1. Introduction

2. Results and discussion

DMON-PS1-4 were then prepared by mixing the corresponding triethoxysilylated photosensitizers (Figures 1A, 2A, 3A and 4A) in the presence of tetraethoxysilane, bis(triethoxysilylpropyl)tetrasulfide, following a one-pot known procedure using NaSal (sodium salicylate) and cationic surfactant CTAB as structure directing agents and triethanolamine as a catalyst. [29] The dendritic structure and the presence of radial mesopores were clearly shown with transmission electron microscopy (TEM) (Figures 1B, 2B, 3B and 4B) of DMONPS1-4. DLS showed well-dispersed nanoparticles from 95-100 nm, hydrodynamic diameters in agreement with TEM images. The photosensitizers were clearly incorporated inside the structure of DMONPS1-4 as shown by UV-Vis spectra. (Figures 1C, 2C, 3C and 4C). With PS1 possessing four triethoxysilyl groups, the Q bands were visible after incorporation in DMONPS1 despite light scattering, which was not the case for DMONPS2, DMONPS3 due to a lower amount of incorporation. The Q1 band was present for the chlorin e6 derivative (DMONPS4) showing that the structure was not damaged during the mild sol-gel method used for the preparation of the nanoparticles. N₂ adsorption-desorption was studied for all the DMONPS. (Figures 1D, 2D, 3D and 4D, Table 1). All the nanoparticles showed type IV isotherms. The Brunauer−Emmett−Teller (BET) surface area and the total pore volume of DMONPS1 were 110 m².g⁻¹ and 0.44 cm³.g⁻¹ respectively. The capillary condensation step occurred in the relative pressure (P/P0) of 0.8−0.9, corresponding to a large pore size of ∼24.4 nm (inset of Figure 1D). Interestingly, with DMONPS2 and DMONPS3, the BET-specific surface area increased to 356, 353 m².g⁻¹, with an increase of the pore volumes to 1.78, 1.65 cm³.g⁻¹ and a decrease of the pore size to 19.5 and 18.2 nm respectively. The structure of DMONPS4 was between DMONPS1 and DMONPS2-3 with a BET-specific surface area of 266 m².g⁻¹ a pore volume of 1.52 cm³.g⁻¹ and a pore size of 22.6 nm. In order to complex siRNA, functionalization of DMONPS1-4 with lysine (Scheme 1), by amination with aminopropyltriethoxysilane (APTES), coupling with protected lysine, and deprotection was then performed. DMONPS1-4 showed a negative zeta potential in agreement with the deprotonation of Si-OH in water. After amination, the zeta potential turned positive (Table 1) and after functionalization with lysine, high zeta potential values were observed indicating that the functionalization was successful, except for DMONNPS4-Lys.

Figure 1. A) The tetraaminophenylporphyrin with four triethoxysilyl groups used for the preparation of DMONPS1. B) DMONPS1 as shown by TEM, the dendritic structure is visible. C) UV-Vis spectra in EtOH of the silylated photosensitizer(PS1) and the corresponding DMONPS1, the photosensitizer is encapsulated inside the framework of DMONPS1, the Soret and four Q bands are visible. D) Nitrogen adsorption–desorption at 77 K (BET). Insert BJH adsorption (dV/dw) Pore Volume.

Figure 1. A) The tetraaminophenylporphyrin with four triethoxysilyl groups used for the preparation of DMONPS1. B) DMONPS1 as shown by TEM, the dendritic structure is visible. C) UV-Vis spectra in EtOH of the silylated photosensitizer(PS1) and the corresponding DMONPS1, the photosensitizer is encapsulated inside the framework of DMONPS1, the Soret and four Q bands are visible. D) Nitrogen adsorption–desorption at 77 K (BET). Insert BJH adsorption (dV/dw) Pore Volume.

Figure 2. A) The monosilylated aminophenylporphyrin used for the preparation of DMONPS2. B) DMONPS2 as shown by TEM, the dendritic structure is visible, the nanoparticles seem aggregated. C) UV-Vis spectra in EtOH of the silylated photosensitizer(PS2) and the corresponding DMONPS2, the photosensitizer is encapsulated inside the framework of DMONPS2, the Soret band is visible. D) Nitrogen adsorption–desorption at 77 K (BET). Insert BJH adsorption (dV/dw) Pore Volume.

