Light-induced antibiotic release from a coumarin-caged compound on the ultrafast timescale
Literature Information
L.-M. Herzig, I. Elamri, H. Schwalbe, J. Wachtveitl
A synthesis route for puromycin caged with the photo-responsive 7-diethylaminocoumarinyl protecting group carbamate was developed. The inactivation and recovery of the cytotoxic effect of puromycin was tested with a XTT cell viability assay. The uncaging mechanism was studied by ultrafast transient absorption spectroscopy and by time-correlated single photon counting. The combination of these results with quantum-chemical calculations provided detailed insights in dynamics upon excitation. Interestingly, a change of the dipole moment due to structural rearrangements of the amino moiety led to an intermolecular charge transfer on the picosecond time-scale. IR measurements marked the successful uncaging via the release of CO2, resulting from the carbamate linker. This decarboxylation constituted the rate-limiting step of the uncaging reaction and occurred on the subsecond timescale. DEACM-puromycin, thus, represents an efficient photo-activatable antibiotic for in-cell applications.
Recommended Journals
Related Literature
Synthesis of functionalized diarylbenzofurans via Ru-catalyzed C–H activation and cyclization under air: rapid access to the polycyclic scaffold of diptoindonesin G
Lufeng Ouyang, Zhigeng Lin, Shiqi Li, Baoyin Chen, Jidan Liu, Wen-Jing Shi, Liyao Zheng
DOI: 10.1039/D1QO01242H
Mixed carboxylic–sulfonic anhydride in reaction with imines: a straightforward route to water-soluble β-lactams via a Staudinger-type reaction
Olga Bakulina, Dmitry Dar'in, Mikhail Krasavin
DOI: 10.1039/C8OB00768C
Aziridine based electrophilic handle for aspartic acid ligation
Kiran Bajaj, Devesh S. Agarwal, Rajeev Sakhuja, Girinath G. Pillai
DOI: 10.1039/C8OB00676H
Recent advances in catalytic enantioselective direct C–H bond functionalization of electron-deficient N-containing heteroarenes
Xiao-Lan Liu, Luo-Bin Jiang, Mu-Peng Luo, Zhi Ren, Shou-Guo Wang
DOI: 10.1039/D1QO01223A
Tetra-substituted furans by a gold-catalysed tandem C(sp3)–H alkynylation/oxy-alkynylation reaction
Chunyu Han, Xianhai Tian, Lina Song, Yaowen Liu
DOI: 10.1039/D1QO01401C
Figure-eight arylene ethynylene macrocycles: facile synthesis and specific binding behavior toward Hg2+
Hui Nie, Qian-Hui Li, Siqi Zhang, Chuan-Ming Wang, Wen-Hui Lin, Ke Deng, Li-Jin Shu, Qing-Dao Zeng, Jun-Hua Wan
DOI: 10.1039/D1QO00812A
Rhodium(iii)-catalyzed annulation of 3-arylquinazolinones with alkynes via double C–H activation: an efficient route for quinolino[2,1-b]quinazolinones
Jian Huang, Wei Chen, Jiazhi Liang, Qin Yang, Zhihong Deng, Zhibin Song, Yiyuan Peng
DOI: 10.1039/D1QO01186C
Asymmetric cycloisomerization/[3 + 2] cycloaddition for the synthesis of chiral spiroisobenzofuran-1,3′-pyrrolidine derivatives
Pei Dong, Long Chen, Zhendong Yang, Shunxi Dong, Xiaoming Feng
DOI: 10.1039/D1QO01194D
Alkylsulfonium salts for the photochemical desulphurizative functionalization of heteroarenes
Xiaolong Zhu, Xuan Li, Enjie Zhu, Qirong Deng, Xiuyan Song, Jian Lv
DOI: 10.1039/D1QO01570B
You might also like
What industries use (1R,3S)-1,3-Cyclopentanediol (CAS: 16326-97-9)?
(1R,3S)-1,3-Cyclopentanediol finds applications in various industries. In the ph...
What precautions should be taken when handling N'-[4-(Dimethylamino)phenyl]-N,N-dimethyl-1,4-benzenediamine (CAS: 637-31-0)?
When handling N'-[4-(Dimethylamino)phenyl]-N,N-dimethyl-1,4-benzenediamine, it i...
Are there alternatives to 5-(2,4-Difluorophenyl)-2-methoxypyrimidine (CAS: 1352318-16-1) in synthesis?
There are several alternatives to 5-(2,4-Difluorophenyl)-2-methoxypyrimidine in ...
What regulatory guidelines apply to 1-(3-Methoxyphenoxy)propan-2-ol (CAS: 382141-68-6)?
1-(3-Methoxyphenoxy)propan-2-ol (CAS: 382141-68-6) must comply with the Globally...
Is Tetrodotoxin Citrate (CAS: 18660-81-6) safe?
Tetrodotoxin Citrate is extremely dangerous and should be handled with extreme c...
What are the main uses of 2-Methyl-2-propanyl [(1R,3S)-3-hydroxycyclopentyl]carbamate (CAS: 225641-84-9)?
2-Methyl-2-propanyl [(1R,3S)-3-hydroxycyclopentyl]carbamate (CAS: 225641-84-9) i...
How should waste containing 4-(2-Hydroxyhexafluoroisopropyl)Benzoic Acid (CAS: 16261-80-6) be handled?
Waste containing 4-(2-Hydroxyhexafluoroisopropyl)Benzoic Acid (CAS: 16261-80-6) ...
How is 2-Methyl-2-proanyl {(2S)-1-[(benzyloxy)amino]-3-hydroxy-3-methyl-1-oxo-2-butanyl}carbamate (CAS: 102507-19-7) typically synthesized?
2-Methyl-2-proanyl {(2S)-1-[(benzyloxy)amino]-3-hydroxy-3-methyl-1-oxo-2-butanyl...
What is Benzeneethanamine, α-ethyl-, hydrochloride (1:1) (CAS: 20735-15-3)?
Benzeneethanamine, α-ethyl-, hydrochloride (1:1) is an organic compound with the...
Are there alternatives to 3-{(E)-[4-(Dimethylamino)phenyl]diazenyl}benzoic acid (CAS: 20691-84-3) in synthesis?
In the synthesis of compounds similar to 3-{(E)-[4-(Dimethylamino)phenyl]diazeny...
Source Journal
Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics (PCCP) is an international journal co-owned by 19 physical chemistry and physics societies from around the world. This journal publishes original, cutting-edge research in physical chemistry, chemical physics and biophysical chemistry. To be suitable for publication in PCCP, articles must include significant innovation and/or insight into physical chemistry; this is the most important criterion that reviewers and Editors will judge against when evaluating submissions. The journal has a broad scope and welcomes contributions spanning experiment, theory, computation and data science. Topical coverage includes spectroscopy, dynamics, kinetics, statistical mechanics, thermodynamics, electrochemistry, catalysis, surface science, quantum mechanics, quantum computing and machine learning. Interdisciplinary research areas such as polymers and soft matter, materials, nanoscience, energy, surfaces/interfaces, and biophysical chemistry are welcomed if they demonstrate significant innovation and/or insight into physical chemistry. Joined experimental/theoretical studies are particularly appreciated when complementary and based on up-to-date approaches.














![N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-beta-phenyl-L-phenylalanine structure N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-beta-phenyl-L-phenylalanine structure](https://static.chemtradehub.com/structs/201/201484-50-6-c2fc.webp)