22917-75-5

Basic information

• Product Name: 1,1'-(1,3-Propanediyl)dithymine
• Synonyms: 1,1'-(1,3-Propanediyl)dithymine;1,1'-Trimethylenedithymine;1,1'-Trimethylenebis
• CAS NO: 22917-75-5
• Molecular Formula: C13H16 N4 O4
• Molecular Weight: 292.2905
• Mol File: 22917-75-5.mol
• Article Data: 10

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.294g/cm³
• CAS DataBase Reference: 1,1'-(1,3-Propanediyl)dithymine(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1'-(1,3-Propanediyl)dithymine(22917-75-5)
• EPA Substance Registry System: 1,1'-(1,3-Propanediyl)dithymine(22917-75-5)

Safety Data

• Hazardous Substances Data: 22917-75-5(Hazardous Substances Data)

Upstream product

• 65-71-4 thymin 
• 22919-50-2 1-(3-bromopropyl)-5-methylpyrimidine-2,4(1H,3H)-dione 
• 109-64-8 1,3-dibromo-propane 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 
• 25878-29-9 cis,syn-3,3'-dimethyl-1,1'-trimethylenebis(thymine) cyclobutadipyrimidine 

Relevant articles and documents

NMR and UV Study of 1,1′-(α,ω-Alkanediyl)bis[thymine] and l,1′-(α,ω-Alkanediyl)bis[uracil]

Treatment of thymine or uracil with Br(CH2)nBr (n = 3-10) in the presence of t-BuOK gave 1,1′-(α,ω-alkanediyl)bis[thymine] or 1,1′-(α,ω-alkanediyl)bis[uracil] together with l-(ω-bromoalkyl)thymine or l-(ω-bromoalkyl)uracil. The structures of these products were determined on the basis of the coupling constants between 5- and 3-positions of uracil ring on the 1H NMR spectra. Molecular aggregation of the thymine and uracil rings of these compounds in aqueous solution was studied on the basis of their 1H NMR and UV spectra. A stacking interaction of the two thymine rings linked by shorter polymethylene chains such as trimethylene and tetramenthylene groups was observed.

Lignin Nanoparticles Deliver Novel Thymine Biomimetic Photo-Adducts with Antimelanoma Activity

We report here the synthesis of novel thymine biomimetic photo-adducts bearing an alkane spacer between nucleobases and characterized by antimelanoma activity against two mutated cancer cell lines overexpressing human Topoisomerase 1 (TOP1), namely SKMEL28 and RPMI7951. Among them, Dewar Valence photo-adducts showed a selectivity index higher than the corresponding pyrimidine-(6-4)-pyrimidone and cyclobutane counterpart and were characterized by the highest affinity towards TOP1/DNA complex as evaluated by molecular docking analysis. The antimelanoma activity of novel photo-adducts was retained after loading into UV photo-protective lignin nanoparticles as stabilizing agent and efficient drug delivery system. Overall, these results support a combined antimelanoma and UV sunscreen strategy involving the use of photo-protective lignin nanoparticles for the controlled release of thymine dimers on the skin followed by their sacrificial transformation into photo-adducts and successive inhibition of melanoma and alert of cellular UV machinery repair pathways.

SUNLESS TANNING COMPOUNDS AND COMPOSITIONS

The invention provides sunless tanning compositions comprising a compounds of formula (I): or a salt thereof as described herein as well as methods for tanning mammalian skin by contacting the skin with the compounds of formula (I) or compositions comprising compounds of formula (I).