Iron Oxide Nanoparticles are a promising option as drug-delivery agents due to their biocompatibility, low cost, stability, and size. They have the potential to be applied in a variety of areas in the medical field. This study aimed to develop a simple, novel, and reproducible method for coating Superparamagnetic Iron Oxide Nanoparticles (SPIONs) with Chitosan (CH) and Chitosan Hydrochloride (CHL) and loading drugs (Quercetin, Resveratrol, and Doxycycline) to compare these coatings effectiveness and potential applications that can be applied inside dentinal tubules to facilitate dental treatments. 17 nm SPIONs were coated CH and CHL using a one-pot synthesis with an overhead stirrer overnight, followed by loading with resveratrol (RES), quercetin (QUE), and doxycycline (DOXY). Synthesized samples presented a spherical shape, and NPs size was obtained through Transmission Electron Microscopy (TEM). QUE-CH-SPIONs, RES-CH-SPIONs, and DOXY-CH-SPIONs presented an increase in size to 28, 26, and 25 nm, respectively. While QUE-CHL-SPIONs, RES-CHL-SPIONs, and DOXY-CHL-SPIONs increased to 20, 23, and 23 nm, respectively. Nanoparticles' Zeta Potential and polydispersity confirmed NPs' stability and that samples were extremely anionic, and Fourier Transform infrared spectroscopy (FTIR) proved NPs' successful coating synthesis. Drug-loading characteristics were obtained through Drug loading (DL) and encapsulation efficiency (EE) equations. All loaded NPs presented EE higher than 88 %, and DL confirmed the particles' surface modification. All samples' in vitro release profile was conducted, and a successful release of DOXY from CH-coated and CHL-coated NPs was confirmed. Kirb-diffusion test demonstrated DOXY-CH-SPIONs and DOXY-CHL-SPIONs' antimicrobial potential. Results from the experiments confirmed nanoparticles' successful coating and drug loading, confirming nanoparticles' potential in the biomedical field. Nanoparticles were inserted inside dentinal tubules and FTIR results along with confocal microscopy presented the high potential these nanoparticles have for applications inside the dentine.