Bicinchoninic acid: Difference between revisions

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	{{chembox		{{chembox
			\| Watchedfields = changed
	\| verifiedrevid = 413897454		\| verifiedrevid = 413897454
	\| Name = Bicinchoninic acid		\| Name = Bicinchoninic acid
	\| ImageFile = ~~Bicinchoninic~~ acid.~~svg~~		\| ImageFile = Structure of bicinchoninic acid.png
		⚫	\| ImageName =
	<!-- \| ImageSize = 200px -->
			\| PIN = -4,4′-dicarboxylic acid
⚫	\| ImageName =
		⚫	\| OtherNames = Bicinchoninic acid<br>4,4′-Dicarboxy-2,2′-biquinoline<br>2,2'-Biquinoline-4,4'-dicarboxylic acid
	\| IUPACName = 2-(4-carboxyquinolin-2-yl)quinoline-4-carboxylic acid
		⚫	\|Section1={{Chembox Identifiers
⚫	\| OtherNames = Bicinchoninic acid</br>4,4'-Dicarboxy-2,2'-Biquinoline
		⚫	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
⚫	\| Section1 = {{Chembox Identifiers
⚫	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| ChemSpiderID = 64223		\| ChemSpiderID = 64223
	\| InChI = 1/C20H12N2O4/c23-19(24)13-9-17(21-15-7-3-1-5-11(13)15)18-10-14(20(25)26)12-6-2-4-8-16(12)22-18/h1-10H,(H,23,24)(H,25,26)
	\| SMILES = O=C(O)c1cc(nc2c1cccc2)c3nc4ccccc4c(c3)C(=O)O		\| SMILES = O=C(O)c1cc(nc2c1cccc2)c3nc4ccccc4c(c3)C(=O)O
	\| InChIKey = AFYNADDZULBEJA-UHFFFAOYAF
	\| PubChem = 71068		\| PubChem = 71068
	\| ChEMBL_Ref = {{ebicite\|correct\|EBI}}		\| ChEMBL_Ref = {{ebicite\|correct\|EBI}}
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	\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChIKey = AFYNADDZULBEJA-UHFFFAOYSA-N		\| StdInChIKey = AFYNADDZULBEJA-UHFFFAOYSA-N
			\| CASNo_Ref = {{cascite\|correct\|??}}
	\| CASNo = 1245-13-2		\| CASNo = 1245-13-2
			\| CASNo_Comment = (free acid)
⚫	\| RTECS =
			\| CASNo2_Ref = {{cascite\|unknown\|CAS}}
			\| CASNo2 = 979-88-4
			\| CASNo2_Comment = (disodium salt)
			\| UNII_Ref = {{fdacite\|correct\|FDA}}
			\| UNII = CX56TX9Y1I
		⚫	\| RTECS =
	}}		}}
	\| Section2 = {{Chembox Properties		\|Section2={{Chembox Properties
			\| C=20\|H=12\|N=2\|O=4
	\| Formula = (HO<sub>2</sub>CC<sub>9</sub>H<sub>5</sub>N)<sub>2</sub>
			\| Appearance = Cream colored powder
	\| MolarMass = 344.33 g/mol
	\| ~~Appearance~~ = ~~Cream powder.~~ Characteristic odor.		\| Odor = Characteristic odor{{vague\|date=October 2013}}
			\| Density =
	\| Density = Solid in pure form.</br>Density not available.
	\| Solubility = Partially soluble in cold water, hot water.		\| Solubility = Partially soluble in cold water, hot water{{vague\|date=October 2013}}
			\| MeltingPtC = 352
	\| MeltingPt = 365 to 367 °C
			\| MeltingPt_notes = decomposes
	\| BoilingPt = Not available.
	\| ~~pKa~~ =		\| BoilingPt =
			\| pKa =
	}}		}}
	\| Section3 = {{Chembox Structure		\|Section3={{Chembox Structure
	\| CrystalStruct =		\| CrystalStruct =
	\| Dipole =		\| Dipole =
	}}		}}
	\| Section7 = {{Chembox Hazards		\|Section7={{Chembox Hazards
	\| ~~ExternalMSDS~~ =		\| ExternalSDS =
			\| MainHazards = Will irritate eyes and mucous membranes.
	\| MainHazards = Will irritate eyes and mucous membranes.<br />The chemical, physical and toxicological<br />properties have not been fully investigated.<br />Presume moderate toxicity internally. LD/TD<br />no data. OSHA PEL/ACGIH TLV not established.<br />No evidence of carcinogenicity.
	\| NFPA-H = 1		\| NFPA-H = 1
	\| NFPA-R =		\| NFPA-R =
	\| NFPA-F =		\| NFPA-F =
	\| FlashPt = ~~N/A~~		\| FlashPt =
	}}		}}
	}}		}}

