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MICROCHIMICA ACTA · 2020 ·Vol. 187 ·期 2 ·1-8 · IF 6.232

Colorimetric captopril assay based on oxidative etching-directed morphology control of silver nanoprisms

Zhang Pu,Wang Li,Zeng Jing,Tan Juan,Long Yunfei,Wang Yi

Oxidative etching is an effective approach to control the morphology of nanomaterials. Taking silver nanocrystals (AgNCs) as an example, oxidative etching-directed morphological transformation from a triangular prism shape to a disk shape is achieved and then applied to the determination of captopril. As a mediator, trace amount of halides play important roles in the shape-controlled evolution of AgNCs. Etching causes the color of the triangular silver nanoprims (AgNPRs) to change from blue to yellow on formation of round nanodisks. On addition of captopril, the oxidative etching of the AgNPRs is prevented owing to the protection by the drug via Ag-S bonding. In this case, the solution color does not change. This finding was used to design an assay of captopril that has a linear response in the 10–600 nM concentration range and a 2 nM limit of detection. This method also allows digital camera read-out. It was successfully applied to quality control of captopril in tablets. Oxidative etching-directed morphological transformation of silver nanocrystals is well manipulated and successfully applied in colorimetric determination of captopril in tablets.

研究领域: 分析化学 · 药物分析 · 纳米技术
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MICROCHEMICAL JOURNAL · 2023 · IF 4.8

A practical electrochemical method for determining the inhibitory activity of New Delhi Metallo-β-lactamase-1 inhibitors

Hongyu Gan,Yaowen Liang,Yun Tang,Manna Huang,Yiqian Wan

A practical electrochemical method for the determination of the inhibitory activity of New Delhi metallo-β-lactamase-1 (NDM-1) inhibitors was established with a bare pencil graphite electrode (PGE) as the working electrode and imipenem as the substrate. To validate the method, the well-known NDM-1 inhibitors EDTA and L -captopril were selected for the corresponding assays with IC 50 values of 1.22 ± 0.20 μM and 22.92 ± 1.19 μM, respectively. These results were consistent with those (5.48 ± 0.32 μM for EDTA and 69.13 ± 6.01 μM for L- captopril) from the UV–vis high-throughput assay method. Further investigation regarding the steady kinetics of a typical competitive inhibitor of L -captopril showed that the two methods provided K i values at the same level, i.e., they are 41.5 ± 3.8 μM (DPV-PGE) and 52.5 ± 2.5 μM (UV–vis), respectively.

CAS / MDL: 13746-66-2 7664-38-2
研究领域: 生物化学 · 药物化学
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2022 · IF 4.831

Quantitative detection of captopril in urine by smartphone-assisted ratiometric fluorescence sensing platform

Lixia Han,Ting Liu,Di Cui,Jiaqi Yi,Wei Jiang,Xiaoshuang Li,Na Niu,Ligang Chen

Captopril (CP) is a widely used antihypertensive drug. In this study, a smartphone-assisted sensing platform on the basis of ratiometric fluorescent test strips was developed, which can accomplish visualization for the quantitative detection of captopril. Ratiometric fluorescent probe was constructed from carbon dots (CDs) and gold nanoclusters (Au NCs). After adding Cu 2+ to fluorescent probe, Cu 2+ can complex the amino and carboxyl groups on the surface of Au NCs and aggregate Au NCs, which will quench the fluorescence of Au NCs. Compared with amino and carboxyl groups, -SH in CP has a higher affinity for Cu 2+ and can capture Cu 2+ to restore Au NCs fluorescence. In this process, CDs remained essentially unchanged as background fluorescence. As CP concentration increased, the fluorescence color showed a distinct change from blue to purple to orange. Based on this principle, a sensing platform combining smartphone and fluorescent test strips was constructed to visualize the quantitative detection of CP by RGB values. Under optimal conditions, the wide linear range of CP detection for both fluorescence spectrometer and smartphone paper-based sensing platform was 0.25–50 μM. The limits of detection were as low as 76 nM and 101.3 nM, respectively. Furthermore, it was implemented successfully for the detection of CP in urine. The satisfactory recoveries were 96.0–103.3% and 92.0–108.0% for fluorescence spectrometer and smartphone platform, respectively. This smartphone-assisted platform provided a new approach for visual detection of CP, which showed its great potential in bioanalytical assays.

