207395-85-5
Chemical Structure
L 377202
- CAS No.: 207395-85-5
- Formula:C65H89N9O25
- Molecular Weight:1396.45
IUPAC Name: 5-((2S,4R)-2-(((2S,5S,8S,11S,14S,17S)-11-(3-amino-3-oxopropyl)-8-cyclohexyl-17-(((2S,3S,4S,6R)-3-hydroxy-2-methyl-6-(((1S,3S)-3,5,12-trihydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl)oxy)tetrahydro-2H-pyran-4-yl)carbamoyl)-5,14-bis(hydroxymethyl)-19-methyl-3,6,9,12,15-pentaoxo-4,7,10,13,16-pentaazaicosan-2-yl)carbamoyl)-4-hydroxypyrrolidin-1-yl)-5-oxopentanoic acid
InChIKey: CZXGBIFEWYVYJY-NPLULESDSA-N
SMILES: OC1=C2C([C@H](C[C@@](C(CO)=O)(O)C2)O[C@@]3([H])C[C@@H]([C@H](O)[C@H](C)O3)NC([C@H](CC(C)C)NC([C@H](CO)NC([C@H](CCC(N)=O)NC([C@H](C4CCCCC4)NC([C@H](CO)NC([C@H](C)NC([C@H]5N(C[C@H](O)C5)C(CCCC(O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=C(O)C6=C1C(C7=CC=CC(OC)=C7C6=O)=O
Biological Activity: L 377202 is a conjugate of Doxorubicin (HY-15142A) and a PSA substrate peptide. L 377202 is cleaved at its peptide precursor portion by prostate-specific antigen PSA, releasing N-(L-leucyl) doxorubicin and cytotoxic Doxorubicin. L 377202 is internalized via endocytosis and endosomal escape. L 377202 can be used for research on prostate cancer[1][2][3][4][5][6][7].
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L 377202 | L 377202 is a conjugate of Doxorubicin (HY-15142A) and a PSA substrate peptide. L 377202 is cleaved at its peptide precursor portion by prostate-specific antigen PSA, releasing N-(L-leucyl) doxorubicin and cytotoxic Doxorubicin. L 377202 is internalized via endocytosis and endosomal escape. L 377202 can be used for research on prostate cancer. | |||||||||||||||||||||
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References
- [1]. Graeser R, et al. Synthesis and biological evaluation of an albumin-binding prodrug of doxorubicin that is cleaved by prostate-specific antigen (PSA) in a PSA-positive orthotopic prostate carcinoma model (LNCaP). International journal of cancer. 2008 Mar 01;122(5):1145-54. [Content Brief]
- [2]. Aloysius H. Design and synthesis of prostate specific antigen-activated prodrugs[M]. Rutgers The State University of New Jersey, School of Graduate Studies, 2014.
- [3]. Sha J. Design, synthesis and evaluation of doxorubicin based anti-cancer drug conjugates[D]. Department of Medicinal Chemistry, University of Utah, 2006.
- [4]. Denny WA, et al. Tumor-activated prodrugs--a new approach to cancer therapy. Cancer investigation. 2004;22(4):604-19. [Content Brief]
- [5]. Gill J H, et al. Development of Tumour-Selective and Endoprotease-Activated Anticancer[J]. The Cancer Degradome, 853.
- [6]. Pereira S, et al. Encapsulation of doxorubicin prodrug in heat-triggered liposomes overcomes off-target activation for advanced prostate cancer therapy. Acta biomaterialia. 2022 Mar 01;140:530-546. [Content Brief]
- [7]. Jiang Y. Novel cyclophosphamide prodrugs for site-specific activation in tumor cells[M]. Rutgers The State University of New Jersey, School of Graduate Studies, 2005.
