1. A compound of formula (I):
wherein: R\u2032 independently is OH, NH2, or OR\u2033, wherein R\u2033 independently is alkyl, tert-butyl, allyl, or benzyl; k is 1 or 2; m is 0 or 1; Y is a structure of formula (a-1), (a-2), (a-3), or (a-4):
where p is 0 or 1; n is 1 to 10; W is OH, SH, or NZ2; each of R1-18 and Z independently is or includes hydrogen, carboxyalkyl, alkylamido, alkyl, allyl, benzyl, benzyloxyalkyl, cycloalkyl, alkoxy, hydroxyalkyl, aryl, aryloxy, hydroxyaryl, heteroaryl, phenyl, vinyl, alkynyl, alkenyl, furannylalkyl, alkylthioalkyl, arylhydroxyalkyl, indanyl, inolylalkyl, naphthylalkyl, imidazolylalkyl, pyridiylalkyl, benzothiophenylalkyl, thiophenylalkyl, thioalkyl, thioaryl, thiobenzyl, hydroxy, carboxyl, carboxyalkyloxy, amino, carboxylic acid, or holoalkylamido, aldehyde, ester, amido, tosyl, phthalimidyl, trityl, tert-butyloxycarbonyl, carbobenzyloxy, o-nosyl, acetyl, fluoroacetyl, dimethoxybenzyl, p-methoxybenzyl, an amide containing group, a thioamide containing group, an amino acid-containing group, an ester containing group, a protecting group, or a group of formula (a-5), (a-6), or (a-7);
and X is or includes hydrogen, halo, cyano, alkyl, hydroxy, nitro, amino, alkylamino, thiocyano, isothiocyano, alkoxy, aryloxy, carboxyl, carboxyalkyl, carboxyalkyloxy, ester, amido, aldehydro, alkylamido, holoalkylamido, an ester containing group, an carbonyl containing group, an amide containing group, a thioamide containing group, or an amino acid-containing group;
provided that wherein m is 0, k is 1, R\u2032 is OH, Y is (a-1), Z is carboxyalkyl, then one of R14-15 is not a compound of the formula of (a-5), (a-6), or (a-7), at least one of R12-17 is not a hydrogen, or one of R1-11 is a compound of the formula (a-5), (a-6), or (a-7).
2. The compound according to claim 1, wherein at least one of R1-9 or R12-17 comprises a cycloalkyl formed with a neighboring carbon.
3. A complex comprising the compound of claim 1 and a metal ion, a radioactive isotope of the metal ion, or a radioactive isotope of carbon, nitrogen, iodine, fluorine, oxygen, or helium.
4. The complex of claim 3, wherein the metal ion is selected from the group consisting of Ac, Bi, Pb, Y, Mn, Cr, Fe, Co, Zn, Ni, Tc, Gd, In, Ga, Cu, Re, Sm, Pm, Ho, Zr, a lanthanide, and an actinide.
5. A conjugate comprising the compound of claim 1 and a targeting moiety, a fluorescence moiety, or a nanoparticle.
6. The conjugate according to claim 5, comprising the targeting moiety, wherein the targeting moiety comprises a biomolecule selected from a hormone, a bile acid, an amino acid, a peptide, a peptidomimetic, a protein, a deoxyribonucleic acid (DNA), a ribonucleic acid (RNA), a lipid, an albumin, a receptor molecule, a receptor binding molecule, a hapten, a monoclonal antibody, a polyclonal antibody, a peptide, an aptamer, a folic acid, an estrogen, or a transferrin.
7. A complex comprising the conjugate of claim 5 and a metal ion, a radioactive isotope of the metal ion, or a radioactive isotope of carbon, nitrogen, iodine, fluorine, oxygen, or helium.
