9-Aminocamptothecin CAS 91421-43-1

Introduction：Basic information about 9-Aminocamptothecin CAS 91421-43-1, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

9-Aminocamptothecin Basic information

• Product Name: 9-Aminocamptothecin
• Synonyms: 4':6,7)indolizino(1,2-B)quinoline-3,14(4H,12H)-dione;4':6,7)indolizino(1,2-B)quinoline-3,14(4H,12H)-dione, 10-amino-4-ethyl-4-hydroxy-, (S)-;CAMPTOTHECIN, 9-AMINO-(RG);(S)-10-AMino-4-ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione;(S)-10-Amino-4-ethyl-4-hydroxy-1H-pyrano[3',4':6,7]-indolizino[1,2-b]quinoline-3,14(4H,12H)-di;CAMPTOTHECIN, 9-AMINO-;AMinocaMptothecin;9-AMINO-CAMPTOTHECIN
• CAS: 91421-43-1
• MF: C20H17N3O4
• MW: 363.37
• Product Categories: Pharmaceutical Raw Materials;Alkaloids;Natural Anti-cancer Medical Materials and It's Derivatives
• Mol File: 91421-43-1.mol

9-Aminocamptothecin Chemical Properties

• Melting point: 142.0-145.0 °C
• Boiling point: 819.6±65.0 °C(Predicted)
• density: 1.55±0.1 g/cm3(Predicted)
• storage temp.: 2-8°C(protect from light)
• solubility: ≤1mg/ml in DMSO;1mg/ml in dimethyl formamide
• pka: 11.23±0.20(Predicted)
• form: powder to crystal
• color: Light yellow to Yellow to Orange
• Merck: 14,431
• InChI: InChI=1S/C20H17N3O4/c1-2-20(26)13-7-16-17-10(6-11-14(21)4-3-5-15(11)22-17)8-23(16)18(24)12(13)9-27-19(20)25/h3-7,26H,2,8-9,21H2,1H3/t20-/m0/s1
• InChIKey: FUXVKZWTXQUGMW-FQEVSTJZSA-N
• SMILES: N1C2C(=C(N)C=CC=2)C=C2CN3C(C=12)=CC1[C@](CC)(O)C(=O)OCC=1C3=O
• CAS DataBase Reference: 91421-43-1(CAS DataBase Reference)

Safety Information

• RTECS: UQ0490500
• HS Code: 29349990

9-Aminocamptothecin Usage And Synthesis

Chemical Properties

Yellow crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO. It is derived from the fruit of Camptotheca acuminata Decne., a plant of the Davidiaceae family.

Uses

9-Amino Camptothecin is a derivative of Camptothecin (C175150), as antitumor agent.

Definition

ChEBI: 9-Aminocamptothecin is a pyranoindolizinoquinoline.

Biological Activity

9-amino camptothecin is a topoisomerase i inhibitor [1][2].dna topoisomerases relax dna torsional strain generated during replication, transcription, recombination, repair, and chromosome condensation. the relaxation of dna supercoiling by topoisomerase i is enabled by a mechanism of controlled rotation around a transient dna single-strand break. camptothecin (cpt) is isolated from the bark of the chinese tree camptotheca accuminata [3].9-amino camptothecin, a water-soluble camptothecin analogue, is a topoisomerase i inhibitor. in human ht-29 colon adenocarcinoma, 9-amino camptothecin (9-ac) exhibited cytotoxicity with ic50 value of 19 nm. 9-ac also induced dna damage in whole cells and nuclei at a concenstration of 85 nm and 21 nm, respectively [1].9-amino camptothecin had greater activity than camptothecin against human tumour xenografts, including lewis lung carcinoma and b16 melanoma. 9-ac had entered phase ii trials. in patients with advanced solid tumours, 9-amino camptothecin exhibited anti-tumor activity [1][2].

in vivo

9-Aminocamptothecin (9-Amino-CPT) inhibits tumor growth at the lowest oral dose (0.35 mg/kg/day), whereas higher oral doses (0.75 and 1 mg/kg/day) and s.c. administration (4 mg/kg/week) causes tumor regression. 9-Aminocamptothecin is well tolerated at all doses, with no toxic death or weight loss of more than 10% observed in any group^[2]. 9-Aminocamptothecin induces complete remissions in 55 % of SCID mice engrafted with human myeloid leukemia. The oral and intravenous routes are equally effective. The results with this pre-clinical model support the evaluation of 9-Aminocamptothecin as antileukemic agent in a phase I trial in patients with AML^[3].

IC 50

Topoisomerase I

references

[1]. rothenberg, m.l. topoisomerase i inhibitors: review and update. annals of oncology 8(9), 837-855 (1997).
[2]. dancey j, eisenhauer ea. current perspectives on camptothecins in cancer treatment. br j cancer. 1996 aug;74(3):327-38.
[3]. drwal mn1, agama k, wakelin lp, et al. exploring dna topoisomerase i ligand space in search of novel anticancer agents. plos one. 2011;6(9):e25150.