(-)-Cryptopleurine (Synonyms: (R)-Cryptopleurine; NSC 19912)

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(–)-Cryptopleurine is an alkaloid that has been found in Lauraceae and has diverse biological activities. It inhibits the growth of human A375 melanoma, A431 epidermoid carcinoma, A549 lung, MES-SA uterine sarcoma, and MCF-7 breast cancer cells (IC₅₀=3 nM for all).2 (–)-Cryptopleurine inhibits hypoxia-induced gene expression in a hypoxia response element (HRE) reporter assay (IC₅₀=8.7 nM).3 (–)-Cryptopleurine (500 μg/mL) prevents lesion formation in tobacco (N. tabacum) plants infected with tobacco mosaic virus (TMV). It also inhibits protein synthesis by yeast and mammalian ribosomes.

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(-)-Cryptopleurine Chemical Structure

CAS No. : 482-22-4

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Description

Cellular Effect

Cell Line	Type	Value	Description	References
A-375	IC₅₀	1.2 nM Compound: (-)-1	Antiproliferative activity against human A375 cells after 72 hrs by ATPlite assay Antiproliferative activity against human A375 cells after 72 hrs by ATPlite assay	[PMID: 25499434]
A549	GI₅₀	< 0.001 μM Compound: 36	Antiproliferative activity against human A549 cells after 72 hrs by MTT assay Antiproliferative activity against human A549 cells after 72 hrs by MTT assay	[PMID: 22417638]
A549	IC₅₀	0.94 nM Compound: 2	Cytotoxicity against human A549 cells assessed as growth inhibition after 72 hrs by SRB assay Cytotoxicity against human A549 cells assessed as growth inhibition after 72 hrs by SRB assay	[PMID: 26393416]
A549	GI₅₀	1.38 nM Compound: R-cryptopleurine	Anticancer activity against human A549 cells after 72 hrs by sulforhodamine B assay Anticancer activity against human A549 cells after 72 hrs by sulforhodamine B assay	[PMID: 21668000]
A549	IC₅₀	1.38 nM Compound: cryptopleurine	Cytotoxicity against human A549 cells after 2 hrs by methylene blue staining-based spectrophotometric analysis Cytotoxicity against human A549 cells after 2 hrs by methylene blue staining-based spectrophotometric analysis	[PMID: 22823514]
A549	IC₅₀	1.9 nM Compound: (-)-1	Antiproliferative activity against human A549 cells after 72 hrs by ATPlite assay Antiproliferative activity against human A549 cells after 72 hrs by ATPlite assay	[PMID: 25499434]
A549	IC₅₀	1.9 nM Compound: cryptopleurine	Cytotoxicity against human A549 cells assessed as cell viability after 48 hrs by SRB assay Cytotoxicity against human A549 cells assessed as cell viability after 48 hrs by SRB assay	[PMID: 22823514]
AGS	IC₅₀	8.7 nM Compound: 1	Inhibition of hypoxia-induced HIF1 activation in human AGS cells after 16 hrs by pGL3-HRE-luciferase reporter gene assay Inhibition of hypoxia-induced HIF1 activation in human AGS cells after 16 hrs by pGL3-HRE-luciferase reporter gene assay	[PMID: 16872154]
CAKI-1	IC₅₀	0.86 nM Compound: 2	Cytotoxicity against human Caki1 cells assessed as growth inhibition after 72 hrs by SRB assay Cytotoxicity against human Caki1 cells assessed as growth inhibition after 72 hrs by SRB assay	[PMID: 26393416]
CL1-0	IC₅₀	5 nM Compound: cryptopleurine	Cytotoxicity against human CL1-0 cells assessed as cell viability after 48 hrs by SRB assay Cytotoxicity against human CL1-0 cells assessed as cell viability after 48 hrs by SRB assay	[PMID: 22823514]
DU-145	GI₅₀	1.59 nM Compound: R-cryptopleurine	Anticancer activity against human DU145 cells after 72 hrs by sulforhodamine B assay Anticancer activity against human DU145 cells after 72 hrs by sulforhodamine B assay	[PMID: 21668000]
DU-145	IC₅₀	1.59 nM Compound: cryptopleurine	Cytotoxicity against human DU145 cells after 2 hrs by methylene blue staining-based spectrophotometric analysis Cytotoxicity against human DU145 cells after 2 hrs by methylene blue staining-based spectrophotometric analysis	[PMID: 22823514]
HCT-116	IC₅₀	0.7 nM Compound: (-)-1	Antiproliferative activity against human HCT116 cells after 72 hrs by ATPlite assay Antiproliferative activity against human HCT116 cells after 72 hrs by ATPlite assay	[PMID: 25499434]
HCT-116	IC₅₀	1.04 nM Compound: 2	Cytotoxicity against human HCT116 cells assessed as growth inhibition after 72 hrs by SRB assay Cytotoxicity against human HCT116 cells assessed as growth inhibition after 72 hrs by SRB assay	[PMID: 26393416]
HCT-8	GI₅₀	1.09 nM Compound: R-cryptopleurine	Anticancer activity against human HCT8 cells after 72 hrs by sulforhodamine B assay Anticancer activity against human HCT8 cells after 72 hrs by sulforhodamine B assay	[PMID: 21668000]
HCT-8	IC₅₀	1.91 nM Compound: cryptopleurine	Cytotoxicity against human HCT8 cells after 2 hrs by methylene blue staining-based spectrophotometric analysis Cytotoxicity against human HCT8 cells after 2 hrs by methylene blue staining-based spectrophotometric analysis	[PMID: 22823514]
HL-60	GI₅₀	< 0.001 μM Compound: 36	Antiproliferative activity against human HL60 cells after 72 hrs by SRB assay Antiproliferative activity against human HL60 cells after 72 hrs by SRB assay	[PMID: 22417638]
KB	GI₅₀	1.51 nM Compound: R-cryptopleurine	Anticancer activity against human KB cells after 72 hrs by sulforhodamine B assay Anticancer activity against human KB cells after 72 hrs by sulforhodamine B assay	[PMID: 21668000]
KB	IC₅₀	1.51 nM Compound: cryptopleurine	Cytotoxicity against human KB cells after 2 hrs by methylene blue staining-based spectrophotometric analysis Cytotoxicity against human KB cells after 2 hrs by methylene blue staining-based spectrophotometric analysis	[PMID: 22823514]
MDA-MB-231	IC₅₀	0.89 nM Compound: 2	Cytotoxicity against human MDA-MB-231 cells assessed as growth inhibition after 72 hrs by SRB assay Cytotoxicity against human MDA-MB-231 cells assessed as growth inhibition after 72 hrs by SRB assay	[PMID: 26393416]
MRC5	IC₅₀	14 nM Compound: cryptopleurine	Cytotoxicity against human MRC5 cells assessed as cell viability after 48 hrs by SRB assay Cytotoxicity against human MRC5 cells assessed as cell viability after 48 hrs by SRB assay	[PMID: 22823514]
NAMALVA	IC₅₀	2.6 nM Compound: (-)-1	Antiproliferative activity against human NAMALWA cells after 72 hrs by ATPlite assay Antiproliferative activity against human NAMALWA cells after 72 hrs by ATPlite assay	[PMID: 25499434]
PC-3	IC₅₀	2.55 nM Compound: 2	Cytotoxicity against human PC3 cells assessed as growth inhibition after 72 hrs by SRB assay Cytotoxicity against human PC3 cells assessed as growth inhibition after 72 hrs by SRB assay	[PMID: 26393416]
PC-9	IC₅₀	5.5 nM Compound: cryptopleurine	Cytotoxicity against human PC9 cells assessed as cell viability after 48 hrs by SRB assay Cytotoxicity against human PC9 cells assessed as cell viability after 48 hrs by SRB assay	[PMID: 22823514]
SK-HEP1	IC₅₀	0.83 nM Compound: 2	Cytotoxicity against human SKHEP1 cells assessed as growth inhibition after 72 hrs by SRB assay Cytotoxicity against human SKHEP1 cells assessed as growth inhibition after 72 hrs by SRB assay	[PMID: 26393416]
SNU-638	IC₅₀	1.26 nM Compound: 2	Cytotoxicity against human SNU638 cells assessed as growth inhibition after 72 hrs by SRB assay Cytotoxicity against human SNU638 cells assessed as growth inhibition after 72 hrs by SRB assay	[PMID: 26393416]

