T:Toxic;
305-03-3Relevant articles and documents
A two-photon responsive naphthyl tagged: P -hydroxyphenacyl based drug delivery system: Uncaging of anti-cancer drug in the phototherapeutic window with real-time monitoring
Kundu, Moumita,Mondal, Mahitosh,Nair, Asha V,Pal, Bipul,Roy, Biswajit,Roy, Samrat,Shah, Sk. Sheriff,Singh, Amit Kumar,Singh, N. D. Pradeep
, p. 9986 - 9989 (2020)
We report a two-photon responsive drug delivery system (DDS), namely, p-hydroxyphenacyl-naphthalene-chlorambucil (pHP-Naph-Cbl), having a two-photon absorption (TPA) cross-section of ≥20 GM in the phototherapeutic window (700 nm). Our DDS exhibited both AIE and ESIPT phenomena, which were utilized for the real-time monitoring of anti-cancer drug release.
Upconversion-like Photolysis of BODIPY-Based Prodrugs via a One-Photon Process
Lv, Wen,Li, Yafei,Li, Feiyang,Lan, Xin,Zhang, Yaming,Du, Lili,Zhao, Qiang,Phillips, David L.,Wang, Weiping
, p. 17482 - 17486 (2019)
Photochemical reactions at lower energy than the absorption window are currently achieved by multi-photon processes, including two-photon absorption and photon upconversion, which have limited energy utilization efficiency. Here, we report a one-photon strategy based on triplet-triplet energy transfer (TTET) between a photosensitizer and a photocleavable molecule to achieve photolysis at low energy. To verify this concept, we chose platinum(II) tetraphenyltetrabenzoporphyrin (PtTPBP) as the photosensitizer and synthesized a boron-dipyrromethene (BODIPY)-based prodrug as the photocleavable molecule. Photolysis of the prodrug is achieved by TTET upon excitation of PtTPBP at 625 nm with a photolysis quantum yield of 2.8%. Another demonstration shows an unexpected higher photolysis quantum yield than the direct excitation at 530 nm. This strategy opens a new path for achieving photolysis at long wavelengths, benefiting the applications in biological studies, photopharmacology, and photoresponsive drug delivery.
Single component photoresponsive fluorescent organic nanoparticles: a smart platform for improved biomedical and agrochemical applications
Chaudhuri, Amrita,Paul, Amrita,Sikder, Antara,Pradeep Singh
, p. 1715 - 1733 (2021)
In the last two decades, light responsive nano drug delivery systems (DDSs) have gained considerable importance, particularly in the area of biology and medicine. In general, light responsive nano DDSs are bicomponent and constructed using two ingredients, namely a nanocarrier and a phototrigger. The synthesis of these bicomponent nano DDSs requires multiple steps, which limits their applications. Hence, we have reported single component light responsive nano DDSs using fluorescent organic nanoparticles (FONPs) which acted both as a nanocarrier and a phototrigger. This feature article provides an overview of recently developed light responsive single component FONPs and their applications in the regulated release of anticancer drugs, gasotransmitters, antibacterial agents, and pesticides, and also as efficient PDT agents. We have summarised the synthesis, characterisation, and photophysical, photochemical, andin vitrobehaviours of these light responsive FONPs. In addition, we also discussed the advantages of using FONPs as a nano DDS for cellular studies like: excellent biocompatibility, efficient cellular internalisation, real time monitoring of the drug release ability inside the cells, and enhanced cytotoxicity due to regulated release of bioactive molecules inside the cells.
Three-Arm, Biotin-Tagged Carbazole–Dicyanovinyl–Chlorambucil Conjugate: Simultaneous Tumor Targeting, Sensing, and Photoresponsive Anticancer Drug Delivery
Venkatesh, Yarra,Karthik,Rajesh,Mandal, Mahitosh,Jana, Avijit,Singh, N. D. Pradeep
, p. 3482 - 3486 (2016)
The design, synthesis, and in vitro biological studies of a biotin–carbazole–dicyanovinyl–chlorambucil conjugate (Bio-CBZ-DCV-CBL; 6) are reported. This conjugate (6) is a multifunctional single-molecule appliance composed of a thiol-sensor DCV functionality, a CBZ-derived phototrigger as well as fluorescent reporter, and CBL as the anticancer drug, and Bio as the cancer-targeting ligand. In conjugate 6, the DCV bond undergoes a thiol–ene click reaction at pH7 with intracellular thiols, thereby shutting down internal charge transfer between the donor CBZ and acceptor DCV units, resulting in a change of the fluorescence color from green to blue, and thereby, sensing the tumor microenvironment. Subsequent photoirradiation results in release of the anticancer drug CBL in a controlled manner.
