2,2'-Dipyridyl disulfide
featured

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 581011

CAS#: 2127-03-9

Description: 2,2'-Dipyridyl disulfide, also known as OPSS, is a useful reagent for determination of sulfhydryl groups, preparation of amino acid active esters and the thio esters of phosphoric acid. It acts as a peptide coupling reagent and as an oxidizing agent. It is also used for the activation of glycosides.


Chemical Structure

img
2,2'-Dipyridyl disulfide
CAS# 2127-03-9

Theoretical Analysis

MedKoo Cat#: 581011
Name: 2,2'-Dipyridyl disulfide
CAS#: 2127-03-9
Chemical Formula: C10H8N2S2
Exact Mass: 220.01
Molecular Weight: 220.300
Elemental Analysis: C, 54.52; H, 3.66; N, 12.72; S, 29.10

Price and Availability

Size Price Availability Quantity
5g USD 210 2 Weeks
25g USD 400 2 Weeks
250g USD 1210 2 Weeks
Bulk inquiry

Synonym: 2,2'-Dipyridyl disulfide; Orthopyridyl disulfide; Aldrithiol 2; OPSS.

IUPAC/Chemical Name: 2,2"-Dithiodipyridine

InChi Key: HAXFWIACAGNFHA-UHFFFAOYSA-N

InChi Code: InChI=1S/C10H8N2S2/c1-3-7-11-9(5-1)13-14-10-6-2-4-8-12-10/h1-8H

SMILES Code: C1(SSC2=NC=CC=C2)=NC=CC=C1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 220.30 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Watanabe D, Kanzaki K, Kuratani M, Matsunaga S, Yanaka N, Wada M. Contribution
of impaired myofibril and ryanodine receptor function to prolonged low-frequency force depression after in situ stimulation in rat skeletal muscle. J Muscle Res
Cell Motil. 2015 Jun;36(3):275-86. doi: 10.1007/s10974-015-9409-1. Epub 2015 Feb 20. PubMed PMID: 25697123.


2: Miller E, Spadaccia M, Sabado R, Chertova E, Bess J, Trubey CM, Holman RM,
Salazar A, Lifson J, Bhardwaj N. Autologous aldrithiol-2-inactivated HIV-1
combined with polyinosinic-polycytidylic acid-poly-L-lysine
carboxymethylcellulose as a vaccine platform for therapeutic dendritic cell
immunotherapy. Vaccine. 2015 Jan 3;33(2):388-95. doi:
10.1016/j.vaccine.2014.10.054. Epub 2014 Nov 15. PubMed PMID: 25444812; PubMed
Central PMCID: PMC4272884.


3: Kanishchev OS, Dolbier WR Jr. Synthesis and characterization of
2-pyridylsulfur pentafluorides. Angew Chem Int Ed Engl. 2015 Jan 2;54(1):280-4.
doi: 10.1002/anie.201409990. Epub 2014 Nov 6. PubMed PMID: 25376393.


4: Basak D, Kumar R, Ghosh S. Telechelic Poly(disulfide)s and Related Block
Copolymer. Macromol Rapid Commun. 2014 Aug;35(15):1340-4. doi:
10.1002/marc.201400237. Epub 2014 May 20. PubMed PMID: 24840860.


5: Clausen A, McClanahan T, Ji SG, Weiss JH. Mechanisms of rapid reactive oxygen species generation in response to cytosolic Ca2+ or Zn2+ loads in cortical
neurons. PLoS One. 2013 Dec 10;8(12):e83347. doi: 10.1371/journal.pone.0083347.
eCollection 2013. PubMed PMID: 24340096; PubMed Central PMCID: PMC3858366.


6: Lee YM, Wang YT, Duh Y, Yuan HS, Lim C. Identification of labile Zn sites in
drug-target proteins. J Am Chem Soc. 2013 Sep 25;135(38):14028-31. doi:
10.1021/ja406300c. Epub 2013 Sep 11. PubMed PMID: 24010488.


7: McCord MC, Aizenman E. Convergent Ca2+ and Zn2+ signaling regulates apoptotic Kv2.1 K+ currents. Proc Natl Acad Sci U S A. 2013 Aug 20;110(34):13988-93. doi:
10.1073/pnas.1306238110. Epub 2013 Aug 5. PubMed PMID: 23918396; PubMed Central
PMCID: PMC3752224.


8: Gökce H, Bahçeli S. FT-IR, micro-Raman and UV-vis spectroscopic and quantum
chemical investigations of free 2,2'-dithiodipyridine and its metal (Co, Cu and
Zn) halide complexes. Spectrochim Acta A Mol Biomol Spectrosc. 2013
Oct;114:61-73. doi: 10.1016/j.saa.2013.04.112. Epub 2013 May 9. PubMed PMID:
23751221.


9: Fateixa S, Pinheiro PC, Nogueira HI, Trindade T. Composite blends of gold
nanorods and poly(t-butylacrylate) beads as new substrates for SERS. Spectrochim Acta A Mol Biomol Spectrosc. 2013 Sep;113:100-6. doi: 10.1016/j.saa.2013.04.070. Epub 2013 May 3. PubMed PMID: 23714187.