研究领域: 分析化学 · 生物医学工程 · 药物分析
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RESEARCH ON CHEMICAL INTERMEDIATES · 2012 ·Vol. 39 ·期 2 ·621-629 · IF 0.697

Synthesis and characterization of captopril derivatives

Li He-ping,Zhang Juan-juan,Qin Long,Zhao Ming-dong

To develop more potential angiotensin converting enzyme (ACE) inhibitors, a series of captopril (Cap) derivatives were synthesized, including Cap-glycine methyl ester, Cap- l -alanine methyl ester, Cap- l -aspartic acid dimethyl ester, Cap- l -lysine methyl ester, Cap- O -acylisourea, acetyl captopril, and benzoyl captopril. The resulting products were characterized by IR and UV–visible spectroscopy and MS, which showed the desired products were successfully synthesized. This could serve as a guide for rational design of highly potent ACE inhibitors.

研究领域: 药物化学 · 生物化学
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WATER RESEARCH · 2016 · IF 5.991

Transformation and products of captopril with humic constituents during laccase-catalyzed oxidation: Role of reactive intermediates

Penghui Du,He Zhao,Chenming Liu,Qingguo Huang,Hongbin Cao

The transformation of captopril (CAP), a widely-used thiol drug, was studied with the presence of dissolved model humic constituents (HCs) in a laccase-catalyzed system. Reaction products were analyzed by ultra-performance liquid chromatography coupled to time-of-flight mass spectrometry and condensed fukui function computation. CAP reacted with different model HCs in the enzymatic system for 1 h, ranging from 75% (syringic acid) to 96% ( p -coumaric acid). In the absence of HCs, only 15% of CAP was removed through self-coupling. The presence of HCs apparently changed the transformation of CAP in aqueous environment, and the HC reactive intermediates played an important role. First, during laccase catalysis, HCs with different structures were oxidized to produce reactive intermediates, including phenoxyl radical cation, ortho -, and para -quinone intermediates. Second, these intermediates were readily attacked by CAP via nucleophilic reactions, forming C–S–C covalent conjugates. More importantly, the standard reduction potential of these intermediates is a critical parameter, as PCA showed the highest reactivity to the nucleophilic addition reaction with CAP by forming phenoxy radical cations. While SYR showed the least reactivity due to the formation of para -quinone intermediates. Therefore, the functional groups on HCs could greatly influence the cross-coupling with CAP, as well as the type and stability of the coupling products. This work clearly demonstrated the transformation of CAP and other thiol drugs with the presence of HCs in aqueous environment, which is similar to the natural humification process.

研究领域: 环境科学 · 药物化学
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2018 · IF 3.412

Novel Antihypertensive Prodrug from Grape Seed Proanthocyanidin Extract via Acid-Mediated Depolymerization in the Presence of Captopril: Synthesis, Process Optimization, and Metabolism in Rats

Can Cui,Ailong Shi,Shuang Bai,Pengyu Yan,Qing Li,Kaishun Bi

Grape seed extract contains a high content of proanthocyanidins that can be depolymerized into C-4-substituted (epi)catechin derivatives in the presence of nucleophiles. However, the biological and medicinal values of depolymerization products have been rarely investigated. Recently, we developed a novel depolymerization product (−)-epicatechin-4β-S-captopril methyl ester (ECC) derived from the reaction of grape seed proanthocyanidin extract with captopril in the presence of acidified methanol. A central composite design was employed to select the most appropriate depolymerization temperature and time to obtain the target product ECC with a high yield. A total of 16 metabolites of ECC in rat urine, feces, and plasma were identified using liquid chromatography quadrupole time-of-flight tandem mass spectrometry. The in vivo results suggested that ECC could release captopril methyl ester and epicatechin, followed by the generation of further metabolites captopril and epicatechin sulfate conjugates. Therefore, ECC may be used as a potential prodrug with synergistic or additive hypotensive effects.

