Bioconjugation Reagents and Tools – ChemiMart

6-Maleimidohexanehydrazide trifluoroacetate

mzaug — Tue, 08 Dec 2020 13:00:09 +0000

These crosslinkers contain a maleimido functionality and a hydrazine group, and are often used for preparing enzyme conjugates or immunotoxins.

AEAETS

mzaug — Tue, 08 Dec 2020 12:56:29 +0000

AEAETS (2-Aminoethyl 2-aminoethanethiosulfonate dihydrochloride salt) is a doubly positively charged alkanethiosulfonate.

Ref.:

1) The intrinsic electrostatic potential and the intermediate ring of charge in the acetylcholine receptor channel.

G. G. Wilson, J .Gen. Physiol. 2000, 115(2); 93-106.

DOI:10.1085/jgp.115.2.9

2) Substituted-cysteine accessibility method.

A. Karlin, Methods Enzymol. 1998, 293; 123-145.

DOI:10.1016/s0076-6879(98)93011-7

4-[4-(1-Hydroxyethyl)-2-methoxy-5-nitrophenoxy]butyric acid

mzaug — Tue, 08 Dec 2020 12:52:48 +0000

Hydroxyethyl photolinker which can be bound to amino- and hydroxymethyl resins. Synthesis of sensitive acids.

Ref.:

1) Model Studies for New o-Nitrobenzyl Photolabile Linkers: Substituent Effects on the Rates of Photochemical Cleavage.

C. P. Holmes, J. Org. Chem. 1997, 62(8); 2370-2380.

DOI:10.1021/jo961602x

2) Optical control of cell differentiation on synthetic collagen-like scaffolds.

M. Kobayashi, J. Biomater. Sci. Polym. Ed. 2019, 30(13); 1161-1171.

DOI:10.1080/09205063.2019.1622845

Sulfo-SIAB

mzaug — Tue, 08 Dec 2020 12:49:33 +0000

Sulfo-SIAB is supplied as a sodium salt and is water-soluble to ~10mM. SIAB must be first dissolved in an organic solvent, such as DMSO or DMF, and then added to the aqueous reaction mixture. SIAB is lipophilic, membrane-permeable and does not possess a charged group.

Bearing the sulfo-NHS ester and iodoacetyl reactive groups, which react selectively with amino and sulfhydryl groups repsectively. This is a non-cleavable linker and is a more soluble alternaive to SIAB.

SIAB

mzaug — Tue, 08 Dec 2020 12:46:08 +0000

SIAB sulfhydryl and amino reactive heterobifunctional protein crosslinking reagent ideal for labelling peptides and proteins with various labels (ligands or dyes).

Ref.:

1) N-succinimidyl-(4-iodoacetyl)aminobenzoate: A new heterobifunctional crosslinker.

Weltman, J. K., Biotechniques, 1983, 1, 148-152

DOI: N/A

N-(2-Iodoethyl)trifluoroacetamide

mzaug — Tue, 08 Dec 2020 12:42:54 +0000

Reagent for aminoethylation of sulfhydryl groups in proteins. Also useful for the introduction of the aminoethyl group into various molecules.

Ref.:

1) N-(β-Iodoethyl)trifluoroacetamide: a new reagent for the aminoethylation of thiol groups in proteins.

W.E. Schwartz, P.K. Smith, G.P. Royer, Anal. Biochem., 1980, 106, 43.

DOI: 10.1016/0003-2697(80)90116-5

FlAsH-EDT2, Fluorescein Arsenical Hairpin Binder

mzaug — Tue, 08 Dec 2020 12:39:09 +0000

Used in bioanalytical research as a fluorescent label for visualising proteins in living cells. It is excited at 508 nm and emits at 528 nm.

FlAsH-EDT2 selectively binds to proteins containing the tetracysteine (TC) motif CCPGCC and becomes fluorescent when bound. Also can be used to study the processes of protein trafficking in situ.

Ref.:

1) Preparation of the membrane-permeant biarsenicals FlAsH-EDT2 and ReAsH-EDT2 for fluorescent labeling of tetracysteine-tagged proteins.

S.R. Adams, R.Y. Tsien, Nat. Protoc. 2008, 3(9), 1527–1534.

DOI:10.1038/nprot.2008.144

2) New biarsenical ligands and tetracysteine motifs for protein labeling in vitro and in vivo: synthesis and biological applications.

S.R.Adams, R.E. Campbell, L.A. Gross, B.R. Martin, G.K. Walkup, Y. Yao, J. Llopis, R. Y. Tsien, J. Am. Chem. Soc. 2002, 124(21), 6063–6076.

DOI:10.1021/ja017687n

SATA, N-succinimidyl-S-acetyl-thioacetate

mzaug — Tue, 08 Dec 2020 12:35:32 +0000

Other names: N-Succinimidyl (acetylthio)acetate, S-Acetylthioglycolic acid NHS ester.

Thiolating reagent for primary amines; thiol can be liberated from protected form under mild conditions.

Can be coupled to molecules containing primary amine by amide bond. The reaction proceeds in buffered solution at pH 7.5.

Deprotection with 0.05M hydroxylamine may be accomplished at neutral pH.

Useful for preparation of enzyme immunoconjugates and hapten carrier molecule conjugates.

Ref.:

1) A new reagent which may be used to introduce sulfhydryl groups into proteins, and its use in the preparation of conjugates for immunoassay.

R.J Duncan, Anal. Biochem. 1983, 132(1), 68-73.

DOI: 10.1016/0003-2697(83)90426-8

Sulfo-MBS, m-Maleimidobenzoyl-N-hydroxysulfosuccinimide ester

mzaug — Tue, 08 Dec 2020 12:23:48 +0000

Sulfo-MBS is a water-soluble derivatives of MBS, an amine-to-sulfhydryl bioconjugation reagent with NHS-ester and maleimide reactive groups at opposite ends of an aromatic system. The linker provides 7.3Å separation of the reactive functionalities.

Ref.:

More useful maleimide compounds for the conjugation of Fab’ to horseradish peroxidase through thiol groups in the hinge.

H. Seiichi et. al, J. Appl. Biochem. 1984, 6, 56.

PMID: 6490581

MBS, m-Maleimidobenzoyl-N-hydroxysuccinimide ester

mzaug — Tue, 08 Dec 2020 11:40:30 +0000

MBS is a short, amine-to-sulfhydryl bioconjugation reagent that contains NHS-ester and maleimide in meta-positions of an aromatic ring. It provides approximately 7.3Å spacer lenght between reactive functionalities.

Can be used to link a drug to a protein or peptide.

Ref.:

1) Optimization of a Stable Linker Involved DEVD Peptide-Doxorubicin Conjugate that is Activated upon Radiation-Induced Caspase-3-Mediated Apoptosis.

S.W. Chung, J. Med. Chem. 2015, 58(16); 6435-6447.

DOI: 10.1021/acs.jmedchem.5b00420.

2) Conjugation of Peptide to Carrier Proteins via m-Maleimidobenzoyl-N-Hydroxysuccinimide Ester (MBS).

J.M. Carter, The Protein Protocols Handbook, 689-692.
DOI: 10.1007/978-1-60327-259-9_118.