MedKoo Cat#: 208258 | Name: Gnidimacrin

Description:

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

Gnidimacrin activated HIV-1 replication and killed persistently-infected cells at picomolar concentrations. In addition to its potential to purge HIV-1 from latently infected cells, gnidimacrin potently inhibited a panel of HIV-1 R5 virus infection of peripheral blood mononuclear cells (PBMCs) at an average concentration lower than 10 pM. These results suggest that gnidimacrin could activate latent HIV-1, specifically kill HIV-1 persistently infected cells, and inhibit R5 viruses at picomolar concentrations

Chemical Structure

Gnidimacrin
Gnidimacrin
CAS#60796-70-5

Theoretical Analysis

MedKoo Cat#: 208258

Name: Gnidimacrin

CAS#: 60796-70-5

Chemical Formula: C44H54O12

Exact Mass: 774.3615

Molecular Weight: 774.90

Elemental Analysis: C, 68.20; H, 7.02; O, 24.78

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Gnidi-macrin, gnidimacrin
IUPAC/Chemical Name
Chemical Name: [(1R,2S,4R,5R,6S,7S,9R,10S,11S,12S,13S,14S,15R,22R,23S,25R)-12-Benzoyloxy-10,11,22-trihydroxy-9-(hydroxymethyl)-13,15-dimethyl-4-prop-1-en-2-yl-8,24,26,27-tetraoxaheptacyclo[12.10.1.14,23.15,23.01,6.07,9.011,25]heptacosan-2-yl]methyl benzoate
InChi Key
SSXCVTWCXHGTLK-VFZTWJSWSA-N
InChi Code
InChI=1S/C44H54O12/c1-24(2)40-21-29(22-51-37(47)27-16-10-7-11-17-27)43-32-35(40)54-44(55-40,56-43)30(46)20-14-6-5-9-15-25(3)31-26(4)34(52-38(48)28-18-12-8-13-19-28)42(50,33(31)43)39(49)41(23-45)36(32)53-41/h7-8,10-13,16-19,25-26,29-36,39,45-46,49-50H,1,5-6,9,14-15,20-23H2,2-4H3/t25-,26+,29+,30-,31+,32-,33-,34+,35-,36+,39-,40-,41+,42-,43-,44-/m1/s1
SMILES Code
O=C(OC[C@H]1[C@@]2([C@]34[H])O[C@](O5)(O6)[C@H](O)CCCCCC[C@@H](C)[C@@]3([H])[C@H](C)[C@H](OC(C7=CC=CC=C7)=O)[C@@]4(O)[C@H](O)[C@@]8(CO)O[C@@]8([H])[C@@]2([H])[C@]5([H])[C@]6(C(C)=C)C1)C9=CC=CC=C9
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 774.90 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
1: Otsuki K, Li W, Asada Y, Chen CH, Lee KH, Koike K. Daphneodorins A-C, Anti- HIV Gnidimacrin Related Macrocyclic Daphnane Orthoesters from Daphne odora. Org Lett. 2020 Jan 3;22(1):11-15. doi: 10.1021/acs.orglett.9b03539. Epub 2019 Nov 4. PMID: 31680527; PMCID: PMC7437546. 2: Liu Q, Cheng YY, Li W, Huang L, Asada Y, Hsieh MT, Morris-Natschke SL, Chen CH, Koike K, Lee KH. Synthesis and Structure-Activity Relationship Correlations of Gnidimacrin Derivatives as Potent HIV-1 Inhibitors and HIV Latency Reversing Agents. J Med Chem. 2019 Aug 8;62(15):6958-6971. doi: 10.1021/acs.jmedchem.9b00339. Epub 2019 Jul 25. PMID: 31343875; PMCID: PMC7442216. 3: Huang L, Ho P, Yu J, Zhu L, Lee KH, Chen CH. Picomolar dichotomous activity of gnidimacrin against HIV-1. PLoS One. 2011;6(10):e26677. doi: 10.1371/journal.pone.0026677. Epub 2011 Oct 24. PMID: 22039528; PMCID: PMC3200356. 4: Lai W, Huang L, Zhu L, Ferrari G, Chan C, Li W, Lee KH, Chen CH. Gnidimacrin, a Potent Anti-HIV Diterpene, Can Eliminate Latent HIV-1 Ex Vivo by Activation of Protein Kinase C β. J Med Chem. 2015 Nov 12;58(21):8638-46. doi: 10.1021/acs.jmedchem.5b01233. Epub 2015 Nov 3. PMID: 26509731; PMCID: PMC4767159. 5: Huang L, Lai WH, Zhu L, Li W, Wei L, Lee KH, Xie L, Chen CH. Elimination of HIV-1 Latently Infected Cells by Gnidimacrin and a Selective HDAC Inhibitor. ACS Med Chem Lett. 2018 Feb 6;9(3):268-273. doi: 10.1021/acsmedchemlett.8b00012. PMID: 29541372; PMCID: PMC5846048. 6: Yoshida M, Yokokura H, Hidaka H, Ikekawa T, Saijo N. Mechanism of antitumor action of PKC activator, gnidimacrin. Int J Cancer. 1998 Jul 17;77(2):243-50. doi: 10.1002/(sici)1097-0215(19980717)77:2<243::aid-ijc13>3.0.co;2-c. PMID: 9650560. 7: Yoshida M, Feng W, Nishio K, Takahashi M, Heike Y, Saijo N, Wakasugi H, Ikekawa T. Antitumor action of the PKC activator gnidimacrin through cdk2 inhibition. Int J Cancer. 2001 Nov 1;94(3):348-52. doi: 10.1002/ijc.1476. PMID: 11745413. 8: Yoshida M, Matsui Y, Iizuka A, Ikarashi Y. G2-phase arrest through p21(WAF1 / Cip1) induction and cdc2 repression by gnidimacrin in human hepatoma HLE cells. Anticancer Res. 2009 Apr;29(4):1349-54. PMID: 19414386. 9: Yoshida M, Heike Y, Ohno S, Ikekawa T, Wakasugi H. Involvement of PKC betaII in anti-proliferating action of a new antitumor compound gnidimacrin. Int J Cancer. 2003 Jul 10;105(5):601-6. doi: 10.1002/ijc.11157. PMID: 12740906. 10: Yoshida M, Feng W, Saijo N, Ikekawa T. Antitumor activity of daphnane-type diterpene gnidimacrin isolated from Stellera chamaejasme L. Int J Cancer. 1996 Apr 10;66(2):268-73. doi: 10.1002/(SICI)1097-0215(19960410)66:2<268::AID- IJC22>3.0.CO;2-7. PMID: 8603823.