Lankacidinol

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MedKoo CAT#: 598206

CAS#: 23498-37-5

Description: Lankacidinol is an antibiotic with antitumor and immunosuppressive activities.


Price and Availability

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Pricing updated 2020-08-15. Prices are subject to change without notice.

Lankacidinol 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#: 598206
Name: Lankacidinol
CAS#: 23498-37-5
Chemical Formula: C25H35NO7
Exact Mass: 461.2414
Molecular Weight: 461.55
Elemental Analysis: C, 65.06; H, 7.64; N, 3.03; O, 24.26


Synonym: Lankacidinol; T-2636 F; T 2636 F; T2636 F; Antibiotic T 2636F;

IUPAC/Chemical Name: (R)-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-hydroxypropanamide

InChi Key: FUDDPCATVZFGCZ-SQFDTGPGSA-N

InChi Code: InChI=1S/C25H35NO7/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/h6-8,10-12,16-21,27-29H,9,13H2,1-5H3,(H,26,31)/b10-8+,11-7+,14-6+,15-12+/t16-,17-,18+,19-,20-,21-,25+/m1/s1

SMILES Code: O[C@H](C)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


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).

HS Tariff Code:
2934.99.03.00


References

1: Oostu K, Matsumoto T, Harada S, Kishi T. Antitumor and immunosuppressive activities of lankacidin-group antibiotics: structure-activity relationships. Cancer Chemother Rep. 1975 Sep-Oct;59(5):919-28. PubMed PMID: 1148.

2: Hayashi T, Okada J, Kondo S, Yamazaki T. Role of intestinal excretion in the effect of subcutaneously administered sedecamycin on cecal infection caused by Treponema hyodysenteriae in mice. Antimicrob Agents Chemother. 1991 Aug;35(8):1601-4. PubMed PMID: 1929332; PubMed Central PMCID: PMC245226.

3: Okada J, Kondo S. Liquid chromatographic method for determining the macrolide antibiotic sedecamycin and its major metabolites in swine plasma and tissues. J Assoc Off Anal Chem. 1987 Sep-Oct;70(5):818-24. PubMed PMID: 3680117.

4: 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.

5: 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.

6: Yamauchi Y, Nindita Y, Hara K, Umeshiro A, Yabuuchi Y, Suzuki T, Kinashi H, Arakawa K. Quinoprotein dehydrogenase functions at the final oxidation step of lankacidin biosynthesis in Streptomyces rochei 7434AN4. J Biosci Bioeng. 2018 Jun 2. pii: S1389-1723(18)30057-4. doi: 10.1016/j.jbiosc.2018.03.006. [Epub ahead of print] PubMed PMID: 29871824.

7: Zheng K, Shen D, Hong R. Biomimetic Synthesis of Lankacidin Antibiotics. J Am Chem Soc. 2017 Sep 20;139(37):12939-12942. doi: 10.1021/jacs.7b08500. Epub 2017 Sep 6. PubMed PMID: 28853876.

8: Lu C, Li JM, Qi H, Zhang H, Zhang J, Xiang WS, Wang JD, Wang XJ. Two new lankacidin-related metabolites from Streptomyces sp. HS-NF-1178. J Antibiot (Tokyo). 2018 Mar;71(3):397-401. doi: 10.1038/s41429-017-0004-0. Epub 2018 Jan 18. PubMed PMID: 29348529.