			'''Bicinchoninic acid''' ({{IPAc-en\|b\|aɪ\|s\|ɪ\|n\|k\|ɔː\|n\|ɪ\|n\|ɪ\|k}}) or '''BCA''' is a ] composed of two ]ated ] rings. It is an organic compound with the formula (C<sub>9</sub>H<sub>5</sub>NCO<sub>2</sub>H)<sub>2</sub>. The molecule consists of a pair of ] rings, each bearing a ] group. Its ] forms a purple complex with ] ions.<ref>{{Cite journal\|year=1985\|title=Measurement of Protein Using Bicinchoninic Acid\|journal=Analytical Biochemistry\|volume=150\|issue=1\|pages=76–85\|doi=10.1016/0003-2697(85)90442-7\|last1=Smith \|first1=P.K. \|last2=Krohn \|first2=R.I. \|last3=Hermanson \|first3=G.T. \|last4=Mallia \|first4=A.K. \|last5=Gartner \|first5=F.H. \|last6=Provenzano \|first6=M.D. \|last7=Fujimoto \|first7=E.K. \|last8=Goeke \|first8=N.M. \|last9=Olson \|first9=B.J. \|last10=Klenk \|first10=D.C. \|pmid=3843705 }}</ref><ref>{{cite journal \|doi=10.1016/0003-2697(89)90101-2\|title=Protein measurement using bicinchoninic acid: Elimination of interfering substances \|year=1989 \|last1=Brown \|first1=Rhoderick E. \|last2=Jarvis \|first2=Kari L. \|last3=Hyland \|first3=Kristi J. \|journal=Analytical Biochemistry \|volume=180 \|issue=1 \|pages=136–139 \|pmid=2817336 }}</ref><ref>{{cite book \|doi=10.1016/S0076-6879(09)63008-1\|chapter=Chapter 8 Quantitation of Protein \|title=Guide to Protein Purification, 2nd Edition \|series=Methods in Enzymology \|year=2009 \|last1=Noble \|first1=James E. \|last2=Bailey \|first2=Marc J.A. \|volume=463 \|pages=73–95 \|pmid=19892168 \|isbn=9780123745361 }}</ref>
	'''Bicinchoninic acid''' is a weak acid composed of two ]ated ] rings.

	Bicinchoninic acid is most commonly employed ~~by biochemists~~ in the ], which is used to determine the total ~~level~~ of protein in a solution. In this assay, two molecules of bicinchoninic acid ] a single ]<sup>1+</sup> ion, forming a purple water-soluble complex that strongly absorbs light at 562 ].<ref></ref>		Bicinchoninic acid is most commonly employed in the ], which is used to determine the total concentration of ] in a solution. Bicinchoninic acid is used to detect the presence of cuprous ions, due to its purple coloration via a ]. In this assay, two molecules of bicinchoninic acid ] a single ]<sup>+</sup> ion, forming a purple water-soluble complex that strongly absorbs light at 562 ].<ref></ref>

	==References==		==References==
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Latest revision as of 10:10, 12 August 2024

Bicinchoninic acid
Names

Preferred IUPAC name -4,4′-dicarboxylic acid
Other names Bicinchoninic acid 4,4′-Dicarboxy-2,2′-biquinoline 2,2'-Biquinoline-4,4'-dicarboxylic acid
Identifiers
CAS Number	1245-13-2 (free acid) 979-88-4 (disodium salt)
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL431482
ChemSpider	64223
ECHA InfoCard	100.013.628
PubChem CID	71068
UNII	CX56TX9Y1I
CompTox Dashboard (EPA)	DTXSID8061638
InChI InChI=1S/C20H12N2O4/c23-19(24)13-9-17(21-15-7-3-1-5-11(13)15)18-10-14(20(25)26)12-6-2-4-8-16(12)22-18/h1-10H,(H,23,24)(H,25,26)Key: AFYNADDZULBEJA-UHFFFAOYSA-N
SMILES O=C(O)c1cc(nc2c1cccc2)c3nc4ccccc4c(c3)C(=O)O
Properties
Chemical formula	C₂₀H₁₂N₂O₄
Molar mass	344.326 g·mol
Appearance	Cream colored powder
Odor	Characteristic odor
Melting point	352 °C (666 °F; 625 K) decomposes
Solubility in water	Partially soluble in cold water, hot water
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Will irritate eyes and mucous membranes.
NFPA 704 (fire diamond)	1
Safety data sheet (SDS)	External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is ?) Infobox references

Chemical compound

Bicinchoninic acid (/baɪsɪnkɔːnɪnɪk/) or BCA is a weak acid composed of two carboxylated quinoline rings. It is an organic compound with the formula (C₉H₅NCO₂H)₂. The molecule consists of a pair of quinoline rings, each bearing a carboxylic acid group. Its sodium salt forms a purple complex with cuprous ions.

Bicinchoninic acid is most commonly employed in the bicinchoninic acid (BCA) assay, which is used to determine the total concentration of protein in a solution. Bicinchoninic acid is used to detect the presence of cuprous ions, due to its purple coloration via a biuret reaction. In this assay, two molecules of bicinchoninic acid chelate a single Cu ion, forming a purple water-soluble complex that strongly absorbs light at 562 nm.

References

Smith, P.K.; Krohn, R.I.; Hermanson, G.T.; Mallia, A.K.; Gartner, F.H.; Provenzano, M.D.; Fujimoto, E.K.; Goeke, N.M.; Olson, B.J.; Klenk, D.C. (1985). "Measurement of Protein Using Bicinchoninic Acid". Analytical Biochemistry. 150 (1): 76–85. doi:10.1016/0003-2697(85)90442-7. PMID 3843705.
Brown, Rhoderick E.; Jarvis, Kari L.; Hyland, Kristi J. (1989). "Protein measurement using bicinchoninic acid: Elimination of interfering substances". Analytical Biochemistry. 180 (1): 136–139. doi:10.1016/0003-2697(89)90101-2. PMID 2817336.
Noble, James E.; Bailey, Marc J.A. (2009). "Chapter 8 Quantitation of Protein". Guide to Protein Purification, 2nd Edition. Methods in Enzymology. Vol. 463. pp. 73–95. doi:10.1016/S0076-6879(09)63008-1. ISBN 9780123745361. PMID 19892168.
Pierce BCA Protein Assay Kit

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