Novel phosphoramidates with porphine and nitrogenous drug: one-pot synthesis and orientation to cancer cells.
One-pot synthesis of novel phosphoramidates with porphine and nitrogenous drug was accomplished. In the absence of light, MTT test showed that they killed the BEL-7402 liver cancer cells effectively in vitro. The cell viability studied on normal liver and cancer cells showed that porphine phosphoramidates selectively kill the cancer cells, which was in sharp contrast with the non-porphine containing compound 4-formylphenyl N,N-bis(2-chloroethyl)-phosphoramidate. These results, coupled with the cell uptake test showing that they could differentiate the tumor cells from the normal cells by their selective accumulation in cancer cells, gave strong support to the notion that the introduction of porphine moiety in these molecules was responsible for the effectiveness and cell differentiability of these porphine phosphoramidates.
Wang
Zhi-Wei
ZW
College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, PR China.
Guo
Can-Cheng
CC
Xie
Wen-Zhong
WZ
Liu
Chao-Zhou
CZ
Xiao
Chun-Guang
CG
Tan
Ze
Z
D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D002460:Cell Line; D045744:Cell Line, Tumor; D015195:Drug Design; D006801:Humans; D008113:Liver Neoplasms / Q000188:drug therapy; D015394:Molecular Structure; D010756:Phosphoric Acids / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology
D000577:Amides; D000970:Antineoplastic Agents; D010756:Phosphoric Acids; D011166:Porphyrins; C107018:porphine; C011067:phosphoramidic acid