8. A pharmaceutical composition comprising the compound of claim 1 and a pharmaceutically acceptable carrier.
9. The compound according to claim 1, further comprising the compound of formula (II):
wherein: R\u2032 independently is OH, NH2, or OR\u2033, wherein R\u2033 independently is alkyl, tert-butyl, allyl, or benzyl; m is 0 or 1; Y is a structure of formula (a-1), (a-2), (a-3), or (a-4):
where p is 0 or 1; W is OH, SH, or NZ2; n is 1 to 10; each of R1-18 and Z independently is or includes hydrogen, carboxyalkyl, alkylamido, alkyl, allyl, benzyl, benzyloxyalkyl, cycloalkyl, alkoxy, hydroxyalkyl, aryl, aryloxy, hydroxyaryl, heteroaryl, phenyl, vinyl, alkynyl, alkenyl, furannylalkyl, alkylthioalkyl, arylhydroxyalkyl, indanyl, inolylalkyl, naphthylalkyl, imidazolylalkyl, pyridiylalkyl, benzothiophenylalkyl, thiophenylalkyl, thioalkyl, thioaryl, thiobenzyl, hydroxy, carboxyl, carboxyalkyloxy, amino, carboxylic acid, or holoalkylamido, aldehyde, ester, amido, tosyl, phthalimidyl, trityl, tert-butyloxycarbonyl, carbobenzyloxy, o-nosyl, acetyl, fluoroacetyl, dimethoxybenzyl, p-methoxybenzyl, an amide containing group, a thioamide containing group, an amino acid-containing group, an ester containing group, a protecting group, or a group of formula (a-5), (a-6), or (a-7);
and X is or includes hydrogen, halo, cyano, alkyl, hydroxy, nitro, amino, alkylamino, thiocyano, isothiocyano, alkoxy, aryloxy, carboxyl, carboxyalkyl, carboxyalkyloxy, ester, amido, aldehydro, alkylamido, holoalkylamido, an ester containing group, an carbonyl containing group, an amide containing group, a thioamide containing group, or an amino acid-containing group;
provided that wherein m is 0, k is 1, R\u2032 is OH, Y is (a-1), Z is carboxyalkyl, then one of R14-15 is not a compound of the formula of (a-5), (a-6), or (a-7), at least one of R12-17 is not a hydrogen, or one of R1-11 is a compound of the formula (a-5), (a-6), or (a-7).
10. The compound according to claim 9, further comprising the compound of formula (II-a), (II-b), or (II-c), wherein p is 1 or 2 and n is 1 to 10:
11. A complex comprising the compound of claim 9 and a metal ion, radioactive isotope of the metal ion, or radioactive isotope of carbon, nitrogen, iodine, fluorine, oxygen, or helium.
12. The compound according to claim 1, further comprising the compound of formula (III):
wherein: R\u2032 independently is OH, NH2, or OR\u2033, wherein R\u2033 independently is alkyl, tert-butyl, allyl, or benzyl; m is 0 or 1; Y is a structure of formula (a-1), (a-2), (a-3), or (a-4):
where p is 0 or 1; W is OH, SH, or NZ2; n is 1 to 10; each of R1-21 and Z independently is or includes hydrogen, carboxyalkyl, alkylamido, alkyl, allyl, benzyl, benzyloxyalkyl, cycloalkyl, alkoxy, hydroxyalkyl, aryl, aryloxy, hydroxyaryl, heteroaryl, phenyl, vinyl, alkynyl, alkenyl, furannylalkyl, alkylthioalkyl, arylhydroxyalkyl, indanyl, inolylalkyl, naphthylalkyl, imidazolylalkyl, pyridiylalkyl, benzothiophenylalkyl, thiophenylalkyl, thioalkyl, thioaryl, thiobenzyl, hydroxy, carboxyl, carboxyalkyloxy, amino, carboxylic acid, or holoalkylamido, aldehyde, ester, amido, tosyl, phthalimidyl, trityl, tert-butyloxycarbonyl, carbobenzyloxy, o-nosyl, acetyl, fluoroacetyl, dimethoxybenzyl, p-methoxybenzyl, an amide containing group, a thioamide containing group, an amino acid-containing group, an ester containing group, a protecting group, or a group of formula (a-5), (a-6), or (a-7);
and X is or includes hydrogen, halo, cyano, alkyl, hydroxy, nitro, amino, alkylamino, thiocyano, isothiocyano, alkoxy, aryloxy, carboxyl, carboxyalkyl, carboxyalkyloxy, ester, amido, aldehydro, alkylamido, holoalkylamido, an ester containing group, an carbonyl containing group, an amide containing group, a thioamide containing group, or an amino acid-containing group; or wherein at least one of R1-9, R19-21, or R12-17 comprises a cycloalkyl formed with a neighboring carbon.
13. The compound according to claim 12, further comprising the compound of formula (III-a), wherein p is 1 or 2 and n is 1 to 10:
14. A complex comprising the compound of claim 12 and a metal ion, radioactive isotope of the metal ion, or radioactive isotope of carbon, nitrogen, iodine, fluorine, oxygen, or helium.
