Lankacidins

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

MedKoo CAT#: 598296

CAS#: 23623-31-6

Description: Lankacidins is an antitumor antibiotic of the macrolide tetraenes family, isolated from Streptomyces.


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Lankacidins is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 598296
Name: Lankacidins
CAS#: 23623-31-6
Chemical Formula: C25H33NO7
Exact Mass: 459.2257
Molecular Weight: 459.53
Elemental Analysis: C, 65.34; H, 7.24; N, 3.05; O, 24.37


Synonym: Lankacidins; Lankacidin C; Lankacidin; Antibiotic T-2636 C; Bundlin A; NSC 145118; NSC-145118; NSC145118; T-2636C; T 2636C; T2636C;

IUPAC/Chemical Name: N-((1S,2R,3E,5E,7S,9E,11E,13S,15R,19R)-7,13-dihydroxy-1,4,10,19-tetramethyl-17,18-dioxo-16-oxabicyclo[13.2.2]nonadeca-3,5,9,11-tetraen-2-yl)-2-oxopropanamide

InChi Key: ATDILMLBOZKFGI-JUTMVFGESA-N

InChi Code: InChI=1S/C25H33NO7/c1-14-6-9-18(28)10-8-15(2)12-21(26-23(31)17(4)27)25(5)22(30)16(3)20(33-24(25)32)13-19(29)11-7-14/h6-8,10-12,16,18-21,28-29H,9,13H2,1-5H3,(H,26,31)/b10-8+,11-7+,14-6+,15-12+/t16-,18+,19-,20-,21-,25+/m1/s1

SMILES Code: CC(C(N[C@H](/C=C(C)/C=C/[C@@H](O)C/C=C(C)/C=C/[C@@H](O)C[C@@]1([H])O2)[C@](C([C@@H]1C)=O)(C)C2=O)=O)=O


Technical Data

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:
>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).

Harmonized System Code:
2934.99.03.00


References

1: He HY, Yuan H, Tang MC, Tang GL. An unusual dehydratase acting on glycerate and a ketoreducatse stereoselectively reducing α-ketone in polyketide starter unit biosynthesis. Angew Chem Int Ed Engl. 2014 Oct 13;53(42):11315-9. doi: 10.1002/anie.201406602. Epub 2014 Aug 27. PubMed PMID: 25160004.

2: Cao Z, Yoshida R, Kinashi H, Arakawa K. Blockage of the early step of lankacidin biosynthesis caused a large production of pentamycin, citreodiol and epi-citreodiol in Streptomyces rochei. J Antibiot (Tokyo). 2015 May;68(5):328-33. doi: 10.1038/ja.2014.160. Epub 2014 Dec 3. PubMed PMID: 25464973.

3: Ayoub AT, Abou El-Magd RM, Xiao J, Lewis CW, Tilli TM, Arakawa K, Nindita Y, Chan G, Sun L, Glover M, Klobukowski M, Tuszynski J. Antitumor Activity of Lankacidin Group Antibiotics Is Due to Microtubule Stabilization via a Paclitaxel-like Mechanism. J Med Chem. 2016 Oct 27;59(20):9532-9540. Epub 2016 Oct 18. PubMed PMID: 27718573.

4: Arakawa K. Genetic and biochemical analysis of the antibiotic biosynthetic gene clusters on the Streptomyces linear plasmid. Biosci Biotechnol Biochem. 2014;78(2):183-9. doi: 10.1080/09168451.2014.882761. Epub 2014 Apr 16. Review. PubMed PMID: 25036669.

5: Williams DR, Rojas CM, Bogen SL. Studies of Acyl Nitrene Insertions. A Stereocontrolled Route toward Lankacidin Antibiotics. J Org Chem. 1999 Feb 5;64(3):736-746. PubMed PMID: 11674141.

6: Dickschat JS, Vergnolle O, Hong H, Garner S, Bidgood SR, Dooley HC, Deng Z, Leadlay PF, Sun Y. An additional dehydratase-like activity is required for lankacidin antibiotic biosynthesis. Chembiochem. 2011 Nov 4;12(16):2408-12. doi: 10.1002/cbic.201100474. Epub 2011 Sep 27. PubMed PMID: 21953738.

7: Arakawa K, Tsuda N, Taniguchi A, Kinashi H. The butenolide signaling molecules SRB1 and SRB2 induce lankacidin and lankamycin production in Streptomyces rochei. Chembiochem. 2012 Jul 9;13(10):1447-57. doi: 10.1002/cbic.201200149. Epub 2012 Jun 14. PubMed PMID: 22761035.

