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Silibinin (SB) is a flavonoid with an eminent anticancer activity but poorwater solubility, whichrestricts its biomedical applications. Considering this as a potential challenge, the SB binding and release were studied usingtrimesoyl 1, 3, 5-tridipropyl malonate (TTDPM), trimesoyl 1, 3, 5- tridibutyl malonate (TTDBM) and trimesoyl 1, 3, 5-tridihexyl malonate (TTDHM)1sttier dendrimers. The SB binding with TTDPM, TTDBM and TTDHM having dipropyl (- CH2CH2CH2)2, dibutyl (-CH2CH2CH2-CH2-)2 and dihexyl (- CH2CH2CH2CH2CH2CH2)2dialkyl chainsare attained from FTIR, DSC, DLS and SEM studies. UV-Vis spectroscopy has depicted in vitro4 %/h release of SBin PBS + 10 % DMSO (PD) medium at 37 0C. The SB release from TTDPM, TTDBM and TTDHM with dipropyl, dibutyl and dihexyl dialkyl chains are in1.61: 1.43: 1.12% ratio.The results of this study can provide new insights in the development of 1st tier dendrimers as drug delivery systems for SB with a controlled and sustained release tendency.