Figure 2. A) The monosilylated aminophenylporphyrin used for the preparation of DMONPS2. B) DMONPS2 as shown by TEM, the dendritic structure is visible, the nanoparticles seem aggregated. C) UV-Vis spectra in EtOH of the silylated photosensitizer(PS2) and the corresponding DMONPS2, the photosensitizer is encapsulated inside the framework of DMONPS2, the Soret band is visible. D) Nitrogen adsorption–desorption at 77 K (BET). Insert BJH adsorption (dV/dw) Pore Volume.

Figure 3. A) The monosilylated aminoporphyrin used for the preparation of DMONPS3. B) DMONP3 as shown by TEM, the dendritic structure is visible. C) UV-Vis spectra in EtOH of the silylated photosensitizer(PS3) and the corresponding DMONPS3, the photosensitizer is encapsulated inside the framework of DMONPS3, the Soret band is visible. D) Nitrogen adsorption–desorption at 77 K (BET). Insert BJH adsorption (dV/dw) Pore Volume.

Figure 3. A) The monosilylated aminoporphyrin used for the preparation of DMONPS3. B) DMONP3 as shown by TEM, the dendritic structure is visible. C) UV-Vis spectra in EtOH of the silylated photosensitizer(PS3) and the corresponding DMONPS3, the photosensitizer is encapsulated inside the framework of DMONPS3, the Soret band is visible. D) Nitrogen adsorption–desorption at 77 K (BET). Insert BJH adsorption (dV/dw) Pore Volume.

Table 1. Data for DMON.

Table 1. Data for DMON.

DMONPS	DLS (nm)	ZETA Potential (mV)	BET (m2.g-1)	Pore size (nm)	Pore volume cm3.g-1
DMONPS1	100	-8.1	110	24.4	0.44
DMONPS2	92	-8.5	356	19.5	1.78
DMONPS3	96	-10.4	353	18.2	1.65
DMONPS4	95	-7.5	265	22.6	1.52
DMONPS1-NH2	100	6.0	/	/	/
DMONPS2-NH2	99	4.8	/	/	/
DMONPS3-NH2	100	5.1	/	/	/
DMONPS4-NH2	100	6.3	/	/	/
DMONPS1-Lys	99	42.0	/	/	/
DMONPS2-lys	99	26.3	/	/	/
DMONPS3-Lys	100	26.4	/	/	/
DMONPS4-Lys	100	6.0	/	/	/

Figure 4. A) The trisilylated chlorin e6 used for the preparation of DMONPS4. B) DMONP4 as shown by TEM, the dendritic structure is visible. C) UV-Vis spectra in EtOH of the silylated photosensitizer(PS4) and the corresponding DMONPS4, the photosensitizer is encapsulated inside the framework of DMONPS4, the Soret and Q1 bands are visible. D) Nitrogen adsorption–desorption at 77 K (BET). Insert BJH adsorption (dV/dw) Pore Volume.

Figure 4. A) The trisilylated chlorin e6 used for the preparation of DMONPS4. B) DMONP4 as shown by TEM, the dendritic structure is visible. C) UV-Vis spectra in EtOH of the silylated photosensitizer(PS4) and the corresponding DMONPS4, the photosensitizer is encapsulated inside the framework of DMONPS4, the Soret and Q1 bands are visible. D) Nitrogen adsorption–desorption at 77 K (BET). Insert BJH adsorption (dV/dw) Pore Volume.

Scheme 1. Functionalization of DMONPS1-4 with lysine amino acid (DMONPS1-4-Lys) in order to complex siRNA.

Scheme 1. Functionalization of DMONPS1-4 with lysine amino acid (DMONPS1-4-Lys) in order to complex siRNA.

The nanoparticles were then incubated with cancer cells for 24 h, at a concentration of 50 µg.mL^-1, which was adequate for imaging, and confocal microscopy was performed (Figure 5). The nanoparticles were excited at 420 nm, in the Soret band of the porphyrin and chlorin.

Figure 5. Confocal microscopy imaging of MCF-7 cancer cells incubated with DMONPS1-4, DMONPS1-4-NH₂ or DMONPS1-4-Lys, for 24h. ℷ_excitation = 420 nm ℷ_emission = 630-670 nm. Membranes were stained with a cell mask 15 Min. before observation. ℷ_excitation = 561 nm ℷ_emission = 565-629 nm.

