Design, Synthesis, Biological Evaluation of New Porphyrin and Metalloporphyrin Derivatives

References

• C. P. Tidwell, P. Bharara, G. Rudeseal, T. Rudeseal, F. H. Rudeseal, C. A. Simmer, D. McMillan, K. Lanier, D. Fondren, L. L. Folmar, et al, “Synthesis and Characterization of 5, 10, 15, 20-Tetra [3-(3-Trifluoromethyl) Phenoxy],” Molecules 12, no. 7 (2007): 1389–98.
   PubMed Web of Science ®Google Scholar
• C. Spangler, “Fluorimetric and Mass-spectrometric Methods for Analysis of GTP-converting Signal-transducing Proteins and Enzymes” (Doctoral dissertation, 2010). Thesis of the University of Regensburg (PhD); Chemistry and Pharmacy > Institut für Analytische Chemie, Chemo- und Biosensorik
   Google Scholar
• K. I. Ozoemena, “Anodic Oxidation and Amperometric Sensing of Hydrazine at a Glassy Carbon Electrode Modified with Cobalt (II) Phthalocyanine–Cobalt (II) Tetraphenylporphyrin (CoPc-(CoTPP) 4) Supramolecular Complex,” Sensors 6, no. 8 (2006): 874–91.
   Web of Science ®Google Scholar
• O. Ikeda, K. Yoshinaga, and J. Lei, “Nitric Oxide Detection with Glassy Carbon Electrodes Coated with Charge-Different Polymer Films,” Sensors 5, no. 4 (2005): 161–70.
   Web of Science ®Google Scholar
• J. Yu, X. Wang, B. Zhang, Y. Weng, and L. Zhang, “Prolonged Excited-State Lifetime of Porphyrin Due to the Addition of Colloidal SiO2 to Triton X-100 Micelles,” Langmuir 20, no. 5 (2004): 1582–6.
   Web of Science ®Google Scholar
• E. De Clercq, “The Role of Non-Nucleoside Reverse Transcriptase Inhibitors (NNRTIs) in the Therapy of HIV-1 Infection,” Antiviral Research 38, no. 3 (1998): 153–79.
   PubMed Web of Science ®Google Scholar
• E. De Clercq and G. Li, “Approved Antiviral Drugs over the past 50 Years,” Clinical Microbiology Reviews 29, no. 3 (2016): 695–747.
   PubMed Web of Science ®Google Scholar
• K. J. Barnham, C. L. Masters, and A. I. Bush, “Neurodegenerative Diseases and Oxidative Stress,” Nature Reviews. Drug Discovery 3, no. 3 (2004): 205–14.
   PubMed Web of Science ®Google Scholar
• M. S. Cooke, M. D. Evans, M. Dizdaroglu, and J. Lunec, “Oxidative DNA Damage: mechanisms, Mutation, and Disease,” FASEB Journal 17, no. 10 (2003): 1195–214. b) T. Finkel and N. J. Holbrook. “Oxidants, Oxidative Stress and the Biology of Ageing,” Nature; 408, no. 6809 (2000), 239–47.‏
   PubMed Web of Science ®Google Scholar
• C. Frochot and S. Mordon, “Update of the Situation of Clinical Photodynamic Therapy in Europe in the 2003–2018 Period,” Journal of Porphyrins and Phthalocyanines 23, no. 04n05 (2019), 347–357.
   Google Scholar
• Y. J. Cai, L. P. Ma, L. F. Hou, B. Zhou, L. Yang, and Z. L. Liu, “Antioxidant Effects of Green Tea Polyphenols on Free Radical Initiated Peroxidation of Rat Liver Microsomes,” Chemistry and Physics of Lipids 120, no. 1–2 (2002): 109–17.
