161321-34-2

Basic information

• Product Name: <4S-(4α,12aα)>-9-amino-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide
• Synonyms: <4S-(4α,12aα)>-9-amino-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide
• CAS NO: 161321-34-2
• Molecular Weight: 459.456
• Mol File: 161321-34-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: <4S-(4α,12aα)>-9-amino-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: <4S-(4α,12aα)>-9-amino-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide(161321-34-2)
• EPA Substance Registry System: <4S-(4α,12aα)>-9-amino-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide(161321-34-2)

Safety Data

• Hazardous Substances Data: 161321-34-2(Hazardous Substances Data)

Downstream Products

• 295356-14-8 (4S,4aR,5S,5aR,6R,12aS)-9-Amino-4-dimethylamino-3,5,10,12,12a-pentahydroxy-6-methyl-8-(4-nitro-phenyl)-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide 
• 295356-13-7 (4S,4aR,5S,5aR,6R,12aS)-9-Amino-4-dimethylamino-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-8-phenyl-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide 

Relevant articles and documents

Synthesis and Characterization of Photoactivatable Doxycycline Analogues Bearing Two-Photon-Sensitive Photoremovable Groups Suitable for Light-Induced Gene Expression

We report the synthesis and photolytic properties of caged 9-aminodoxycycline derivatives modified with 2-{4′-bis-[2-(2methoxyethoxy)ethyl]-4-nitrobiphenyl-3-yl}prop-1-oxy (EANBP) and PEG7-ylated (7-diethylamino-2-oxo-2H-chromen-4-yl)methyl (PEG7-DEACM) groups. 9-Aminodoxycycline is a tetracycline analogue capable of activating transcription through the inducible TetOn transgene expression system and can be regioselectively coupled to two-photon-sensitive photo-removable protecting groups by carbamoylation. The EANBP-based caged 9-aminodoxycycline showed complex photochemical reactions but did release 10 % of 9-aminodoxycycline. However, 9-(PEG7-DEACMamino)doxycycline exhibited excellent photolysis efficiency at 405 nm with quantitative release of 9-aminodoxycycline and a 0.21 uncaging quantum yield. Thanks to the good two-photon sensitivity of the DEACM chromophore, 9-aminodoxycycline release by two-photon photolysis is possible, with calculated action cross-sections of up to 4.0 GM at 740 nm. Therefore, 9-(PEG7-DEACMamino)doxycycline represents a very attractive tool for the development of a light-induced gene expression method in living cells.