Herein, we report the successful multi-step syntheses of new two-photon responsive octupolar-shaped fluorophores with pendant propanol groups, abbreviated as F1 and F2. Mass spectrometry 1H NMR measurements confirmed they were pure isolated. This type compounds has already proven good biocompatibility internalization in HEK293 cells, well high absorption cross-sections near infra-red region, which are interesting aspects for bioapplications 1. Thus, can serve bioimaging markers. In addition, studied potential fluorophore a donor Fӧrster Resonance Energy Transfer (FRET) tetraaminophenylporphyrin acceptor (POR). The porphyrin photosensitizer displayed significant efficiency anticancer Two-Photon Excited Photodynamic Therapy (TPE-DPT) when integrated Periodic Mesoporous Organosilica Nanoparticles (PMO NPs), due to J-aggregations inside mesostructured that enhancing properties material 2-3.Thus, trisilylated tetrasilylated POR both sol-gel synthesis PMO alongside ethylene (E) or ethenylene (ENE)-based organoalkoxysilane precursors. Biodegradable (BPMO) made bis(triethoxysilyl)propyl)tetrasulfide (4S) also prepared, 80:20 E:4S ENE:4S molar ratio, order compare their therapeutic capability. Glutathione, biomolecule responsible redox cleavage S-S bonds, is present rates at bacteria membrane interface cancer leading BPMO biodegradation 4. Moreover, physico-chemical being noticeably different (morphology, surface charge, porosity), it could affect positively negatively 1O2 transport systems. Next, NPs further modified PEG-silane bring better colloidal stability biocompatibility. final step, post-grafted squarate mannose derivative (sqMAN) through primary amine function previously functionalized aminoundecyltriethoxysilane. mannoside presents numerous advantages: an active targeting lectins over-expressed by facilitating nanoparticle 5, spontaneous interaction 1 fimbrial H bacteria, inhibiting infection host cells 6-7. sqMAN concentration induce aggregation, thus considerably reducing proliferation. Naked F1-POR-E induced mortality MCF-7 TPE-PDT irradiated 780 860 nm. (E, ENE) (E-4S, ENE-4S), grafted not PEG sqMAN, will be compared together assess best conditions. Silica-based suitable carriers protecting drugs against chemical enzymatic degradation, controlled delivery lower systemic/topical toxicity. With objective perform dual therapy (antibiotic antibacterial TPE-PDT), vancomycin hydrochloride antibiotic was loaded pores F1-POR NPs. displaying pH-dependent drug loading content variable between pH 5 7 8. Vancomycin release observed on E. coli S. aureus strains total growth inhibition concentrations 1-2 fold higher than minimum inhibitory (MIC).In perspective, those VAN-loaded would used vivo wound healing studies mices, antitumoral zebrafish embryo excited fluorescence tracking via fluorescence.