   PubMed Web of Science ®Google Scholar
• A. N. Vzorov, D. W. Dixon, J. S. Trommel, L. G. Marzilli, and R. W. Compans, “Inactivation of Human Immunodeficiency Virus Type 1 by Porphyrins,” Antimicrobial Agents and Chemotherapy 46, no. 12 (2002): 3917–25.
   PubMed Web of Science ®Google Scholar
• K. A. Zhdanova, I. O. Savelyeva, A. V. Ezhov, A. P. Zhdanov, K. Y. Zhizhin, A. F. Mironov, N. A. Bragina, A. A. Babayants, I. S. Frolova, N. I. Filippova, et al, “Cationic Meso-Arylporphyrins and Their Antiviral Activity against HSV-1,” Pharmaceuticals 14, no. 3 (2021): 242.
   Web of Science ®Google Scholar
• D. Sengupta, U. Timilsina, Z. H. Mazumder, A. Mukherjee, D. Ghimire, M. Markandey, K. Upadhyaya, D. Sharma, N. Mishra, T. Jha, et al, “Dual Activity of Amphiphilic Zn (II) Nitroporphyrin Derivatives as HIV-1 Entry Inhibitors and in Cancer Photodynamic Therapy,” European Journal of Medicinal Chemistry 174 (2019): 66–75.
   PubMed Web of Science ®Google Scholar
• N. M. Moura, M. Esteves, C. Vieira, G. M. Rocha, M. A. Faustino, A. Almeida, J. A. Cavaleiro, C. Lodeiro, and M. G. Neves, “Novel β-Functionalized Mono-Charged Porphyrinic Derivatives: Synthesis and Photoinactivation of Escherichia coli,” Dyes and Pigments 160 (2019): 361–71.
   Web of Science ®Google Scholar
• E. Ruggiero, and S. N. Richter, “G-Quadruplexes and G-Quadruplex Ligands: targets and Tools in Antiviral Therapy,” Nucleic Acids Research 46, no. 7 (2018): 3270–83.
   PubMed Web of Science ®Google Scholar
• M. S. Rodríguez-Morgade, M. Planells, T. Torres, P. Ballester, and E. Palomares, “A Colorimetric Molecular Probe for Cu (ii) Ions Based on the Redox Properties of Ru (ii) Phthalocyanines,” Journal of Materials Chemistry. 18, no. 2 (2008): 176–81.
   Web of Science ®Google Scholar
• A. A. Fadda, E. El-Gendy, H. M. Refat, and E. H. Tawfik, “Utility of Dipyrromethane in the Synthesis of Some New A2B2 Porphyrin and Their Related Porphyrin like Derivatives with Their Evaluation as Antimicrobial and Antioxidant Agents,” Dyes and Pigments 191 (2021): 109008.
   Web of Science ®Google Scholar
• D. Holten, D. F. Bocian, and J. S. Lindsey, “Probing Electronic Communication in Covalently Linked Multiporphyrin Arrays. A Guide to the Rational Design of Molecular Photonic Devices,” Accounts of Chemical Research 35, no. 1 (2002): 57–69.
   PubMed Web of Science ®Google Scholar
• P. Rothemund, and A. R. Menotti, “Porphyrin Studies. IV. The Synthesis of α, β, γ, δ-Tetraphenylporphine,” Journal of the American Chemical Society 63, no. 1 (1941): 267–70.
   Google Scholar
• A. D. Adler, F. R. Longo, and W. Shergalis, “Mechanistic Investigations of Porphyrin Syntheses. I. Preliminary Studies on ms-Tetraphenylporphin,” Journal of the American Chemical Society 86, no. 15 (1964): 3145–9.
   Web of Science ®Google Scholar
• X. Huang, and J. T. Groves, “Oxygen Activation and Radical Transformations in Heme Proteins and Metalloporphyrins,” Chemical Reviews 118, no. 5 (2018): 2491–553.