Targeted photoresponsive carbazole–coumarin and drug conjugates for efficient combination therapy in leukemia cancer cells
Chang, Wen-Wei,Chu, Chih-Chien,Lai, Yi-Ting,Lin, Yen-Cheng,Ou, Jia-Yu,Wang, Bing-Yen
, (2020)
Phototriggered drug delivery systems (PTDDSs) facilitate controlled delivery of drugs loaded on photoactive platform to the target region under light stimulation. The present study investigated the synthesis and efficacy of carbazole–coumarin (CC)-fused heterocycles as a PTDDS platform for the photocontrolled release of a chemotherapeutic agent, chlorambucil, in an in vitro model of human breast and leukemia cancer cells. CC-fused heterocycles were constructed using 4-hydroxycarbazole as the starting material, and further modification of these heterocycles yielded two CC derivatives. CC-7 with an additional ? COOH group and CC-8 with the triphenylphosphonium (TPP) group, a mitochondria-targeting ligand introduced in the carbazole ring, dissolved in polar solvents and exhibited emission bands at 360 and 450 nm, respectively. The results indicate that visible light of 405 nm triggers the photolysis of the CC–drug conjugate and efficiently delivers the drug in both in vitro cancer cell models. Cytotoxicity evaluation indicates the suppression of proliferation of both types of cells treated with CC-8 under synergy effect combining drug potency and photosensitization. Further, the lower IC50 of CC-8 toward leukemia cells suggests the efficacy of the TPP ligand in increasing the bioavailability of CC–drug conjugates in leukemia treatment. Studies on mitochondria-targeting drug delivery systems are required for improving the performance of anticancer drugs.
A dual-analyte probe: Hypoxia activated nitric oxide detection with phototriggered drug release ability
Biswas, Sandipan,Rajesh,Barman, Shrabani,Bera, Manoranjan,Paul, Amrita,Mandal, Mahitosh,Pradeep Singh
, p. 7940 - 7943 (2018)
A new strategy for the detection of hypoxia and NO succeeded by photocontrolled delivery of an anticancer agent has been demonstrated. The developed system is able to produce distinct responses (dual channel) upon interaction with hypoxia and NO. This probe can also release anticancer drugs upon photoirradiation acting potentially as both a dual-analyte imaging agent and a prodrug.
Method for synthesizing chlorambucil
-
Paragraph 0028; 0031-0032; 0035-0036, (2021/07/17)
The invention discloses a method for synthesizing chlorambucil, which relates to the technical field of organic chemistry, and comprises the following steps: S1, adding a mixture of 4-bromo-N, N-bis (2-chloroethyl) aniline, N-(quinolin-8-yl) butyl 3-enamide, palladium chloride, tri-n-butylphosphine tetrafluoroborate, potassium carbonate and benzoic acid at ratio of 10.83%: 10.83%-32.50%: 0.22%-2.17%: 0.43%-2.17%: 10.83%-54.17%: 10.83%-54.17% and dimethyl sulfoxide at molar volume ratio of 0.1 mmol: 2 mL to a reaction vessel for uniform mixing; and S2, placing the reaction container in an oil bath at 135-145 DEG C, and violently stirring to react for 24 hours. According to the invention, through the coupling reaction, 8-aminoquinoline is designed as a compound of a leaving group to control regioselectivity and chemical selectivity in the reaction, so that the problem of excessive steps in the existing synthesis process of chlorambucil is effectively solved; the method has the characteristics of high reaction region selectivity and yield, mild reaction conditions and simple reaction and post-treatment purification processes.
PHOTOLYTIC COMPOUNDS AND TRIPLET-TRIPLET ANNIHILATION MEDIATED PHOTOLYSIS
-
Paragraph 0026; 00254, (2021/04/17)
The invention provides novel photolytic compounds and prodrugs, nanoparticles and compositions thereof, and methods of conducting photolysis mediated by triplet-triplet annihilation.
Cys fluorescent molecular probe for detecting DNA targeting under reduction stress as well as preparation method and application of Cys fluorescent molecular probe
-
Paragraph 0067-0068, (2021/06/26)
The invention relates to a Cys fluorescent molecular probe for detecting DNA targeting under reduction stress as well as a preparation method and application of the Cys fluorescent molecular probe. The structural formula of the fluorescent molecular probe is as shown in the formula (1). The prominent light control characteristic of the fluorescent molecular probe is beneficial to real-time monitoring of diseases caused by errors in the DNA replication process due to abnormal expression of Cys under DNA peripheral reduction stress, and the fluorescent molecular probe is expected to be applied to prevention, treatment and the like of gene diseases caused by abnormal expression of Cys.
Mitochondria-localized: In situ generation of rhodamine photocage with fluorescence turn-on enabling cancer cell-specific drug delivery triggered by green light
Bera, Manoranjan,Jana, Avijit,Mengji, Rakesh,Ojha, Mamata,Paul, Amrita,Singh, N. D. Pradeep
, p. 8412 - 8415 (2020/08/13)
In this work, we have developed a rhodamine dye based water-soluble, mitochondria-indicating photocage, which gets activated in the mitochondria producing a fluorescent signal and on-demand releases the caged anticancer drug, chlorambucil, in the cancer cells selectively upon irradiation of green light.
