6602-90-0

Basic information

• Product Name: (1S,3Z,4aS,11S,11aS,12aS)-3-[amino(hydroxy)methylidene]-4a,6,7,11-tetrahydroxy-N,N,N,11-tetramethyl-2,4,5-trioxo-1,2,3,4,4a,5,11,11a,12,12a-decahydrotetracen-1-aminium iodide
• CAS NO: 6602-90-0
• Molecular Formula: C₂₃H₂₇IN₂O₈
• Molecular Weight: 586.3735
• Mol File: 6602-90-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (1S,3Z,4aS,11S,11aS,12aS)-3-[amino(hydroxy)methylidene]-4a,6,7,11-tetrahydroxy-N,N,N,11-tetramethyl-2,4,5-trioxo-1,2,3,4,4a,5,11,11a,12,12a-decahydrotetracen-1-aminium iodide(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,3Z,4aS,11S,11aS,12aS)-3-[amino(hydroxy)methylidene]-4a,6,7,11-tetrahydroxy-N,N,N,11-tetramethyl-2,4,5-trioxo-1,2,3,4,4a,5,11,11a,12,12a-decahydrotetracen-1-aminium iodide(6602-90-0)
• EPA Substance Registry System: (1S,3Z,4aS,11S,11aS,12aS)-3-[amino(hydroxy)methylidene]-4a,6,7,11-tetrahydroxy-N,N,N,11-tetramethyl-2,4,5-trioxo-1,2,3,4,4a,5,11,11a,12,12a-decahydrotetracen-1-aminium iodide(6602-90-0)

Safety Data

• Hazardous Substances Data: 6602-90-0(Hazardous Substances Data)

Upstream product

• 60-54-8 TETRACYCLINE 
• 74-88-4 methyl iodide 

Downstream Products

• 2444-65-7 4-de(dimethylamino)tetracycline 

Relevant articles and documents

Synthesis and in vitro evaluation of targeted tetracycline derivatives: Effects on inhibition of matrix metalloproteinases

Among other non-antibiotic properties, tetracyclines inhibit matrix metalloproteinases and are currently under study for the treatment of osteoarthritis. Quaternary ammonium conjugates of tetracyclines were synthesized by direct alkylation of the amine function at the 4-position with methyl iodide. When tested in vitro, they inhibited cytokine-induced MMP expression to a lesser extent than parent tetracyclines. This was compensated by an improved inhibition of MMP catalytic activity. Since inhibition of collagen degradation was maintained these derivatives could be potent drug candidates for cartilage-targeted chondroprotective treatment.