A p-Hydroxyphenacyl-Benzothiazole-Chlorambucil Conjugate as a Real-Time-Monitoring Drug-Delivery System Assisted by Excited-State Intramolecular Proton Transfer

被引：63

作者：

Barman, Shrabani ^{[1
]}

Mukhopadhyay, Sourav K. ^{[2
]}

Biswas, Sandipan ^{[1
]}

Nandi, Surajit ^{[1
]}

Gangopadhyay, Moumita ^{[1
]}

Dey, Satyahari ^{[2
]}

Anoop, Anakuthil ^{[1
]}

Singh, N. D. Pradeep ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kharagpur 721302, W Bengal, India

[2] Indian Inst Technol, Dept Biotechnol, Kharagpur 721302, W Bengal, India

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 13期

关键词：

drug delivery; fluorescence; phototriggers; real-time monitoring; theranostics; LARGE STOKES SHIFT; PROTECTING GROUPS; TRANSFER ESIPT; RELEASE; PHOTOTRIGGERS; FLUORESCENCE; ABSORPTION; MECHANISMS;

D O I：

10.1002/anie.201508901

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Among the well-known phototriggers, the p-hydroxyphenacyl (pHP) group has consistently enabled the very fast, efficient, and high-conversion release of active molecules. Despite this unique behavior, the pHP group has been ignored as a delivery agent, particularly in the area of theranostics, because of two major limitations: Its excitation wavelength is below 400nm, and it is nonfluorescent. We have overcome these limitations by incorporating a 2-(2-hydroxyphenyl)benzothiazole (HBT) appendage capable of rapid excited-state intramolecular proton transfer (ESIPT). The ESIPT effect also provided two unique advantages: It assisted the deprotonation of the pHP group for faster release, and it was accompanied by a distinct fluorescence color change upon photorelease. Invitro studies showed that the p-hydroxyphenacyl-benzothiazole-chlorambucil conjugate presents excellent properties, such as real-time monitoring, photoregulated drug delivery, and biocompatibility.

引用

页码：4194 / 4198

页数：5

共 26 条

[11] New phototriggers 9:: p-hydroxyphenacyl as a C-terminal photoremovable protecting group for oligopeptides [J].

Givens, RS ;

Weber, JFW ;

Conrad, PG ;

Orosz, G ;

Donahue, SL ;

Thayer, SA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (12) :2687-2697

[12] Perylene-3-ylmethanol: Fluorescent Organic Nanoparticles as a Single-Component Photoresponsive Nanocarrier with Real-Time Monitoring of Anticancer Drug Release [J].

Jana, Avijit ;

Devi, K. Sanjana P. ;

Maiti, Tapas K. ;

Singh, N. D. Pradeep .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (18) :7656-7659

[13] Photoresponsive quinoline tethered fluorescent carbon dots for regulated anticancer drug delivery [J].

Karthik, S. ;

Saha, Biswajit ;

Ghosh, Sudip Kumar ;

Singh, N. D. Pradeep .

CHEMICAL COMMUNICATIONS, 2013, 49 (89) :10471-10473

[14] Photoremovable Protecting Groups in Chemistry and Biology: Reaction Mechanisms and Efficacy [J].

Klan, Petr ;

Solomek, Tomas ;

Bochet, Christian G. ;

Blanc, Aurelien ;

Givens, Richard ;

Rubina, Marina ;

Popik, Vladimir ;

Kostikov, Alexey ;

Wirz, Jakob .

CHEMICAL REVIEWS, 2013, 113 (01) :119-191

[15] Hybrids consisting of the pharmacophores of salmeterol and roflumilast or phthalazinone: Dual β2-adrenoceptor agonists-PDE4 inhibitors for the treatment of COPD [J].

Liu, Anqiu ;

Huang, Ling ;

Wang, Zhiren ;

Luo, Zonghua ;

Mao, Fei ;

Shan, Wenjun ;

Xie, Jiaxing ;

Lai, Kefang ;

Li, Xingshu .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (05) :1548-1552

[16] Photoresponsive Poly(S-(o-nitrobenzyl)-L-cysteine)-b-PEO from a L-Cysteine N-Carboxyanhydride Monomer: Synthesis, Self-Assembly, and Phototriggered Drug Release [J].

Liu, Gang ;

Dong, Chang-Ming .

BIOMACROMOLECULES, 2012, 13 (05) :1573-1583

[17] A novel HBT-based Schiff base for colorimetric detection of aluminum: Synthesis, characterization, spectral and DFT computational studies [J].

Liu, Shudi ;

Zhang, Liangwei ;

Zan, Wenyan ;

Yao, Xiaojun ;

Yang, Ying ;

Liu, Xiang .

SENSORS AND ACTUATORS B-CHEMICAL, 2014, 192 :386-392

[18] Ultrafast time-resolved transient absorption and resonance Raman spectroscopy study of the photodeprotection and rearrangement reactions of p-hydroxyphenacyl caged phosphates [J].

Ma, CS ;

Kwok, WM ;

Chan, WS ;

Du, Y ;

Kan, JTW ;

Toy, PH ;

Phillips, DL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (08) :2558-2570

[19] Real-time electrochemical monitoring of drug release from therapeutic nanoparticles [J].

Mora, Laura ;

Chumbimuni-Torres, Karin Y. ;

Clawson, Corbin ;

Hernandez, Lucas ;

Zhang, Liangfang ;

Wang, Joseph .

JOURNAL OF CONTROLLED RELEASE, 2009, 140 (01) :69-73

[20] Tuning of Excited-State Intramolecular Proton Transfer (ESIPT) Fluorescence of Imidazo[1,2-a]pyridine in Rigid Matrices by Substitution Effect [J].

Mutai, Toshiki ;

Sawatani, Hirotaka ;

Shida, Toshihide ;

Shono, Hideaki ;

Araki, Koji .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (06) :2482-2489

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