Luminescence and charge transfer. Part 2. Aminomethyl anthracene derivatives as fluorescent PET (photoinduced electron transfer) sensors for protons

Bissell, Richard A.; Calle, Emilio; Silva, A. Prasanna de; Silva, Saliya A. de; Gunaratne, H. Q. Nimal; Habib‐Jiwan, Jean‐Louis; Peiris, S. L. A.; Rupasinghe, R. A. D. Dayasiri; Shantha, T.K.; Samarasinghe, Diyanath; Sandanayake, K. R. A. Samankumara; Soumillion, Jean‐Philippe

doi:10.1039/p29920001559

Cited by 94 publications

(65 citation statements)

References 63 publications

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“…395-548. † Corresponding author receptor systems [5,12]. At alkaline pH values, the tertiary amine units quench the anthracene fluorescence essentially completely.…”

Section: Simple Pet Sensorsmentioning

confidence: 99%

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Luminescent sensors and photonic switches

Silva

Fox

Moody

et al. 2001

Pure and Applied Chemistry

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The principles of photochemistry continue to fuel progress in luminescent sensors and photonic switches. Examples of sensors based on photoinduced electron transfer (PET) are discussed, including those which form the basis of successful systems used in physiology and medicine. More complex formats usually involve multiple receptors. One progression takes us to lanthanide complexes enabled with sensory capabilities. Another path takes us to molecular-scale implementation of logic gates such as AND and INHIBIT. Such luminescent switches can be enriched by combination with nonluminescent cousins. The latter are based on internal charge-transfer excited states (ICT). An example of rudimentary arithmetic at the molecular scale is presented by running a luminescent AND gate in parallel with a nonluminescent XOR gate. Thus, small molecules can process small numbers for the first time outside of our brains.

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“…395-548. † Corresponding author receptor systems [5,12]. At alkaline pH values, the tertiary amine units quench the anthracene fluorescence essentially completely.…”

Section: Simple Pet Sensorsmentioning

confidence: 99%

“…Acidification produces a visually dramatic fluorescence enhancement. In fact, fluorescence enhancement factors of 1000 are common for 1 and its congeners [12]. The visual impact accompanying protonation of 1 is a major reason for its use to track acidic lysosomal compartments in living cells [8].…”

Section: Simple Pet Sensorsmentioning

confidence: 99%

Luminescent sensors and photonic switches

Silva

Fox

Moody

et al. 2001

Pure and Applied Chemistry

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“…11 They are made by alkylation of monoaza crowns with 9-(chloromethyl)anthracene. Anthracylmethyl crowns 3-5 were prepared similarly, by alkylation of monoaza crowns 6-8, as shown in Scheme 1.…”

Section: Synthesismentioning

confidence: 99%

“…15 The equation describes a hyperbolic binding isotherm, and the binding constant, K 11 , is obtained by a nonlinear least-squares curve fitting program. One of the isotherms for saxitoxin binding to 5 is shown in Figure 2.…”

Section: Titrationsmentioning

confidence: 99%

Effect of crown ether ring size on binding and fluorescence response to saxitoxin in anthracylmethyl monoazacrown ether chemosensors

Mao¹,

Thorne²,

Pharr³

et al. 2006

Can. J. Chem.

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Convenient macrocyclization synthetic routes for the preparation of different-sized monoaza anthracylmethyl crown ether chemsensors (15-crown-5, 18-crown-6, 21-crown-7, 24-crown-8 and 27-crown-9) are described. Evaluation of these crowns as chemosensors for saxitoxin revealed that the larger crowns have moderately higher binding constants, with the 27-crown-9 chemosensor having the largest binding constant: 2.29×10 5 M −1 . Fluorescence enhancements of 100% were observed at saxitoxin concentrations of 5 μM, which is close to the detection limit in mouse bioassay. KeywordsAnthracene; Crown ethers; Saxitoxin; PSP; binding constants; chemsensors Harmful algal blooms (HABs) are linked to many cases of human poisoning each year. Economic losses and costs to the fishing industry, public health, and tourism are estimated to be $40,000,000 annually, as of the late 1990s 1 . The toxins produced by HABs, as well as many other analytes of interest to members of the biomedical community are "small molecules". Saxitoxin (STX) (Figure 1) is such a small molecule because of its neurotoxicity, and is the most toxic component of the paralytic shellfish poisons (PSPs). 2 Its activity is manifested through the binding of the toxin to voltage-gated sodium channels and blocking sodium ion transport across neuronal membranes. In 1996, Saxitoxin was included on the United States government's list of "Select Agents" (potential terrorist weapons). It is one of only 3 small molecules on the list; the rest are viruses (e.g., ebola), bacteria (e.g., Yersenia pestis), and proteins (e.g., ricin, abrin). Mouse bioassay is the current method used by government agencies to detect saxitoxin and its derivatives (known collectively as paralytic shellfish poisons, or PSPs), 3 but for both ethical and economic reasons, an alternative would be highly beneficial. We have been working for several years to develop fluorescent chemosensors for the detection of saxitoxin, and have recently made significant advances. Specifically, we have shown that arylmethylcrowns are selective for the detection of saxitoxin over sodium, potassium, and calcium ions, 4 as well as several organic analytes, 5 including tetrodotoxin (Figure 1). 6 The latter point is clinically relevant since saxitoxin and ‡ This paper is dedicated to Alfred Bader, in recognition of his many contributions, both personal and professional, to the chemical enterprise. Until now we have focussed on the 18-crown-6 monoaza or diaza crown ethers, with anthracene, coumarin, or acridine fluorophores. In early work, Cram, showed that 27-crown-9 crown ether is the optimum size to host a guanidinium guest. 9,10 Since saxitoxin ( Figure 1) is a bis-guanidinium dication, we explored larger crown sizes to determine the effect on binding, using the anthracene fluorophore as sensor. Thus, crown ethers 1-5 were prepared and evaluated for fluorescence response to saxitoxin: 15-crown-5 (1, n=1), 18-crown-6 (2, n = 2), 21-crown-7 (3, n=3), 24-crown-8 (4, n=4) and 27-crown-9 (5, n=5) ( Figure 1). Synthes...

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“…22 So the emission output follows the H + input 14 (Table 1), corresponding to H + -driven YES logic. The analysis of the outputinput profile 23 gives the H + -binding constant (pK a ) of 2 as 5.8.…”

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confidence: 99%