15. A method of generating a diagnostic image or measurement, the method comprising:
administering to an animal a composition comprising the complex of claim 3; and
imaging or measuring an amount of the composition in a tissue or organ of the animal using magnetic resonance imaging (MRI), fluorescence imaging (FI), x-ray contrast imaging, transmission electron microscopy imaging, a positron emission tomography (PET) imaging, or single photon emission computed spectroscopy (SPECT).
16. A method of treating cancer, iron overload disease, or neurodegenerative or infectious diseases including Alzheuner’s disease (AD), Parkinson’s disease (PD), tuberculosis, HIV, fungal disease, or amalaria disease in a mammal, comprising the step of administering to the mammal a composition comprising the compound of claim 1 in an amount effective to treat the cancer, the iron overload disease, the neutrodegenerative or infectious diseases, wherein the cancer is selected from the group consisting of lymphomas, leukemias, hepatic, colo-rectal cancer, ovarian cancer, breast cancer, and prostate cancer.
17. The method of claim 16, wherein the compound of claim 1 further comprises a complex with 90Y, 86Y, 111In, 213Bi, 212Bi, 212Pb, 225Ac, 177Lu, 68Ga, 166Ho, 153Sm, 149Pm, or 67Cu.
18. A method of preparing the compound of claim 1, comprising:
reacting a compound of formula (Ib-1) or (Ib-2):
wherein: m is 0 or 1; each of R1-21 is as defined for R1-21 in formulas (I)-(IV); each of R22-24 is as defined for R1-22 in formulas (I)-(IV), or a protecting group or a structure of (a-1), (a-2), (a-3), (a-4), or (a-5), or a structure of formula (b-1), (b-2), or (b-3):
where R18 and R22-23 are as defined above; R25 independently is or includes hydrogen, allyl, alkyl, ter t-butyl, benzyl, dimethoxybenzyl, p-methoxybenzyl, p-nitrobenzyl, benzhydryl, trityl, cycloalkyl, aryl, tert-butyldimethylsilyl, or a protecting group; with a compound of formula (Ib-4), (Ib-5), (Ib-6), (Ib-7), (Ib-8), (Ib-9), or (Ib-10):
where m is 0 or 1; p is 0 or 1; R22-23 are as defined above; R26 is a leaving group and includes tosylate, chloride, bromide, mesylate, triflate, or iodide; and R27-28 independently is or includes hydrogen, carboxyalkyl, alkylamido, alkyl, allyl, benzyl, benzyloxyalkyl, cycloalkyl, alkoxy, hydroxyalkyl, aryl, aryloxy, hydroxyaryl, heteroaryl, phenyl, vinyl, alkynyl, alkenyl, furannylalkyl, alkylthioalkyl, arylhydroxyalkyl, indanyl, inolylalkyl, naphthylalkyl, imidazolylalkyl, pyridiylalkyl, benzothiophenylalkyl, thiophenylalkyl, thioalkyl, thioaryl, thiobenzyl, carboxyl, carboxyalkyloxy, aldehyde, ester, amido, an amide containing group, a thioamide containing group, an amino acid-containing group, an ester containing group, a protecting group.
19. The method of claim 18, further comprising providing a compound of formula (f-1) or (f-2):
converting the compound of formula (f-1) or (f-2), wherein R22-24 is a protecting group, to a compound of the formula (f-3) or (f-4), respectively:
alkylating a compound of the formula (f-3) or (f-4) to provide the compound of the formula (I)
20. A method of preparing a compound of one of formulas (I)-(IV), comprising:
chemically reacting a compound of formula (c-1) with a compound of (d-1) or (d-2)
where, k is 0 or 1; m is 0 or 1; n is 1 to 10; p is 0 or 1; R1-9 is defined as R1-21 in formulas (I)-(IV). R22-23 is defined as R1-22 in formulas (I)-(IV). R26 is a leaving group and includes tosylate, chloride, bromide, mesylate, triflate, or iodide; R27-28 is independently is or includes hydrogen, alkyl, allyl, benzyl, cycloalkyl, hydroxyalkyl, aryl, heteroaryl, phenyl, vinyl, or an oxo group; to provide a compound of formula (e-1) or (e-2):
converting a compound of the formula (e-1) or (e-2), wherein R22-23 is a protecting group, to a compound of the formula (e-3) or (e-4):
alkylating the compound of the formula (e3) or (e-4) to provide a compound according to one of formulas (I)-(IV).
