Expanding a fluorescent RNA alphabet: synthesis, photophysics and utility of isothiazole-derived purine nucleoside surrogates.

نویسندگان

  • Alexander R Rovira
  • Andrea Fin
  • Yitzhak Tor
چکیده

A series of emissive ribonucleoside purine mimics, all comprised of an isothiazolo[4,3-d]pyrimidine core, was prepared using a divergent pathway involving a key Thorpe-Ziegler cyclization. In addition to an adenosine and a guanosine mimic, analogues of the noncanonical xanthosine, isoguanosine, and 2-aminoadenosine were also synthesized and found to be emissive. Isothiazolo 2-aminoadenosine, an adenosine surrogate, was found to be particularly emissive and effectively deaminated by adenosine deaminase. Competitive studies with adenosine deaminase with each analogue in combination with native adenosine showed preference for the native substrate while still deaminating the isothiazolo analogues.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Electronic structure and absorption spectra of fluorescent nucleoside analogues.

This work presents a systematic investigation of the electronic and conformational properties of five new fluorescent nucleobases belonging to the alphabet based on the isothiazole[4,3-d]pyrimidine molecule, very recently synthesized. This is of particular importance in the characterization of the main electronic aspects of these fluorescent nucleosides. The solvent effects of 1,4-dioxane and w...

متن کامل

P-51: A Purine Nucleoside Analogue_Acyclovir Impairs Testicular Functions in Male Rats

Background: Acyclovir (ACV) is a synthetic purine nucleoside analog drived from guanosine. ACV possesses antiviral activity against Herpes Simplex Virus types 1 and 2 (HSV-1 and HSV-2 ), Varicella Zoster virus (VZV) , Epstein Barr virus (EBV) and Cytomegalovirus (CMV). ACV exert its effects by interfering with DNA synthesis,thus inhibiting viral replication. ACV is khown to be toxic to gonads,t...

متن کامل

Cellular activity of siRNA oligonucleotides containing synthetic isomorphic nucleoside surrogates.

Singly and multiply modified synthetic siRNA oligonucleotides, containing isomorphic surrogate nucleobases, show high interference potency in cell culture, suggesting the highly isomorphic RNA alphabet, based on a thieno[3,4-d]-pyrimidine core, is tolerated well by the cellular silencing machinery.

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:
  • Chemical science

دوره 8 4  شماره 

صفحات  -

تاریخ انتشار 2017