NDLI: Synthesis of F16 conjugated with 5-fluorouracil and biophysical investigation of its interaction with bovine serum albumin by a spectroscopic and molecular modeling approach.

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Synthesis of F16 conjugated with 5-fluorouracil and biophysical investigation of its interaction with bovine serum albumin by a spectroscopic and molecular modeling approach.

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Xiang, Chen Li, Dong-Wei Qi, Zu-De Jiang, Feng-Lei Ge, Yu-Shu Liu, Yi
Description	Author Affiliation: Xiang C ( State Key Laboratory of Virology & Key Laboratory of Analytical Chemistry for Biology and Medicine (MOE), College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072, People's Republic of China.)
Abstract	5-Fluorouracil (5-FU) has been widely used as a chemotherapy agent in the treatment of many types of solid tumors. Investigation of its antimetabolites led to the development of an entire class of fluorinated pyrimidines. However, the toxicity profile associated with 5-FU is significant and includes diarrhea, mucositis, hand-foot syndrome and myelosuppression. In aiming at reducing of the side effects of 5-FU, we have designed and synthesized delocalized lipophilic cations (DLCs) as a vehicle for the delivery of 5-FU. DLCs accumulate selectively in the mitochondria of cancer cells because of the high mitochondrial transmembrane potential (ΔΨm). Many DLCs exhibited anti-cancer efficacy and were explored as potential anti-cancer drugs based on their selective accumulation in the mitochondria of cancer cells. F16, the DLC we used as a vehicle, is a small molecule that selectively inhibits tumor cell growth and dissipates mitochondrial membrane potential. The binding of the conjugate F16-5-FU to bovine serum albumin (BSA) was investigated using spectroscopic and molecular modeling approaches. Fluorescence quenching constants were determined using the Stern-Volmer equation to provide a measure of the binding affinity between F16-5-FU and BSA. The activation energy of the interaction between F16-5-FU and BSA was calculated and the unusually high value was discussed in terms of the special structural block indicated by the molecular modeling approach. Molecular modeling showed that F16-5-FU binds to human serum albumin in site II, which is consistent with the results of site-competitive replacement experiments. It is suggested that hydrophobic and polar forces played important roles in the binding reaction, in accordance with the results of thermodynamic experiments.
File Format	HTM / HTML
ISSN	15227235
Issue Number	6
Volume Number	28
e-ISSN	15227243
Journal	Luminescence
Language	English
Publisher	Wiley-Blackwell
Publisher Date	2013-11-01
Publisher Place	Great Britain (UK)
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Discipline Biophysics Discipline Biochemistry Fluorouracil Chemistry Indoles Chemical Synthesis Pyridinium Compounds Serum Albumin, Bovine Animals Cattle Models, Molecular Molecular Structure Spectrometry, Fluorescence Spectrophotometry, Ultraviolet Journal Article Research Support, Non-u.s. Gov't
Content Type	Text
Resource Type	Article
Subject	Chemistry Biophysics

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