8: Harada S, Okada J, Takeda M, Yamazaki T. Inclusion compounds of lankacidin-group antibiotics with cyclodextrins. J Antibiot (Tokyo). 1985 Jul;38(7):877-85. PubMed PMID: 4030501.

9: Belousoff MJ, Shapira T, Bashan A, Zimmerman E, Rozenberg H, Arakawa K, Kinashi H, Yonath A. Crystal structure of the synergistic antibiotic pair, lankamycin and lankacidin, in complex with the large ribosomal subunit. Proc Natl Acad Sci U S A. 2011 Feb 15;108(7):2717-22. doi: 10.1073/pnas.1019406108. Epub 2011 Jan 31. PubMed PMID: 21282615; PubMed Central PMCID: PMC3041097.

10: Solenberg PJ, Baltz RH. Transposition of Tn5096 and other IS493 derivatives in Streptomyces griseofuscus. J Bacteriol. 1991 Feb;173(3):1096-104. PubMed PMID: 1846854; PubMed Central PMCID: PMC207229.

11: Auerbach T, Mermershtain I, Davidovich C, Bashan A, Belousoff M, Wekselman I, Zimmerman E, Xiong L, Klepacki D, Arakawa K, Kinashi H, Mankin AS, Yonath A. The structure of ribosome-lankacidin complex reveals ribosomal sites for synergistic antibiotics. Proc Natl Acad Sci U S A. 2010 Feb 2;107(5):1983-8. doi: 10.1073/pnas.0914100107. Epub 2010 Jan 11. PubMed PMID: 20080686; PubMed Central PMCID: PMC2804743.

12: McFarland JW, Pirie DK, Retsema JA, English AR. Side chain modifications in lankacidin group antibiotics. Antimicrob Agents Chemother. 1984 Feb;25(2):226-33. PubMed PMID: 6370129; PubMed Central PMCID: PMC185479.

13: Tatsuno S, Arakawa K, Kinashi H. Extensive mutational analysis of modular-iterative mixed polyketide biosynthesis of lankacidin in Streptomyces rochei. Biosci Biotechnol Biochem. 2009 Dec;73(12):2712-9. Epub 2009 Dec 7. PubMed PMID: 19966473.

14: Kinashi H, Mori E, Hatani A, Nimi O. Isolation and characterization of linear plasmids from lankacidin-producing Streptomyces species. J Antibiot (Tokyo). 1994 Dec;47(12):1447-55. PubMed PMID: 7844039.

15: Tatsuno S, Arakawa K, Kinashi H. Analysis of modular-iterative mixed biosynthesis of lankacidin by heterologous expression and gene fusion. J Antibiot (Tokyo). 2007 Nov;60(11):700-8. PubMed PMID: 18057700.

16: Sawada H, Suzuki T, Akiyama S, Nakao Y. Mechanism of the stimulatory effect of cyclodextrins on lankacidin-producing Streptomyces. Appl Microbiol Biotechnol. 1990 Feb;32(5):556-9. PubMed PMID: 1366439.

17: Arakawa K, Mochizuki S, Yamada K, Noma T, Kinashi H. gamma-Butyrolactone autoregulator-receptor system involved in lankacidin and lankamycin production and morphological differentiation in Streptomyces rochei. Microbiology. 2007 Jun;153(Pt 6):1817-27. PubMed PMID: 17526839.

18: Arakawa K, Sugino F, Kodama K, Ishii T, Kinashi H. Cyclization mechanism for the synthesis of macrocyclic antibiotic lankacidin in Streptomyces rochei. Chem Biol. 2005 Feb;12(2):249-56. PubMed PMID: 15734652.

19: Mochizuki S, Hiratsu K, Suwa M, Ishii T, Sugino F, Yamada K, Kinashi H. The large linear plasmid pSLA2-L of Streptomyces rochei has an unusually condensed gene organization for secondary metabolism. Mol Microbiol. 2003 Jun;48(6):1501-10. PubMed PMID: 12791134.

20: Suwa M, Sugino H, Sasaoka A, Mori E, Fujii S, Shinkawa H, Nimi O, Kinashi H. Identification of two polyketide synthase gene clusters on the linear plasmid pSLA2-L in Streptomyces rochei. Gene. 2000 Apr 4;246(1-2):123-31. PubMed PMID: 10767533.