Quinocarcin | 84573-33-1 | antitumor antibiotics

MedKoo Cat#: 581279 | Name: Quinocarcin

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Description:

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

Quinocarcin are from Streptomyces melanovinaceus nov.sp. (-)-Quinocarcin are potent antitumor antibiotics that plays a key role in the construction of tetracyclic THIQ-pyrrolidine core scaffold.

Chemical Structure

Quinocarcin

CAS#84573-33-1

Theoretical Analysis

MedKoo Cat#: 581279

Name: Quinocarcin

CAS#: 84573-33-1

Chemical Formula: C18H22N2O4

Exact Mass: 330.1580

Molecular Weight: 330.38

Elemental Analysis: C, 65.44; H, 6.71; N, 8.48; O, 19.37

Price and Availability

Size	Price	Availability
5mg	USD 6,200.00	2 weeks
15mg	USD 17,000.00	2 weeks
25mg	USD 20,500.00	2 weeks

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Related CAS #

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Synonym

Quinocarcin; Antibiotic DC 52; DC52; DC-52;

IUPAC/Chemical Name

3,6-Imino-1H-2-oxa-11c-azanaphth(1,2,3-cd)azulene-5-carboxylic acid, 2a,3,4,5,6,6a,7,11b-octahydro-11-methoxy-12-methyl-, (2a-alpha,3-alpha,5-alpha,6-alpha,6a-alpha,11b-alpha)-, (-)-

InChi Key

VOUMVHRRAVBACH-MQZHMRIFSA-N

InChi Code

InChI=1S/C18H22N2O4/c1-19-12-7-10(18(21)22)16(19)11-6-9-4-3-5-14(23-2)15(9)13-8-24-17(12)20(11)13/h3-5,10-13,16-17H,6-8H2,1-2H3,(H,21,22)/t10-,11+,12+,13+,16-,17-/m0/s1

SMILES Code

O=C([C@@H]1[C@@]2([H])[C@](CC3=C4C(OC)=CC=C3)([H])N5[C@]4([H])CO[C@@]5([H])[C@@](N2C)([H])C1)O

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

To be determined

Shelf Life

>3 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

2934.99.03.00

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

(-)-Quinocarcin are potent antitumor antibiotics that plays a key role in the construction of tetracyclic THIQ-pyrrolidine core scaffold.

In vitro activity:

Quinocarcin and SF-1739, potent antitumor antibiotics, share a common tetracyclic tetrahydroisoquinoline (THIQ)-pyrrolidine core scaffold. This study propose that a biosynthetic pathway comprising a three-component NRPS/MbtH family protein complex, plays a key role in the construction of THIQ-pyrrolidine core scaffold involving sequential Pictet-Spengler and intramolecular Mannich reactions. Data derived from gene inactivation experiments led this study to propose late-modification steps of quinocarcin. Reference: Chem Biol. 2013 Dec 19;20(12):1523-35. https://pubmed.ncbi.nlm.nih.gov/24269153/

In vivo activity:

TBD

	Solvent	mg/mL	mM
Solubility
	Soluble in DMSO	0.0	0.00

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 330.38 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.

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:

1. Hiratsuka T, Koketsu K, Minami A, Kaneko S, Yamazaki C, Watanabe K, Oguri H, Oikawa H. Core assembly mechanism of quinocarcin/SF-1739: bimodular complex nonribosomal peptide synthetases for sequential mannich-type reactions. Chem Biol. 2013 Dec 19;20(12):1523-35. doi: 10.1016/j.chembiol.2013.10.011. Epub 2013 Nov 21. PMID: 24269153. 2. Herberich B, Scott JD, Williams RM. Synthesis of a netropsin conjugate of a water-soluble epi-quinocarcin analogue: the importance of stereochemistry at nitrogen. Bioorg Med Chem. 2000 Mar;8(3):523-32. doi: 10.1016/s0968-0896(99)00314-4. PMID: 10732968.

In vitro protocol:

In vivo protocol:

