gamma-Lumicolchicine

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

MedKoo CAT#: 527978

CAS#: 6901-14-0

Description: gamma-Lumicolchicine is three, alpha, beta, and gamma isomers of ultraviolet degradation products of colchicine that lack many of the physiological actions of the parent; used as experimental control for colchicine actions.


Chemical Structure

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gamma-Lumicolchicine
CAS# 6901-14-0

Theoretical Analysis

MedKoo Cat#: 527978
Name: gamma-Lumicolchicine
CAS#: 6901-14-0
Chemical Formula: C22H25NO6
Exact Mass: 399.17
Molecular Weight: 399.443
Elemental Analysis: C, 66.15; H, 6.31; N, 3.51; O, 24.03

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: gamma-Lumicolchicine

IUPAC/Chemical Name: (7S-(7alpha,7balpha,10aalpha))-N-(5,6,7,7b,8,10a-Hexahydro-1,2,3,9-tetramethoxy-8-oxobenzo(a)cyclopenta(3,4)cyclobuta(1,2-c)cyclohepten-7-yl)acetamide

InChi Key: VKPVZFOUXUQJMW-LXIYXOSZSA-N

InChi Code: InChI=1S/C22H25NO6/c1-10(24)23-13-7-6-11-8-15(27-3)21(28-4)22(29-5)16(11)17-12-9-14(26-2)20(25)18(12)19(13)17/h8-9,12-13,18H,6-7H2,1-5H3,(H,23,24)/t12-,13-,18-/m0/s1

SMILES Code: CC(N[C@@H]1C([C@]2([H])[C@@]3([H])C=C(OC)C2=O)=C3C4=C(OC)C(OC)=C(OC)C=C4CC1)=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: 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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 399.44 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:
In vitro protocol:
In vivo protocol:

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1: Bondi CD, McKeon RM, Bennett JM, Ignatius PF, Brydon L, Jockers R, Melan MA, Witt-Enderby PA. MT1 melatonin receptor internalization underlies melatonin-induced morphologic changes in Chinese hamster ovary cells and these processes are dependent on Gi proteins, MEK 1/2 and microtubule modulation. J Pineal Res. 2008 Apr;44(3):288-98. doi: 10.1111/j.1600-079X.2007.00525.x. PubMed PMID: 18339124.

2: Cacelli I, D'Auria M, Villani V. Theoretical Study of the Photochemical Isomerization of Colchicine. J Chem Theory Comput. 2007 Mar;3(2):649-56. doi: 10.1021/ct600306t. PubMed PMID: 26637043.

3: Morimoto T, Liu W, Woda C, Carattino MD, Wei Y, Hughey RP, Apodaca G, Satlin LM, Kleyman TR. Mechanism underlying flow stimulation of sodium absorption in the mammalian collecting duct. Am J Physiol Renal Physiol. 2006 Sep;291(3):F663-9. Epub 2006 Apr 25. PubMed PMID: 16638910.

4: Alali FQ, El-Elimat T, Li C, Qandil A, Alkofahi A, Tawaha K, Burgess JP, Nakanishi Y, Kroll DJ, Navarro HA, Falkinham JO 3rd, Wani MC, Oberlies NH. New colchicinoids from a native Jordanian meadow saffron, colchicum brachyphyllum: isolation of the first naturally occurring dextrorotatory colchicinoid. J Nat Prod. 2005 Feb;68(2):173-8. PubMed PMID: 15730238.

5: Mottino AD, Crocenzi FA, Pozzi EJ, Veggi LM, Roma MG, Vore M. Role of microtubules in estradiol-17beta-D-glucuronide-induced alteration of canalicular Mrp2 localization and activity. Am J Physiol Gastrointest Liver Physiol. 2005 Feb;288(2):G327-36. Epub 2004 Sep 16. PubMed PMID: 15374814.

6: Riley NE, Bardag-Gorce F, Montgomery RO, Li J, Lungo W, Lue YH, French SW. Microtubules are required for cytokeratin aggresome (Mallory body) formation in hepatocytes: an in vitro study. Exp Mol Pathol. 2003 Apr;74(2):173-9. PubMed PMID: 12710949.