Figure 5. Confocal microscopy imaging of MCF-7 cancer cells incubated with DMONPS1-4, DMONPS1-4-NH₂ or DMONPS1-4-Lys, for 24h. ℷ_excitation = 420 nm ℷ_emission = 630-670 nm. Membranes were stained with a cell mask 15 Min. before observation. ℷ_excitation = 561 nm ℷ_emission = 565-629 nm.

Cytotoxicity studies were then performed (Figure 6). 25 µg.mL^-1 was the adequate concentration to carry out photodynamic therapy (PDT) experiments as the nanoparticles presented low toxicity above 75% after three days. The cells were classically irradiated [26] at 405 nm in the Soret band, for 5 min. or at 650 nm for 20 min. in the QI band, but PDT effects were not observed (data not shown). Indeed we believe that the tetrasulfide group quenches the formation of singlet oxygen through oxidation. [30] The photosensitizers allow only imaging of cancer cells.

Figure 6. Cytotoxicity studies of MCF-7 cancer cells were performed through incubation with DMONPS1-4, DMONPS1-4-NH₂ or DMONPS1-4-Lys, for 72h. The cytotoxicity was monitored with the MTT assay.

Figure 6. Cytotoxicity studies of MCF-7 cancer cells were performed through incubation with DMONPS1-4, DMONPS1-4-NH₂ or DMONPS1-4-Lys, for 72h. The cytotoxicity was monitored with the MTT assay.

Complexation of DMONPS1-4-Lys with siRNA (Inhibitor Apoptotic Protein) IAP was then performed (Figure 7) and monitored with a gel retardation assay. Proapoptotic siRNA would inhibit the production of anti-apoptotic proteins, with the activation of the apoptotic pathway, leading to cell death. A very good complexation was noticed at concentrations of 1/25 for DMONPS1-2-lys, and 1/10 for DMONPS3-4-lys.

Figure 7. Agarose gel-retardation assay with DMONPS1-4-Lys, complexed with siRNA (negative control (A)), at different weight ratios ranging from 1/10 to 1/50. Electrophoresis was immediately performed after complex formation for 30 min at 37 °C.

Figure 7. Agarose gel-retardation assay with DMONPS1-4-Lys, complexed with siRNA (negative control (A)), at different weight ratios ranging from 1/10 to 1/50. Electrophoresis was immediately performed after complex formation for 30 min at 37 °C.

After having determined the complexation of the siRNA/nanoparticles ratio, we then investigated the siRNA IAP delivery in MCF-7 breast cancer cells (Figure 8). We incubated the DMONPS1-4-Lys-siRNA complexes or siRNA alone with MCF-7 cancer cells for three days. MTT assay was carried out to monitor the siRNA effect (Figure 8).

Figure 8. Anticancer effect of DMONPS1-4 complexed with siRNA inhibitor of apoptosis protein (IAP). MCF-7 cells were treated (or not) with free DMONPS1-4 (at 25 µg.mL^-1) or DMONPS1-4 complexed with siRNA at a 1/15 ratio. The killing effect was monitored with the MTT assay.

Figure 8. Anticancer effect of DMONPS1-4 complexed with siRNA inhibitor of apoptosis protein (IAP). MCF-7 cells were treated (or not) with free DMONPS1-4 (at 25 µg.mL^-1) or DMONPS1-4 complexed with siRNA at a 1/15 ratio. The killing effect was monitored with the MTT assay.

After that, we tested the encapsulation of the FVIII protein factor as a model protein, in DMONPS1-Lys and DMONPS3-Lys. FVIII factor is a protein that plays a crucial role in blood clotting. [31] It is produced in the liver and circulates in the blood. FVIII deficiency is the cause of hemophilia A, a genetic bleeding disorder Hemophilia A patients require regular infusions of FVIII to prevent bleeding episodes. FVIII is administered intravenously. The half-life of FVIII in the body is approximately 8-12 hours. Therefore, encapsulation of FVIII could be of high interest. Furthermore, the global charge of factor VIII is negative. This is because FVIII is a glycoprotein, [32] and the carbohydrate component contains negatively charged molecules, such as sialic acid and sulfate groups, which contribute to the overall negative charge of the protein.

Table 2. Data for the encapsulation of FVIII factor in DMONPS1-Lys and DMONPS3-Lys.

