151889-83-7Relevant articles and documents
Coumarin-benzothiazole-chlorambucil (Cou-Benz-Cbl) conjugate: An ESIPT based pH sensitive photoresponsive drug delivery system
Barman, Shrabani,Mukhopadhyay, Sourav K.,Gangopadhyay,Biswas, Sandipan,Dey, Satyahari,Singh, N.D.Pradeep
, p. 3490 - 3497 (2015)
We have developed an ESIPT based drug delivery system (DDS), Cou-Benz-Cbl conjugate, by incorporating a benzothiazole group at the 8th position of the 7-hydroxy-coumarin moiety for pH sensitive fluorescence properties and photocontrolled release of the anticancer drug chlorambucil. The Cou-Benz-Cbl conjugate exhibited unique photophysical properties like good absorbance at around 350 nm, a large Stokes shift (～151 nm) and pH sensitive fluorescence properties. The pH sensitive fluorescence properties of the Cou-Benz-Cbl conjugate can be ascribed to an ESIPT turn "on and off" mechanism. At physiological pH, the ESIPT gets turned "off" and a blue fluorescence of the coumarin moiety was observed, but at acidic pH, the ESIPT gets turned "on" and a green fluorescence was noted. Photolysis of the Cou-Benz-Cbl conjugate using UV light of wavelength ≥365 nm resulted in the efficient release of the anticancer drug chlorambucil. Cellular uptake studies revealed that the Cou-Benz-Cbl conjugate was easily internalized inside the cancer cells. Further, an MTT assay showed that the Cou-Benz-Cbl conjugate has a good biocompatibility and low cytotoxicity towards the MDA-MB-231 cell line, whereas upon exposure to UV light, the Cou-Benz-Cbl conjugate exhibited enhanced cytotoxicity compared to the free drug due to the effective release of the anticancer drug chlorambucil inside the cancer cell.
Photoresponsive coumarin polyesters that exhibit cross-linking and chain scission properties
Maddipatla, Murthy V.S.N.,Wehrung, Daniel,Tang, Chuan,Fan, Weizheng,Oyewumi, Moses O.,Miyoshi, Toshikazu,Joy, Abraham
, p. 5133 - 5140 (2013)
The synthesis and properties of a new class of photoresponsive coumarin polyesters are described. Incorporation of the coumarin chromophore in the polymer chain provides interesting properties such as polymer chain cross-linking upon irradiation at 350 nm and chain un-cross-linking when irradiated at 254 nm. In addition, irradiation at 254 nm also results in polymer chain scission. The cross-linking, un-cross-linking, and chain scission properties were studied by ssNMR, ATR-IR, and GPC measurements. These properties enable the fabrication of 2D surfaces having complementary micropatterned features. Also, initial biocompatibility profiles of the polymers and their irradiation products were demonstrated using MTT assays.
Structures of human monoamine oxidase B complexes with selective noncovalent inhibitors: Safinamide and coumarin analogs
Binda, Claudia,Wang, Jin,Pisani, Leonardo,Caccia, Carla,Carotti, Angelo,Salvati, Patricia,Edmondson, Dale E.,Mattevi, Andrea
, p. 5848 - 5852 (2007)
Structures of human monoamine oxidase B (MAO B) in complex with safinamide and two coumarin derivatives, all sharing a common benzyloxy substituent, were determined by X-ray crystallography. These compounds competitively inhibit MAO B with Ki v
Synthesis and photobiological properties of 4-hydroxymethyl-4'-methylpsoralen derivatives.
Zagotto,Gia,Baccichetti,Uriarte,Palumbo
, p. 486 - 491 (1993)
The synthesis and the photobiological activity of two new hydroxymethyl derivatives of psoralen namely 4-hydroxymethyl-4'-methyl- and 4-hydroxymethyl-4'-methyl-8-methoxypsoralen are described. Both compounds exhibited efficient photobinding to DNA and RNA. The DNA-photobinding process was investigated using different nucleic acid structures such as double-helical DNA, ribosomal RNA, bacterial DNA and DNA organized in the nucleosomal arrangement. The test derivatives were able to induce cross-links to a similar extent as 8-methoxypsoralen (8-MOP), used as a reference photochemotherapeutic drug. In contrast to 8-MOP, they produced relatively high levels of 1O2. Most photobiological effects (DNA synthesis inhibition, T2 phage sensitization, inhibition of tumor transmitting capacity) showed a good correlation with the extent of covalent photoaddition. On the other hand, the new 4-hydroxymethylpsoralens were unable to induce skin erythema, in striking contrast with 8-MOP. Thus, neither cross-linking of the nucleic acid nor 1O2 production were coupled with skin phototoxicity in this class of compounds. The new derivatives appear to represent an important beginning to development of new active photochemotherapeutic agents devoid of undesired phototoxic side effects.
Practical and Scalable Synthesis of 7-Azetidin-1-yl-4-(hydroxymethyl)coumarin: An Improved Photoremovable Group
Bassolino, Giovanni,Halabi, Elias A.,Rivera-Fuentes, Pablo
, p. 846 - 852 (2018)
7-Substituted 4-methylcoumarin derivatives are widely employed as photoprotecting groups in chemistry and biology. We have recently shown that the 7-azetidinylated version of this photocage releases carboxylic acids in aqueous solution more efficiently than the traditionally used 7-diethylamino variant. Here we present a robust and scalable route to prepare the 7-azetidinylated alcohol, a useful precursor for the photoprotection of a variety of leaving groups, and its use in the preparation of model phosphate, sulfonate, and carbamate derivatives.
Ethylenic conjugated coumarin thiazolidinediones as new efficient antimicrobial modulators against clinical methicillin-resistant Staphylococcus aureus
Hu, Chun-Fang,Zhang, Peng-Li,Sui, Yan-Fei,Lv, Jing-Song,Ansari, Mohammad Fawad,Battini, Narsaiah,Li, Shuo,Zhou, Cheng-He,Geng, Rong-Xia
, (2019/12/24)
In an effort for the development of novel antimicrobial agents, ethylenic conjugated coumarin thiazolidinediones as potential multi-targeting new antimicrobial compounds were synthesized through convenient procedures from commercially available resorcinol and were evaluated for their antimicrobial potency. Bioactive evaluation revealed that some of the prepared compounds showed strong antimicrobial activities towards the tested microorganisms including clinically drug-resistant strains. Especially, propargyl derivative 12b exhibited effective anti-MRSA potency with MIC value of 0.006 μmol/mL, which was highly advantageous over clinical antibacterial drug norfloxacin. Compound 12b showed rapid killing effect, low toxicity against hepatocyte LO2 cell line, and no obvious drug resistance development against MRSA. Preliminary exploration of action mechanism manifested that molecule 12b acted upon MRSA through forming stable supramolecular complex with bacterial DNA which might impede DNA replication. Molecular docking showed that compound 12b could bind with DNA-gyrase through hydrogen bonds.
O -Hydroxycinnamate for sequential photouncaging of two different functional groups and its application in releasing cosmeceuticals
Paul, Amrita,Bera, Manoranjan,Gupta, Prakhar,Singh, N. D. Pradeep
supporting information, p. 7689 - 7693 (2019/08/30)
We demonstrated a new approach for the sequential photouncaging of two different functional groups from o-hydroxycinnamate. The second caged molecule initially remains in the locked state and is released only after attaining its unlocked state upon in situ generation of the second phototrigger, i.e., coumarin, thereby leading to the sequential release of alcohol and carboxylic acid. We have utilised the above strategy for the controlled release of cosmeceutical agents.
