Taste sensor for detecting non-charged bitter substances: Xanthine derivatives of pharmaceutical applications

Zhao, Zeyu; Song, Fang; Kimura, Shunsuke; Onodera, Takeshi; Uchida, Takahiro; Toko, Kiyoshi

doi:10.1016/j.microc.2024.110248

Cited by 1 publication

(7 citation statements)

References 52 publications

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“…Conversely, the 3-Br-2,6-DHBA-treated sensor showed significant responses to non-charged bitter substances, including caffeine (75.12 mV), acefylline (31.29 mV), doxofylline (25.25 mV), and pentoxifylline (69.61 mV). The response to the caffeine sample was consistent with a previous paper [ 40 ]. These results show that the BT0 sensor had limitations in detecting certain non-charged bitter substances, such as caffeine and other pharmaceuticals.…”

Section: Resultssupporting

confidence: 91%

“…Certain substances with a xanthine scaffold, such as caffeine and etofylline, were detectable by the 3-Br-2,6-DHBA-treated sensor [ 30 , 39 , 40 ], operating through an allosteric mechanism discussed in the Introduction. Since acefylline possesses the same xanthine scaffold (as shown in Figure 1 ), the authors propose that the detection mechanism underlying the acefylline detection was also an allosteric one.…”

Section: Resultsmentioning

confidence: 99%

“…Previous studies [ 39 , 40 ] marked a significant advancement through employing 3-Br-2,6-DHBA-treated taste sensors to detect a wide range of xanthine derivatives. These include natural xanthine derivatives like caffeine, theobromine, and theophylline, as well as pharmaceuticals synthesized with xanthine scaffolds such as etofylline, proxyphylline, and diprophylline.…”

Section: Resultsmentioning

confidence: 99%

“…Based on these understandings, our group explored additional modifiers to enhance the sensor’s sensitivity to caffeine, such as 3-bromo-2,6-dihydroxybenzoic acid (3-Br-2,6-DHBA) [ 39 ]. Utilizing the sensor modified with 3-Br-2,6-DHBA, the authors detected xanthine derivatives used in pharmaceuticals, including etofylline [ 40 ].…”

Section: Introductionmentioning

confidence: 99%

“…The scaffold of xanthine, with its structural rigidity and versatility, offers significant potential for molecular diversity when creating xanthine derivatives in combinatorial chemistry [ 47 , 48 ]. Our previous research [ 40 ] identified three APIs with xanthine scaffolds, etofylline, proxyphylline, and diprophylline, prompting further investigation into other non-charged pharmaceuticals, particularly acefylline and doxofylline, which are known for their bronchodilation effects [ 49 , 50 ]. This study also involves the examination of two additional non-charged pharmaceuticals possessing extra pharmacological properties: pentoxifylline, with potential benefits in preterm neonates with necrotizing enterocolitis [ 51 ], and allopurinol, used in the treatment of hyperuricemia [ 52 ].…”

Section: Introductionmentioning

confidence: 99%

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Assessment of Bitterness in Non-Charged Pharmaceuticals with a Taste Sensor: A Study on Substances with Xanthine Scaffold and Allopurinol

Zhao,

Song,

Kimura

et al. 2024

Molecules

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Taste sensors with an allostery approach have been studied to detect non-charged bitter substances, such as xanthine derivatives, used in foods (e.g., caffeine) or pharmaceuticals (e.g., etofylline). In this study, the authors modified a taste sensor with 3-bromo-2,6-dihydroxybenzoic acid and used it in conjunction with sensory tests to assess the bitterness of non-charged pharmaceuticals with xanthine scaffolds (i.e., acefylline and doxofylline), as well as allopurinol, an analogue of hypoxanthine. The results show that the sensor was able to differentiate between different levels of sample bitterness. For instance, when assessing a 30 mM sample solution, the sensor response to acefylline was 34.24 mV, which corresponded to the highest level of bitterness (τ = 3.50), while the response to allopurinol was lowest at 2.72 mV, corresponding to relatively weaker bitterness (τ = 0.50). Additionally, this study extended the application of the sensor to detect pentoxifylline, an active pharmaceutical ingredient in pediatric medicines. These results underscore the taste sensor’s value as an additional tool for early-stage assessment and prediction of bitterness in non-charged pharmaceuticals.

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Section: Resultssupporting

confidence: 91%