Table 2. Data for the encapsulation of FVIII factor in DMONPS1-Lys and DMONPS3-Lys.

DMONPS	DLC 2 mg/mL FVIII	DLE 2 mg/mL FVIII	DLC 4 mg/mL FVIII	DLE 4 mg/mL FVIII
DMONPS1-Lys	14 %	40 %	/	/
DMONPS3-Lys	12%	35%	25%	42%

3. Materials and Methods

3.1. Silylation of PS1-4

Firstly, a mixture of 5,10,15,20-meso-tetra(4-aminophenyl)porphyrin (200 mg,(0.3mmol) 1.4*10-2 mmol), DIPEA (11.2 mg), isocyanatopropyltriethoxysilane (362.8 mg (1.47mmol)) was stirred in anhydrous THF (7 mL) under argon at 80°C overnight (Scheme 1). After evaporation of the solvent, the POR precursor was washed with AcOEt and recrystallized in hexane. This process was repeated 4 times. Finally, the precursor was dried under vacuum. 1H NMR (300 MHz, DMSO-d6) was done to prove the silylation of the porphyrin (Figure). (δ (ppm) 8.88 (s, 8H, Hβpyrrole), 8.86 (s, 4H,CO-NH-CH₂ ), 8.06 (d, 3 J=9.0 Hz, 8H, H3,5 aryl), 7.84 (d, 3 J=9.0 Hz, 8H, H2,6 aryl), 6.40 (t, 4H, 3 J=4.5 Hz, CO-NH-Ph), 3.81 (q, 3 J=7.5 Hz, 24H, O-CH₂-CH₃ ), 1.20 (t, 3 J= 7.5 Hz, 36H, O-CH₂-CH₃ ), 0.66 (t, 3 J=9.0 Hz, 8H, CH₂-Si)

Table 5. aminophenyl)-2,3,7,8,12,18-(hexamethyl)-13,17-(diethyl)porphyrin precursor (25 mg, 0.0456 mmol) in anhydrous THF (7 mL) and DIPEA (0.015 mL, 11.2 mg, ), 3-isocyanatopropyltriethoxysilane (17 mg, 17 µl, 0.0684 mmol) was slowly added, and the mixture was stirred under argon at 80°C overnight. Volatiles were evaporated

To a solution of 2,3,7,8,12,13,17,18-octaethylporphyrin-5-amine precursor (25 mg, 0.0455 mmol) in anhydrous THF (7 mL) and DIPEA (0.015 mL, 11.2 mg, ), 3-isocyanatopropyltriethoxysilane (17 mg, 17 µl, 0.0684 mmol) was slowly added, and the mixture was stirred under argon at 80°C overnight. Volatiles were evaporated.

2.2 mg of conjugated chlorin e6 (Ce6) pre-dissolved in 0.5 mL of DMSO were mixed with 12 µL of APTES, in the presence of 6 mg of EDC-HCl, and 4 mg of NHS. The mixture was stirred overnight at room temperature.

4. Biological studies

4.6. FVIII encapsulation

For the encapsulation of FVIII in DMONPSI-Lys, 5 mg of powdered nanoparticles were mixed with 5 mL of FVIII previously diluted in PBS (10mM, pH 7.4) to obtain a final concentration of 2 mg/mL. For the encapsulation of FVIII in DMONPS3-Lys, two batches of 5 mg of powdered nanoparticles were mixed with 5 mL of FVIII previously diluted in order to have final concentrations of 2 mg/mL or 4 mg/mL. To suspend the solution, a sonication of 5 seconds was carried out then the solution was incubated at room temperature at 200 rpm for 24 hours

$$\mathrm{DLC} (\%)=\frac{\mathrm{M}\mathrm{a}\mathrm{s}\mathrm{s}\mathrm{o}\mathrm{f}\mathrm{F}\mathrm{V}\mathrm{I}\mathrm{I}\mathrm{I}\mathrm{i}\mathrm{n}\mathrm{t}\mathrm{h}\mathrm{e}\mathrm{D}\mathrm{M}\mathrm{O}\mathrm{N}\mathrm{P}\mathrm{S}\mathrm{1,3}-\mathrm{L}\mathrm{y}\mathrm{s}}{\mathrm{M}\mathrm{a}\mathrm{s}\mathrm{s}\mathrm{o}\mathrm{f}\mathrm{D}\mathrm{M}\mathrm{O}\mathrm{N}\mathrm{P}\mathrm{S}\mathrm{1,3}-\mathrm{L}\mathrm{y}\mathrm{s}}$$

