Phosphonate-linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates: synthesis, DNA-binding affinity and cytotoxicity

  • Bioorg Med Chem. 2008 Apr 1;16(7):3895-906. doi: 10.1016/j.bmc.2008.01.040.
Ahmed Kamal  1 ,  P Praveen Kumar ,  B N Seshadri ,  O Srinivas ,  M Shiva Kumar ,  Subrata Sen ,  Nisha Kurian ,  Aarti S Juvekar ,  Surekha M Zingde
Affiliations
  • 1. Biotransformation Laboratory, Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad, Andhra Pradesh 500 007, India. [email protected]
PMID: 18262426 DOI: 10.1016/j.bmc.2008.01.040
Abstract

Pyrrolobenzodiazepine-diethylphosphonate conjugates have been designed and synthesized that link through two different types of spacers that are simple alkane chain and also a piperazine moiety side-armed with the alkane chains. These pyrrolobenzodiazepine conjugates have exhibited remarkable DNA-binding affinity and improved solubility in water, a representative compound 7d showing promising in vitro cytotoxicity.