Flexible Synthesis of Cationic Peptide-porphyrin Derivatives for Light-triggered Drug Delivery and Photodynamic Therapy

Overview

Journal Org Biomol Chem

Publisher Royal Society of Chemistry

Specialties Biochemistry
Chemistry

Date 2016 Nov 26

PMID 27886311

Citations 13

Authors

R Dondi

E Yaghini

K M Tewari

L Wang

F Giuntini

M Loizidou

A J MacRobert

I M Eggleston

Affiliations

Soon will be listed here.

Abstract

Efficient syntheses of cell-penetrating peptide-porphyrin conjugates are described using a variety of bioconjugation chemistries. This provides a flexible means to convert essentially hydrophobic tetrapyrolle photosensitisers into amphiphilic derivatives which are well-suited for use in light-triggered drug delivery by photochemical internalisation (PCI) and targeted photodynamic therapy (PDT).

Citing Articles

Cellular Imaging and Time-Domain FLIM Studies of Meso-Tetraphenylporphine Disulfonate as a Photosensitising Agent in 2D and 3D Models.

Balukova A, Bokea K, Barber P, Ameer-Beg S, MacRobert A, Yaghini E Int J Mol Sci. 2024; 25(8).

PMID: 38673807 PMC: 11050357. DOI: 10.3390/ijms25084222.

Targeting Zika Virus with New Brain- and Placenta-Crossing Peptide-Porphyrin Conjugates.

Todorovski T, Mendonca D, Fernandes-Siqueira L, Cruz-Oliveira C, Guida G, Valle J Pharmaceutics. 2022; 14(4).

PMID: 35456572 PMC: 9032516. DOI: 10.3390/pharmaceutics14040738.

Synthesis and Applications of Porphyrin-Biomacromolecule Conjugates.

Pathak P, Zarandi M, Zhou X, Jayawickramarajah J Front Chem. 2021; 9:764137.

PMID: 34820357 PMC: 8606752. DOI: 10.3389/fchem.2021.764137.

Structural Investigations, Cellular Imaging, and Radiolabeling of Neutral, Polycationic, and Polyanionic Functional Metalloporphyrin Conjugates.

Ciaffaglione V, Waghorn P, Exner R, Cortezon-Tamarit F, Godfrey S, Sarpaki S Bioconjug Chem. 2021; 32(7):1374-1392.

PMID: 33525868 PMC: 8299459. DOI: 10.1021/acs.bioconjchem.0c00691.

Photoinduced Endosomal Escape Mechanism: A View from Photochemical Internalization Mediated by CPP-Photosensitizer Conjugates.

Soe T, Watanabe K, Ohtsuki T Molecules. 2020; 26(1).

PMID: 33374732 PMC: 7793540. DOI: 10.3390/molecules26010036.

References

Kaiser P, Boyer D, Cruess A, Slakter J, Pilz S, Weisberger A . Verteporfin plus ranibizumab for choroidal neovascularization in age-related macular degeneration: twelve-month results of the DENALI study. Ophthalmology. 2012; 119(5):1001-10. DOI: 10.1016/j.ophtha.2012.02.003. View

Ikawa Y, Harada H, Toganoh M, Furuta H . Synthesis and protonation behavior of a water-soluble N-fused porphyrin: conjugation with an oligoarginine by click chemistry. Bioorg Med Chem Lett. 2009; 19(9):2448-52. DOI: 10.1016/j.bmcl.2009.03.066. View

Pereira P, Korsak B, Sarmento B, Schneider R, Fernandes R, Tome J . Antibodies armed with photosensitizers: from chemical synthesis to photobiological applications. Org Biomol Chem. 2015; 13(9):2518-29. DOI: 10.1039/c4ob02334j. View

Wagner J, Mercadante D, Nikic I, Lemke E, Grater F . Origin of Orthogonality of Strain-Promoted Click Reactions. Chemistry. 2015; 21(35):12431-5. PMC: 4600239. DOI: 10.1002/chem.201501727. View

Meerovich I, Muthukrishnan N, Johnson G, Erazo-Oliveras A, Pellois J . Photodamage of lipid bilayers by irradiation of a fluorescently labeled cell-penetrating peptide. Biochim Biophys Acta. 2013; 1840(1):507-15. PMC: 3918956. DOI: 10.1016/j.bbagen.2013.10.011. View