$$\mathrm{DLE} (\%)=\frac{\mathrm{M}\mathrm{a}\mathrm{s}\mathrm{s}\mathrm{o}\mathrm{f}\mathrm{F}\mathrm{V}\mathrm{I}\mathrm{I}\mathrm{I}\mathrm{i}\mathrm{n}\mathrm{t}\mathrm{h}\mathrm{e}\mathrm{D}\mathrm{M}\mathrm{O}\mathrm{N}\mathrm{P}\mathrm{S}\mathrm{1,3}-\mathrm{L}\mathrm{y}\mathrm{s}}{\mathrm{M}\mathrm{a}\mathrm{s}\mathrm{s}\mathrm{o}\mathrm{f}\mathrm{F}\mathrm{V}\mathrm{I}\mathrm{I}\mathrm{I}\mathrm{i}\mathrm{n}\mathrm{t}\mathrm{h}\mathrm{e}\mathrm{f}\mathrm{e}\mathrm{e}\mathrm{d}\mathrm{i}\mathrm{n}\mathrm{g}\mathrm{s}\mathrm{o}\mathrm{l}\mathrm{u}\mathrm{t}\mathrm{i}\mathrm{o}\mathrm{n}}$$

DLC and DLE were calculated after centrifugation and titration of the supernatant with UV-Vis spectra at 280 nm, using two calibration curves.

Calibration curves were determined at 2 mg/mL and 4 mg/mL of FVIII respectively

Figure 9. Calibration curve of FVIII at 2 mg/mL in PBS.

Figure 9. Calibration curve of FVIII at 2 mg/mL in PBS.

Figure 10. Calibration curve of FVIII at 4 mg/mL in PBS.

Figure 10. Calibration curve of FVIII at 4 mg/mL in PBS.