10: Nagao R, Tsutsui H, Mochizuki T, Takayama T, Kuwabara T, Min JZ, Inoue K,
Todoroki K, Toyo'oka T. Novel chiral derivatization reagents possessing a
pyridylthiourea structure for enantiospecific determination of amines and
carboxylic acids in high-throughput liquid chromatography and
electrospray-ionization mass spectrometry for chiral metabolomics identification.
J Chromatogr A. 2013 Jun 28;1296:111-8. doi: 10.1016/j.chroma.2013.03.019. Epub
2013 Mar 26. PubMed PMID: 23582770.


11: Tsutsui H, Mochizuki T, Maeda T, Noge I, Kitagawa Y, Min JZ, Todoroki K,
Inoue K, Toyo'oka T. Simultaneous determination of DL-lactic acid and
DL-3-hydroxybutyric acid enantiomers in saliva of diabetes mellitus patients by
high-throughput LC-ESI-MS/MS. Anal Bioanal Chem. 2012 Oct;404(6-7):1925-34. doi: 10.1007/s00216-012-6320-0. Epub 2012 Aug 16. PubMed PMID: 22895741.


12: Ismaylova SR, Matsulevich ZV, Borisova GN, Borisov AV, Khrustalev VN.
Dichloridobis(pyridine-2-thiol-ato-κ²N,S)tin(IV): a new polymorph. Acta
Crystallogr Sect E Struct Rep Online. 2012 Jul 1;68(Pt 7):m875-6. doi:
10.1107/S1600536812024026. Epub 2012 Jun 13. PubMed PMID: 22807723; PubMed
Central PMCID: PMC3393155.


13: Cotella D, Hernandez-Enriquez B, Wu X, Li R, Pan Z, Leveille J, Link CD, Oddo
S, Sesti F. Toxic role of K+ channel oxidation in mammalian brain. J Neurosci.
2012 Mar 21;32(12):4133-44. doi: 10.1523/JNEUROSCI.6153-11.2012. Erratum in: J
Neurosci. 2012 Jul 4;32(27):9449. PubMed PMID: 22442077.


14: Mollica JP, Dutka TL, Merry TL, Lamboley CR, McConell GK, McKenna MJ, Murphy RM, Lamb GD. S-glutathionylation of troponin I (fast) increases contractile
apparatus Ca2+ sensitivity in fast-twitch muscle fibres of rats and humans. J
Physiol. 2012 Mar 15;590(6):1443-63. doi: 10.1113/jphysiol.2011.224535. Epub 2012
Jan 16. PubMed PMID: 22250211; PubMed Central PMCID: PMC3382333.


15: Gibon J, Richaud P, Bouron A. Hyperforin changes the zinc-storage capacities of brain cells. Neuropharmacology. 2011 Dec;61(8):1321-6. doi:
10.1016/j.neuropharm.2011.08.002. Epub 2011 Aug 12. PubMed PMID: 21854792.


16: Dallas ML, Boyle JP, Milligan CJ, Sayer R, Kerrigan TL, McKinstry C, Lu P,
Mankouri J, Harris M, Scragg JL, Pearson HA, Peers C. Carbon monoxide protects
against oxidant-induced apoptosis via inhibition of Kv2.1. FASEB J. 2011
May;25(5):1519-30. doi: 10.1096/fj.10-173450. Epub 2011 Jan 19. PubMed PMID:
21248240.


17: Lewis DJ, Glover PB, Solomons MC, Pikramenou Z. Purely heterometallic
lanthanide(III) macrocycles through controlled assembly of disulfide bonds for
dual color emission. J Am Chem Soc. 2011 Feb 2;133(4):1033-43. doi:
10.1021/ja109157g. Epub 2010 Dec 23. PubMed PMID: 21182290.


18: Dutka TL, Mollica JP, Posterino GS, Lamb GD. Modulation of contractile
apparatus Ca2+ sensitivity and disruption of excitation-contraction coupling by
S-nitrosoglutathione in rat muscle fibres. J Physiol. 2011 May 1;589(Pt
9):2181-96. doi: 10.1113/jphysiol.2010.200451. Epub 2010 Nov 29. PubMed PMID:
21115647; PubMed Central PMCID: PMC3098697.


19: Mochida K, Amano H, Onduka T, Kakuno A, Fujii K. Toxicity and metabolism of
copper pyrithione and its degradation product, 2,2'-dipyridyldisulfide in a
marine polychaete. Chemosphere. 2011 Jan;82(3):390-7. doi:
10.1016/j.chemosphere.2010.09.074. Epub 2010 Oct 20. PubMed PMID: 20965543.


20: Che KF, Sabado RL, Shankar EM, Tjomsland V, Messmer D, Bhardwaj N, Lifson JD,
Larsson M. HIV-1 impairs in vitro priming of naïve T cells and gives rise to
contact-dependent suppressor T cells. Eur J Immunol. 2010 Aug;40(8):2248-58. doi:
10.1002/eji.201040377. PubMed PMID: 20455275; PubMed Central PMCID: PMC3258541.