   PubMed Web of Science ®Google Scholar
• P. M. R. Pereira, “Galactose-Conjugated Photosensitizers for Targeted Cancer Photodynamic Therapy” (Doctoral dissertation, Universidade de Aveiro (Portugal), 2018).‏
   Google Scholar
• W. Zhang, W. Lai, and R. Cao, “Energy-Related Small Molecule Activation Reactions: oxygen Reduction and Hydrogen and Oxygen Evolution Reactions Catalyzed by Porphyrin-and Corrole-Based Systems,” Chemical Reviews 117, no. 4 (2017): 3717–97.
   PubMed Web of Science ®Google Scholar
• Y. Ding, W.-H. Zhu, and Y. Xie, “Development of Ion Chemosensors Based on Porphyrin Analogues,” Chemical Reviews 117, no. 4 (2017): 2203–56.
   PubMed Web of Science ®Google Scholar
• A. J. Harte, and T. Gunnlaugsson, “Synthesis of α-Chloroamides in Water,” Tetrahedron Letters. 47, no. 35 (2006): 6321–4.
   Web of Science ®Google Scholar
• J. Micky, N. Saleh, S. Mohamed, S. Mohameda, and M. Salem, “Reaction and Antimicrobial Activity of 1-Arylethylene Benzofuranyl Ketone Derivatives,” CSIR 37, no. 40 (2006). doi:10.1002/chin.200640166
   Google Scholar
• C. A. Duckworth, “ Stable Emulsion Flowable Formulation of a 2-Chloroacetamide Herbicide and an Imidazolinone Herbicide” (U.S. Patent No. 5,538,938, Washington, DC: U.S. Patent and Trademark Office, 1996).
   Google Scholar
• T. Ikeuchi, T. Ohkawa, S. Ohno, Y. Yamaji, and Y. Ogawa, “Phytotoxicity Controlling Agent for Upland Farming and Phytotoxicity Controlling Method” (U.S. Patent No. 8,318,635. Washington, DC: U.S. Patent and Trademark Office, 2012.)
   Google Scholar
• F. Zaragoza, and H. Stephensen, “Solid-Phase Synthesis of Substituted 4-Acyl-1, 2, 3, 4-Tetrahydroquinoxalin-2-Ones,” The Journal of Organic Chemistry 64, no. 7 (1999): 2555–7.
   Web of Science ®Google Scholar
• G. Sirasani, and R. B. Andrade, “Sequential One-Pot Cyclizations: Concise Access to the ABCE Tetracyclic Framework of Strychnos Alkaloids,” Organic Letters 11, no. 10 (2009): 2085–8.
   PubMed Web of Science ®Google Scholar
• T. Kaoudi, L. D. Miranda, and S. Z. Zard, “An Easy Entry into Berbane and Alloyohimbane Alkaloids via a 6-Exo Radical Cyclization,” Organic Letters 3, no. 20 (2001): 3125–7.
   PubMed Web of Science ®Google Scholar
• M. J. Evans, and B. F. Cravatt, “Mechanism-Based Profiling of Enzyme Families,” Chemical Reviews 106, no. 8 (2006): 3279–301.
   PubMed Web of Science ®Google Scholar
• M. Shaul, G. Abourbeh, O. Jacobson, Y. Rozen, D. Laky, A. Levitzki, and E. Mishani, “Novel Iodine-124 Labeled EGFR Inhibitors as Potential PET Agents for Molecular Imaging in Cancer,” Bioorganic & Medicinal Chemistry 12, no. 13 (2004): 3421–9.
   PubMed Web of Science ®Google Scholar
• H. Tang, Z. Dong, Z. Merican, D. Margetić, Ž. Marinić, M. J. Gunter, R. N. Warrener, D. Officer, D. N. Butler, and R. N. Warrener, “Hinged Bis-Porphyrin Scaffolds I. The Synthesis of a New Porphyrin Diene and Its Role in Constructing Hinged Porphyrin Dyads and Cavity Systems,” Tetrahedron Letters. 50, no. 6 (2009): 667–70.