7: Lee CH. Differential regulation of P-glycoprotein genes in primary rat hepatocytes by collagen sandwich and drugs. J Cell Biochem. 2002;86(1):12-20. PubMed PMID: 12112011.

8: Stumptner C, Fuchsbichler A, Lehner M, Zatloukal K, Denk H. Sequence of events in the assembly of Mallory body components in mouse liver: clues to the pathogenesis and significance of Mallory body formation. J Hepatol. 2001 May;34(5):665-75. PubMed PMID: 11434612.

9: Nery AL, Quina FH, Moreira PF Jr, Medeiros CE, Baader WJ, Shimizu K, Catalani LH, Bechara EJ. Does the photochemical conversion of colchicine into lumicolchicines involve triplet transients? A solvent dependence study. Photochem Photobiol. 2001 Mar;73(3):213-8. PubMed PMID: 11281015.

10: Feng G, Kaplowitz N. Colchicine protects mice from the lethal effect of an agonistic anti-Fas antibody. J Clin Invest. 2000 Feb;105(3):329-39. PubMed PMID: 10675359; PubMed Central PMCID: PMC377439.

11: Rogler G, Aschenbrenner E, Gross V, Stange EF, Schölmerich J. Intracellular transport of high-density lipoprotein 3 in intestinal epithelial cells (Caco-2) is tubulin associated. Digestion. 2000;61(1):47-58. PubMed PMID: 10671774.

12: Marinelli RA, Tietz PS, Pham LD, Rueckert L, Agre P, LaRusso NF. Secretin induces the apical insertion of aquaporin-1 water channels in rat cholangiocytes. Am J Physiol. 1999 Jan;276(1 Pt 1):G280-6. PubMed PMID: 9887005.

13: Gröne A, Weckmann MT, Capen CC, Rosol TJ. Regulation of parathyroid hormone-related protein expression in a canine squamous carcinoma cell line by colchicine. Exp Toxicol Pathol. 1998 Sep;50(4-6):365-70. PubMed PMID: 9784008.

14: Saldías F, Lecuona E, Friedman E, Barnard ML, Ridge KM, Sznajder JI. Modulation of lung liquid clearance by isoproterenol in rat lungs. Am J Physiol. 1998 May;274(5 Pt 1):L694-701. PubMed PMID: 9612284.

15: Ikeda T, Sawada N, Satoh M, Mori M. Induction of tyrosine aminotransferase of primary cultured rat hepatocytes depends on the organization of microtubules. J Cell Physiol. 1998 Apr;175(1):41-9. PubMed PMID: 9491779.

16: Weiner JL, Buhler AV, Whatley VJ, Harris RA, Dunwiddie TV. Colchicine is a competitive antagonist at human recombinant gamma-aminobutyric acidA receptors. J Pharmacol Exp Ther. 1998 Jan;284(1):95-102. PubMed PMID: 9435166.

17: Crocenzi FA, Sisti A, Pellegrino JM, Roma MG. Role of bile salts in colchicine-induced hepatotoxicity. Implications for hepatocellular integrity and function. Toxicology. 1997 Aug 15;121(2):127-42. PubMed PMID: 9230445.

18: Pruzanski W, Kennedy BP, van den Bosch H, Stefanski E, Vadas P. Microtubule depolymerization selectively down-regulates the synthesis of proinflammatory secretory nonpancreatic phospholipase A2. Lab Invest. 1997 Feb;76(2):171-8. PubMed PMID: 9042153.

19: Michel MC, Kaldenberg-Stasch S, Wieland T. Cytoskeletal inhibitors impair Ca2+ elevations via neuropeptide Y and other Gi-coupled receptors. Eur J Pharmacol. 1996 Aug 1;309(1):87-94. PubMed PMID: 8864698.

20: Butta N, Martin-Requero A, Urcelay E, Parrilla R, Ayuso MS. Modulation of the hepatic alpha 1-adrenoceptor responsiveness by colchicine: dissociation of free cytosolic Ca(2+)-dependent and independent responses. Br J Pharmacol. 1996 Aug;118(7):1797-805. PubMed PMID: 8842446; PubMed Central PMCID: PMC1909855.