2389-60-8Relevant articles and documents
Structure-delivery relationships of lysine-based gemini surfactants and their lipoplexes
Damen, Mark,Cristobal-Lecina, Edgar,Sanmarti, Gloria Colom,Van Dongen, Stijn F.M.,Garcia Rodriguez, Cristina L.,Dolbnya, Igor P.,Nolte, Roeland J.M.,Feiters, Martin C.
, p. 5702 - 5714 (2014)
The synthesis and properties of gemini surfactants of the type (R 1(CO)-Lys(H)-NH)2(CH2)n are reported. For a spacer length of n = 6, the hydrophobic acyl tail was varied in length (R1 = C8, C10, C12, C14, C16, and C18) and, for R1 = C18, the degree of unsaturation. For R1(CO) = oleoyl (C18:1 Z) the spacer length (n = 2-8) and the stereochemistry of the lysine building block were varied; a 'half-gemini' derivative with a single oleoyl tail and head group was also prepared. The potential of the gemini surfactants to transfer polynucleotides across a cell membrane was investigated by transfection of HeLa cells with beta-galactosidase, both in the presence and absence of the helper lipid DOPE. Oleoyl was found to be by far the best hydrophobic tail for this biological activity, whereas the effect of the lysine stereochemistry was less pronounced. The effect of an optimum spacer length (n = 6) was observed only in the absence of helper lipid. The most active surfactant, i.e. the one with oleoyl chains and n = 6, formed liposomes with sizes in the range of 60-350 nm, and its lipoplex underwent a transition from a lamellar to a hexagonal morphology upon lowering the pH from 7 to 3. the Partner Organisations 2014.
Serine- and threonine-derived diamine equivalents for site-specific incorporation of platinum centers in peptides, and the anticancer potential of these conjugates
Kumbhakonam, Sateeshkumar,Vellaisamy, Kasipandi,Saroj, Soumya,Venkatesan, Nalini,Karunagaran,Manheri, Muraleedharan Kannoth
supporting information, p. 2450 - 2458 (2018/02/19)
A modular strategy that allows introduction of one or more reactive platinum units at chosen locations along a peptide sequence is presented. This makes use of diazides generated from serine and threonine as diamine equivalents which can be conjugated to the peptide under standard coupling conditions. Reduction of these diazides using Pd/C and H2 followed by platination affords the final products in good yields. Following this, we prepared a new class of peptide-platinum conjugates and carried out preliminary cytotoxicity evaluation and DNA interaction studies. Inclusion of lysine residues in the sequence was found to improve DNA interaction and anticancer activities compared to analogous conjugates with hydrophobic side chains.
Macrocyclic hexaoxazoles: Influence of aminoalkyl substituents on RNA and DNA G-quadruplex stabilization and cytotoxicity
Satyanarayana, Mavurapu,Kim, Young-Ah,Rzuczek, Suzanne G.,Pilch, Daniel S.,Liu, Angela A.,Liu, Leroy F.,Rice, Joseph E.,LaVoie, Edmond J.
scheme or table, p. 3150 - 3154 (2010/09/10)
A series of 24-membered macrocyclic hexaoxazoles containing one or two aminoalkyl substituents was synthesized and evaluated for cytotoxicity and for their ability to selectively stabilize G-quadruplex DNA and RNA. The most cytotoxic analog 4a, with IC50 values of 25 and 130 nM using KB3-1 and RPMI 8402 cells, is efficacious in vivo in athymic nude mice with a human tumor xenograft from the breast cancer cell line MDA-MB-435.