The claims below are in addition to those above.
All refrences to claim(s) which appear below refer to the numbering after this setence.
1. A method for making a photonic crystal structure at a temperature compatible with a substrate comprising a material selected from the group consisting of III-V compounds, silicon, glass, copper and aluminum, said method comprising:
depositing a first amorphous silicon layer on said substrate at said temperature;
patterning said first amorphous silicon layer to correspond to a first layer of said photonic crystal structure;
depositing a first sacrificial filler layer to planarize said first amorphous silicon layer;
depositing a second amorphous silicon layer on said first amorphous silicon layer;
patterning said second amorphous silicon layer to correspond to a second layer of said photonic crystal structure;
depositing a second sacrificial filler layer to planarize said second amorphous silicon layer; and
removing said first and said second sacrificial filler layer from said photonic crystal structure using an etching process.
2. The method of claim 1 wherein said first amorphous silicon layer is a hydrogenated amorphous silicon layer.
3. The method of claim 1 further comprising polishing said first sacrificial filler layer.
4. The method of claim 1 wherein said first amorphous silicon layer is deposited using plasma enhanced chemical vapor deposition.
5. The method of claim 1 wherein said temperature is less than about 330 degrees Celsius.
6. The method of claim 1 wherein said etching process is a hydrofluoric acid wet dip.
7. The method of claim 1 wherein said first sacrificial layer is silicon oxide.
8. The method of claim 1 wherein said first sacrificial layer is deposited using ozone TEOS.
9. The method of claim 1 wherein said first and said second amorphous silicon layers are doped to modify the refractive index.
10. The method of claim 9 wherein said first and said second amorphous silicon layers are doped with boron.
11. The method of claim 1 wherein said material is GaAs.
12. The method of claim 1 wherein said second amorphous silicon layer is deposited using sputtering.
13. The method of claim 1 further comprising deposition of an adhesion layer to said substrate.
14. The method of claim 13 wherein said adhesion layer is silicon nitride.
15. A method for making a two-dimensional photonic crystal structure at a temperature compatible with a substrate comprising a material selected from the group consisting of III-V compounds, silicon, glass and aluminum, said method comprising:
depositing an amorphous silicon layer on said substrate at said temperature; and
patterning said amorphous silicon layer to correspond to a layer of said two dimensional photonic crystal structure.
16. The method of claim 15 wherein said material is GaAs.
17. The method of claim 15 wherein said amorphous silicon layer comprises non-hydrogenated amorphous silicon.
18. The method of claim 15 wherein said amorphous silicon layer is deposited using sputtering.
19. The method of claim 15 further comprising deposition of an adhesion layer to said substrate.
20. A method for making a photonic crystal structure at a temperature compatible with a substrate comprising a material selected from the group consisting of 11V compounds, silicon, glass, copper and aluminum, said method comprising:
depositing a first amorphous silicon layer on said substrate at said temperature;
patterning said first amorphous silicon layer to correspond to a first layer of said photonic crystal structure;
depositing a sacrificial filler layer to planarize said first amorphous silicon layer;
depositing a second amorphous silicon layer on said first amorphous silicon layer;
patterning said second amorphous silicon layer to correspond to a second layer of said photonic crystal structure; and
removing said sacrificial filler layer from said photonic crystal structure using an etching process.
21. The method of claim 20 wherein said first amorphous silicon layer is a hydrogenated amorphous silicon layer.
22. The method of claim 20 further comprising polishing said sacrificial filler layer.
23. The method of claim 20 wherein said first amorphous silicon layer is deposited using plasma enhanced chemical vapor deposition.
24. The method of claim 20 wherein said temperature is less than about 330 degrees Celsius.
25. The method of claim 20 wherein said etching process is a hydrofluoric acid wet dip.
26. The method of claim 20 wherein said sacrificial layer is deposited using ozone TEOS.
27. The method of claim 20 wherein said first and said second amorphous silicon layers are doped to modify the refractive index.
28. The method of claim 27 wherein said first and said second amorphous silicon layers are doped with boron.
29. The method of claim 20 wherein said second amorphous silicon layer is deposited using sputtering.
30. The method of claim 20 further comprising deposition of an adhesion layer to said substrate.