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MedKoo Cat#: 598572 | Name: Lentiginosine

Description:

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

Lentiginosine is a selective and powerful inhibitor of amyloglucosidases.

Chemical Structure

Lentiginosine
Lentiginosine
CAS#125279-72-3

Theoretical Analysis

MedKoo Cat#: 598572

Name: Lentiginosine

CAS#: 125279-72-3

Chemical Formula: C8H15NO2

Exact Mass: 157.1103

Molecular Weight: 157.21

Elemental Analysis: C, 61.12; H, 9.62; N, 8.91; O, 20.35

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Lentiginosine;
IUPAC/Chemical Name
(1S,2S,8aS)-octahydroindolizine-1,2-diol
InChi Key
SQECYPINZNWUTE-FXQIFTODSA-N
InChi Code
InChI=1S/C8H15NO2/c10-7-5-9-4-2-1-3-6(9)8(7)11/h6-8,10-11H,1-5H2/t6-,7-,8-/m0/s1
SMILES Code
O[C@@H]1[C@@H](O)CN2CCCC[C@@]12[H]
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
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Lentiginosine is a selective and powerful inhibitor of amyloglucosidases.
In vitro activity:
The results showed that D(-)lentiginosine increased caspase 9 expression at 18 h in all the cell lines from 1.5-3.1 folds. U937Bcl-2 transfectants, highly expressing Bcl-2, were reluctant to undergo apoptosis even following treatment with 500 μM D(-)lentiginosine, whereas apoptosis by D(-)lentiginosine was induced also in U937 cells, naturally deficient in P53. Reference: Cell Death Dis. 2012 Jul 26;3(7):e358. https://pubmed.ncbi.nlm.nih.gov/22833097/
In vivo activity:
TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 157.21 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:
1. Minutolo A, Grelli S, Marino-Merlo F, Cordero FM, Brandi A, Macchi B, Mastino A. D(-)lentiginosine-induced apoptosis involves the intrinsic pathway and is p53-independent. Cell Death Dis. 2012 Jul 26;3(7):e358. doi: 10.1038/cddis.2012.97. PMID: 22833097; PMCID: PMC3406596. 2. Macchi B, Minutolo A, Grelli S, Cardona F, Cordero FM, Mastino A, Brandi A. The novel proapoptotic activity of nonnatural enantiomer of Lentiginosine. Glycobiology. 2010 May;20(5):500-6. doi: 10.1093/glycob/cwp202. Epub 2010 Jan 5. PMID: 20053629.
In vitro protocol:
1. Minutolo A, Grelli S, Marino-Merlo F, Cordero FM, Brandi A, Macchi B, Mastino A. D(-)lentiginosine-induced apoptosis involves the intrinsic pathway and is p53-independent. Cell Death Dis. 2012 Jul 26;3(7):e358. doi: 10.1038/cddis.2012.97. PMID: 22833097; PMCID: PMC3406596. 2. Macchi B, Minutolo A, Grelli S, Cardona F, Cordero FM, Mastino A, Brandi A. The novel proapoptotic activity of nonnatural enantiomer of Lentiginosine. Glycobiology. 2010 May;20(5):500-6. doi: 10.1093/glycob/cwp202. Epub 2010 Jan 5. PMID: 20053629.
In vivo protocol:
TBD
1: Cordero FM, Giomi D, Brandi A. Recent syntheses and biological activity of lentiginosine and its analogues. Curr Top Med Chem. 2014;14(10):1294-307. Review. PubMed PMID: 24758428. 2: Cordero FM, Vurchio C, Brandi A. A Stereoselective Synthesis of Lentiginosine. J Org Chem. 2016 Feb 19;81(4):1661-4. doi: 10.1021/acs.joc.5b02804. Epub 2016 Feb 3. PubMed PMID: 26800332. 3: Dal Piaz F, Vassallo A, Chini MG, Cordero FM, Cardona F, Pisano C, Bifulco G, De Tommasi N, Brandi A. Natural iminosugar (+)-lentiginosine inhibits ATPase and chaperone activity of hsp90. PLoS One. 2012;7(8):e43316. doi: 10.1371/journal.pone.0043316. Epub 2012 Aug 20. PubMed PMID: 22916240; PubMed Central PMCID: PMC3423353. 4: Kauloorkar SV, Jha V, Jogdand G, Kumar P. A stereoselective approach to indolizidine and pyrrolizidine alkaloids: total synthesis of (-)-lentiginosine, (-)-epi-lentiginosine and (-)-dihydroxypyrrolizidine. Org Biomol Chem. 2014 Jul 7;12(25):4454-60. doi: 10.1039/c4ob00461b. PubMed PMID: 24850083. 