Light-triggered CO delivery by a water-soluble and biocompatible manganese photoCORM

Jimenez, Jorge; Chakraborty, Indranil; Carrington, Samantha J.; Mascharak, Pradip K.

doi:10.1039/c6dt01358a

Cited by 39 publications

(22 citation statements)

References 44 publications

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“…2-(Quinonyl)iminotriazaadamante (qyTAm) was synthesized by following a procedure reported by us in a previous account [21]. The yield of the ligand (white solid) was 668 mg (68.8%).…”

Section: Methodsmentioning

confidence: 99%

Silver complexes of ligands derived from adamantylamines: Water-soluble silver-donating compounds with antibacterial properties

Jimenez

Chakraborty

Rojas‐Andrade

et al. 2017

Journal of Inorganic Biochemistry

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Two new silver(I) complexes, namely [Ag(qyAm)2](CF3SO3) (1) and [Ag(qyTAm)2](CF3SO3) (2), (qyAm = 2-(quinonyl)iminoadamantane, qyTAm = 2-(quinonyl)iminotriazaadamantane) have been synthesized and characterized by elemental analyses, 1H NMR, IR, electronic absorption spectroscopy, and X-ray diffraction. The coordination geometry of the silver center in both complexes is distorted tetrahedral where their respective qyAm and qyTAm ligand bind in a bidentate fashion using the imine and quinoline nitrogen atoms. Complex 2 is soluble in water and exhibits strong antimicrobial actions on both Gram-negative (E. coli, and P. aeruginosa) and Gram-positive (S. aureus) bacteria. The minimal inhibitory concentration (MIC) values for complex 2 (4, 4, and 8 μg for E. coli, P. aeruginosa, and S. aureus, respectively) are comparable to MIC values of silver nitrate and silver sulfadiazine.

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“…2-(Quinonyl)iminotriazaadamante (qyTAm) was synthesized by following a procedure reported by us in a previous account [21]. The yield of the ligand (white solid) was 668 mg (68.8%).…”

Section: Methodsmentioning

confidence: 99%

Silver complexes of ligands derived from adamantylamines: Water-soluble silver-donating compounds with antibacterial properties

Jimenez

Chakraborty

Rojas‐Andrade

et al. 2017

Journal of Inorganic Biochemistry

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“…Complexes 232 , 233 , and 234 ( Table 14 ) containing α-diimine ligands were designed to be more soluble in water. 1148 Irradiation of 233 released 3 equiv of CO, but the quantum yield of this process declined by factors of ∼2 and 3 in dichloromethane and aqueous solutions, respectively. The CO release efficiency of these complexes increased in the order 232 < 233 < 234 , paralleling the increase in the electron-donating abilities of their ligands.…”

Section: Photorelease Of Gasotransmittersmentioning

confidence: 99%

Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

et al. 2020

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Photoactivatable (alternatively, photoremovable, photoreleasable, or photocleavable) protecting groups (PPGs), also known as caged or photocaged compounds, are used to enable non-invasive spatiotemporal photochemical control over the release of species of interest. Recent years have seen the development of PPGs activatable by biologically and chemically benign visible and near-infrared (NIR) light. These long-wavelength-absorbing moieties expand the applicability of this powerful method and its accessibility to non-specialist users. This review comprehensively covers organic and transition metal-containing photoactivatable compounds (complexes) that absorb in the visible- and NIR-range to release various leaving groups and gasotransmitters (carbon monoxide, nitric oxide, and hydrogen sulfide). The text also covers visible- and NIR-light-induced photosensitized release using molecular sensitizers, quantum dots, and upconversion and second-harmonic nanoparticles, as well as release via photodynamic (photooxygenation by singlet oxygen) and photothermal effects. Release from photoactivatable polymers, micelles, vesicles, and photoswitches, along with the related emerging field of photopharmacology, is discussed at the end of the review.

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“…More recently, the group of Mascharak published visible light-induced CO release by a biocompatible tris-carbonyl Mn-based photoCORM showing good water-solubility [67]. Three α-diimines ligand-based complexes were prepared (20-22, Figure 4) and one of them (21, Figure 4) demonstrated carbon monoxide delivery to myoglobin in PBS solution.…”

Section: Inorganic and Organometallic Photocormsmentioning

confidence: 99%

Visible Light-Activated PhotoCORMs

Kottelat

Zobi

2017

Inorganics

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Despite its well-known toxicity, carbon monoxide (CO) is now recognized as a potential therapeutic agent. Its inherent toxicity, however, has limited clinical applications because uncontrolled inhalation of the gas leads to severe systemic derangements in higher organisms. In order to obviate life-threatening effects and administer the gas by bypassing the respiratory system, CO releasing molecules (CORMs) have emerged in the last decades as a plausible alternative to deliver controlled quantities of CO in cellular systems and tissues. As stable, solid-storage forms of CO, CORMs can be used to deliver the gas following activation by a stimulus. Light-activated CORMs, known as photoCORMs, are one such example. This class of molecules is particularly attractive because, for possible applications of CORMs, temporal and spatial control of CO delivery is highly desirable. However, systems triggered by visible light are rare. Most currently known photoCORMs are activated with UV light, but red light or even infrared photo-activation is required to ensure that structures deeper inside the body can be reached while minimizing photo-damage to healthy tissue. Thus, one of the most challenging chemical goals in the preparation of new photoCORMs is the reduction of radiation energy required for their activation, together with strategies to modulate the solubility, stability and nontoxicity of the organic or organometallic scaffolds. In this contribution, we review the latest advances in visible light-activated photoCORMs, and the first promising studies on near-infrared light activation of the same.

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Light-triggered CO delivery by a water-soluble and biocompatible manganese photoCORM

Cited by 39 publications

References 44 publications

Silver complexes of ligands derived from adamantylamines: Water-soluble silver-donating compounds with antibacterial properties

Silver complexes of ligands derived from adamantylamines: Water-soluble silver-donating compounds with antibacterial properties

Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

Visible Light-Activated PhotoCORMs

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