   Web of Science ®Google Scholar
• S. Rai, and M. Ravikanth, “Synthesis of Covalently Linked Unsymmetrical Porphyrin Pentads Containing Three Different Porphyrin Subunits,” The Journal of Organic Chemistry 73, no. 21 (2008): 8364–75.
   PubMed Web of Science ®Google Scholar
• C.-S. Chan, AK-S. Tse, and K. S. Chan, “Highly Versatile Methods for the Synthesis of Quinonylporphyrins via Benzannulation of Fischer Carbene Complexes and Palladium-Catalyzed Cross-Coupling Reactions,” The Journal of Organic Chemistry 59, no. 20 (1994): 6084–9.
   Web of Science ®Google Scholar
• A. A. Fadda, R. E. El‐Mekawy, A. I. El‐Shafei, and H.Freeman, “Synthesis and Pharmacological Screening of Novel Meso‐Substituted Porphyrin Analogs,” Archiv Der Pharmazie 346, no. 1 (2013): 53–61.
   PubMed Web of Science ®Google Scholar
• M. Amaravathi, M. M. Babu, and G. Chandramouli, “Synthesis of Meso-Tetrakis (2-Chloroquinolin-3-yl) Porphyrins,” Arkivoc 2007, no. 1 (2007): 148–53.
   Google Scholar
• A. Amer, W. I. El-Eraky, and S. Mahgoub, “Synthesis, Characterization and Antimicrobial Activity of Some Novel Quinoline Derivatives Bearing Pyrazole and Pyridine Moieties,” Egyptian Journal of Chemistry 0, no. 0 (2018): 0.
   Google Scholar
• A. S. Munde, A. N. Jagdale, S. M. Jadhav, and T. K. Chondhekar, “Synthesis and Characterization of Some Transition Metal Complexes of Unsymmetrical Tetradentate Schiff Base Ligand,” Journal of the Korean Chemical Society. 53, no. 4 (2009): 407–14.
   Google Scholar
• S. J. Thompson, M. R. Brennan, S. Y. Lee, and G. Dong, “Synthesis and Applications of Rhodium Porphyrin Complexes,” Chemical Society Reviews 47, no. 3 (2018): 929–981.
   PubMed Web of Science ®Google Scholar
• Z. Bıyıklıoğlu, H. Kantekin, and M. Özil, “Microwave-Assisted Synthesis and Characterization of Novel Metal-Free and Metallophthalocyanines Containing Four 14-Membered Tetraaza Macrocycles,” Journal of Organometallic Chemistry 692, no. 12 (2007): 2436–40.
   Web of Science ®Google Scholar
• M. Brewis, G. J. Clarkson, P. Humberstone, S. Makhseed, and N. B. McKeown, “The Synthesis of Some Phthalocyanines and Napthalocyanines Derived from Sterically Hindered Phenols,” Chemistry - A European Journal 4, no. 9 (1998): 1633–40.
   Web of Science ®Google Scholar
• (a) E. Manoj, M. P. Kurup, and A. Punnoose, “Preparation, Magnetic and EPR Spectral Studies of Copper (II) Complexes of an Anticancer Drug Analogue,” Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy 72, no. 3 (2009): 474–483.
   PubMed Web of Science ®Google Scholar
  (b) M. Nonoyama, “Five-Coordinate Nickel (II) and Copper (II) Complexes of Quinquedentate Acid Amides,” Inorganica Chimica Acta. 10 (1974): 59–63.
   Web of Science ®Google Scholar
• B. Singh, B. P. Yadava, and R. C. Aggarwal, “Synthesis & Characterization of 1-Phenyl-5-Benzoyl-4-Thiobiuret Complexes with Oxovanadium (IV), Cobalt (II & III), Nickel (II), Copper (II), Cadmium (II) & Mercury (II),” Indian Journal of Chemistry 23A (1984): 441–444.
