Related CAS #
81531-57-9 (cation)
105118-14-7 (chloride)
81531-58-0 (acetate)
157000-76-5 (chloride HCl)
958863-79-1 (mesylate)
Synonym
Datelliptium chloride; SR 95156A; SR95156A; SR-95156A; SR 95156; SR95156; SR-95156; NSC 311152; NSC-311152; NSC311152;
IUPAC/Chemical Name
2-(2-(Diethylamino)ethyl)-9-hydroxy-5,11-dimethyl-6H-pyrido(4,3-b)carbazolium chloride
InChi Key
UCICRVXYPSKKJK-UHFFFAOYSA-N
InChi Code
InChI=1S/C23H27N3O.ClH/c1-5-25(6-2)11-12-26-10-9-18-16(4)23-22(15(3)20(18)14-26)19-13-17(27)7-8-21(19)24-23;/h7-10,13-14,27H,5-6,11-12H2,1-4H3;1H
SMILES Code
CC1=C2C(NC3=C2C=C(O)C=C3)=C(C)C4=CC=[N+](CCN(CC)CC)C=C41.[Cl-]
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 and water
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
2934.99.9001
Biological target:
Datelliptium chloride has been shown to inhibit tumor growth by inhibiting cell growth and inducing apoptosis. Datelliptium chloride interferes with the absorption process of glucose in the body, leading to increased serum bilirubin and decreased serum glucose levels.
In vitro activity:
Datelliptium (35 mg/kg i.p. days 1 and 8) was active against 2 of 6 small cell lung cancer lines.
Reference: Cancer Res. 1992 Nov 1;52(21):5940-7. https://pubmed.ncbi.nlm.nih.gov/1394220/
In vivo activity:
Datelliptium exerts antitumor activity against medullary thyroid carcinoma (MTC) cells by reducing the EMT program, migratory ability, and self-renewal capacity of TT cells, thus preventing invasive and metastatic behavior of MTC. Datelliptium inhibited approximately 75% of MTC xenograft growth with minimal systemic toxicity.
Reference: Cancers (Basel). 2021 Jun 30;13(13):3288. https://pubmed.ncbi.nlm.nih.gov/34209165/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
5.0 |
12.56 |
| Water |
41.7 |
104.71 |
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
397.95
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. Boven E, Winograd B, Berger DP, Dumont MP, Braakhuis BJ, Fodstad O, Langdon S, Fiebig HH. Phase II preclinical drug screening in human tumor xenografts: a first European multicenter collaborative study. Cancer Res. 1992 Nov 1;52(21):5940-7. PMID: 1394220.
2. Donato MT, Goethals F, Gómez-Lechón MJ, Deboyser D, De Coster I, Roberfroid M, Castell JV. Toxicity of the antitumoral drug datelliptium in hepatic cells: Use of models in vitro for the prediction of toxicity in vivo. Toxicol In Vitro. 1992 Jul;6(4):295-302. doi: 10.1016/0887-2333(92)90019-n. PMID: 20732126.
3. Alqahtani T, Alswied A, Sun D. Selective Antitumor Activity of Datelliptium toward Medullary Thyroid Carcinoma by Downregulating RET Transcriptional Activity. Cancers (Basel). 2021 Jun 30;13(13):3288. doi: 10.3390/cancers13133288. PMID: 34209165; PMCID: PMC8267783.
In vitro protocol:
1. Boven E, Winograd B, Berger DP, Dumont MP, Braakhuis BJ, Fodstad O, Langdon S, Fiebig HH. Phase II preclinical drug screening in human tumor xenografts: a first European multicenter collaborative study. Cancer Res. 1992 Nov 1;52(21):5940-7. PMID: 1394220.
2. Donato MT, Goethals F, Gómez-Lechón MJ, Deboyser D, De Coster I, Roberfroid M, Castell JV. Toxicity of the antitumoral drug datelliptium in hepatic cells: Use of models in vitro for the prediction of toxicity in vivo. Toxicol In Vitro. 1992 Jul;6(4):295-302. doi: 10.1016/0887-2333(92)90019-n. PMID: 20732126.
In vivo protocol:
1. Alqahtani T, Alswied A, Sun D. Selective Antitumor Activity of Datelliptium toward Medullary Thyroid Carcinoma by Downregulating RET Transcriptional Activity. Cancers (Basel). 2021 Jun 30;13(13):3288. doi: 10.3390/cancers13133288. PMID: 34209165; PMCID: PMC8267783.
1: Kriaa W, Sghaier-Hammami B, Masmoudi-Allouche F, Benjemaa-Masmoudi R, Drira N.
The date palm (Phoenix dactylifera L.) micropropagation using completely mature
female flowers. C R Biol. 2012 Mar;335(3):194-204. doi:
10.1016/j.crvi.2012.01.005. Epub 2012 Mar 15. PubMed PMID: 22464427.
2: Djuric Z, Everett CK, Valeriote FA. DNA damage and cytotoxicity in L1210 cells
by ellipticine and a structural analogue,
N-2-(diethylaminoethyl)-9-hydroxyellipticinium chloride. Cancer Res. 1992 Mar
15;52(6):1515-9. PubMed PMID: 1540960.
3: Khayat D, Borel C, Azab M, Paraisot D, Malaurie E, Bouloux C, Weil M. Phase I
study of Datelliptium chloride, hydrochloride given by 24-h continuous
intravenous infusion. Cancer Chemother Pharmacol. 1992;30(3):226-8. PubMed PMID:
1628372.
4: Mucci-LoRusso P, Polin L, Biernat LA, Valeriote FA, Corbett TH. Activity of
datelliptium acetate (NSC 311152; SR 95156A) against solid tumors of mice. Invest
New Drugs. 1990 Aug;8(3):253-61. PubMed PMID: 2177044.
5: Multon E, Riou JF, LeFevre D, Ahomadegbe JC, Riou G. Topoisomerase II-mediated
DNA cleavage activity induced by ellipticines on the human tumor cell line N417.
Biochem Pharmacol. 1989 Jul 1;38(13):2077-86. PubMed PMID: 2544183.
6: Auclair C, Pierre A, Voisin E, Pepin O, Cros S, Colas C, Saucier JM,
Verschuere B, Gros P, Paoletti C. Physicochemical and pharmacological properties
of the antitumor ellipticine derivative 2-(diethylamino-2-ethyl)9-hydroxy
ellipticinium-chloride, HCl. Cancer Res. 1987 Dec 1;47(23):6254-61. PubMed PMID:
3677074.