5. Conclusions

References

1. Manzano, M.; Vallet-Regi, M. Mesoporous silica nanoparticles for drug delivery. Adv. Funct. Mater. 2019, 10.1002/adfm.201902634, Ahead of Print. [CrossRef]
2. Li, Z.; Zhang, Y.; Feng, N. Mesoporous silica nanoparticles: synthesis, classification, drug loading, pharmacokinetics, biocompatibility, and application in drug delivery. Expert Opin. Drug Delivery 2019, 16, 219–237. [Google Scholar] [CrossRef]
3. Li, T.; Shi, S.; Goel, S.; Shen, X.; Xie, X.; Chen, Z.; Zhang, H.; Li, S.; Qin, X.; Yang, H. , et al. Recent advancements in mesoporous silica nanoparticles towards therapeutic applications for cancer. Acta Biomater. 2019, 89, 1–13. [Google Scholar] [CrossRef] [PubMed]
4. Castillo, R.R.; Lozano, D.; Gonzalez, B.; Manzano, M.; Izquierdo-Barba, I.; Vallet-Regi, M. Advances in mesoporous silica nanoparticles for targeted stimuli-responsive drug delivery: an update. Expert Opin. Drug Delivery 2019, 16, 415–439. [Google Scholar] [CrossRef]
5. Chinnathambi, S.; Tamanoi, F. Recent Development to Explore the Use of Biodegradable Periodic Mesoporous Organosilica (BPMO) Nanomaterials for Cancer Therapy. Pharmaceutics 2020, 12, 890. [Google Scholar] [CrossRef]
6. Mai, N.X.D.; Nguyen, T.-H.T.; Vong, L.B.; Dang, M.-H.D.; Nguyen, T.T.T.; Nguyen, L.H.T.; Ta, H.K.T.; Nguyen, T.-H.; Phan, T.B.; Doan, T.L.H. Tailoring chemical compositions of biodegradable mesoporous organosilica nanoparticles for controlled slow release of chemotherapeutic drug. Materials Science and Engineering: C 2021, 127, 112232. [Google Scholar] [CrossRef] [PubMed]
7. Guan, L.; Chen, J.; Tian, Z.; Zhu, M.; Bian, Y.; Zhu, Y. Mesoporous organosilica nanoparticles: Degradation strategies and application in tumor therapy. VIEW 2021, 2, 20200117. [Google Scholar] [CrossRef]
8. Guimarães, R.S.; Rodrigues, C.F.; Moreira, A.F.; Correia, I.J. Overview of stimuli-responsive mesoporous organosilica nanocarriers for drug delivery. Pharmacol.. Res. 2020, 155, 104742. [Google Scholar] [CrossRef]
9. Cheng, Y.; Jiao, X.; Fan, W.; Yang, Z.; Wen, Y.; Chen, X. Controllable synthesis of versatile mesoporous organosilica nanoparticles as precision cancer theranostics. Biomaterials 2020, 256, 120191. [Google Scholar] [CrossRef]
10. Yang, B.; Chen, Y.; Shi, J. Mesoporous silica/organosilica nanoparticles: Synthesis, biological effect and biomedical application. Materials Science and Engineering: R: Reports 2019, 137, 66–105. [Google Scholar] [CrossRef]
11. Yu, L.; Chen, Y.; Lin, H.; Du, W.; Chen, H.; Shi, J. Ultrasmall mesoporous organosilica nanoparticles: Morphology modulations and redox-responsive biodegradability for tumor-specific drug delivery. Biomaterials 2018, 161, 292–305. [Google Scholar] [CrossRef]
12. Croissant, J.G.; Fatieiev, Y.; Almalik, A.; Khashab, N.M. Mesoporous Silica and Organosilica Nanoparticles: Physical Chemistry, Biosafety, Delivery Strategies, and Biomedical Applications. Adv. Healthc. Mater. 2018, 7, 1700831. [Google Scholar] [CrossRef]
13. Du, X.; Li, X.; Xiong, L.; Zhang, X.; Kleitz, F.; Qiao, S.Z. Mesoporous silica nanoparticles with organo-bridged silsesquioxane framework as innovative platforms for bioimaging and therapeutic agent delivery. Biomaterials 2016, 91, 90–127. [Google Scholar] [CrossRef]
14. Chen, Y.; Shi, J. Chemistry of Mesoporous Organosilica in Nanotechnology: Molecularly Organic-Inorganic Hybridization into Frameworks. Adv. Mater. 2016, 28, 3235–3272. [Google Scholar] [CrossRef]
15. Croissant, J.G.; Cattoen, X.; Wong Chi Man, M.; Durand, J.-O.; Khashab, N.M. Syntheses and applications of periodic mesoporous organosilica nanoparticles. Nanoscale 2015, 7, 20318–20334. [Google Scholar] [CrossRef] [PubMed]
16. Yang, S.; Chen, S.; Fan, J.; Shang, T.; Huang, D.; Li, G. Novel mesoporous organosilica nanoparticles with ferrocene group for efficient removal of contaminants from wastewater. J. Coll. Int. Sci. 2019, 554, 565–571. [Google Scholar] [CrossRef]
17. Hoffmann, F.; Cornelius, M.; Morell, J.; Froeba, M. Silica-based mesoporous organic-inorganic hybrid materials. Angew. Chem., Int. Ed. 2006, 45, 3216–3251. [Google Scholar] [CrossRef] [PubMed]
