoyl)oxyphenyl)porphyrin tetrabromide (3b) and known 5,10,15,20-tetrakis(1-methyl-4-pyridinio)porphyrin tetraiodide (TMePyP) were synthesized, and their dark antiviral activity in vitro against HSV-1 was studied. The influence of porphyrin’s nanosized delivery vehicles based on Pluronic F127 on anti-HSV-1 activity was estimated. All the received compounds 3a, 3b and TMePyP showed virucidal efficiency and had an effect on viral replication stages. The new compound 3b showed the highest antiviral activity, close to 100%, with the lowest concentration, while the maximum TMePyP activity was observed with a high concentration; porphyrin 3a was the least active. The inclusion of the synthesized compounds in Pluronic F-127 polymeric micelles had a noticeable effect on antiviral activity only at higher porphyrin concentrations. Action of the received compounds differs by influence on the early or later reproduction stages. While 3a and TMePyP acted on all stages of the viral replication cycle, porphyrin 3b inhibited viral replication during the early stages of infection. The resulting compounds are promising for the development of utilitarian antiviral agents and, possibly, medical antiviral drugs.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Novel Cationic Meso-Arylporphyrins and Their Antiviral Activity against HSV-1

et al. 2021

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“…A comparison of the results of studies [ 12 , 13 ] allows us to conclude that the charge of porphyrins and their analogues is not determining in linking with viral gp120, since both cationic [ 12 ] and anionic [ 13 ] porphyrins showed a similar high virucidal activity. It can be assumed that the electrostatic interactions in the MGC-gp120 system are not significant, and it is logical, since the outer part of gp120 consists of sites that are very variable and carry multiple sugars (the basis for the virus to evade the immune response to this protein in the body).…”

Section: Porphyrins and Their Analogues Structurementioning

confidence: 99%

The Application of Porphyrins and Their Analogues for Inactivation of Viruses

et al. 2020

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The problem of treating viral infections is extremely relevant due to both the emergence of new viral diseases and to the low effectiveness of existing approaches to the treatment of known viral infections. This review focuses on the application of porphyrin, chlorin, and phthalocyanine series for combating viral infections by chemical and photochemical inactivation methods. The purpose of this review paper is to summarize the main approaches developed to date in the chemical and photodynamic inactivation of human and animal viruses using porphyrins and their analogues and to analyze and discuss the information on viral targets and antiviral activity of porphyrins, chlorins, of their conjugates with organic/inorganic compounds obtained in the last 10–15 years in order to identify the most promising areas.

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“…Therefore, the research of blocking human immunodeficiency virus infection from the source and preventing the occurrence of the disease is necessary. Contemporarily, antiretrovirals are the best option for maximal viral suppression, which include reverse transcriptase inhibitors, integrase strand transfer inhibitors, protease inhibitors, and entry inhibitors (CCR5 antagonists and fusion inhibitors) [6–9]. HIV fusion inhibitors can effectively block HIV from getting into and infecting CD 4 + T cells, which stops HIV multiplication in the human body at the first stage and exerts greater preventive effect [10,11].…”

Section: Introductionmentioning

confidence: 99%

Preparation and evaluation of amphipathic lipopeptide‐loaded PLGA microspheres as sustained‐release system for AIDS prevention

Jin

Chong

Zhu

et al. 2020

Engineering in Life Sciences

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At present, AIDS drugs are typical inhibitors that cannot achieve permanent effects. Therefore, the research of blocking HIV infection is essential. Especially for people in the high‐risk environment, long‐term prevention is important, because HIV can easily infect cells once the drug is interrupted. However, there is still no long‐acting AIDS prevention drug approved. Hence, the purpose of this study is to prepare a fusion inhibitor loaded poly(d, l‐lactic‐co‐glycolic acid) (PLGA) microspheres as a sustained‐release system for long‐term AIDS prevention. As the HIV membrane fusion inhibitor (LP‐98) used in this research is amphiphilic lipopeptide, W1/O/W2 double‐emulsion method was chosen, and premix membrane emulsification technique was used for controlling the uniformity of particle size. Several process parameters that can impact drug loading efficiency were summarized: the concentration of LP‐98 and PLGA, and the preparation condition of primary emulsion. Finally, the microspheres with high loading efficiency (>8%) and encapsulation efficiency (>90%) were successfully prepared under optimum conditions. Pharmacokinetic studies showed that LP‐98‐loaded microspheres were capable to continuously release for 24 days in rats. This research can promote the application of sustained‐release microspheres in AIDS prevention, and the embedding technique used in this study can also provide references for the loading of other amphipathic drugs.

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Dual activity of amphiphilic Zn(II) nitroporphyrin derivatives as HIV-1 entry inhibitors and in cancer photodynamic therapy

Cited by 37 publications

References 37 publications

Novel Cationic Meso-Arylporphyrins and Their Antiviral Activity against HSV-1

Novel Cationic Meso-Arylporphyrins and Their Antiviral Activity against HSV-1

The Application of Porphyrins and Their Analogues for Inactivation of Viruses

Preparation and evaluation of amphipathic lipopeptide‐loaded PLGA microspheres as sustained‐release system for AIDS prevention

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