Effect of hydrogen bonding and complexation with metal ions on the fluorescence of luotonin A

Miskolczy, Zsombor; Biczók, László

doi:10.1039/c3pp50011j

Cited by 5 publications

(5 citation statements)

References 45 publications

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“…Miskolczy et al . have reported the acceleration of the photochemical conversion of PMCH to SP, which they attribute to the modification of the electron distribution and a decrease in interaction between PMCH and H 2 O by the addition of cucurbit[7]uril . Further, Muthu et al .…”

Section: Resultsmentioning

confidence: 99%

Light‐Driven Proton Release of Spirobenzopyran‐Derived Protonated Photomerocyanine in Cyclodextrin Aqueous Solution

2017

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Protonated photomerocyanine (PMCH), which is a ring‐opening isomer of spirobenzopyran, functions as a metastable‐state photoacid (PAH) driven by blue or visible light. Enhancement of the proton photodissociation efficiency and thermal stability of the deprotonated isomer facilitates pH adjustments and control by light irradiation. In this article, we report the proton photodissociation of PMCH based on 1,3,3‐trimethylindolino‐8’‐methoxybenzopyrylospiran (1) in an aqueous cyclodextrin (CD) solution. In the aqueous solution, the spirobenzopyran form of 1 underwent a spontaneous ring‐opening reaction and formed the thermodynamically stable PMCH form of 1 (PMCH‐1). After a laser flash at 355 nm, the photomerocyanine form of 1 (PMC‐1) was generated by proton photodissociation from the singlet excited state of PMCH‐1. The quantum yield of the proton photodissociation was changed by the stoichiometry or binding constant of the inclusion complex between PMCH‐1 and CD. Additionally, the encapsulation effects of CD inhibited the re‐protonation of PMC‐1. We conclude that these findings are useful for pH adjustment and control using PAHs based on PMCH.

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Section: Resultsmentioning

confidence: 99%

Light‐Driven Proton Release of Spirobenzopyran‐Derived Protonated Photomerocyanine in Cyclodextrin Aqueous Solution

2017

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“…At regular time intervals, 40 µL of LuA solution was taken out and diluted to 2 mL using distilled water. The concentration of LuA in the supernatant solution was calculated using ultraviolet‐visible spectrophotometer at 358 nm . The LuA loading efficiency of mCS and mCS‐PVA hydrogel beads was calculated using the following equation:

normalL normalo normala normald normali normaln normalg normale normalf normalf normali normalc normali normale normaln normalc normaly (|, %) = \frac{C_{0} - C_{normalt}}{C_{0}} \times 100

where

C_{0}

is the initial concentration of LuA (before loading) and

C_{normalt}

is the concentration of LuA (after loading) at time

t

.…”

Section: Methodsmentioning

confidence: 99%

One pot synthesis of new poly(vinyl alcohol) blended natural polymer based magnetic hydrogel beads: Controlled natural anticancer alkaloid delivery system

Kesavan¹,

Ayyanaar²,

Lenin³

et al. 2017

J Biomedical Materials Res

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Facile one-pot synthesis has been demonstrated for new biocompatible and dual responsive magnetic iron oxide nanoparticles cross-linked poly(vinyl alcohol) (PVA) blended natural polymer chitosan (CS) based hydrogel beads (mCS-PVA) as a controlled natural anticancer alkaloid Luotonin A (LuA) delivery system. The prepared magnetic hydrogel beads were characterized using powder X-ray diffraction measurement, Fourier transform-infrared spectroscopy, scanning electron microscopy, energy dispersive X-ray spectroscopy, and vibrating sample magnetometer. The magnetic hydrogel beads are exhibited significant water retention and follow the second order kinetic model in swelling study. The swelling ratio of the magnetic gel beads increased by the addition of PVA and showed a maximum swelling ratio of 40.83 ± 1.01 g/g and follows non-Fickian water transport mechanism. Stimuli responsive mCS and mCS-PVA hydrogel beads functionalized with LuA is demonstrated for controlled release at physiological pH and under magnetic field. The magnetic hydrogel beads show highest LuA releasing efficacy at acidic medium (pH = 5.0) with maximum efficiency of 73.33 ± 1.44%. This efficacy may also be tuned by altering the external magnetic field as well as the weight percentage (wt %) of polyethylene glycol. It is clearly that the newly produced magnetic hydrogel beads can be served as an effective intestinal LuA delivery system. © 2017 Wiley Periodicals, Inc. J Biomed Mater Res Part A: 106A: 543-551, 2018.

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“…Furthermore, the use of commercially available chiral stationary phases or the inverted chirality columns approach, has made possible the chiral resolution of enantiomers of the drugs [21]. Luotonin A derivatives also exhibit a strong fluorescence [22,23], although the literature about the separation of luotonin A analogues is very scarce [24,25]. We have previously reported a methodology for the quantification of luotonin A derivatives in human serum samples [24].…”

Section: Introductionmentioning

confidence: 98%

Challenging core-shell stationary phases with the separation of closely related anti-cancer compounds: performance studies and application to drug quantitation in cell cultures with multi-well plate clean-up

González‐Ruiz

Olives

Martín

2014

Journal of Chromatography A

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Effect of hydrogen bonding and complexation with metal ions on the fluorescence of luotonin A

Cited by 5 publications

References 45 publications

Light‐Driven Proton Release of Spirobenzopyran‐Derived Protonated Photomerocyanine in Cyclodextrin Aqueous Solution

Light‐Driven Proton Release of Spirobenzopyran‐Derived Protonated Photomerocyanine in Cyclodextrin Aqueous Solution

One pot synthesis of new poly(vinyl alcohol) blended natural polymer based magnetic hydrogel beads: Controlled natural anticancer alkaloid delivery system

Challenging core-shell stationary phases with the separation of closely related anti-cancer compounds: performance studies and application to drug quantitation in cell cultures with multi-well plate clean-up

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