Nof Corporation

Hokkaido University

Chiba University

Kota Tange

Hidetaka Akita

Hideyoshi Harashima

Yuta Nakai

Kazuhiro Kubo

Hiroki Tanaka

Hiroki Yoshioka

Hiroto Hatakeyama

Naoya Miura

Masaya Arai

Takuma Tsubusaki

Masaki Kamiya

Masaki Ota

Shinya Tamagawa

Shota Sasaki

Manami Konishi

Nae Takata

Masaki Ohta

Tatsunari Takahashi

Nayuta Shimizu

Masami Ukawa

Ryohei Ishiba

Yuki Noguchi

Mio Maeta

Ryohei Togashi

Ayaka Watanabe

The invention provides a cationic lipid, a lipid membrane structure containing same, and use thereof. The cationic lipid is represented by the formula (1) wherein R, R, R, R, R, R, X, X, Y, Y, Z, and Zare as defined in the specification.

Cationic lipid exhibiting improved intracellular dynamics

The present invention provides an O/W type emulsion having a volume median diameter of not more than 100 nm and containing a compound represented by the formula (1) wherein Xand Xare each independently X, Xor a 1,4-piperazinediyl group; s is 1 or 2,Ris an alkyl group having 1-6 carbon atoms,nand nare each independently 0 or 1,R, R, Rand Rare each independently an alkylene group having 1-6 carbon atoms,Yand Yare each independently an ester bond, or the like, andRand Rare each independently a liposoluble vitamin residue or the like.

O/W type emulsion

A degradable polyethylene glycol derivative represented by formula (1). R, R, and Rrepresent each independently a hydrogen atom or a hydrocarbon group having from 1 to 6 carbon atoms, and at least one of R, R, Rand Ris the hydrocarbon group; Pis a straight-chain or branched polyethylene glycol chain having a number of ethylene glycol units of 3 or more; Pis a straight-chain polyethylene glycol chain having a number of ethylene glycol units of 3 or more; w is an integer of 1 to 8; u is an integer of 1 to 10; Xis a chemically reactive functional group; and Z, Zand Zare each independently a selected divalent spacer. 

Degradable polyethylene glycol derivative having disulfide linker

The present invention aims to provide a cationic lipid that can be used as a nucleic acid delivery carrier, a lipid membrane structure using a cationic lipid, a nucleic acid-introducing agent using a cationic lipid, and a method of achieving nucleic acid introduction by using a nucleic acid-introducing agent containing a cationic lipid. A lipid membrane structure containing a cationic lipid represented by the formula (1) wherein each symbol is as defined in the DESCRIPTION, is superior in the stability in blood and tumor accumulation property. A nucleic acid-introducing agent using the cationic lipid can achieve high nucleic acid delivery efficiency of nucleic acid to be delivered into the cytoplasm.

Cationic lipid

The invention provides a cationic lipid capable of achieving higher intracellular delivery efficiency than conventional cationic lipids, when used as a lipid membrane structure which is a carrier for delivering functional nucleic acid. The cationic lipid is represented by the formula (1): 

Cationic lipid for nucleic acid delivery

The present invention relates to a compound represented by the formula (1) wherein Xand Xare each independently Xor X; s is 1 or 2,Ris an alkyl group having 1-6 carbon atoms,nand nare each independently 0 or 1,Rand Rare each independently an alkylene group having 1-6 carbon atoms,Rand Rare each independently an alkylene group having 1-6 carbon atoms,Yand Yare each independently an ester bond, an amide bond, a carbamate bond, an ether bond or a urea bond, andRand Rare each independently a sterol residue, a liposoluble vitamin residue or an aliphatic hydrocarbon group having 12-22 carbon atoms,and use thereof.

Cationic lipid having improved intracellular kinetics

In production of a cationic lipid having at least one methylene group sandwiched between adjacent two cis form double bonds in the molecule, isomerization from a cis form to a trans form is suppressed. A compound represented by the following formula (I):R&#x2014;X&#x2003;&#x2003;(I)(in Formula, Rrepresents a hydrocarbon group having at least one methylene group sandwiched between adjacent two cis form double bonds in the molecule and having the carbon number of 8 to 24 and X represents a releasing group) is reacted with (B) a compound having at least one of each of tertiary amino group and hydroxyl group in the molecule in a saturated hydrocarbon solvent having the carbon number of 5 to 10 in the presence of an alkali catalyst.

Method for manufacturing tertiary amino group-containing lipid

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Kawasaki, Japan

Kota Tange