Super-resolution imaging compositions and methods using same

Patent metadata

Field	Value
Publication number	US-10087199-B2
Application number	US-201514919216-A
Country	US
Kind code	B2
Filing date	Oct 21, 2015
Priority date	Oct 22, 2014
Publication date	Oct 2, 2018
Grant date	Oct 2, 2018

Abstract

The invention provides compositions that may be used for imaging intracellular structures. The invention further provides methods of imaging intracellular structures. In certain embodiments, the compositions of the invention include trans-cyclooctene-containing ceramide lipids and tetrazine-containing rhodamine-related dyes.

First claim

What is claimed:

1. A trans-cyclooctene-containing lipid, or a salt, solvate, stereoisomer, or any mixtures thereof, wherein the lipid comprises TCO-LINK-LIPID, wherein TCO is a trans-cyclooctene group, LINK is a bivalent linker, and wherein LIPID comprises at least one selected from the group consisting of a sphingolipid, phospholipid, sterol lipid and fatty acid
wherein LINK comprises:
—X(CR′R″) n C(═O)—, wherein

X is covalently conjugated to TCO and is selected from the group consisting of a covalent bond, —C(═O)—, —C(═O)O— and —C(═O)NR′—;
each occurrence of R′ and R″ is independently selected from the group consisting of H and optionally substituted C 1 -C 6 alkyl; and
n is an integer ranging from 1 to 20.

2. The trans-cyclooctene-containing lipid of claim 1 , wherein TCO is selected from the group consisting of:

wherein R′ is H or optionally substituted C 1 -C 6 alkyl, and wherein the heteroatom is not attached to the ring double bond.

3. The trans-cyclooctene-containing lipid of claim 2 , wherein TCO is selected from the group consisting of:

wherein R′ is H or optionally substituted C 1 -C 6 alkyl.

4. The trans-cyclooctene-containing lipid of claim 1 , wherein LIPID comprises at least one selected from the group consisting of sphingosine, 1-phosphocholine-sphingosine, 1-phosphoethanolamine-sphingosine, and a 1-glycosyl-sphingosine.

5. The trans-cyclooctene-containing lipid of claim 4 , wherein LIPID comprises sphingosine.

6. The trans-cyclooctene-containing lipid of claim 5 , wherein LIPID comprises sphingosine and is covalently conjugated to LINK through the 2-amino group of sphingosine.

7. The trans-cyclooctene-containing lipid of claim 1 , wherein n is 5.

8. The trans-cyclooctene-containing lipid of claim 1 , which is Cer-TCO or a salt, solvate, stereoisomer, or any mixtures thereof:

Assignees

• Univ Yale

Inventors

• Erdmann Roman
• Shrader Alanna Schepartz
• Toomre Derek

Classifications

• C07F7/0816

  said ring comprising Si as a ring atom · CPC title

• C07C271/34 Primary

  with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms · CPC title

• C07F7/0807 Primary

  comprising Si as a ring atom · CPC title

• C07C2601/18

  with a ring being at least seven-membered · CPC title

• G01N33/582

  with fluorescent label · CPC title