研究领域: 药理学 · 分析化学 · 药物化学
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MICROCHIMICA ACTA · 2018 ·Vol. 185 ·期 9 ·1-9 · IF 5.705

Photoluminescent coral-like carbon-branched polymers as nanoprobe for fluorometric determination of captopril

Wang Zhong-Xia,Gao Yuan-Fei,Yu Xian-He,Kong Fen-Ying,Lv Wei-Xin,Wang Wei

The authors describe the synthesis of fluorescent coral-like carbon nano-branched polymers (PCNBPs) co-doped with nitrogen and phosphorus. Uric acid and phosphoric acid act as nitrogen and phosphorus sources, respectively. The PCNBPs have a coral-like branched structure, are cross-connected, and < 20 nm in skeleton diameter. Their blue fluorescence, best measured at excitation/emission wavelengths of 330/425 nm, is quenched by mercury (II) ions due to the specifically restricted rigid conformation caused by the interaction of phosphorus, nitrogen, and oxygen groups on the surface of the PCNBPs. Fluorescence is selectivity quenched by Hg(II) but restored in addition of the hypertension drug captopril (CAP) in the range 50 nM to 40 μM concentration range. Fluorescence recovery is attributed to the effectively specific interactions between the thiol group of CAP and Hg(II). The method was applied to the determination of the concentration of Cap in pharmaceutical samples, and recoveries were between 97.6 and 105.1%. Fluorescent coral-like carbon nano-branched polymers (PCNBPs) co-doped with nitrogen and phosphorus are described. Their fluorescence is selectivity quenched by Hg(II) but restored in addition of the hypertension drug captopril (Cap) in the range 50 nM to 40 μM concentration range.

研究领域: 分析化学 · 材料科学 · 药物分析
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Journal of Pharmaceutical Analysis · 2021 · IF 4.769

Reversible regulation of enzyme-like activity of molybdenum disulfide quantum dots for colorimetric pharmaceutical analysis

Juan Tan,Shiyue Wu,Qingqing Cai,Yi Wang,Pu Zhang

Regulating the catalytic activity of nanozymes is significant for their applications in various fields. Here, we demonstrate a new strategy to achieve reversible regulation of the nanozyme's activity for sensing purpose. This strategy involves the use of zero-dimensional MoS 2 quantum dots (MQDs) as the building blocks of nanozymes which display very weak peroxidase (POD)-like activity. Interestingly, such POD-like activity of the MQDs largely enhances in the presence of Fe 3+ while diminishes with the addition of captopril thereafter. Further investigations identify the mechanism of Fe 3+ -mediated aggregation-induced enhancement of the POD-like activity and the inhibitory effect of captopril on the enhancement, which is highly dependent on their concentrations. Based on this finding, a colorimetric method for the detection of captopril is developed. This sensing approach exhibits the merits of simplicity, rapidness, reliability, and low cost, which has been successfully applied in quality control of captopril in pharmaceutical products. Moreover, the present sensing platform allows smartphone read-out, which has promising applications in point-of-care testing devices for clinical diagnosis and drug analysis.

CAS / MDL: 7689-03-4 64285-73-0
研究领域: 纳米生物学 · 药物分析 · 生物传感
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ACS Applied Materials & Interfaces · 2025 · IF 8.2

Enzyme-Responsive Peptide-Prodrug Integrated Biphasic Microneedle Patch for Enhanced Transdermal Delivery and Hypertension Therapy

Shibo Zhang,Bing Dong,Yao Shuai,Shuyue Deng,Jun Luo,Caixia Sun,Xing Ge,Lilin Chen,Hai Qian,Jianjun Dai,Yanmin Ju

Hypertension is a major risk factor for cardiovascular diseases and needs effective blood pressure reduction. Current antihypertensive drugs, such as captopril, face challenges, including the enzymatic degradation and the liver first-pass effect. Here, we developed a dissolving microneedle (MN) loaded with a peptide-based enzyme-responsive prodrug peptide-captopril (PC) to enhance the stability of captopril and enable efficient transdermal delivery. Kinetic studies revealed that PC exhibited a lower Km value (1.1 × 10–5 M) for esterase-mediated hydrolysis compared to free captopril (2.1 × 10–5 M), indicating improved enzymatic stability. Meanwhile, PC was encapsulated stably in microneedle tips to form the PC MN, achieving approximately 90% transdermal drug delivery. In spontaneously hypertensive rat models, PC MN elicited a rapid and potent blood-pressure-lowering effect, outperforming oral captopril administration. This study presents a promising self-administering strategy to enhance hypertension treatment through efficient transdermal drug delivery.