18. Kickelbick, G. Hybrid inorganic-organic mesoporous materials. Angew. Chem., Int. Ed. 2004, 43, 3102–3104. [Google Scholar] [CrossRef]
19. Tao, J.; Su, X.; Li, J.; Shi, W.; Teng, Z.; Wang, L. Intricately structured mesoporous organosilica nanoparticles: synthesis strategies and biomedical applications. Biomaterials Science 2021, 9, 1609–1626. [Google Scholar] [CrossRef] [PubMed]
20. Wang, Y.; Zhang, B.; Ding, X.; Du, X. Dendritic mesoporous organosilica nanoparticles (DMONs): Chemical composition, structural architecture, and promising applications. Nano Today 2021, 39, 101231. [Google Scholar] [CrossRef]
21. Wang, Y.; Song, H.; Liu, C.; Zhang, Y.; Kong, Y.; Tang, J.; Yang, Y.; Yu, C. Confined growth of ZIF-8 in dendritic mesoporous organosilica nanoparticles as bioregulators for enhanced mRNA delivery in vivo. National science review 2021, 8, nwaa268. [Google Scholar] [CrossRef] [PubMed]
22. Mezghrani, B.; Ali, L.M.A.; Richeter, S.; Durand, J.-O.; Hesemann, P.; Bettache, N. Periodic Mesoporous Ionosilica Nanoparticles for Green Light Photodynamic Therapy and Photochemical Internalization of siRNA. ACS Appl. Mater. Interfaces. 2021, 13, 29325–29339. [Google Scholar] [CrossRef] [PubMed]
23. Pham, T.C.; Nguyen, V.-N.; Choi, Y.; Lee, S.; Yoon, J. Recent Strategies to Develop Innovative Photosensitizers for Enhanced Photodynamic Therapy. Chem. Rev. 2021, 121, 13454–13619. [Google Scholar] [CrossRef] [PubMed]
24. Tsuboi, M.; Matsuo, K.; Ts'o, P.O.P. Interaction of poly-l-lysine and nucleic acids. Journal of Molecular Biology 1966, 15, 256–267. [Google Scholar] [CrossRef] [PubMed]
25. Daurat, M.; Rahmani, S.; Bouchal, R.; Akrout, A.; Budimir, J.; Nguyen, C.; Charnay, C.; Guari, Y.; Richeter, S.; Raehm, L. , et al. Organosilica Nanoparticles for Gemcitabine Monophosphate Delivery in Cancer Cells. ChemNanoMat 2019, 5, 888–896. [Google Scholar] [CrossRef]
26. Aggad, D.; Mauriello Jimenez, C.; Dib, S.; Croissant, J.G.; Lichon, L.; Laurencin, D.; Richeter, S.; Maynadier, M.; Alsaiari, S.K.; Boufatit, M. , et al. Gemcitabine Delivery and Photodynamic Therapy in Cancer Cells via Porphyrin-Ethylene-Based Periodic Mesoporous Organosilica Nanoparticles. ChemNanoMat 2018, 4, 46–51. [Google Scholar] [CrossRef]
27. Jimenez, C.M.; Rubio, Y.G.; Saunier, V.; Warther, D.; Stojanovic, V.; Raehm, L.; Frochot, C.; Arnoux, P.; Garcia, M.; Morère, A. , et al. 20-nm-sized mesoporous silica nanoparticles with porphyrin photosensitizers for in vitro photodynamic therapy. J. Sol-Gel Sci. Technol. 2016, 79, 447–456. [Google Scholar] [CrossRef]
28. Yang, G.; Gong, H.; Qian, X.; Tan, P.; Li, Z.; Liu, T.; Liu, J.; Li, Y.; Liu, Z. Mesoporous silica nanorods intrinsically doped with photosensitizers as a multifunctional drug carrier for combination therapy of cancer. Nano Research 2015, 8, 751–764. [Google Scholar] [CrossRef]
29. Yang, Y.; Wan, J.; Niu, Y.; Gu, Z.; Zhang, J.; Yu, M.; Yu, C. Structure-Dependent and Glutathione-Responsive Biodegradable Dendritic Mesoporous Organosilica Nanoparticles for Safe Protein Delivery. Chem. Mater. 2016, 28, 9008–9016. [Google Scholar] [CrossRef]
30. Lacombe, S.; Cardy, H.; Simon, M.; Khoukh, A.; Soumillion, J.P.; Ayadim, M. Oxidation of sulfides and disulfides under electron transfer or singlet oxygen photosensitization using soluble or grafted sensitizers. Photochem. Photobiol. Sci. 2002, 1, 347–354. [Google Scholar] [CrossRef] [PubMed]
31. Samuelson Bannow, B.; Recht, M.; Négrier, C.; Hermans, C.; Berntorp, E.; Eichler, H.; Mancuso, M.E.; Klamroth, R.; O'Hara, J.; Santagostino, E. , et al. Factor VIII: Long-established role in haemophilia A and emerging evidence beyond haemostasis. Blood Reviews 2019, 35, 43–50. [Google Scholar] [CrossRef] [PubMed]
32. Qu, J.; Ma, C.; Xu, X.-Q.; Xiao, M.; Zhang, J.; Li, D.; Liu, D.; Konkle, B.A.; Miao, C.H.; Li, L. , et al. Comparative glycosylation mapping of plasma-derived and recombinant human factor VIII. PLoS One 2020, 15, e0233576. [Google Scholar] [CrossRef] [PubMed]