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Fullerene derivatives for biological investigations

Part I. Carboxylic acids

Material purity: 98-99.5+%.
Supplementary spectroscopicdata: data: 1H NMR
Optimal solvents: THF, 1,4-dioxane, CS₂, DMF

Part II. Fullerenols

C60(OH)6 (ca. 80%, 20% - C60(OH)4 Fl-06-1	C60(OH)~24 prepared from C60Br24 Fl-06-2
C60(OH)22-26Fl-06-3	C60(OH)18-22(OK)4Fl-06-3

Solubility info: Fl-06-01, Fl-06-02, and Fl-06-03are soluble in polar organic solvents like DMSO, DMF, 1,4-dioxane, and some alcohols; Fl-06-04 is highly soluble in water
Supplementary data: FT-IR spectra, chemical analysis data

References:

1. "Tissue-protective effects of FULLERENOL C60(OH)24 and aminostine in irradiated rats "
S.Trajkovic et al., - Colloids Surf. B Biointerfaces, 2007 Jan.16, : 17317115

2. "Fullerenes in Biomedicine"
A.Djordjevic et al., - J.Buon., 2006 Oct-Dec., 11(4): 391-404

3."Cytotoxicity of Water-Soluble Fullerene in vascular endothelial cells "
H.Yamawaki, N.Iwai " Am.J.Physiol.Cell Physiol., 2006 Jun., 290(6): C1495-502

4. "Distinct cytotoxic mechanisms of pristine versus Hydroxylated Fullerene "
A.Isakovic et al., - Toxicol. Sci., 2006 May, 91(1): 173-83

5. "Radioprotection by FULLERENOLS of Stylonychia mytilus exposed to gamma-rays "
Q.Zhao et al., - Int.J.Radiat.Biol., 2005 Feb., 81(2): 169-75

6. " Nanotechnology Approaches for the Regeneration and Neuroprotection of the Central Nervous System "
G.A.Silva " Surgical Neurology, 63 (2005), 301-306
www.silva.ucsd.edu/Nanotechnology

7. " Modulating activity of FULLEROL C60(OH)22 on doxorubicin-induced cytotoxicity "
G.Bogdanovic et al., - Toxicol. In Vitro, 2004 Oct.,18(5):629-37

8. " Fullerene Derivatives protect against Oxidative Stress in RAW 264.7 cells and Ischemia-reperfused Lungs "
Y.W.Chen et al., -Am.J.Physiol.Regul.Integr.Comp.Physiol., 2004 Jul., 287(1):R21-6

9. " Antioxidative Activity and Hypothetic Radical Mechanism of FULLERENOLS "
A.Dordevic et al., - J. of Annals of the Academy of Studenica,
10-th Intern. Univ. Sci. Meeting " Nanotechnology in Biomedicine " " Content 7/2004
www.onk.ns.ac.yu/Letopis/Lsa2004/S2-3-3-djordjevic.htm

10." In vivo study of Radioprotective Potential of FULLERENES" S.Dobric et al.,
J. of Annals of the Academy of Studenica, 10-th Intern. Univ. Sci.
Meeting " Nanotechnoligy in Biomedicine " " Content 7/2004
www.onk.ns.ac.yu/Letopis/Lsa2004/S2-3-4-dobric.htm

11."FULLERENOL Inhibit Antitumor Drug-Induced Cytotoxicity
G.Bogdanovic et al., - J. of Annals of the Academy of Studenica,
10-th Intern. Univ. Sci. Meeting "Nanotechnology in Biomedicine" - Content 7/2004
www.onk.ns.ac.yu/Letopis/Lsa2004/S2-3-1-bogdanovic.htm

12. " FULLEROL C60(OH)24 modulates adryamicin induced cytotoxity on Human Breast Cancer Cell Lines "
A.Djordjevic et al., - 1st Intern.Viennes Conference on Clinical Exper.Oncology;
Vienna, Austria (11-13th March), 1999.