   Google Scholar
• D. Kivelson and R. Neiman, “ESR Studies on the Bonding in Copper Complexes,” Journal of Chemical Physics. 35, no. 1 (1961): 149–55.
   Web of Science ®Google Scholar
• I. Procter, B. Hathaway, and P. Nicholls, “The Electronic Properties and Stereochemistry of the Copper (II) Ion. Part I. Bis (Ethylenediamine) Copper (II) Complexes,” Journal of the Chemical Society A: Inorganic, Physical, Theoretical (1968): 1678–84.
   Google Scholar
• B. Hathaway and D. Billing, “The Electronic Properties and Stereochemistry of Mono-Nuclear Complexes of the Copper (II) Ion,” Coordination Chemistry Reviews 5, no. 2 (1970): 143–207.
   Web of Science ®Google Scholar
• L. Zao-Ying, Z. Yue-Ning, X. Wei, Z. Xun-Jin, G. Zhen-Ting, and L. Yi, “Study on Synthesis and Biological Activities of Novel Water-Soluble Metalloporphyrins,” Wuhan University Journal of Natural Sciences 6, no. 4 (2001): 841–5.
   Google Scholar
• B. J. Day, I. Batinic-Haberle, and J. D. Crapo, “Metalloporphyrins Are Potent Inhibitors of Lipid Peroxidation,” Free Radical Biology & Medicine 26, no. 5–6 (1999): 730–736.
   PubMed Web of Science ®Google Scholar
• F. I. Abdullaev, “Cancer Chemopreventive and Tumoricidal Properties of Saffron (Crocus Sativus L.),” Experimental Biology and Medicine 227, no. 1 (2002): 20–525.
   Web of Science ®Google Scholar
• G. A. Cordell, C. K. Angerhofer, and J. M. Pezzuto, “Recent Studies on Cytotoxic, anti-HIV and Antimalarial Agents from Plants,” Pure and Applied Chemistry 66, no. 10–11 (1994): 2283–2286.
   Web of Science ®Google Scholar
• J. Singh, K. B. Ashok, R. Rajapandi, T. Ghosh, A. Mondal, and B. Maiti, “Synthesis and Anticancer Activity of Some 1, 3, 4-Oxadiazole Derivatives against Ehlirch Ascites Carcinoma Bearing Mice Model,” Asian Journal of Chemistry 22, no. 5 (2010): 4099–103.
   Google Scholar
• D. K. Dash, S. S. Nayak, S. Samanta, T. Ghosh, T. Jha, and B. C. Maiti, “Antitumor Activity and Antioxidant Role of Ichnocarpus Frutescens against Ehrlich Ascites Carcinoma in Swiss Albino Mice,” Natural Product Sciences. 13, no. 1 (2007): 54–60.
   Google Scholar
• G. Bischoff and S. Hoffmann, “DNA-Binding of Drugs Used in Medicinal Therapies,” Current Medicinal Chemistry 9, no. 3 (2002): 321–48.
   Web of Science ®Google Scholar
• R. Martinez and L. Chacon-Garcia, “The Search of DNA-Intercalators as Antitumoral Drugs: what It Worked and What Did Not Work,” Current Medicinal Chemistry 12, no. 2 (2005): 127–51.
   PubMed Web of Science ®Google Scholar
• E. Abdel-Latif, M. M. Fahad, and M. A. Ismail, “Synthesis of N-Aryl 2-Chloroacetamides and Their Chemical Reactivity towards Various Types of Nucleophiles,” Synthetic Communications. 50, no. 3 (2020): 289–314.
   Web of Science ®Google Scholar
• A. A. Fadda, R. E. El-Mekawy, and A. I. El-Shafei, “Synthesis, Antiviral, Cytotoxicity and Antitumor Evaluations of A4 Type of Porphyrin Derivatives,” Journal of Porphyrins and Phthalocyanines 19, no. 06 (2015): 753–768.
   Google Scholar