- Real-time monitoring of a photoactivated hydrogen persulfide donor for biological entities
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Hydrogen persulfide (H2S2) plays an important role in sulfur-based redox signaling mechanisms. Herein, we developed a visible light activated ESIPT based H2S2 donor using a p-hydroxyphenacyl phototrigger. The unique feature of the designed H2S2 donor system is the ability to monitor the H2S2 release in real time through a non-invasive fluorescence color change approach, with the color changing from green to blue. Next, we demonstrated the detection and quantification of H2S2 using a fluorescein based "turn-on" fluorescent probe. Furthermore, in vitro studies of the designed H2S2 donor demonstrated the real-time monitored H2S2 release and cytoprotective ability in the highly oxidizing cellular environment of MDA-MB-468 cells.
- Chaudhuri, Amrita,Venkatesh, Yarra,Jena, Bikash Chandra,Behara, Krishna Kalyani,Mandal, Mahitosh,Singh, N.D. Pradeep
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- A chromatography-free synthesis of racemic salbutamol hemisulfate
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Our efforts to achieve an efficient synthesis of racemic salbutamol hemisulfate are described. The selected chemical route starts from commodity chemicals and allows the generation of salbutamol hemisulfate in 5 steps and 44% overall yield without any purification by column chromatography. The reaction sequence has been optimized to provide the title compound using robust procedures. Emphasis on reproducibility and experimental simplicity drove the work described herein.
- Vanoost, Agathe,Petit, Laurent
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- Tetraphenylethylene conjugated: P -hydroxyphenacyl: Fluorescent organic nanoparticles for the release of hydrogen sulfide under visible light with real-time cellular imaging
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Hydrogen sulfide (H2S) behaves like a two-edged sword, at low concentrations it has beneficial and cytoprotective effects, while at higher concentrations it exhibits toxicity. Hence there is a keen interest in developing light responsive H2S donors with a spatio-temporal controlled release. Herein, we report visible light activatable tetraphenylethylene conjugated p-hydroxyphenacyl (TPE-pHP-H2S) nanoparticles for the release of hydrogen sulfide (H2S) with a real time monitoring ability. Our newly designed photoresponsive single component organic nanoparticle based H2S donor is built by integrating the tetraphenylethylene (TPE) moiety and p-hydroxyphenacyl (pHP) group so that it can display both aggregation-induced emission (AIE) and excited state intramolecular proton transfer (ESIPT) properties. Aggregation-induced emission enhancement was exhibited by our TPE-pHP-H2S NP donor, which was then explored for the cellular imaging application. The ESIPT by the pHP moiety provided unique advantages to our TPE-pHP-H2S NP donor which include (i) the excitation wavelength extended to >410 nm (ii) a large Stokes shift (iii) a low inner filter effect and (iv) real-time monitoring of H2S release by a simple fluorescent colour change. In vitro studies showed that the TPE-pHP-H2S NP donor presents excellent properties like real-time monitoring, photoregulated H2S release and biocompatibility.
- Parthiban,Pavithra,Reddy, L. Vinod Kumar,Sen, Dwaipayan,Samuel, Melvin S.,Singh, N. D. Pradeep
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- A new synthetic approach to salmeterol
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In the present work a short and convenient route for the synthesis of salmeterol from salicylaldehyde has been developed.
- Rong, Yajing,Ruoho, Arnold E.
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- A p-Hydroxyphenacyl-Benzothiazole-Chlorambucil Conjugate as a Real-Time-Monitoring Drug-Delivery System Assisted by Excited-State Intramolecular Proton Transfer
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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 400 nm, 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. In vitro studies showed that the p-hydroxyphenacyl-benzothiazole-chlorambucil conjugate presents excellent properties, such as real-time monitoring, photoregulated drug delivery, and biocompatibility.