A Highly Water-Soluble Metallated Form of FULLERENOLS As Stable Radical Anions

1. " FULLERENOLS Revisited as Stable Radical Anions "
L.O.Husebo et al., - JACS, 2004, 126, 12055-12064
pubs.acs.org/cgi-bin/abstract.cgi/jacsat/2004/126/i38/abs/ja047593o.html

2. " The Differential Cytotoxicity of Water-Soluble Fullerenes "
C.M.Sayes et al., - Nano Letters, 2004, v.4 (10), 1881-1887
pubs.acs.org/cgi-bin/sample.cgi/nalefd/2004/4/10/pdf/nl0489586.pdf

Fullerene Derivatives for Bio-Medicine: Carboxylic Acids

1. " Anti-Inflammatory and Anti-Oxidant Activity of a New Class of Phenyl-Pyrazolone Derivatives "
C.Cusan et al., - Curr.Drug Discov.Technol., 2006 Mar., 3(1): 67-73

2. " Design and Activity of CATIONIC FULLERENE DERIVATIVES as Inhibitors of Acetylcholinesterase "
G.Pastorin et al., - Org.Biomol.Chem., 2006 Jul. 7, 4(13): 2556-62

3. " Pharmacological Studies on FULLERENE C60, a novel carbon allotrope and its Derivatives "
M.Satoh et al., - J.Pharmacol.Sci., 2006, 100(5):513-518

4. " Anti-HIV properties of CATIONIC FULLERENE DERIVATIVES "
S.Marchesan et al., - Bioorg.Med.Chem.Lett., 2005 Aug., 15(15): 3615-3618

5. " Human Immunodeficiency Virus-Reverse Transcriptase Inhibition and Hepatitis C Virus RNA-dependent RNA Polymerase Inhibition Activities of FULLERENE DERIVATIVES "
T.Mashino et al., - Bioorganic & Medicinal Chemistry Letters, Vol.15, Issue 4, 15 February 2005, 1107-1109

6. " Synthesis and Anti-HIV properties of new Water-Soluble Bis-functionalized/60/ FULLERENE DERIVATIVES "
S.Bosi et al., - Bioorganic & Medicinal Chemistry Letters, Vol.13, Issue 24, 15 December 2003, 4437-4440

7. " FULLERENE DERIVATIVES: an Attractive Tool for Biological Applications "
S.Bosi et al., - Eur.J.Med.Chem., 2003 Nov-Dec., 38(11-12): 913-923

8. " Local CARBOXYFULLERENE Protects Cortical Infarction in Rat Brain "
A.M-Y. Lin et al., - Neuroscience Research, Vol. 43, Issue 4, August 2002, 317-321

9. " In Vitro Action of CARBOXYFULLERENE "
N.Tsao et al., -J.Antimicrobial Chemotherapy (2002), 49, 641-649

10. " Inhibition of Group A Streptococcus Infection by CARBOXYFULLERENE "
N.Tsao et al.,- Antimicrobial Agents and Chemotheraphy, June 2001, Vol.45 (6), 1788-1793

11. " BIOILOGICAL APPLICATIONS of FULLERENE DERIVATIVES: A Brief Overview "
T. Da Ros et al., - Croatica Chemica Acta, 74(4), 743-755 ( 2001 )

12." CARBOXYFULLERENES Protect Human Keratinocytes from Ultraviolet-B-Induced Apoptosis "
C.Fumelli et al., - J.Invest. Dermatol., 2000 Nov., 115(5): 835-841

13. " C60 CARBOXYFULLERENE Exerts a Protective Activity Against Oxidative Stress-Induced Apoptosis in Human Peripheral Blood Mononuclear Cells "
D.Monti et al., - Biochem. Biophys. Res. Commun., 2000 Nov. 2, 277 (3): 711-717

14."MEDICAL APPLICATIONS of FULLERENES & METALLO-FULLERENES"
L.J.Wilson - The Electrochemical Society Interface, Winter 1999 15.CARBOXYFULLERENES as NEUROPROTECTIVE AGENTS " L.L.Dugan et al., - Proc.Natl.Acad.Sci.USA, Vol.94, 9434-9439, August 1997