Porphyrin-peptoid conjugate and the preparation process thereof

Patent metadata

Field	Value
Publication number	US-9263194-B2
Application number	US-201414199317-A
Country	US
Kind code	B2
Filing date	Mar 6, 2014
Priority date	Sep 6, 2013
Publication date	Feb 16, 2016
Grant date	Feb 16, 2016

Abstract

Disclosed are a porphyrin-peptoid conjugate and a method for preparing the same. The porphyrin-peptoid conjugate according to the present disclosure has porphyrins arranged face-to-face on a helical peptoid. The porphyrin-peptoid conjugate according to the present disclosure is a new-concept photosensitizing dye material wherein the distance, arrangement and number of porphyrins are controllable. Since the porphyrin-peptoid conjugate is monodisperse and has a precisely defined structure, selective decoration of dyes is easy and dyes can be arranged on the peptoid helix sequence and space specifically. Accordingly, a new high-efficiency photosensitizing dye molecule system having wide absorption spectrum including the visible and near-infrared range and high absorption coefficient can be prepared.

First claim

What is claimed is:

1. A conjugate represented by Chemical Formula 1, which has a helical structure wherein at least two R groups are R 2 , and wherein T's are arranged face-to-face:

wherein
n is 9 or 12,
R is R 1 or R 2 ,
R 1 is

R 2 is selected from

m is an integer from 1 to 5,
T is selected from

each of X 1 , X 2 , X 3 , which are identical or different, is

Y is selected from C—H, N, C—COOH, C—SO 3 H and C—NH 2 , and
the tilde symbol indicates a chemical bond.

2. The conjugate according to claim 1 , wherein the conjugate has a structure selected from Chemical Formulas 2-5:

3. The conjugate according to claim 2 , wherein the conjugate has a structure selected from Chemical Formulas 6-9:

4. The conjugate according to claim 3 , wherein R 2 's have the same structure.

5. The conjugate according to claim 1 , wherein the conjugate has a structure selected from Chemical Formulas 10-13:

wherein
TPP represents

each of X 1 , X 2 and X 3 is

Y is C—H, and
the tilde symbol indicates a chemical bond.

6. The conjugate according to claim 1 , wherein each R is independently chosen from R 2 .

7. The conjugate according to claim 1 , wherein each R is the same R 2 .

8. A method for preparing a porphyrin-peptoid conjugate, comprising:
preparing a helical peptoid by microwave-assisted solid-phase submonomer protocol synthesis;
acetylating the N-terminal amine of the helical peptoid;
removing a methoxytrityl group from the N-terminal acetylated helical peptoid by treating repeatedly with trifluoroacetic acid (TFA);
preparing tetraphenylporphyrin (TPP) carboxylic acid according to the Lindsey's protocol;
preparing TTP-NHS ester by esterifying the tetraphenylporphyrin (TPP) carboxylic acid; and
conjugating the TPP-NHS ester with the methoxytrityl-removed helical peptoid.

9. The method for preparing a porphyrin-peptoid conjugate according to claim 8 , which further comprises purifying the porphyrin-peptoid conjugate by reversed-phase HPLC.

Assignees

• Kwangju Inst Sci & Tech

Inventors

• Seo Jiwon
• Kang Bo Yeong

Classifications

• H01G9/2059 Primary

  comprising an organic dye as the active light absorbing material, e.g. adsorbed on an electrode or dissolved in solution · CPC title

• H01L51/0077

  Electricity · mapped topic

• H01L51/0093

  Electricity · mapped topic

• C07K14/001

  by chemical synthesis · CPC title

• C07D487/22

  in which the condensed system contains four or more hetero rings · CPC title