- Barman, Shrabani,Mukhopadhyay, Sourav K.,Biswas, Sandipan,Nandi, Surajit,Gangopadhyay, Moumita,Dey, Satyahari,Anoop, Anakuthil,Singh, N.D. Pradeep
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- 'AIE + ESIPT' assisted photorelease: Fluorescent organic nanoparticles for dual anticancer drug delivery with real-time monitoring ability
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'Aggregation Induced Emission + Excited State Intramolecular Proton Transfer (AIE + ESIPT)'-assisted photorelease of an anticancer drug by a p-hydroxyphenacyl (pHP) phototrigger with real-time monitoring has been demonstrated.
- Biswas, Sandipan,Mengji, Rakesh,Barman, Shrabani,Venugopal, Vangala,Jana, Avijit,Singh, N. D. Pradeep
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- Synthesis method of salbutamol sulfate intermediate
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The invention discloses a synthesis method of a salbutamol sulfate intermediate, which comprises the following steps: by taking salicylaldehyde as a raw material, carrying out three-step reaction of Friedel-Crafts acylation, reduction, propylidene protection and N alkylation, and obtaining the target product salbutamol intermediate with the reaction yield of more than 60% in each step. The synthesis method of the salbutamol sulfate intermediate has the advantages of few reaction steps, simple post-treatment and high product purity.
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Paragraph 0028-0032
(2021/05/05)
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- Synthesis method of 5-(2-bromoacetyl)-2-hydroxybenzaldehyde
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The invention discloses a synthesis method of 5-(2-bromoacetyl)-2-hydroxybenzaldehyde, and belongs to the field of medicine synthesis. According to the method, the acylation reaction is conducted withsalicylaldehyde as the raw material to obtain 2-(acetoxyl)-benzaldehyde, then the rearrangement reaction is conducted, and finally the bromination reaction is conducted to obtain 5-(2-bromoacetyl)-2-hydroxybenzaldehyde. The preparing method has the advantages of being high in product purity and high in yield.
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Paragraph 0014; 0016; 0017; 0019; 0020; 0022
(2019/06/12)
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- Light triggered uncaging of hydrogen sulfide (H2S) with real-time monitoring
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An ESIPT based light activated hydrogen sulfide (H2S) donor using a p-hydroxyphenacyl phototrigger has been developed. The unique feature of our H2S donor system is that it provides real-time monitoring of H2S release by a non-invasive fluorescence colour change approach.
- Venkatesh, Yarra,Das, Joyjyoti,Chaudhuri, Amrita,Karmakar, Anupam,Maiti, Tapas K.,Singh, N. D. Pradeep
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supporting information
p. 3106 - 3109
(2018/03/28)
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- Levalbuterol intermediate and synthetic method of levalbuterol hydrochloride
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The invention provides a levalbuterol intermediate and a levalbuterol hydrochloride synthesis method, and relates to a levalbuterol intermediate and a method for preparing levalbuterol hydrochloride from the intermediate. The method comprises steps as follows: 2-halogenate-1-(2,2-dimelthyl-4-hydrogen-benzo [d][1,3] dioxane)-butanone and organic amine have a Hoffman alkylation reaction to prepare a compound in the formula 2, the structural formula of the compound is shown in the specification, and the compound in the formula 2 is subjected to a reduction reaction, optically pure organic acid resolution and deprotection by hydrochloric acid to obtain levalbuterol hydrochloride. The method does not need processes of protection or deprotection and the like of hydroxyl groups on a benzene ring, protection, deprotection and purification processes are reduced, the synthesis route is short, operation is simple, meanwhile, borane-thioether does not need to be used as a reduction agent, and safety and environmental protection are realized.