Sultan A, Jerjes W, Berg K, Hogset A, Mosse C, Hamoudi R . Disulfonated tetraphenyl chlorin (TPCS2a)-induced photochemical internalisation of bleomycin in patients with solid malignancies: a phase 1, dose-escalation, first-in-man trial. Lancet Oncol. 2016; 17(9):1217-29. DOI: 10.1016/S1470-2045(16)30224-8. View

King M, Wagner A . Developments in the field of bioorthogonal bond forming reactions-past and present trends. Bioconjug Chem. 2014; 25(5):825-39. DOI: 10.1021/bc500028d. View

Maisch T . Anti-microbial photodynamic therapy: useful in the future?. Lasers Med Sci. 2006; 22(2):83-91. DOI: 10.1007/s10103-006-0409-7. View

Acherar S, Colombeau L, Frochot C, Vanderesse R . Synthesis of Porphyrin, Chlorin and Phthalocyanine Derivatives by Azide-Alkyne Click Chemistry. Curr Med Chem. 2015; 22(28):3217-54. DOI: 10.2174/0929867322666150716115832. View

10.

Martinez de Pinillos Bayona A, Moore C, Loizidou M, MacRobert A, Woodhams J . Enhancing the efficacy of cytotoxic agents for cancer therapy using photochemical internalisation. Int J Cancer. 2015; 138(5):1049-57. PMC: 4973841. DOI: 10.1002/ijc.29510. View

11.

Thandu M, Rapozzi V, Xodo L, Albericio F, Comuzzi C, Cavalli S . "Clicking" Porphyrins to Magnetic Nanoparticles for Photodynamic Therapy. Chempluschem. 2020; 79(1):90-98. DOI: 10.1002/cplu.201300276. View

12.

Kitagishi H, Hatada S, Itakura T, Maki Y, Maeda Y, Kano K . Cellular uptake of octaarginine-conjugated tetraarylporphyrin included by per-O-methylated β-cyclodextrin. Org Biomol Chem. 2013; 11(19):3203-11. DOI: 10.1039/c3ob27248f. View

13.

Sletten E, Bertozzi C . Bioorthogonal chemistry: fishing for selectivity in a sea of functionality. Angew Chem Int Ed Engl. 2009; 48(38):6974-98. PMC: 2864149. DOI: 10.1002/anie.200900942. View

14.

Muthukrishnan N, Donovan S, Pellois J . The photolytic activity of poly-arginine cell penetrating peptides conjugated to carboxy-tetramethylrhodamine is modulated by arginine residue content and fluorophore conjugation site. Photochem Photobiol. 2014; 90(5):1034-42. PMC: 4855509. DOI: 10.1111/php.12288. View

15.

Jinadasa R, Zhou Z, Vicente M, Smith K . Syntheses and cellular investigations of di-aspartate and aspartate-lysine chlorin e(6) conjugates. Org Biomol Chem. 2015; 14(3):1049-64. PMC: 4701634. DOI: 10.1039/c5ob02241j. View

16.

Valeur E, Bradley M . Amide bond formation: beyond the myth of coupling reagents. Chem Soc Rev. 2009; 38(2):606-31. DOI: 10.1039/b701677h. View

17.

Angell Y, Alsina J, Albericio F, Barany G . Practical protocols for stepwise solid-phase synthesis of cysteine-containing peptides. J Pept Res. 2002; 60(5):292-9. DOI: 10.1034/j.1399-3011.2002.02838.x. View

18.

Castano A, Mroz P, Hamblin M . Photodynamic therapy and anti-tumour immunity. Nat Rev Cancer. 2006; 6(7):535-45. PMC: 2933780. DOI: 10.1038/nrc1894. View

19.

Sibrian-Vazquez M, Jensen T, Vicente M . Synthesis, characterization, and metabolic stability of porphyrin-peptide conjugates bearing bifunctional signaling sequences. J Med Chem. 2008; 51(10):2915-23. DOI: 10.1021/jm701050j. View

20.

Stewart K, Horton K, Kelley S . Cell-penetrating peptides as delivery vehicles for biology and medicine. Org Biomol Chem. 2008; 6(13):2242-55. DOI: 10.1039/b719950c. View