S-Nitroso-N-acetyl-D-penicillamine covalently linked to polydimethylsiloxane (SNAP–PDMS) for use as a controlled photoinitiated nitric oxide release polymer

Abstract

Nitric oxide (NO) plays a critical role in the regulation of a wide variety of physiological processes. It is a potent inhibitor of platelet adhesion and aggregation, inhibits bacterial adhesion and proliferation, is implicated in mediating the inflammatory response toward implanted devices, plays a role in tumor growth and proliferation, and is a neurotransmitter. Herein, we describe the synthesis and NO-release properties of a modified polydimethylsiloxane that contains S-nitroso-N-acetyl-D-penicillamine covalently attached to the cross-linking agent (SNAP-DMS). Light from a C503B-BAN-CY0C0461 light-emitting diode (470 nm) was used as an external trigger to allow precise control over level and duration of NO release ranging from a surface flux of zero to approximately 3.5 × 10 −10 mol cm −2 min −1 . SNAP-PDMS films stored in the dark released NO after 297 days, indicating the long-term stability of SNAP-PDMS.

Recent advances in thromboresistant and antimicrobial polymers for biomedical applications: just say yes to nitric oxide (NO)

“…243 The ability to generate programmable sequences of NO flux from these light-sensitive materials can offer precise spatial and temporal control of the NO release and potentially provides a platform to systematically study, at a fundamental level, the in vivo physiological response to implanted devices. 226 Of note, SNAP-cyclam is capable of releasing physiological relevant levels of NO for up to 3 months in vitro when blended into poly(L-lactic acid) thin films, and this represents the longest NO release from SNAP-based polymer films reported to date. 243 …”

“…These include micelles, 138,190,191 microbubbles, 192 proteins, 193–197 liposomes, 126,198 inorganic nanoparticles (such as silica, 70,199–203 gold, 204,205 microparticles, 198,206 zeolites, 207,208 ), metal-organic frameworks (MOFs), 209–212 dendrimers, 71,213,214 xerogels, 215–217 electrospun fibers, 88,100,218 natural polymers (chitosan, 85–87,219–221 gelatin, 222 etc. ), and other organic polymers (polymethacrylate, 223 polyester, 224,225 polydimethylsiloxane (PDMS), 226 polysaccharides, 227,228 hydrogel, 178,179,229,230 PVA, 49,231,232 polyurethanes, 161,162,233,234 and PVC 154 ). The approaches and benefits of different NO-delivery materials have been highlighted in numerous reviews.…”

“…Evidence suggested that 67 % of the photoinitiated NO was accounted for by the longer wavelength (590 nm) and 33 % by shorter wavelengths (centered around 340 nm). SNAP has also been covalently attached to PDMS, 226 gelatin 222 and a macrocycle (e.g., cyclam). 243 The ability to generate programmable sequences of NO flux from these light-sensitive materials can offer precise spatial and temporal control of the NO release and potentially provides a platform to systematically study, at a fundamental level, the in vivo physiological response to implanted devices.…”

“…Frost et al successfully develop a S -nitroso- N -acetyl-D-penicillamine functionalized polymer matrix (e.g., PDMS, 226 cyclam 243 and gelatin 222 ) that can release NO via light-initiated SNAP decomposition. SNAP modified purified gelatin can release NO up to 1 × 10 −8 µmol mg −1 s −1 under a 527 nm wavelength light-emitting diode (LED,) and it also shows continuous and light intensity-responsive NO release over 24 h, with a total payload of 0.06 µmol NO mg −1 .…”

Wireless platform for controlled nitric oxide releasing optical fibers for mediating biological response to implanted devices

“…Detailed synthesis of this material has been described elsewhere [21], briefly: 1.6 g of hydroxy-terminated PDMS was mixed with 0.3 g of aminopropyl trimethoxysilane, 2.4 mg of dibutyltin dilaurate and 8 mL of toluene. The solution was stirred for 24 h to cross link the PDMS.…”