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Paragraph 0041; 0042; 0043; 0044
(2017/08/25)
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- (R)- albuterol hydrochloride asymmetric preparation method (by machine translation)
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The present invention relates to a high-efficient chiral catalyst synthesis of (R)- albuterol hydrochloride the asymmetric synthesis of the new method, the synthesis step includes: 1) salicylaldehyde with a halo of acetyl halogen crafts acylation reaction halo; 2) obtained after the the halogenated ketone uses unclebutylamine amine solution obtained after hydrolysis to the protection of the salicylaldehyde aminoketone; 3) this aminoketone in chiral amino alcohol derivative of the chiral borane the presence of a catalyst, is reduced to (R)- albuterol crude product, then the purified hydrochloric salt to obtain the high purity of the (R)- albuterol hydrochloride. (by machine translation)
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Paragraph 0040; 0041
(2017/08/25)
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- Hybrids consisting of the pharmacophores of salmeterol and roflumilast or phthalazinone: Dual β2-adrenoceptor agonists-PDE4 inhibitors for the treatment of COPD
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A novel class of dual pharmacology bronchodilators targeting both β2-adrenoceptor and PDE4 was designed and synthesised by combining the pharmacophores of salmeterol and roflumilast or phthalazinone. All the compounds exhibited better β2-adrenoceptor agonist activities (pEC50 = 8.47-9.20) than the reference compound salmeterol (pEC50 = 8.3) and good inhibitory activity on PDE4B2 (IC 50 = 0.235-1.093 μM).
- Liu, Anqiu,Huang, Ling,Wang, Zhiren,Luo, Zonghua,Mao, Fei,Shan, Wenjun,Xie, Jiaxing,Lai, Kefang,Li, Xingshu
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p. 1548 - 1552
(2013/03/28)
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- A convenient synthesis of (R)-salmeterol via Rh-catalyzed asymmetric transfer hydrogenation
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(R)-Salmeterol was synthesized in eight steps with salicaldehyde as the starting material. The key chiral intermediate, alcohol 5, was prepared via Rh-catalyzed asymmetric transfer hydrogenation with (S,S)-PEG-BsDPEN or (S,S)-TsDPEN ligand and sodium formate as the hydrogen donor under mild conditions.
- Liu, Juntao,Zhou, Di,Jia, Xian,Huang, Ling,Li, Xingshu,Chan, Albert S.C.
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p. 1824 - 1828
(2008/12/22)
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- NOVEL PROCESS
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The present invention relates to processes for the preparation of 4- hydroxy-α'' -[[[6-(4-phenylbutoxy)hexyl]amino]methyl]- 1,3-benzenedimethanol 1-hydroxy-2-naphthoate (salmeterol xinafoate) (Formula (12a)), the preparation of 4-hydroxy-α''-[[[6-(4-phenylbutoxy)hexyl]amino]methyl]-1,3-benzenedimethanol (salmeterol) (Formula (11)), the preparation of protected N-[6-(4-phenylbutoxy)hexyl]amine intermediates (Formula (7)), and the preparation of 6-substituted (4-phenylbutoxy)hexane intermediates (Formula (5)), shown below, wherein X is a leaving group and Pg is a protecting group.
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Page/Page column 23; Figure 2
(2010/11/27)
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- BENZYLPHOSPHATE AND SUBSTITUTED BENZYLPHOSPHATE PRODRUGS FOR TRE TREATMENT OF PULMONARY INFLAMMATION
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A prodrug of a corticosteroid, lidocaine or related local anesthetic composition for formulation for delivery by aerosolization to inhibit inflammation in asthmatic lungs is described. The prodrug is preferably formulated in a 5 ml solution of a quarter normal saline having pH between 5.0 and 7.0 for the treatment of respiratory tract inflammation by an aerosol having mass medium average diameter predominantly between 1 to 5 μ produced by nebulization or dry powder inhaler.
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Page/Page column 51
(2010/02/12)
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- Intermediates in the preparation of alpha1(((1,1-dimethylethyl) amino) methyl)-4-hydroxy-1,3-benzenedimethanol
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There is disclosed an improved process for preparing albuterol which comprises reacting a 5-(haloacetyl)-2-hydroxybenzaldehyde with 1,1-dimethylethanamine in an organic solvent and in an inert atmosphere to form 5-[[(1,1-dimethylethyl)amino]acetyl]-2-hydr
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