研究领域: 药剂学 · 生物化学 · 生物医学工程 · 心血管医学
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Analytical Methods · 2025 · IF 2.6

Development of a NS-CDs/Fluorescein Ratiometric Fluorescent Sensor Integrated Smartphone Platform for Rapid and Specific Detection of Mn(VII) and Captopril

Chuntong Liu,Haiyan Qi,Jiayu Zhang,Jun Li,Tao Jing,Qiuying Li,Lixin Qiu,Xiaochen Zhu

The construction of a ratiometric fluorescent sensor based on nitrogen-doped carbon dots (NS-CDs) and fluorescein was reported to detect Mn(VII) and captopril. The detection mechanism of Mn(VII) and captopril were based on inner filter effect (IFE) and redox reaction, respectively. The sensor showed good linearities in the detection range of 0.12-100 μM for Mn(VII) and 0.52-300 μM for captopril, with limits of detection (LODs) of 0.12 μM and 0.52 μM, respectively. Furthermore, a smartphone-based platform for the detection of Mn(VII) and captopril was developed, based on the dual-signal response of color and fluorescence intensity. The system displayed linear signal changes with increasing Mn(VII) and captopril concentration in the ranges of 0.32-100 μM and 0.52-300 μM, with LODs of 0.32 μM and 0.52 μM, respectively. Finally, the ratiometric sensor was validated for the determination of Mn(VII) and captopril in herb and captopril tablet samples, demonstrating its broad applicability and versatility as a portable, sensitive, and specific detector for Mn(VII) and captopril in various sample types. Overall, our ratiometric fluorescent sensor has potential as a portable, on-site detector for Mn(VII) and captopril analysis.

研究领域: 分析化学 · 环境科学 · 药物分析
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JOURNAL OF RAMAN SPECTROSCOPY · 2015 ·Vol. 46 ·期 7 ·605-609 · IF 2.671

Quantitative detection of captopril in tablet and blood plasma samples by the combination of surface-enhanced Raman spectroscopy with multiplicative effects model

Si-Yu Long,Zeng-Ping Chen,Yao Chen,Ru-Qin Yu

With p -thiocresol as internal standard, quantitative analysis of captopril, a synthetic angiotensin converting enzyme inhibitor, was achieved by the combination of the multiplicative effects model with surface-enhanced Raman spectroscopy (SERS). The multiplicative effects model was adopted to correct the detrimental effects caused by the heterogeneity in the physical properties of enhancing substrate (i.e. Ag nano-particles). Experimental results showed that the calibration model built on the SERS spectra of the calibration captopril samples prepared with ultrapure water could attain quite satisfactory concentration predictions for captopril in both real-world tablet samples and plasma samples. The recovery rates were in the range of 94.3% to 109.8%, which were in substantial agreement with the corresponding results of LC-MS/MS. The limit of detection and limit of quantification were estimated to be 0.149 and 0.451 μM, respectively. The proposed approach has advantages of relatively low cost, simplicity, high sensitivity and good accuracy and therefore can be further developed and extended to a routine method for the quantification of captopril in complex systems. Copyright © 2015 John Wiley & Sons, Ltd.

CAS / MDL: 106-45-6
研究领域: 分析化学 · 药物分析 · 生物医学
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2016 · IF 2.653

Reusable fluorescent sensor for captopril based on energy transfer from photoluminescent graphene oxide self-assembly multilayers to silver nanoparticles

Xiangying Sun,Bin Liu,Shuchun Li,Fang Li

In this work we designed a self-assembly multilayers, in which photoluminescent graphene oxide was employed as a fluorescence probe. This multilayers film can effectively recognize captopril by resonance energy transfer from graphite oxide to silver nanoparticles . A new interfacial sensing method for captopril with high signal to noise ratio was established, by means of that multilayers was quenched by silver nanoparticles and subsequently recovered by adding captopril. The linear relation between intensity and captopril concentration was good, and the detection limit was found to be 0.1578   μ M. Also, this novel detection platform demonstrated intriguing reusable properties, and the sensor could be repeated more than ten times without obviously losing its sensing performance.

CAS / MDL: 9012-76-4
研究领域: 分析化学 · 材料科学 · 生物医学工程
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