Molecular Weight

377.48

Formula

C₂₄H₂₇NO₃

CAS No.

482-22-4

SMILES

COC1=CC2=C3C=C(C(OC)=CC3=C4C[C@]5(CCCCN5CC4=C2C=C1)[H])OC

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

Please store the product under the recommended conditions in the Certificate of Analysis.

Purity & Documentation

Handling Instructions (2659 KB)

References

[1]. Cai, et al. Phenanthroquinolizidine alkaloids from the roots of Boehmeria pannosa potently inhibit hypoxia-inducible factor-1 in AGS human gastric cancer cells. J. Nat. Prod. 69(7), 1095-1097 (2006).

(-)-Cryptopleurine Related Classifications

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The dilution calculator equation

Concentration _(start) × Volume _(start) = Concentration _(final) × Volume _(final)

This equation is commonly abbreviated as: C₁V₁ = C₂V₂

Concentration _(start)	×	Volume _(start)	=	Concentration _(final)	×	Volume _(final)
	×		=		×
C1		V1		C2		V2

Help & FAQs

Do most proteins show cross-species activity?
Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

Keywords:

(-)-Cryptopleurine482-22-4(R)-Cryptopleurine NSC 19912NSC19912NSC 19912NSC-19912OthersInhibitorinhibitorinhibit

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