TBD

1: Song T, Wu Y, Ren J, Wang Z. Formal Syntheses of (-)-Quinocarcinamide and (-)-Quinocarcin. Org Lett. 2024 Aug 30;26(34):7100-7104. doi: 10.1021/acs.orglett.4c02267. Epub 2024 Aug 15. PMID: 39145720. 2: Ji KL, He SF, Xu DD, He WX, Zheng JF, Huang PQ. Concise Total Synthesis of (-)-Quinocarcin Enabled by Catalytic Enantioselective Reductive 1,3-Dipolar Cycloaddition of Secondary Amides. Angew Chem Int Ed Engl. 2023 Jun 19;62(25):e202302832. doi: 10.1002/anie.202302832. Epub 2023 May 8. PMID: 37025034. 3: Li L, Shi L, Wei K, Yang YR. Asymmetric Total Synthesis of (+)-Quinocarcinamide. Org Lett. 2021 Oct 15;23(20):7972-7975. doi: 10.1021/acs.orglett.1c02970. Epub 2021 Sep 29. PMID: 34585937. 4: Fang SL, Jiang MX, Zhang S, Wu YJ, Shi BF. Scalable Formal Synthesis of (-)-Quinocarcin. Org Lett. 2019 Jun 21;21(12):4609-4613. doi: 10.1021/acs.orglett.9b01511. Epub 2019 Jun 10. PMID: 31180224. 5: Tang GL, Tang MC, Song LQ, Zhang Y. Biosynthesis of Tetrahydroisoquinoline Antibiotics. Curr Top Med Chem. 2016;16(15):1717-26. doi: 10.2174/1568026616666151012112329. PMID: 26456466. 6: Hiratsuka T, Koketsu K, Minami A, Kaneko S, Yamazaki C, Watanabe K, Oguri H, Oikawa H. Core assembly mechanism of quinocarcin/SF-1739: bimodular complex nonribosomal peptide synthetases for sequential mannich-type reactions. Chem Biol. 2013 Dec 19;20(12):1523-35. doi: 10.1016/j.chembiol.2013.10.011. Epub 2013 Nov 21. PMID: 24269153. 7: Chiba H, Sakai Y, Ohara A, Oishi S, Fujii N, Ohno H. Convergent synthesis of (-)-quinocarcin based on the combination of Sonogashira coupling and gold(I)-catalyzed 6-endo-dig hydroamination. Chemistry. 2013 Jul 1;19(27):8875-83. doi: 10.1002/chem.201300687. Epub 2013 May 16. PMID: 23681666. 8: Chiba H, Oishi S, Fujii N, Ohno H. Total synthesis of (-)-quinocarcin by gold(I)-catalyzed regioselective hydroamination. Angew Chem Int Ed Engl. 2012 Sep 3;51(36):9169-72. doi: 10.1002/anie.201205106. Epub 2012 Aug 13. PMID: 22890756. 9: Peng C, Pu JY, Song LQ, Jian XH, Tang MC, Tang GL. Hijacking a hydroxyethyl unit from a central metabolic ketose into a nonribosomal peptide assembly line. Proc Natl Acad Sci U S A. 2012 May 29;109(22):8540-5. doi: 10.1073/pnas.1204232109. Epub 2012 May 14. PMID: 22586110; PMCID: PMC3365175. 10: Huck L, González JF, de la Cuesta E, Menéndez JC, Avendaño C. 1,3-dipolar cycloadditions from tricyclic hemiaminals. Synthesis of the quinocarcin core through catalyst-free generation of azomethine ylides. Org Biomol Chem. 2011 Sep 21;9(18):6271-7. doi: 10.1039/c1ob05181d. Epub 2011 Jul 19. PMID: 21773620. 11: Kahsai AW, Zhu S, Fenteany G. G protein-coupled receptor kinase 2 activates radixin, regulating membrane protrusion and motility in epithelial cells. Biochim Biophys Acta. 2010 Feb;1803(2):300-10. doi: 10.1016/j.bbamcr.2009.11.002. Epub 2009 Nov 11. PMID: 19913059; PMCID: PMC2838949. 12: Allan KM, Stoltz BM. A concise total synthesis of (-)-quinocarcin via aryne annulation. J Am Chem Soc. 2008 Dec 24;130(51):17270-1. doi: 10.1021/ja808112y. PMID: 19035638. 13: Kahsai AW, Cui J, Kaniskan HU, Garner PP, Fenteany G. Analogs of tetrahydroisoquinoline natural products that inhibit cell migration and target galectin-3 outside of its carbohydrate-binding site. J Biol Chem. 2008 Sep 5;283(36):24534-45. doi: 10.1074/jbc.M800006200. Epub 2008 Jun 13. PMID: 18556657; PMCID: PMC2528994. 14: Wu YC, Liron M, Zhu J. Asymmetric total synthesis of (-)-quinocarcin. J Am Chem Soc. 2008 Jun 4;130(22):7148-52. doi: 10.1021/ja800662q. Epub 2008 May 3. PMID: 18454525. 15: Kahsai AW, Zhu S, Wardrop DJ, Lane WS, Fenteany G. Quinocarmycin analog DX-52-1 inhibits cell migration and targets radixin, disrupting interactions of radixin with actin and CD44. Chem Biol. 2006 Sep;13(9):973-83. doi: 10.1016/j.chembiol.2006.07.011. PMID: 16984887. 16: Kwon S, Myers AG. Synthesis of (-)-quinocarcin by directed condensation of alpha-amino aldehydes. J Am Chem Soc. 2005 Dec 7;127(48):16796-7. doi: 10.1021/ja056206n. PMID: 16316220. 17: Brown LM, Cowen RL, Debray C, Eustace A, Erler JT, Sheppard FC, Parker CA, Stratford IJ, Williams KJ. Reversing hypoxic cell chemoresistance in vitro using genetic and small molecule approaches targeting hypoxia inducible factor-1. Mol Pharmacol. 2006 Feb;69(2):411-8. doi: 10.1124/mol.105.015743. Epub 2005 Oct 27. PMID: 16254058. 18: Herberich B, Scott JD, Williams RM. Synthesis of a netropsin conjugate of a water-soluble epi-quinocarcin analogue: the importance of stereochemistry at nitrogen. Bioorg Med Chem. 2000 Mar;8(3):523-32. doi: 10.1016/s0968-0896(99)00314-4. PMID: 10732968. 19: Yamaguchi K, Fuse E, Takashima M, Yasuzawa T, Kuwabara T, Kobayashi S. Development of a sensitive liquid chromatography-electrospray ionization tandem mass spectrometry method for the measurement of 7-cyanoquinocarcinol in human plasma. J Chromatogr B Biomed Sci Appl. 1998 Aug 25;713(2):447-51. doi: 10.1016/s0378-4347(98)00185-6. PMID: 9746263. 20: Flanagan ME, Rollins SB, Williams RM. Netropsin and spermine conjugates of a water-soluble quinocarcin analog: analysis of sequence-specific DNA interactions. Chem Biol. 1995 Mar;2(3):147-56. doi: 10.1016/1074-5521(95)90069-1. PMID: 9383416.