Biotin derivatives

Patent metadata

Field	Value
Publication number	US-9567346-B2
Application number	US-201113881518-A
Country	US
Kind code	B2
Filing date	Oct 28, 2011
Priority date	Oct 29, 2010
Publication date	Feb 14, 2017
Grant date	Feb 14, 2017

Abstract

Biotin derivatives, methods of using the biotin derivatives and kits comprising the biotin derivatives.

First claim

We claim:

1. A biotin derivative of the formula:

wherein:
X is O;
R 1 is H;
R 2 is a C 2 -C 8 saturated or unsaturated straight or branched chain alkyl group;
Y is absent;
L is absent or is a linker; or
L-R 3 is selected from the group consisting of:

wherein R 5 is H or a saturated or unsaturated straight or branched chain carbon radical
that comprises 1 to 8 carbon atoms, and n is an integer from 0 to 20;

R 3 is selected from —OR 4 , —COOR 4 , and a reactive group, wherein the reactive group is
(a) isothiocyanate, sulfonyl chloride, 4,6-dichlorotriazinyl, a carboxylate, a halo acetyl, hydrazide, a succinimidyl ester, a 4-sulfonyl-3,5-dichlorophenol ester, a maleimide, an iodoacetamide; an azide, an alkyne,

when L is a linker; or
(b) hydrazinyl, N-hydroxysuccinimidyl, 4-sulfonyl-3,5-dichlorophenol,

when L is absent; and
R 4 is a saturated or unsaturated straight or branched chain carbon radical that comprises 2 to 8 carbon atoms.

2. The biotin derivative of claim 1 , wherein L is a linker.

3. The biotin derivative of claim 2 , wherein L is a polyethylene glycol linker.

4. The biotin derivative of claim 2 , wherein the linker comprises a detectable moiety.

5. The biotin derivative of claim 4 , wherein the detectable moiety comprises: a chromophore, a fluorescent dye, a fluorescent protein, a nanocrystal, an enzyme, or a radioisotope.

6. The biotin derivative of claim 5 , wherein the detectable moiety is a fluorescent dye.

7. The biotin derivative of claim 1 , wherein L-R 3 is:

wherein R 5 is H or a saturated or unsaturated straight or branched chain carbon radical that comprises 1 to 8 carbon atoms, and n is an integer from 0 to 20.

8. The biotin derivative of claim 7 , wherein R 3 is —OR 4 or —COOR 4 .

9. The biotin derivative of claim 1 , wherein R 3 is a reactive group.

10. The biotin derivative of claim 9 , wherein R 3 is

when L is a linker; or

when L is absent.

11. The biotin derivative according to claim 1 , wherein the biotin derivative is selected from:

12. A biotin derivative selected from:

wherein R 4 is a saturated or unsaturated straight or branched chain carbon radical that comprises 2 to 8 carbon atoms.

Assignees

• Ying Lai-Qiang
• Branchaud Bruce
• Zhang Yu-Zhong
• Yue Stephen
• Life Technologies Corp

Inventors

• Ying Lai-Qiang
• Branchaud Bruce
• Zhang Yu-Zhong
• Yue Stephen

Classifications

• C07B2200/11

  Compounds covalently bound to a solid support · CPC title

• G01N33/582

  with fluorescent label · CPC title

• C08B37/00

  Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof (cellulose D21; {microbiological processes C12P}) · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C07K2317/92

  Affinity (KD), association rate (Ka), dissociation rate (Kd) or EC50 value · CPC title