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D2388

Sigma-Aldrich

Dimethyl 3,3′-dithiopropionimidate dihydrochloride

powder

Synonyma:

DTBP, Dimethyl 3,3′-dithio-bis(propionimidate) dihydrochloride, Wang/Richards’ reagent

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About This Item

Empirický vzorec (Hillův zápis):
C8H16N2O2S2 · 2HCl
Číslo CAS:
38285-78-8
Molekulová hmotnost:
309.28
MDL number:
MFCD00043245
UNSPSC Code:
12352116
PubChem Substance ID:
57654084
NACRES:
NA.22

form

powder

reaction suitability

reagent type: cross-linking reagent

solubility

H2O: 50 mg/mL

storage temp.

2-8°C

SMILES string

Cl.Cl.COC(=N)CCSSCCC(=N)OC

InChI

1S/C8H16N2O2S2.2ClH/c1-11-7(9)3-5-13-14-6-4-8(10)12-2;;/h9-10H,3-6H2,1-2H3;2*1H

InChI key

CQBCVFHLZAVNPF-UHFFFAOYSA-N

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Application

Reactant for:
  • Synthesis of glutathione-sensitive cross-linked polyethylenimine gene vector
  • Preparation of cyclodextrin-containing polymers designed for gene delivery
  • Crosslinking of chick oviduct progesterone-receptor subunits

Caution

The reagant is readily hydrolyzed at neutral pH. Avoid use of reducing agents during coupling reactions.

Other Notes

Note that the amidine linkage preserves original primary amine positive charge. The disulfide linkage is cleavable by mild reduction. Incorporates an eight atom linker.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H315

Hazard Classifications

Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Osvědčení o analýze (COA)

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John G Lock et al.
Nature cell biology, 20(11), 1290-1302 (2018-10-27)
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Carine F Djuika et al.
Scientific reports, 7(1), 4410-4410 (2017-07-02)
Artemisinins are the current mainstay of malaria chemotherapy. Their exact mode of action is an ongoing matter of debate, and several factors have recently been reported to affect an early stage of artemisinin resistance of the most important human malaria
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A Bu4NI-catalyzed, DTBP-promoted, regioselective C(sp2)-C(sp3) cross dehydrogenative coupling (CDC) protocol for the direct C-3 benzylation of 2H-indazoles is reported. The metal-free protocol is operationally simple and proceeds mechanistically via the generation of stable benzylic free-radicals followed by regioselective addition at
Choong Eun Jin et al.
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Cell-free nucleic acids (cfNAs) are emerging diagnostic biomarkers for monitoring the treatment and recurrence of cancers. In particular, the biological role and clinical usefulness of cfNAs obtained from the plasma of patients with various cancers are popular and still intensely
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Biomacromolecules, 19(6), 2320-2329 (2018-05-17)
Antibody fragment (Fab')-installed polyion complex (PIC) micelles were constructed to improve targetability of small interfering RNA (siRNA) delivery to pancreatic cancer cells. To this end, we synthesized a block copolymer of azide-functionalized poly(ethylene glycol) and poly(l-lysine) and prepared PIC micelles
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