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Photochem Photobiol Sci

Title:		Photoremovable protecting groups as controlled-release device for sex pheromone
Author(s):		Atta S; Ikbal M; Boda N; Gauri SS; Singh ND;
Address:		"Department of Chemistry, Indian Institute of Technology, Kharagpur-721302, India"
Journal Title:		Photochem Photobiol Sci
Year:		2013
Volume:		20121029
Issue:		2
Page Number:		393 - 403
DOI:		10.1039/c2pp25118c
ISSN/ISBN:		1474-9092 (Electronic) 1474-905X (Linking)
Abstract:		"Photoremovable protecting groups (PRPGs) were demonstrated as a delivery device for controlled release of pheromone under both UV light (>/=350 nm) and direct sunlight irradiation. In the present work, (Z)-11-hexadecen-1-ol (sex pheromone of Chilo infuscatellus Snellen) was chemically caged by four different photoremovable protecting groups (7-hydroxy-4-hydroxymethylcoumarin, 1-pyrenemethanol, 9-anthracenemethanol and 2-(hydroxymethyl)anthraquinone) individually. Photophysical studies showed that the caged pheromone with coumarin, pyrene and anthracene derivatives exhibited strong fluorescence. Controlled release of (Z)-11-hexadecen-1-ol was achieved by irradiating the caged compounds in aqueous ethanol both under UV and sunlight. Further, to mimic the environmental conditions, controlled release of (Z)-11-hexadecen-1-ol was also studied in soil medium under direct sunlight. Thermogravimetric analysis showed that caging of (Z)-11-hexadecen-1-ol by PRPGs significantly reduced its volatility. Bioassay experiments indicated that PRPGs are harmless to soil bacteria (Azotobacter sp. and Pseudomonas aeruginosa) and in vitro cytotoxicity studies on eukaryotic L929 cells showed that PRPGs are also non-toxic. Field bioassays were performed using caged pheromone against maize stalk borer (Chilo partellus) and the results showed that the caged alcohol is effective in a number of moths catches instead of free alcohol in a blend for a longer period of time. Our studies indicated that use of PRPGs as delivery device for controlled release of pheromone by sunlight holds great interest for field applications"
Keywords:		"Animals Anti-Bacterial Agents/chemical synthesis/*chemistry/pharmacology Azotobacter/drug effects Cell Line Cell Proliferation/drug effects Cell Survival/drug effects Dose-Response Relationship, Drug Drug Evaluation, Preclinical Ethanol/chemistry Mice Mic;"
Notes:		"MedlineAtta, Sanghamitra Ikbal, Mohammed Boda, Nishitha Gauri, Samiran S Singh, N D Pradeep eng Research Support, Non-U.S. Gov't England 2012/10/31 Photochem Photobiol Sci. 2013 Feb; 12(2):393-403. doi: 10.1039/c2pp25118c. Epub 2012 Oct 29"