5: Minutolo A, Grelli S, Marino-Merlo F, Cordero FM, Brandi A, Macchi B, Mastino A. D(-)lentiginosine-induced apoptosis involves the intrinsic pathway and is p53-independent. Cell Death Dis. 2012 Jul 26;3:e358. doi: 10.1038/cddis.2012.97. PubMed PMID: 22833097; PubMed Central PMCID: PMC3406596. 6: Macchi B, Minutolo A, Grelli S, Cardona F, Cordero FM, Mastino A, Brandi A. The novel proapoptotic activity of nonnatural enantiomer of Lentiginosine. Glycobiology. 2010 May;20(5):500-6. doi: 10.1093/glycob/cwp202. Epub 2010 Jan 5. PubMed PMID: 20053629. 7: Chandra KL, Chandrasekhar M, Singh VK. Total synthesis of (-)- and (+)-lentiginosine. J Org Chem. 2002 Jun 28;67(13):4630-3. PubMed PMID: 12076173. 8: Cardona F, Moreno G, Guarna F, Vogel P, Schuetz C, Merino P, Goti A. New concise total synthesis of (+)-lentiginosine and some structural analogues. J Org Chem. 2005 Aug 5;70(16):6552-5. PubMed PMID: 16050731. 9: Pastuszak I, Molyneux RJ, James LF, Elbein AD. Lentiginosine, a dihydroxyindolizidine alkaloid that inhibits amyloglucosidase. Biochemistry. 1990 Feb 20;29(7):1886-91. PubMed PMID: 2331469. 10: Ayad T, Génisson Y, Baltas M, Gorrichon L. Concise asymmetric syntheses of (-)-lentiginosine and of its pyrrolizidinic analogue. Chem Commun (Camb). 2003 Mar 7;(5):582-3. PubMed PMID: 12669835. 11: Rasmussen MO, Delair P, Greene AE. Enantiocontrolled preparation of indolizidines: synthesis of (-)-2-epilentiginosine and (+)-lentiginosine. J Org Chem. 2001 Aug 10;66(16):5438-43. PubMed PMID: 11485467. 12: Azzouz R, Fruit C, Bischoff L, Marsais F. A concise synthesis of lentiginosine derivatives using a pyridinium formation via the Mitsunobu reaction. J Org Chem. 2008 Feb 1;73(3):1154-7. doi: 10.1021/jo702141b. Epub 2008 Jan 8. PubMed PMID: 18179231. 13: Ayad T, Génisson Y, Baltas M. Asymmetric syntheses of (-)-lentiginosine and an original pyrrolizidinic analogue thereof from a versatile epoxyamine intermediate. Org Biomol Chem. 2005 Jul 21;3(14):2626-31. Epub 2005 Jun 13. PubMed PMID: 15999197. 14: Michael JP. Simple Indolizidine and Quinolizidine Alkaloids. Alkaloids Chem Biol. 2016;75:1-498. doi: 10.1016/bs.alkal.2014.12.001. Epub 2015 Mar 30. Review. PubMed PMID: 26777309. 15: Woźniak Ł, Staszewska-Krajewska O, Michalak M. Diastereoselective synthesis of propargylic N-hydroxylamines via NHC-copper(I) halide-catalyzed reaction of terminal alkynes with chiral nitrones on water. Chem Commun (Camb). 2015 Feb 4;51(10):1933-6. doi: 10.1039/c4cc08742a. PubMed PMID: 25531810. 16: Kim IS, Zee OP, Jung YH. Regioselective and diastereoselective amination of polybenzyl ethers using chlorosulfonyl isocyanate: total syntheses of 1,4-dideoxy-1,4-imino-D-arabinitol and (-)-lentiginosine. Org Lett. 2006 Aug 31;8(18):4101-4. PubMed PMID: 16928084. 17: Angle SR, Bensa D, Belanger DS. New access to indolizidine and pyrrolizidine alkaloids from an enantiopure proline: total syntheses of (-)-lentiginosine and (1R,2R,7aR)-dihydroxypyrrolizidine. J Org Chem. 2007 Jul 20;72(15):5592-7. Epub 2007 Jun 28. PubMed PMID: 17602588. 18: Ajish Kumar KS, Chaudhari VD, Dhavale DD. Efficient synthesis of (+)-1,8,8a-tri-epi-swainsonine, (+)-1,2-di-epi-lentiginosine, (+)-9a-epi-homocastanospermine and (-)-9-deoxy-9a-epi-homocastanospermine from a D-glucose-derived aziridine carboxylate, and study of their glycosidase inhibitory activities. Org Biomol Chem. 2008 Feb 21;6(4):703-11. doi: 10.1039/b712753g. Epub 2008 Jan 3. PubMed PMID: 18264570. 19: Kumar NS, Kuntz DA, Wen X, Pinto BM, Rose DR. Binding of sulfonium-ion analogues of di-epi-swainsonine and 8-epi-lentiginosine to Drosophila Golgi alpha-mannosidase II: the role of water in inhibitor binding. Proteins. 2008 May 15;71(3):1484-96. PubMed PMID: 18076078. 20: Ichikawa Y, Ito T, Isobe M. Stereoselective allyl amine synthesis through enantioselective addition of diethylzinc and [1,3]-chirality transfer: synthesis of lentiginosine and polyoxamic acid derivative. Chemistry. 2005 Mar 4;11(6):1949-57. PubMed PMID: 15672433.